Homes for Sale in Highland Park: Luxury Living on Chicago’s North Shore

Nestled along the picturesque shores of Lake Michigan, Highland Park is one of Chicago’s most sought-after suburbs, known for its beautiful homes, affluent community, and top-rated schools. This historic suburb offers a diverse selection of real estate, including sprawling estates, ranch-style homes, and modern condos. With its beautiful lakefront, vibrant downtown area, and proximity to Chicago, Highland Park provides a serene yet convenient suburban lifestyle.

Why Buy in Highland Park?

Highland Park is renowned for its natural beauty, with expansive parks, ravines, and nature trails. Residents enjoy access to Lake Michigan beaches and the Chicago Botanic Garden, as well as cultural landmarks like Ravinia Festival, the oldest outdoor music festival in the country. The downtown area is bustling with boutiques, restaurants, and cafes, providing a charming shopping and dining experience.

Highland Park also offers excellent schools, making it an ideal choice for families. With access to major highways like US-41 and I-94, as well as Metra train service, commuting to Chicago or other North Shore suburbs is quick and easy. Whether you're looking for a peaceful retreat or proximity to urban amenities, Highland Park provides the perfect balance of luxury, convenience, and community.

Types of Homes for Sale in Highland Park

Single-Family Homes: Highland Park offers an impressive selection of single-family homes, ranging from classic colonial estates to modern luxury residences. Many properties are set on large lots with beautifully landscaped gardens, providing privacy and tranquility.
Ranch Homes: For buyers seeking single-level living, Highland Park features numerous ranch-style homes. These properties are popular among retirees, families, and anyone looking for a spacious home with a convenient layout. Ranch homes in Highland Park often include open floor plans, large yards, and proximity to the area’s parks and beaches.
Condos and Townhomes: Highland Park offers a variety of condos and townhomes, providing low-maintenance living with modern amenities. These properties are ideal for professionals, first-time buyers, and downsizers who want to enjoy a convenient suburban lifestyle. Many condos and townhomes are located near downtown, offering easy access to shopping, dining, and public transportation.
New Construction Homes: Highland Park continues to see growth in new construction developments. These homes offer contemporary designs, energy-efficient features, and high-end finishes, perfect for those looking for a modern home in this historic suburb.

Living in Highland Park: Nature, Culture, and Community

Highland Park is a nature lover's paradise, offering easy access to Lake Michigan, miles of hiking trails, and beautiful parks. Residents can enjoy a day at the beach, explore the stunning ravines, or relax at one of the many community parks, such as Rosewood Beach or Heller Nature Center.

Culturally, Highland Park is a vibrant community, home to Ravinia Festival, where residents can enjoy live music performances under the stars. The downtown area is a hub for dining and shopping, with a variety of restaurants, boutiques, and galleries. With excellent schools, a safe community, and a range of recreational activities, Highland Park is an ideal location for families, retirees, and anyone seeking a suburban oasis with city access.

Explore Nearby Communities

Deerfield: Located just west of Highland Park, Deerfield is known for its family-friendly atmosphere, excellent schools, and beautiful parks. The village offers a range of housing options, from spacious single-family homes to modern condos.
Glencoe: Nestled along Lake Michigan to the north of Highland Park, Glencoe offers luxury homes, a charming downtown, and a strong sense of community. With its own lakefront beaches and proximity to the Chicago Botanic Garden, Glencoe is a nature lover’s paradise.
Northbrook: West of Highland Park, Northbrook is a thriving suburb with a bustling downtown, great shopping options, and highly-rated schools. The village offers a mix of housing options, including single-family homes, townhomes, and condos.
Lake Forest: To the north of Highland Park, Lake Forest is known for its expansive estates, prestigious schools, and lakefront living. The community offers luxury homes, picturesque parks, and historic charm, making it one of the most desirable suburbs on the North Shore.
Highwood: Adjacent to Highland Park, Highwood offers a vibrant downtown with a variety of restaurants and events, including the popular summer farmers' market. This small community has a mix of historic homes and new construction.

Start Your Home Search in Highland Park Today

Whether you're looking for a luxury estate, a ranch-style home, or a modern condo, Highland Park offers an array of housing options that cater to different lifestyles. With its beautiful lakefront setting, top-rated schools, and vibrant community, Highland Park continues to be one of the most desirable suburbs on Chicago's North Shore. Start your home search in Highland Park today and discover why so many people love to call this area home.

Braeside: Known for its luxury homes and proximity to Ravinia Festival, Braeside offers elegant homes on spacious lots near public transit and green spaces.
Hybernia: A newer community featuring modern, upscale homes with access to walking trails, ponds, and natural landscapes.
Highlands: Located near downtown Highland Park, this area includes a mix of historic homes and newer properties, providing easy access to shops and schools.
Sherwood Forest: A charming neighborhood offering ranch homes, historic properties, and newer constructions in a peaceful, tree-lined setting.
Fort Sheridan: A unique lakefront community that features historic homes, townhomes, and stunning views of Lake Michigan, along with easy access to hiking trails.
New Construction in Highland Park: Highland Park offers new developments with modern, energy-efficient homes that combine contemporary design with luxurious finishes.

Latest Highland Park Homes for Sale

$4,700,000

5 Beds ⋅ 6 Baths ⋅ 12778380 MLS ⋅ NEW Status

A distinguished custom Grunsfeld estate, privately set on nearly 2 acres of exceptional tableland and ravine, offers a singular combination of architectural pedigree, uncompromising craftsmanship, and extraordinary privacy. This remarkable 5-bedroom, 5.1-bath residence showcases timeless design, an exceptional floor plan, and the highest quality finishes throughout. Soaring ceilings, dramatic floor-to-ceiling windows, wide-plank oak floors, English sycamore cabinetry, and a striking fossil stone fireplace create interiors of understated elegance and enduring sophistication. The first floor primary suite serves as a private retreat, featuring a walkout to the grounds, an expansive dressing and closet area, and a luxurious spa-inspired bath. Three additional bedrooms and two baths are located on the second floor. Outdoor living is equally impressive, with a swimming pool and expansive bluestone terrace overlooking the beautifully landscaped grounds. Additional amenities include a wine cellar, 6 car garage, 800-amp electrical service, whole-house generator, and fenced ravine. An increasingly rare offering for the discerning buyer seeking refined luxury.

811 Judson Avenue, Highland Park

$1,200,000

4 Beds ⋅ 5 Baths ⋅ 12792177 MLS ⋅ NEW Status

Welcome to this charming multi-level home nestled in the desirable North Deere Park neighborhood in Highland Park. Built in 1950, this spacious residence offers 4 bedrooms and 3 full baths and 2 half baths, perfectly situated on a unique .27-acre lot. With approximately 3,300 square feet of living space, this home provides ample room for both relaxation and entertainment. Beach rights included! MAIN FLOOR: Step inside to a beautifully renovated eat-in kitchen (2016) featuring a stunning wall of windows that overlook the tranquil yard. Relax in the sunken living room, complete with a cozy upgraded Franklin Stove fireplace that radiates warmth throughout the space. Enjoy intimate family dinners in the dining room or bask in natural light in the lovely sunroom adorned with skylights and glass doors on three sides. A tasteful powder room completes this level, ensuring convenience for guests. The LOWER LEVEL boasts a versatile family room that opens to the yard through glass doors. It includes a built-in office area, half bath, and storage closet. This space is perfect for family gatherings or a play area. You'll also find a convenient mud room and laundry facilities on this level. Ascend to the SECOND LEVEL to reach three inviting bedrooms. One bedroom has ensuite bath, and there is a Jack-and-Jill bath for the other two bedrooms. The THIRD LEVEL features a charming loft/office area at the top of the stairs, leading to the luxurious primary suite. This spacious retreat includes an expansive bathroom with skylight, double sinks, abundant storage, jetted Kohler tub, and separate shower. Enjoy the convenience of a dressing room with three closets and a fourth walk-in closet in the bedroom. Take in beautiful views of Lake Michigan from the comfort of your suite. The property includes a hot tub/endless pool, two patios, a fenced backyard, 2.5 car attached garage, and private beach rights to Lake Michigan, perfect for summer enjoyment. Walk to Ravinia Music Festival and Metra or take a short drive to everything else Highland Park has to offer.

361 N Deere Park Drive, Highland Park

$850,000

4 Beds ⋅ 3 Baths ⋅ 12789022 MLS ⋅ NEW Status

A striking mid-century modern home set on three-quarters of an acre of secluded, wooded grounds. Defined by dramatic vaulted and beamed ceilings, expansive floor-to-ceiling windows, and hardwood floors, the home offers a beautiful connection between its architectural design and natural surroundings. The main level features an inviting great room with a fireplace, a spacious dining room, and an updated kitchen with a generous center island, quartz counters, a Sub-Zero refrigerator, and BlueStar range. Upstairs, three bedrooms include a spacious primary suite with a spa-inspired bath, walk-in closet, and convenient second laundry area. The walkout lower level offers gorgeous slate flooring (2026), a family/recreation room, office or fourth bedroom, powder room, laundry, and utility/storage space. Outdoor living is equally appealing, with a screened-in porch overlooking the wooded yard and an adjoining deck that provides additional space for entertaining or simply taking in the peaceful setting. Notable improvements made by the current owner include updated landscaping and new trees (2026), exterior painting (2025), a new roof (2022), and a Sub-Zero refrigerator and BlueStar range (2022). Conveniently situated between Highland Park and Deerfield, with easy access to parks, shopping, dining, and the amenities of both communities. A rare combination of architectural character, privacy, and natural beauty.

1470 Ridge Road, Highland Park

$1,599,500

5 Beds ⋅ 8 Baths ⋅ 12793005 MLS ⋅ NEW Status

Surrounded by the peaceful, natural beauty of the Hybernia Preserve, this luxurious home offers water views and privacy seldom experienced. ***New Roof, Gutters, and Patio - 2020***New Exterior Paint - 2023***Kitchen Renovation - 2018***New Dishwasher - 2021***New Disposal - 2025***New Marble and Hardwood Flooring***Closets Professionally Organized - 2021***Whole House Generator - 2018***New Basement Egress Windows - 2023***A dramatic 2 story, marble floored foyer welcomes you and flows effortlessly to an open floor plan with a gorgeous volume ceiling great room with floor to ceiling windows that flood the residence with loads of natural light! Recently updated, this home offers 5+ Bedrooms (including a first floor primary suite AND a first floor guest suite that includes a dedicated guest bath) 6 full and 3 half baths, and a full basement which treats you to a spa room that rivals your most favored paid luxury spa experience. The attached garage offers parking for 3 cars (plus a lift to accommodate an additional 4th vehicle) and incredible additional storage. Additional updates include ***2018 whole house generator, ***new within 3 years HVAC, new water heaters, ***2018 flooring and new interior paint, 2021 professionally organized closets, 2018 incredible chef's kitchen with sub-zero fridge, wolf range, wine/bev cooler, and much more...while invaluable upgrades include wine cellar, theatre room, professional fitness room, 4 zone heating and cooling, security, irrigation, professional car lift in the garage...simply A+++. Step out to your gorgeous patio outdoor space which includes a gazebo complete with grilling station for your outdoor entertainment. You will feel like you are miles away from everything...and yet be only minutes away from everything that downtown Highland Park has to offer. Award winning schools and easy access to attractions like Lake Michigan beaches, Ravinia Park, Chicago Botanical Gardens, and so much more! This home is an absolute MUST SEE!

1745 Sundrop Circle, Highland Park

$1,795,000

6 Beds ⋅ 7 Baths ⋅ 12770627 MLS ⋅ NEW Status

Steeped in history and beautifully reimagined for modern living, this magnificent Captain's Mansion, dating to 1892, offers a rare opportunity to own a piece of Fort Sheridan's distinguished architectural heritage. Located just three homes from Lake Michigan within the National Historic Landmark District, this exceptional 7,654-square-foot residence seamlessly blends the grandeur and craftsmanship of the late 19th century with extensive contemporary renovations. Soaring ceilings, sun-filled interiors, hardwood floors, two staircases, multiple fireplaces, and seasonal lake views create an extraordinary setting for everyday living and entertaining. A gracious foyer introduces the home's impressive scale and timeless elegance, opening to a beautiful living room with fireplace and a formal dining room, both featuring stunning 11-foot ceilings. The newly redesigned gourmet kitchen combines style and functionality with updated cabinetry, quartz countertops, a generous center island, new stainless steel Wolf double ovens and cooktop, a new Sub Zero refrigerator, and a spacious pantry with a beverage bar and abundant storage. The expansive family room addition offers exceptional gathering space with direct access to a new Trex composite patio and fenced side yard. The second floor features three spacious ensuite bedrooms, including a luxurious primary suite with an oversized custom walk-in closet and a newly renovated spa-inspired bathroom featuring radiant heated floors, quartz countertops, a spacious shower, Jacuzzi tub, and heated towel rack. A comfortable loft and conveniently located laundry room complete this level. The versatile third floor offers a spacious second family room and two additional rooms ideal for bedrooms, home offices, or flexible living spaces. The finished lower level provides even more room to spread out, with a recreation room, additional bedroom, full bathroom, and second laundry room. Extensive recent improvements enhance the home's comfort and functionality, including three new HVAC and air conditioning systems (2025), electrical upgrades, new lower-level luxury vinyl flooring, screen doors, sprinkler system, custom mudroom closets, and window treatments. Freshly painted interiors and an attached three-car garage further complement this exceptional, move-in-ready residence. Originally part of the historic Fort Sheridan military installation, this remarkable home offers the rare opportunity to experience the architectural character and grandeur of a bygone era without sacrificing modern comforts. Surrounded by the natural beauty of Lake Michigan, scenic walking trails, and historic architecture, Fort Sheridan offers a distinctive lifestyle just minutes from the restaurants and shops of Highwood, Highland Park, and Lake Forest, with convenient access to Metra and downtown Chicago. An extraordinary combination of history, architectural beauty, generous living spaces, and modern luxury in one of the North Shore's most distinctive settings.

41 Scott Loop, Highland Park

$589,000

3 Beds ⋅ 2 Baths ⋅ 12792745 MLS ⋅ NEW Status

Ravinia! Completey updated & renovated in 2016! Features a bright and open floor plan! Beautiful New kitchen with great cabinet space, granite countertops, stainless appliances and center island with cool built-in fireplace! All New in 2016: New Kitchen, New Bathrooms, Windows, HVAC, Copper Water Piping, PVC plumbing, 200 Amp Electrical Panel, New Washer & Dryer, New Roof, and more. Solar panels also were installed in 2020 - fantastic with today's ever increasing utility bills. The main level features an open kitchen, dining, and family room space. Upstairs are 3 bedrooms and a full bathroom. The walk-out lower level features a spacious recreation room, full bathroom, laundry/Utility room and a crawl space with concrete floor. Beautifully & Professionally landscaped yard! Great walk to everywhere Ravinia location: Rosewood Beach, Farmer's Truck Wednesdays, Food Truck Thursdays, Green Bay Trail, Schools, Shops & Restaurants, Ravinia Festival, Chicago Botanic Garden and More! Just move right in and enjoy!!

475 Burton Avenue, Highland Park

$1,075,000

4 Beds ⋅ 4 Baths ⋅ 12785762 MLS ⋅ NEW Status

Highest and best due by Monday 2:00 pm. Welcome to 798 Timber Hill, a beautifully updated home situated on a gorgeous street in the highly desirable Braeside area. Offering exceptional finishes, thoughtful improvements, and modern comforts throughout, this sharp and move-in-ready home has undergone extensive renovations between 2023 and 2026. The sought after open floor plan offers seamless flow between living spaces, ideal for everyday living and entertaining. A dramatic two-story foyer welcomes you with a redesigned front entry featuring a new door with sidelights, beautifully honed slate flooring, and a striking staircase. From the foyer, enter the gracious family room, offering generous space for gathering and entertaining. A wet bar with built-ins adds convenience and character, while thoughtfully designed office storage provides additional functionality. The stunning, new kitchen features Fricano Custom soft-close cabinetry with under cab lighting, custom hood, gorgeous quartzite countertops and backsplash, a spacious 3-seat center island, new LG appliances, and slate-tile flooring Additionally, a new window was added along with the new door & storm door accessing the convenient grilling area. The dining room opens to a wonderful screened porch with access to an expansive deck and fenced backyard, creating a seamless connection between indoor and outdoor living. Hardwood floors have replaced carpeting in all four bedrooms on main level, while updated lighting throughout and fresh interior and exterior paint enhance the home's appeal. The luxurious primary suite features a completely remodeled bath with heated floors, frameless glass shower and a newly designed large walk-in closet. The hall bath has also been completely gutted and professionally designed featuring new countertops, stylish wall sconces, mirrors, slate-tile flooring. The newly finished lower level offers flexible living space with luxury vinyl flooring, a finished ceiling, an additional enclosed room ideal for great storage, bright room with adjacent closet perfect for guest room/office and an updated full bath. Additional significant improvements include a new furnace (2026), significant windows replaced (2024), new LG washer and dryer, updated recessed LED lighting, and an EV charger in the garage. Exterior enhancements include a newly paved driveway, rebuilt retaining wall, refreshed screened porch and patio, beautifully landscaped grounds with a sprinkler system, a fully fenced backyard, and a dedicated dog run. Convenient access to the train, highways, shopping, and parks. This house has it all! Fireplace is conveyed as-is. See Additional Information for an extensive list of improvements and updates. Total square footage includes finished basement.

798 Timber Hill Road, Highland Park

$525,000

3 Beds ⋅ 3 Baths ⋅ 12790006 MLS ⋅ NEW Status

This home has all new up to date electrical wiring, a brand new bathroom, house covered with fresh paint, both inside and out. The lower level family room has plush new carpet.The location is close to schools, shopping, restaurants, Highway 41 and the 294 Toll Road. The sidewalks and the patio are new and freshly done. There is a brand new community center close by which offers numerous classes and activities. It is ready for new owners to enjoy!

1751 Clavey Road, Highland Park

240 Whistler Road Unit #1E, Highland Park

$2,100,000

5 Beds ⋅ 6 Baths ⋅ 12791592 MLS ⋅ NEW Status ⋅ Fort Sheridan BLDG.

Built in 1893 and designed by the celebrated Chicago firm Holabird & Roche, this landmark building in the heart of Fort Sheridan began its life as the Infantry Drill Hall and later served as the post gymnasium. Today it holds just 11 distinctive condominiums, and this end unit is one of its most special. With exposures to the east, north, and south, the home is filled with light throughout the day. The building's original wide, arched entrance on the east facade has been reimagined as a dramatic wall of windows, a striking reminder of the building's history. The kitchen pairs clean, contemporary design with serious function, including a Sub-Zero refrigerator and freezer, a Bosch dishwasher, and a six-burner FiveStar range with two ovens. A large marble island with a breakfast bar is the natural gathering spot, and the eating area beside it is surrounded by floor-to-ceiling windows. The kitchen opens to the family room, where 16-foot ceilings and walls of glass lead out to a 38-foot balcony overlooking the meadow and stream, a lovely place to start the morning or unwind at the end of the day. The primary suite has 13-foot ceilings, floor-to-ceiling windows, and its own balcony facing the historic water tower. The primary bath includes a walk-in shower, whirlpool tub, separate Toto toilet room, makeup vanity, and walk-in closet. One of many large closets, professionally built out, throughout the home. The lower level offers remarkable flexibility, with a family room lit by 25 feet of windows, two more bedrooms, two baths, an exercise area, a bonus room and workshop, ideal for guests, a home office, or extended family. Everyday living is easy here, with an elevator just outside the front door, all primary living spaces on the main level, and four assigned spaces in the attached heated garage. Step outside to gravel walking paths and head east for views of Lake Michigan, plus you're just a short walk from Highwood's restaurants, festivals, and food trucks in the park. A rare chance to own a piece of North Shore history, beautifully suited to how we live today.

240 Whistler Road Unit #1E, Highland Park

$2,250,000

4 Beds ⋅ 5 Baths ⋅ 12791828 MLS ⋅ NEW Status

RSTUDIO DESIGN GROUP ONCE AGAIN IS EXCITED TO PRESENT A STUNNINGLY TRANSFORMED ALL BRICK RANCH SET ON 1 ACRE LOT WITH A CIRCULAR DRIVEWAY LOCATED IN HIGHLY DESIRABLE HIGHLAND PARK COMMUNITY. HIGH CEILINGS. 4 BEDROOMS, 4.1 BEAUTIFULLY DESIGNED BATHROOMS. CUSTOM KITCHEN FEATURING TRENDY QUARTZITE COUNTERTOPS, UNIQUE CENTER ISLAND, PREMIUM CABINETRY AND HIGH-END APPLIANCES. THE FAMILY ROOM, COMPLETE WITH A FIREPLACE, OPENS TO A LARGE YARD WITH HUGE PATIO. HARDWOOD FLOORS THROUGHOUT. LUXURIOUS MASTER SUITE WITH A SPA-LIKE ENSUITE BATHROOM. SECOND BEDROOM SUITE. THIS HOME DELIVERS THE PERFECT BLEND OF ELEGANCE, STYLE AND FUNCTIONALITY. HUGE FINISHED BASEMENT. 3 CAR ATTACHED HEATED GARAGE, HOUSE GENERATOR, SPRINLER SYSTEM. ENJOY THE BEST OF SPACIOUS RANCH-STYLE LIVING ON AN EXTRAORDINARY LOT, ALL CONVENIENTLY LOCATED NEAR EXPRESSWAYS, SHOPPING, AND OTHER AMENITIES.

2035 Kipling Court, Highland Park

$1,650,000

5 Beds ⋅ 6 Baths ⋅ 12790920 MLS ⋅ NEW Status

A rare offering in one of Highland Park's most coveted locations - This stunning custom built all brick residence is beautifully positioned on a private tree filled lot and offers six bedrooms & 5.5 bathrooms. The gracious interior begins with an elegant foyer opening to a spectacular living room, where a striking stone fireplace and windows on two exposures fill the space with natural light. French doors transition seamlessly to the family room, complete with a second fireplace and an open connection to the chef's kitchen. Showcasing an oversized island with breakfast bar, granite countertops, premium stainless steel appliances, beverage refrigerator, breakfast area and generous walk-in pantry this is the perfect space for any home chef. A formal dining room with French doors is just off the kitchen along with a main floor bedroom with en suite, & a spacious mudroom with direct access to the attached three car garage. An elegant powder room completes the main level. Upstairs, the primary suite offers a tranquil private retreat with dual walk-in closets, and a luxurious en suite with separate vanities, soaking tub, oversized walk in shower and private water closet. Three additional bedrooms provide exceptional flexibility, including one with a private en suite bath and walk in closet, while two bedrooms share a beautifully designed Jack and Jill bath with dual vanity. The laundry room is just down the hall and features a utility sink and plenty of additional storage space. The finished basement extends the living space with an expansive recreation room with a bar, media room with screen, billiards room with pool table, sixth bedroom, full bath with walk-in shower and versatile bonus room currently used as a gym. Outside, a lush and beautifully backyard creates a private sanctuary, with mature trees, expansive lawn and a sophisticated paver patio ideal for al fresco dining and entertaining. Perfectly positioned just blocks from the Highland Park Metra, downtown shopping, acclaimed dining and farmers markets, with easy access to Lake Michigan, beaches, lakefront paths and Ravinia. Zoned to highly regarded District 112 schools and Highland Park High School. An exceptional opportunity in one of the most desirable locations on the North Shore.

1520 Oakwood Avenue, Highland Park

$460,000

3 Beds ⋅ 3 Baths ⋅ 12786236 MLS ⋅ ACTIVE Status

This move-in ready 3 bedroom, 2.5 bath END-UNIT Chantilly townhome is spacious and bright with an ideal floor plan. First level features expansive family room with marble surround fireplace, formal dining room with bar, versatile den with built-ins and sliding doors to a private patio. The kitchen features Shaker wood cabinetry, stainless steel appliances, Corian countertops, pantry and direct patio access. Luxury vinyl flooring throughout first level. Upstairs, the oversized primary suite offers a walk-in closet, cedar closet, built-in cabinetry and beautiful en-suite bath with decorative tile flooring, double sinks plus vanity area and tub/shower. Two additional generously sized bedrooms, a full hall bath and convenient second-floor laundry complete the upper level. Enjoy outdoor entertaining on the oversized private, fenced patio. Additional highlights include a two-car garage with storage. Residents enjoy a community outdoor pool and a fantastic location near Fink Park, walking paths, recreational facilities and Deer Creek Racquet Club. Easy highway access and just minutes to downtown Highland Park.

737 Orleans Drive, Highland Park

$1,350,000

4 Beds ⋅ 4 Baths ⋅ 12788706 MLS ⋅ ACTIVE Status

A rare opportunity to own a recognized piece of Highland Park architectural history. A locally Landmarked property, the Reisler-Feingold House was designed by noted architect Arthur Dennis Stevens, a protege of Frank Lloyd Wright, with a landscape by distinguished landscape architect Steven Christy. Together, house and grounds create an exceptional Mid-Century Modern setting on nearly 0.84 acres. Thoughtfully renovated in 2017, this four-bedroom, three-and-one-half-bath Split Level residence pairs architectural significance with modern comfort. Extensive improvements-including updated electrical, plumbing and HVAC systems, underfloor heating, new bathrooms, flooring and finishes-were carefully executed while respecting the integrity of the original design. A new patio enhances indoor-outdoor living, and the roof was replaced in 2014. Strong horizontal lines, expansive glass and abundant natural light define the home, framing the landscape through every season. Warm natural materials and beautifully proportioned spaces create an atmosphere that feels intimate, inviting and unmistakably connected to its surroundings. Outside, the landscape is integral to the architecture, providing privacy, beauty and a remarkable sense of retreat. What truly sets the house apart is its rare combination of provenance and livability. This is not a museum or a restoration project waiting to happen. It is an important Mid-Century Modern home, carefully brought forward for contemporary living, ready to move in and enjoy. Architecturally significant. Historically recognized. Beautifully livable. For the buyer who values design, craftsmanship and authenticity, 1120 Ridgewood Drive is a rare opportunity to become the next steward of one of Highland Park's distinctive homes.

1120 Ridgewood Drive, Highland Park

1220 Park Avenue Unit #126, Highland Park

$324,900

2 Beds ⋅ 2 Baths ⋅ 12782094 MLS ⋅ ACTIVE Status

Welcome to Brooke Estates! This bright and spacious 2-bedroom, 2-bathroom end-unit condo offers comfortable, move-in-ready living in a beautifully maintained elevator building. Filled with natural light, this inviting home features an updated kitchen with stainless steel appliances, hardwood flooring, and a convenient breakfast bar that opens to the dining area, complete with vaulted ceilings and skylights. The spacious living room features a cozy gas fireplace and direct access to a private balcony, perfect for relaxing or enjoying your morning coffee. The generously sized primary suite offers plenty of space for a king-sized bed, sitting area, and additional furnishings, along with a private full bathroom and walk-in closet with custom built-ins. The second bedroom features an entire wall of closets, providing exceptional storage. Additional storage can be found throughout the home, including a front entry coat closet and linen closets. A generously sized laundry room features a newer stackable washer and dryer, offering both convenience and additional storage space. Completing this exceptional condo are two heated garage parking spaces and a dedicated storage locker (#31). Brooke Estates offers a wonderful selection of amenities, including two outdoor swimming pools, beautifully landscaped grounds, two picturesque ponds with a fountain, scenic walking paths, and ample guest parking. Located in a highly regarded school district, this home offers an ideal combination of comfort, convenience, and community amenities. The association boasts healthy reserves and no special assessments. Enjoy the ease of maintenance-free living in this desirable Highland Park community!

1220 Park Avenue Unit #126, Highland Park

$649,000

2 Beds ⋅ 3 Baths ⋅ 12785449 MLS ⋅ ACTIVE Status ⋅ Fort Sheridan BLDG.

Discover a distinctive blend of historic character and modern sophistication in this exceptional three-story townhome nestled within the storied Fort Sheridan community along Lake Michigan. An open floor plan, two spacious bedrooms, and two and a half bathrooms create an inviting setting for both everyday living and entertaining. The updated kitchen is beautifully appointed with granite countertops, and a center island, while updated bathrooms offer contemporary style and comfort. Architectural appeal shines through in the dramatic ceiling heights, with 10-foot ceilings on the second floor and soaring 11-foot ceilings on the third, featuring arched windows on the top level. A wooden deck extends the living space outdoors, and a two-car garage and dedicated utility room provide added convenience. Enjoy the distinctive Fort Sheridan lifestyle, where historic surroundings meet the natural beauty of Lake Michigan. Explore nearby scenic trails and lakefront vistas, catch the train at the Fort Sheridan Metra station, or stop by Starbucks just moments away. A rare opportunity to enjoy refined, low-maintenance living in one of the North Shore's most distinctive historic communities.

155 Whistler Road, Highland Park

$575,000

3 Beds ⋅ 3 Baths ⋅ 12786577 MLS ⋅ ACTIVE Status

Set on a serene residential street in the heart of downtown Highland Park, this spacious three-level townhome offers the ideal combination of everyday comfort and easy access to everything the area has to offer. The main level offers a welcoming entry, generous living room with access to a large private fenced patio, separate dining room or den, powder room, and kitchen with stone countertops, subway tile backsplash, abundant cabinetry, and convenient pull-out pantry storage. Hardwood flooring and ample natural light add warmth throughout the space. Upstairs, three bedrooms and two full baths provide a comfortable separation between living and sleeping spaces. The oversized primary bedroom features a walk-in closet and en suite bath with a glass-enclosed walk-in shower. A full-size side-by-side laundry room with additional storage adds everyday convenience. The lower level expands the living space even further with a large family room and direct access to the attached two-car garage, which includes two additional storage rooms. Walk to the Metra, shops, restaurants, coffee, and more, while nearby beaches, Ravinia Festival, country clubs, and golf courses make it easy to enjoy the best of the North Shore.

1454 Glencoe Avenue, Highland Park

$829,000

4 Beds ⋅ 2 Baths ⋅ 12783502 MLS ⋅ ACTIVE Status

Rare opportunity in the heart of Highland Park - an exceptionally deep 50' x 220' professionally landscaped property offering remarkable outdoor space, a 2-car detached garage, and, once inside, classic architectural character with more than 2,600 square feet of living space. A welcoming covered front porch introduces this beautifully maintained brick home, where hardwood floors, 9' ceilings, solid oak doors, and elegant millwork reflect its timeless character. The thoughtfully designed main level offers an inviting flow, beginning with a spacious living room featuring a cozy fireplace. A dedicated first-floor office provides the perfect work-from-home space, while the separate dining room serves as the heart of the home for gatherings and entertaining. The large eat-in kitchen offers abundant cabinetry, plenty of counter space, a breakfast bar with seating for 4, and additional table space. It opens seamlessly to the bright first-floor family room, which has a large window facing the gorgeous yard, creating an ideal layout for everyday living. A full bath is located on the main level. The second floor includes three generously sized bedrooms and a second full bathroom with a walk-in closet. The third floor provides a private fourth bedroom with an adjoining sitting area, making it an excellent retreat for guests, extended family, or a live-in arrangement. The basement is divided into two functional spaces. Imagine one side for a play area, craft room, or a second office. A laundry closet is located on this side. There's a convenient toilet-only bathroom with the possibility of becoming a half bath. The unfinished portion offers a utility room and excellent storage space. With its classic architectural details, generous living areas, and a convenient location close to shopping, dining, downtown amenities, and commuter rail service, this home is ready to welcome its next owners to add their own personal touch.

1538 Oakwood Avenue, Highland Park

$599,000

4 Beds ⋅ 2 Baths ⋅ 12783254 MLS ⋅ ACTIVE Status

RARE OPPORTUNITY IN HIGHLAND PARK! Set on approximately 29,000 square feet across TWO PARCELS, this solidly built 1927 brick home offers incredible possibilities-restore and reimagine a home filled with character, or explore the potential to build new. Beautiful craftsmanship includes black cherry millwork and moldings, red oak hardwood floors throughout (including beneath carpeting), French doors, and two fireplaces, including a striking stone fireplace in the family room/den. Spacious living and dining rooms, a kitchen ready to be expanded and transformed, separate pantry, screened porch, and an attached greenhouse offering additional possibilities. Second-floor bedrooms and full bath, plus a large unfinished basement with shower and toilet. The expansive grounds are surrounded by mature trees with plenty of room to enjoy the property and create your own outdoor oasis. Central air has been added while much of the home's classic 1920s character remains. Walk to Hidden Creek AquaPark and enjoy easy access to vibrant downtown Highland Park with its restaurants, shopping and beautiful library, along with everything this sought-after North Shore lakefront community has to offer. A truly unique opportunity for the buyer who appreciates the craftsmanship of a classic home-or sees the possibilities in the land.

1324 Fredrickson Place, Highland Park

$5,495,000

8 Beds ⋅ 12 Baths ⋅ 12781411 MLS ⋅ ACTIVE Status

Stop dreaming, start living. Rarely does a residence of this magnitude and pedigree become available. Nestled just steps from the whispering shores of Lake Michigan, 86 Prospect Avenue is more than a home-it is a masterpiece of architectural significance. Originally commissioned in 2006 by a prominent local builder as his personal sanctuary, this estate has recently emerged from a multi-year, multi-million dollar transformation, championed by Red Rock Custom Homes and Earth Developments, as well as design carefully curated by Kara Mann Interiors, resulting in a seamless fusion of timeless North Shore grandeur and 2026's most sophisticated modern luxuries. Thoughtfully situated on three hand-selected well-located parcels, the land now totals .87 acres of meticulously manicured grounds. Your approach to the home is cinematic, featuring a brand new circular paver drive, adorned by timeless gas lamps and lush potted plants, which leads to a majestic porte-cochere, a private gated motor court, and a heated five-car garage. The rear grounds are anchored by a 45-foot heated pool recently totally redone and resurfaced, complemented by a stone fire pit and sprawling covered patios. The heart of the home is a bespoke Chef's Atelier featuring a striking marble and walnut island, Viking and Wolf ranges, Traulsen refrigeration with a dedicated commercial walk-in refrigerator, and Sub-Zero integrated drawers. This culinary suite transitions effortlessly from a sun-drenched breakfast room complete with a custom eating area with built-in benches to an expansive formal dining room anchored by a stately wood-burning fireplace. With over 14,000 square feet of finished living space, the home offers a versatile floor plan of eight to ten bedrooms, including a primary suite that serves as a bastion of tranquility with a private balcony, seasonal lake views, dual spa-inspired bathrooms, and two expansive custom dressing rooms. Four additional ensuite bedrooms and a hidden play area grace the second floor, while the third floor is dedicated to wellness with a professional gym, massage/yoga room, and recreation room. The walk-out lower level provides a sophisticated retreat with a second kitchen, three guest suites, three full bathrooms, and a large recreation room with a dedicated cabana bath. Built with a "forever" mindset, the estate includes a full-service elevator, two laundry suites, an executive library, a whole-house generator, and an advanced irrigation system. This is not merely an acquisition of real estate, but the acquisition of a lifestyle without compromise. Step into the perfect blend of timeless architecture and luxury north shore living. Welcome home! A few final touches being completed as we speak. Nearly $2.5m was invested in this home since in the last two years, a full list of improvements available upon request.

86 Prospect Avenue, Highland Park

$439,000

3 Beds ⋅ 3 Baths ⋅ 12773165 MLS ⋅ ACTIVE Status

Rarely available Chantilly END-UNIT ideally situated overlooking the golf course! Lovingly maintained, this spacious and light-filled 3-bedroom, 2.5-bath townhome offers a wonderful floor plan featuring an expansive family room, formal dining room with wet bar and versatile den/office with sliding doors to a private patio. The kitchen features white cabinetry, granite countertops, ceramic tile flooring, a built-in planning desk area, pantry and direct patio access. Upstairs, the oversized primary suite offers a walk-in closet, cedar closet and en-suite bath. Two additional generously sized bedrooms, a full hall bath and convenient second-floor laundry complete the upper level. Enjoy outdoor entertaining on the private, fenced patio. Additional highlights include a two-car garage with abundant storage. Residents enjoy a community outdoor pool and a fantastic location near Fink Park, walking paths, recreational facilities and Deer Creek Racquet Club. Easy highway access and just minutes to downtown Highland Park. Mechanical ages: Bradford White 50-gallon electric water heater - Sept. 2021, Lennox indoor air handler - Sept. 2023, Maytag washer - Jan. 2021, Maytag electric dryer - older, Maytag side-by-side refrigerator/freezer - Jan. 2009, Maytag 30" electric range and microwave - early 2009, Maytag dishwasher - May 1997

1440 Concorde Circle, Highland Park

$2,499,000

6 Beds ⋅ 7 Baths ⋅ 12781765 MLS ⋅ ACTIVE Status

This Beautiful Home on Over an Acre in the Heart of Highland Park Boasts Soaring Barrel Ceilings over 20' High and 5 Fireplaces. Amazing Home for Entertaining with a Magnificent Great Room, a Banquet-Sized Dining Room with a Butlers Pantry, a Wonderful Screened Porch and a Balcony Overlooking the Backyard- which includes Ravines and a Huge Yard, large enough for a tennis/pickleball court, an outdoor pool and more- Accessed by a Bridge! The Double Island Chefs Kitchen has a Fireplace, Walk-in Pantry, Professional Series Appliances, Dumb-waiter and Way Too Many Features to List! The Main Floor has 3 Bedrooms and 3 1/2 Baths and the Entire 2nd Floor is a Romantic Hideaway Primary Suite with its Own Family Room, Fireplace, Huge Walk-in Closet and Spa-like Bath. There is potential to create a 1st Floor Primary if desired. This Home offers over 8000 Sq Ft plus 2330 Sq Ft in the Finished Walkout Basement featuring a 40' Indoor Pool with a Wall of Glass that Open to the Outdoors! 2 Additional Bedrooms and Full Baths, a Massive Workout Room, an Amazing Home Theater, and a Summer Kitchen in the Walkout Basement. 5 Zones of Heat and Air, and a 3+ Car Garage. Located just moments from the Vibrant Shops, Dining, and Cultural Landmarks of Downtown Highland Park, the Metra Train and the Lakefront, this Home offers a Lifestyle of Convenience and Sophisticated Comfort. It's not just a place to live-It's a Place to Thrive. Truly a Must See!

493 Hazel Avenue, Highland Park

$699,999

2 Beds ⋅ 3 Baths ⋅ 12781749 MLS ⋅ ACTIVE Status

Step into this completely renovated (by homeowner) and beautifully appointed Fort Sheridan townhome and prepare to be mesmerized. An unobstructed park view sets the stage for this exceptional home, where 11-foot ceilings, sophisticated design, and state-of-the-art technology come together to create a truly one-of-a-kind living experience. The home has been thoughtfully opened up to create an airy, light-filled floor plan. The first floor features stunning chevron-patterned flooring, a sleek linear modern gas fireplace, and a spectacular custom kitchen. Designed for both everyday living and entertaining, the kitchen showcases 6-foot custom white oak cabinetry, an extra-wide drawer system, a 7-foot island with integrated wine refrigerator and microwave, and gorgeous quartz countertops with a waterfall edge. Additional details include a reverse-osmosis water purification system, under-cabinet toe-kick lighting, and a custom white oak banquette with integrated storage. Even the powder room is gorgeous with hand made cement Moroccan tiles. Smart-home technology is seamlessly integrated throughout, including Lutron Caseta lighting, Sonos surround sound and built-in speakers, and motorized Hunter Douglas window shades. Every detail has been considered, including modern HVAC registers, contemporary outlets with USB-A/C charging ports, and sleek screwless switch plates. Ascend the custom white oak staircase to the second floor, where beautifully appointed bedrooms feature custom wall paneling, spacious closets, extra-wide French doors, and 2 gorgeous bathrooms outfitted with Kohler fixtures. The primary suite offers a generous walk-in closet and a luxurious walk-in shower with floor-to-ceiling tile. The lower level provides exceptional functionality with a new washer and dryer, floating laundry folding cabinet, abundant additional storage, and an epoxy-floored attached two-car garage. Nothing has been overlooked in this extraordinary renovation. Sophisticated, stylish, and exceptionally well executed, this is an effortless way of life in one of the North Shore's most special settings. Living in Fort Sheridan is truly paradise-nestled along Lake Michigan and surrounded by ravines, preserves, and natural beauty. Enjoy beach access, scenic trails, and close proximity to downtown Highwood, Highland Park, and Lake Forest, with an easy commute to Chicago. A rare opportunity to enjoy beautifully designed, completely renovated living in the heart of Fort Sheridan.

271 Whistler Road, Highland Park

$839,000

4 Beds ⋅ 3 Baths ⋅ 12780388 MLS ⋅ ACTIVE Status

IMPROVED PRICE! SELLER IS MOTIVATED. Come see this beautiful craftsman home with a huge backyard in a prime North Shore location. This house is truly a "home", from the dramatic front porch to the BAY WINDOW off the kitchen and CRAFTSMAN DETAILS throughout. MOVE RIGHT IN to this classic home convenient to all the North Shore has to offer! LOVINGLY MAINTAINED and continuously updated by two generations of the same family. GREAT FLOOR PLAN - Kitchen is open to a bright, SPACIOUS EAT-IN AREA, flowing into the formal dining room and then into the front living room.Working GAS FIREPLACE. FOUR GOOD-SIZED BEDROOMS. EN SUITE PRIMARY BATH and full hall bath upstairs, plus powder room downstairs. PARTIAL FINISHED BASEMENT. Spacious BRICK PATIO with gas line to the BBQ. HUGE FULLY-FENCED BACK YARD with gorgeous mature landscaping! Plus an UNBEATABLE CLOSE-TO-EVERYTHING LOCATION ... On a QUIET STREET lined with historic homes but just a block from downtown Highland Park's restaurants, shops, Metra station, coffee, book stores etc. And just a stone's throw to Ravinia District of Highland Park, Ravinia Festival, Chicago Botanic Garden, schools, parks, beaches and more. No central A/C, but many other recent updates and continuously maintained by owners. See the Improvements List under "additional info" or call listing agent Carolyn Cerf!

1530 Oakwood Avenue, Highland Park

1795 Lake Cook Road Unit #211, Highland Park

$338,900

2 Beds ⋅ 2 Baths ⋅ 12779740 MLS ⋅ PRICE CHANGE Status

Bright and spacious, this rarely available 2-bed, 2-bath condo at the Americana in Highland Park offers a sophisticated retreat in a prime location. The moment you step the attention to detail is evident: New flooring, large living area, updated kitchen and bathrooms. The heart of the home is the reimagined eat-in kitchen, a chef's delight featuring crisp cabinetry, expansive counter space, and new stainless steel appliances. Whether you're prepping a quick breakfast or hosting a dinner party, the direct balcony access makes it easy to step out for some fresh air. The open-concept living and dining area feels incredibly airy, anchored by a fireplace that adds a layer of warmth and ambiance to the contemporary design. The primary suite serves as a true sanctuary, complete with a massive walk-in closet and a private en-suite bathroom. The second bedroom is equally impressive, filled with natural light and offering a large walk-in closet-perfect for a guest room or a dedicated creative space. Living at the Americana means enjoying a suite of amenities, including an outdoor pool, exercise room, and a party room with its own kitchen. This unit includes a dedicated storage space on the same floor and one assigned space in the heated garage. With easy access to parks, shopping, and dining, this home perfectly blends updated style with effortless convenience.

1795 Lake Cook Road Unit #211, Highland Park

$625,000

4 Beds ⋅ 2 Baths ⋅ 12779254 MLS ⋅ ACTIVE Status

Updated Highland Park home with distinctive architectural character and exceptional living space. Hardwood floors, vaulted ceilings, exposed beams and abundant natural light create a warm, open feel throughout. The updated kitchen features white cabinetry, stone countertops and stainless-steel appliances, while both bathrooms have been thoughtfully renovated. The home's standout living spaces include a dramatic vaulted great room and a second expansive family room with a soaring wood-plank ceiling and exposed beams-giving the home character and flexibility rarely found at this price point. Four bedrooms provide space for family, guests or a home office, with additional finished space downstairs. Outside, enjoy a large, private backyard and newly expanded deck with plenty of room for dining, entertaining and everyday living. Mature trees and established landscaping add privacy and charm. Located in Highland Park with convenient access to schools, parks, shopping, dining, Metra and everything the North Shore has to offer. Move-in ready, updated where it matters, and filled with architectural details that make this home truly stand apart.

1235 Ferndale Avenue, Highland Park

$975,000

4 Beds ⋅ 5 Baths ⋅ 12767426 MLS ⋅ ACTIVE Status

Sophisticated, spacious, and beautifully updated, this light-filled luxury townhome offers the ease of maintenance-free living with the space, privacy, and functionality of a single-family home. Ideally located just steps from town and Sunset Foods, the residence features 5 bedrooms-including flexible office space, 4 1/2 baths, and more than $350,000 in thoughtful improvements. The main level is designed for both everyday living and entertainment, with a beautifully updated chef's kitchen featuring Viking appliances, new stone countertops, under cabinet lighting & charging station. Brazilian cherry hardwood floors bring warmth and richness throughout the home. The generous living area is anchored by a striking remote controlled gas fireplace and stunning maple cabinets & shelving, creating a warm and inviting gathering space. Upstairs, the second floor offers three bedrooms, including a serene primary suite and en-suite, spa bath outfitted with a steam shower, heated floors, soaking tub, plus two organized walk-in closets. Two additional bedrooms share a Jack-and-Jill bath, while a conveniently located laundry area and built-in homework station, which can also be used as a display area, provides function and style. The third floor is a private, beautifully finished space ideal for a home office, additional bedroom, studio, or quiet retreat, complete with a stunning Bernhardt built-in office. The finished lower level adds even more versatility, with a bedroom featuring a custom closet, full bath, dedicated gym space, and an updated entertainment area with surround sound-perfect for movie nights, guests, or extended family. Speakers are wired throughout the home, organized closets maximize storage, and thoughtful soundproofing between the primary suite and the neighboring residence provides an added level of privacy. A private heated two-car garage with epoxy flooring offers year-round comfort and convenience, while three furnaces and AC units, Ecobee thermostats & video doorbell and remote garage door openers enhance the home's efficiency and ease of living. The beautifully maintained stone and stucco exterior reflect extensive improvements, including a newer roof, brand new garage door, property grading, outdoor fixtures, front steps, landscaping, and select updated windows. The home has been professionally inspected annually. The landscaping, snowplowing, roof and outdoor lighting remain HOA responsibilities going forward. Outside, enjoy meticulously maintained green space and a new Trex deck just off the main level, complete with a gas grill line and outdoor speakers, an effortless extension of the home for entertaining or relaxing. Guest parking and a sprinkler system add even more convenience. With exceptional space, extensive updates, sophisticated finishes, and an unbeatable walk-to-town location, this is a rare opportunity to enjoy luxury townhome living without compromising on the comforts of a single-family home.

930 Central Avenue, Highland Park

$434,000

3 Beds ⋅ 3 Baths ⋅ 12753549 MLS ⋅ ACTIVE Status

Chantilly End Unit on the Golf Course! Bright, sunny, well-loved, and well-maintained, spacious 3-bedroom, 2.1-bath with attached garage, and lovely, fenced private patio facing South and West. The potential and size of the unit and rooms are amazing, with space for entertaining and gatherings, an office, garden room, dining room, or flex space, as well as a living room, dining room, and kitchen, plus a powder room on the first floor. Upstairs, welcome to a huge Primary Suite with year-round views of the golf course, good closets including a separate cedar closet, two more bedrooms with their own substantial closet space, two linen closets, a hall bath, and convenient 2nd-floor laundry. Mechanicals and sliding glass doors updated. Don't miss all that Chantilly has to offer, including parks, a walking path, a dog park nearby, a community pool, and more, plus a great location within the community!

1466 Concorde Circle, Highland Park

$2,400,000

5 Beds ⋅ 4 Baths ⋅ 12775290 MLS ⋅ ACTIVE Status

Completely rebuilt and reimagined in 2021, this stunning 5-bedroom, 4-bath home offers an exceptional open-concept floor plan with high-end finishes throughout. Every major component including the roof, windows, plumbing, mechanicals, flooring, cabinetry, millwork, and appliances is just five years old, providing the feel of new construction. Designed for easy living, the home lives like a ranch with the exception of the family room, recreation room, and garage are located on the lower level. Dual mudrooms and laundry areas on both levels add everyday convenience. Set on a picturesque ravine across from Rosewood Beach on a quiet dead-end street, this exceptional home is ideally located in Highland Park's highly sought-after Ravinia neighborhood.

89 Cary Avenue, Highland Park

$2,195,000

5 Beds ⋅ 6 Baths ⋅ 12774967 MLS ⋅ ACTIVE Status

1398 Sunnyside Avenue, Highland Park

$1,450,000

12773625 MLS ⋅ ACTIVE Status

Gorgeous 3/4-acre East Highland Park ravine lot with breath taking views in every season! Currently features a stunning 1934 English Country home location near Lake Michigan, the train, and highly sought-after Ravinia Elementary School. Quality built, pristine, and exceptionally spacious, this special home has an inviting floor plan - ideal for both entertaining and everyday living, with four bedrooms including a spacious primary suite featuring a fireplace, custom closets, and a private sitting room. Thoughtfully updated while retaining its timeless character, recent improvements include a new cedar roof in 2025, new windows, newly refinished hardwood floors, and a new washer and dryer. A large stone patio with fire pit overlooks the gorgeous natural setting and provides an inviting space for outdoor entertaining and relaxing. A rare opportunity to enjoy the charm and craftsmanship of a classic English Country home, exceptional space, and a truly beautiful setting in one of Highland Park's most desirable locations. Enjoy the current home or build new.

327 Marshman Avenue, Highland Park

1240 Park Avenue Unit #331, Highland Park

$220,000

2 Beds ⋅ 2 Baths ⋅ 12723585 MLS ⋅ PRICE CHANGE Status ⋅ Brooke Estates BLDG.

Bright and spacious second-floor 2-bedroom, 2-bathroom condo in desirable Brooke Estates! Enjoy a private patio overlooking the community pool, creating a pleasant outdoor retreat. Inside, you'll find nicely sized bedrooms, including a primary bedroom with its own private bathroom, along with newer flooring and a newer dishwasher. Enjoy the convenience of an elevator building, one indoor parking space (#19), additional storage, and plenty of guest parking. Brooke Estates offers a beautiful setting with walking paths, a pond, and pool for residents to enjoy. Ideally located just off Route 41 with easy access to expressways, shopping, dining, and downtown Highland Park. A wonderful opportunity to make this condo your own in a convenient and amenity-filled community!

1240 Park Avenue Unit #331, Highland Park

$445,000

3 Beds ⋅ 3 Baths ⋅ 12702457 MLS ⋅ ACTIVE Status

Nestled along the tree-lined streets of sought-after Sherwood Forest, this spacious 1960 split-level offers wonderful potential for buyers ready to bring their decorating and renovation ideas. The light-filled main level features a dramatic vaulted living room with expansive picture windows overlooking the lush backyard, an adjoining formal dining room, and an updated eat-in kitchen. Upstairs, the generously sized primary suite is a rare find for a split-level, offering two large closets and its own private full bath, plus two additional bedrooms and a shared hall bath. The expansive lower-level family room features a wood-burning fireplace and flexible space for recreation, a home office, play area, or game room, along with another full bath, laundry/mechanical room, and abundant storage. With original hardwood floors, an attached one-car garage, a beautiful backyard and patio, and the choice of Highland Park or Deerfield High School, this home offers an exciting opportunity to update, personalize, and build equity in a highly desirable Highland Park neighborhood. While some updating and improvements will allow the next owner to truly make it their own, the home offers wonderful space, character, and potential. Recent improvements include: 2025 - siding, insulation, gutters, downspouts and flashing; 2024 - stove and HVAC; 2023 - microwave and dishwasher; 2018 - roof, vents and shields; 2017 - refrigerator; 2014 - windows. Property is being sold AS-IS as part of an Estate Sale.

1326 Cavell Avenue, Highland Park

$2,500,000

5 Beds ⋅ 7 Baths ⋅ 12771440 MLS ⋅ ACTIVE Status

Introducing The Lincoln Collection - an exclusive offering of nine new construction residences on the former Lincoln School site. Perfectly positioned on a professionally landscaped .31-acre homesite, this exceptional 6-bedroom, 6.1-bath home offers approximately 5,500 square feet of curated living space across three impeccably finished levels. A light filled foyer with statement herringbone hardwood floor sets the tone, flowing into a sophisticated dining room. The home's centerpiece is a sun-drenched, open-concept kitchen and great room designed for effortless living. High ceilings create a dramatic backdrop, along with fireplace flanked by built-ins. The chef's kitchen is outfitted with premium Monogram appliances, sleek quartz counters and backsplash, walk-in pantry, custom rift-cut white oak cabinetry and warm bronze accents-blending timeless elegance with modern sophistication. The main level also features a highly desirable first-floor bedroom suite with en-suite bath, ideal for guests or a private office. A designer powder room and a beautifully appointed mudroom with custom built-ins offering both function and style leads to a 2 car heated garage. Upstairs, the serene primary suite is a true retreat, bathed in natural light, tray ceiling and complemented by dual organized walk-in closets. The spa-inspired bath featuring quartz countertops, bespoke white oak cabinetry, a deep soaking tub, an oversized shower and private commode closet. Three additional bedrooms are generously sized and each include their own private en-suite bath. Large second floor laundry room with built-in cabinetry. The fully finished lower level delivers an elevated lifestyle experience with a sprawling recreation room, dedicated fitness studio, private sauna, additional bedroom, full bath and abundant storage - designed for both relaxation and entertaining. Professionally landscaped fenced yard with patio and large side yard creates the ideal outdoor entertaining spaces. This residence offers a rare combination of new construction, architectural detail and walkable lifestyle, just moments from vibrant downtown Highland Park, the Green Bay Trail and Lake Michigan.

701 Lincoln Avenue, Highland Park

$675,000

3 Beds ⋅ 3 Baths ⋅ 12758851 MLS ⋅ ACTIVE Status

Welcome to 211 Blackhawk Rd, a beautifully appointed 3 bedroom, 3 full bath home in East Highland Park's highly desirable Braeside neighborhood, ideally located just steps from Ravinia and minutes from the Chicago Botanic Garden, Lake Michigan, Green Bay Trail, Metra, and the area's wonderful shops and restaurants. Set on more than 1/3 acre, this inviting home combines distinctive architectural details with an easy, open flow. Natural light fills the main level, with vaulted ceilings, skylights, and beautiful wood beams. The living area is anchored by a striking floor-to-ceiling stone fireplace open to the dining area, while hardwood flooring flows throughout much of the level. The spacious family room provides an ideal gathering space. The kitchen offers generous cabinetry, stone backsplash, granite countertops, bar top seating and direct access outdoors. The second-floor primary suite is a true retreat, featuring a spacious bedroom, private balcony, comfortable sitting area, and built-in wardrobe closets. The primary bath offers dual sinks, a separate soaking tub, and a walk-in shower. Two additional bedrooms are conveniently located on the main level and share a full bath with a walk-in shower. A finished basement adds living space with room for a recreation area, home office, workout space, and more, along with a full bath, dedicated laundry area and storage. Step outside to the large deck with a remote controlled awning, overlooking the expansive yard. Perfect for entertaining, relaxing, and enjoying summer evenings while listening to music drifting from nearby Ravinia. A one-car attached garage adds convenience. Located within Braeside Elementary, Edgewood Middle School and Highland Park High School. Come tour this special home!

211 Blackhawk Road, Highland Park

$1,450,000

4 Beds ⋅ 4 Baths ⋅ 12769637 MLS ⋅ ACTIVE Status

Stunning 1934 English Country home in a prime East Highland Park location near Lake Michigan, the train, and highly sought-after Ravinia Elementary School. Quality built, pristine, and exceptionally spacious, this special home is set on a spectacular 3/4-acre ravine property with stunning views in every season. An inviting floor plan is ideal for both entertaining and everyday living, with four bedrooms including a spacious primary suite featuring a fireplace, custom closets, and a private sitting room. Thoughtfully updated while retaining its timeless character, recent improvements include a new cedar roof in 2025, new windows, newly refinished hardwood floors, and a new washer and dryer. A large stone patio with fire pit overlooks the gorgeous natural setting and provides an inviting space for outdoor entertaining and relaxing. A rare opportunity to enjoy the charm and craftsmanship of a classic English Country home, exceptional space, and a truly beautiful setting in one of Highland Park's most desirable locations.

327 Marshman Avenue, Highland Park

1230 Park Avenue Unit #210, Highland Park

$339,000

2 Beds ⋅ 2 Baths ⋅ 12765641 MLS ⋅ ACTIVE Status ⋅ Brooke Estates BLDG.

Beautifully renovated and exceptionally spacious, this 1st Floor, two-bedroom, two-bath condominium offers an open, light-filled floor plan designed for comfortable everyday living and entertaining. The gorgeous, updated kitchen features crisp white cabinetry, quartz countertops, a stylish subway tile backsplash, stainless steel appliances, generous workspace, and an easy flow into the dining and living areas. The sunny living room features a fireplace with lovely black marble surround and sliding glass doors that open to a private patio overlooking the lawn, creating a wonderful connection between the indoor and outdoor spaces. The separate dining room area provides the perfect space for casual entertaining or holiday meals. The generously sized primary suite offers a large walk-in closet and beautifully updated private bath. The second bedroom is also nicely proportioned and offers the flexibility to serve as a guest room, home office or combination of both. An updated hall bath and convenient in-unit laundry complete the thoughtfully renovated interior. Located in Highland Park's sought-after Brooke Estates, the residence includes one indoor garage parking space. An additional garage space may be rented through the HOA, subject to availability and association requirements. Residents also enjoy two swimming pools, attractive grounds and a picturesque pond. Easy access to route 41 or downtown Highland Park. Spacious, sunny, renovated and move-in ready, this is an exceptional opportunity to enjoy easy condominium living in Highland Park. This is the one to buy!

1230 Park Avenue Unit #210, Highland Park

$800,000

5 Beds ⋅ 3 Baths ⋅ 12747636 MLS ⋅ ACTIVE Status

Nestled on a picturesque hillside lot in the sought-after Braeside school district, this multi-level gem with more than 2,600 square feet of living space above grade offers the perfect blend of comfort and space. Step onto the main level and feel the flow - an expansive L-shaped living and dining room invites easy entertaining, opening off the kitchen and out to a screened porch that's made for lazy mornings and evening get-togethers. From there, step out to the deck and soak in your lush, landscaped backyard bursting with perennials - your own private retreat. The all-white kitchen features granite and Corian countertops, a Sub-Zero refrigerator, KitchenAid double oven, Miele dishwasher, JennAir cooktop, and a brand-new trash compactor. A charming greenhouse window adds a sunny spot to nurture your favorite plants and herbs. Down the hall, you'll find four spacious bedrooms, including a primary suite with three closets and an updated full bath with a walk-in shower, plus an additional updated hall bath for family and guests. Bedrooms have hardwood floors under the carpet. On the entry level, cozy up by the gas fireplace in the inviting family room, or use the fifth bedroom as the perfect home office. An updated powder room adds everyday convenience. Just a few steps down, a versatile recreation/hobby room and a well-equipped utility/laundry room round out the space. Thoughtful touches are everywhere - recently refinished hardwood floors, elegant Prairie Style wood railings, a built-in liquor cabinet/bar in the living room which features stained glass on the doors, a 2.5-car attached garage, lawn sprinkler system, security system, and storage galore. Additional updates include the furnace (2010), A/C (2018), and roof (2018). This home truly has it all - elegance, warmth, and function in every corner, making it a must-see!

822 Timber Hill Road, Highland Park

$595,000

3 Beds ⋅ 2 Baths ⋅ 12756230 MLS ⋅ ACTIVE Status

Built with enduring quality, this solid and brightly lit Highland Park home comes freshly painted and ready for immediate move-in. The main living areas feature stunning hardwood floors and a sunny living room that floods the space with natural light, while the lower-level family room offers a cozy retreat complete with built-in shelving and a beautifully tiled fireplace. Designed for function and entertaining, the spacious kitchen is packed with endless cabinet storage, an expansive breakfast bar, and sliding glass doors that open directly onto a deck overlooking a massive, fully fenced backyard with a dedicated dog run. Beyond the main yard, the side lot boasts your own private fruit orchard, complete with apple, cherry, and peach trees. Comfort extends throughout the home with spacious, high-storage bedrooms and updated bathrooms. On top of its timeless appeal, the property features major recent upgrades for total peace of mind, including a 2-year-old roof, a 2-year-old dishwasher, and a 4-year-old washer and dryer-making it the perfect setting to start building lasting family memories.

1320 Deerfield Place, Highland Park

$2,799,000

6 Beds ⋅ 9 Baths ⋅ 12754915 MLS ⋅ ACTIVE Status

Privately set behind a gated entrance on over 1.3 professionally landscaped acres, this exceptional Highland Park stone and brick estate offers approximately 9,600 square feet of beautifully appointed living space, an attached four-car heated garage, and a rare sense of privacy surrounded by the natural beauty of Chicago's North Shore. Thoughtfully designed to live like a ranch with a luxurious first-floor primary suite, the home offers ultimate flexibility for a variety of lifestyles while still providing exceptional space for family and guests. Designed for both elevated entertaining and effortless everyday living, the home features a spectacular chef's kitchen completely reimagined in 2023 with custom black cabinetry, marble countertops, a dedicated coffee center, two dishwashers, and a striking glass-enclosed, temperature-controlled wine cellar display that creates a dramatic architectural focal point. An expansive accordion door system opens seamlessly to the full-length paved terrace and grounds beyond, creating an exceptional indoor-outdoor connection. The dramatic great room is defined by soaring ceilings, walls of windows, and an impressive double-sided fireplace, while the adjacent family room provides an inviting setting for more relaxed living. The main-level primary suite is a true private retreat, complete with a sitting room, fireplace, wet bar, and serene views of the property. Upstairs, five additional en-suite bedrooms provide exceptional accommodations for family and guests, complemented by an extraordinary 52-by-22-foot bonus room offering endless possibilities. The expansive lower level is designed for recreation and wellness with a private home theater, fully equipped gym, sauna, wet bar with kegerator, and full bath. Recent improvements include a new roof, gutters, and downspouts in 2024, newer HVAC systems, a rebuilt staircase, and a remodeled mudroom with heated floors. Directly behind the property, the forest preserve provides a breathtaking natural backdrop with direct access to a walking path, while dramatic western exposures capture spectacular sunsets across the grounds. Ideally positioned between downtown Highland Park and Deerfield with convenient highway access, owners of this exceptional estate have the unique option to attend either award-winning Highland Park High School or Deerfield High School-an extraordinary advantage within this coveted North Shore setting.

1630 Ridge Road, Highland Park

$3,800,000

4 Beds ⋅ 6 Baths ⋅ 12750752 MLS ⋅ ACTIVE Status

Amazing lakefront property on end Cul De Sac street!!! This home has been totally REMODELED and meticulously curated for modern living with impeccable design. The expansive floor plan features four generous bedrooms, each with its own en-suite bathroom, including a refined primary retreat complete with 12 foot ceiling, a private balcony overlooking iconic Lake Michigan and 2 lavish walk-in closets. Culinary artistry is redefined in the exceptional chef's kitchen, outfitted with professional-grade appliances and a discreet scullery-perfect for both upscale entertaining and daily life. Exceptional amenities include a finished basement with a full bath, second-floor laundry , a first-floor office, a powder room, and expansive living spaces that are bathed in natural light. Perfect indoor-outdoor harmony is achieved through a serene three-season room, and a stone terrace, all providing ideal vantage points to enjoy the tranquil lakefront setting. Enjoy an unbeatable Highland Park location on a commanding .63-acre lot with panoramic Lake Michigan views. Stairs down to the beach are adjacent to back yard, shared with residence on the street.

22 Lakeview Terrace, Highland Park

1795 Lake Cook Road Unit #110, Highland Park

$359,000

2 Beds ⋅ 2 Baths ⋅ 12729689 MLS ⋅ ACTIVE Status

TWO PARKING SPACES! Beautifully updated 2-bedroom, 2-bathroom condo offering modern style, comfort, and convenience. The inviting living room features a gorgeous stone fireplace, creating a warm and welcoming space for relaxing or entertaining. The stylish kitchen boasts crisp white cabinetry, stainless steel appliances, stunning white quart countertops and a clean, contemporary design. Pella windows with integrated blinds for a easy and updated feel. Gorgeous engineered wood throughout the unit.The spacious primary bedroom features a huge walk-in closet and beautifully updated private bath. Both bathrooms have been thoughtfully renovated with gorgeous tilework and modern finishes. A private balcony provides the perfect spot to enjoy your morning coffee or unwind at the end of the day. With two dedicated parking spaces and beautiful updates throughout, this move-in-ready condo is the perfect combination of style and convenience! *50K in Pella windows and doors have been updated in this unit!*

1795 Lake Cook Road Unit #110, Highland Park

$1,599,000

6 Beds ⋅ 7 Baths ⋅ 12733085 MLS ⋅ ACTIVE Status

Just steps from downtown Highland Park's shops, restaurants, library, train, and close to Lake Michigan, Thornycote is a home where location and history come together beautifully. Designed in 1901 by renowned architect Howard Van Doren Shaw, this English Arts and Crafts residence is a remarkable expression of craftsmanship, proportion, and grace. Set on more than an acre of lush, landscaped grounds, Thornycote offers a rare sense of privacy while remaining connected to everything that makes Highland Park special. A handsome foyer sets the tone, introducing the home's elegant proportions, exceptional woodwork, and remarkable architectural integrity. Throughout, Shaw's thoughtful design is evident in the details, from the formal living room anchored by a commanding wood-burning fireplace to the expansive family room, which opens onto a generous terrace. The gracious dining room flows naturally into a bright sunroom, equally suited to morning coffee or evening conversation. A richly detailed library provides a quiet retreat, while the renovated kitchen brings modern function to the historic setting with custom cabinetry, a butler's pantry, coffee bar, and mudroom. An extra-wide staircase leads to the second floor, where the primary suite offers a private retreat with an adjoining sitting and dressing room, wood-burning fireplace, and spacious updated bath overlooking the grounds. Two additional bedrooms share a full bath and connect to a cozy sitting room ideal for reading or play. A second-floor laundry adds everyday convenience. The expansive third floor offers remarkable flexibility, with four bedrooms, two full baths, and a large bonus room that can adapt to whatever life requires, from playroom and home office to media lounge or studio. Beyond the main residence, a 1,600-square-foot coach house adds an extraordinary layer of possibility. With four garage bays, a two-bedroom suite, and a conference room overlooking dramatic ravine views framed by two stone bridges, it is a rare setting where work, creativity, and nature come together. And then there are the discoveries. A hidden speakeasy tucked behind a mirrored door. Secret gardens. Winding pathways made for wandering. At Thornycote, the experience extends well beyond the architecture. More than a residence, Thornycote is a singular piece of Highland Park history, where Howard Van Doren Shaw's artistry remains very much alive.

215 Prospect Avenue, Highland Park

$545,000

4 Beds ⋅ 2 Baths ⋅ 12728137 MLS ⋅ RE-ACTIVATED Status

552 Burton Avenue, Highland Park

$350,000

3 Beds ⋅ 2 Baths ⋅ 12726593 MLS ⋅ ACTIVE Status

Charming townhome in the Ravina neighborhood Boasting FRESH PAINT THROUGHOUT close to parks, shopping, dining, Lake Michigan, and more! Beautifully maintained with a versatile layout, gorgeous natural light, and over 1,100 sq ft of above ground space. Whip up delicious meals in this stylish kitchen equipped with contemporary cabinetry, sleek appliances, and granite countertops. Options are nearly endless for the finished basement just waiting to be transformed into your dream space. Rest easy with INCLUDED lawn and snow removal too! Embrace outdoor living from the comfort of your back deck with a favorite beverage in hand. Convenient location, just a short distance from Metra Station, Greenbay Trail, Chicago Botanical Gardens, and area beaches. Whether you're searching for your next primary residence or looking to expand your investment portfolio, this versatile property offers an exceptional opportunity - Inquire today!

706 Broadview Avenue, Highland Park

$615,000

3 Beds ⋅ 3 Baths ⋅ 12716773 MLS ⋅ ACTIVE Status

LOCATION! LOCATION! LOCATION! INVESTOR & FLIPPER SPECIAL! Rare opportunity to own a historic English Tudor Revival home in one of Highland Park's most desirable neighborhoods. This partially renovated property offers exceptional upside for investors, flippers, rehabbers, or buyers looking to customize a truly one-of-a-kind home while preserving its architectural heritage. This 3-bedroom, 2.5-bath English Tudor Revival home is a rare Krenn-Dato model, showcasing timeless architectural details and rich history. Backed by Edith Rockefeller McCormick, Krenn-Dato homes are celebrated for their distinctive craftsmanship, including decorative half-timbering, a classic brick and stucco facade, steep gables, prominent chimneys, and charming multi-paned windows. Beautifully refinished hardwood floors and fresh paint throughout blend seamlessly with preserved original features, including vintage light fixtures, original windows, doors, hardware, staircase woodwork, and other decorative details that highlight the home's historic charm. The main level features a functional kitchen ready for your personal updates, a spacious living room centered around the original wood-burning fireplace, a formal dining room, a cozy den, a pantry, and a convenient half bath. Upstairs, you'll find three generously sized bedrooms and two full bathrooms. The unfinished basement includes a laundry area and offers outstanding potential for additional living space, a recreation room, home office, fitness area, or ample storage-making it an excellent opportunity for investors, flippers, or buyers looking to add value and customize the home to their vision. Outside, enjoy a large, fully fenced backyard with mature trees, along with a private front yard that enhances the home's curb appeal and serene setting. Ideally located in a top-rated school district, this true showstopper is surrounded by parks and forest preserves and is within walking distance to the Metra station for an easy downtown commute. It is also just minutes from the beach, Fort Sheridan Forest Preserve, restaurants, shopping, and neighborhood playgrounds. This home is proudly featured as part of the Highland Park Historic Homes Bike Tour. The owner, a professional builder, offers a unique opportunity to complete additional renovations-including new windows, bathrooms, a custom kitchen, and a finished basement-for an additional $75,000-$150,000, based on the buyer's preferences. Buyers may also choose to complete the renovations themselves, making this an outstanding value-add opportunity with significant upside. Some images may be virtually enhanced. The home is also available for lease. Property is being sold AS-IS.

3107 Dato Avenue, Highland Park

$4,995,000

9 Beds ⋅ 14 Baths ⋅ 12678213 MLS ⋅ ACTIVE Status

Situated on a prestigious private lane in East Highland Park, this rare lakefront offering is a Mid-Century Modern masterpiece. Designed in 1957 by renowned architect Henry L. Newhouse II for Irving B. Harris, Chicago Philanthropist, this 10,000-square-foot contemporary residence sits on nearly two acres of lush grounds with magnificent, unobstructed views of Lake Michigan. Experience the ultimate wow factor as you enter the dramatic foyer and take in the breathtaking vista. The interior features large expanses of glass and natural light, offering a flexible floor plan that flows effortlessly for entertaining and everyday living. An exquisite foyer leads to custom beveled, imported French Limestone floors and dramatic floor-to-ceiling windows that frame the water. With minimalistic aesthetic, the Chef's Eat-In Kitchen is finished with custom black walnut cabinetry, a wall of granite, gourmet appliances, and a sleek gas fireplace. The home's expansive footprint includes a main floor Primary Bedroom Suite with a secondary Primary Suite on the 2nd level and seven additional Ensuite Bedrooms, providing unparalleled space and privacy. Despite significant renovation since construction, the home still retains the core architectural integrity and mid century character established by Newhouse. For wellness and recreation, an Indoor Pool Pavilion features a Dectron temperature-controlled system, a retractable clerestory roof, a steam room, and a dedicated second kitchen equipped with Viking appliances. Outside, the tranquility of the lakefront setting takes center stage. A sparkling Outdoor Pool overlooks the water, while a private tram and stairs lead down to 150 feet of secluded beach. This is a unique opportunity to own a significant piece of architectural history with unlimited potential on the shores of Lake Michigan!

2441 Woodbridge Lane, Highland Park

$1,399,000

4 Beds ⋅ 5 Baths ⋅ 12696254 MLS ⋅ ACTIVE Status

Welcome to effortless luxurious living in Highland Park. This stunning custom contemporary 6-year-young home offers 5 spacious bedrooms, 4 half baths, and an open floor plan bathed in natural sunlight from every angle. The flexible floor plan blends style, comfort and functionality. Sunny foyer, soaring ceilings, designer finishes, and fixtures throughout. Sun-filled great room flows into chef`s kitchen with stainless steel appliances, pantry, quartz countertop, and storage. A separate dining room sits just off the kitchen and family room, creating the perfect layout. Ideal for family living and entertaining, plus much more. Beautiful hardwood floors throughout the home with all high-end finishes. A custom staircase leads to the second floor. The primary suite includes remote control window treatments, walk in closet, plus a private deck with Trex flooring. The master bath has heated floors, a large shower, and twin sinks. Three additional spacious bedrooms, 2 with jack and jill bath, plus a hall bath with whirlpool tub. The finished basement adds incredible living space with a full bath, bedroom, and large entertainment room, along with a separate professionally soundproofed area ideal for podcasting, recording, or a quiet home office. The garage features epoxy flooring and slat board walls. The home is recently painted and in impeccably maintained. There is also a shared outside area with a play area, fire pit, and walking path. Truly a fabulous home with more features. Taxes do not reflect any exemptions and may be lower for a qualified buyer.

2009 Skyelar Court, Highland Park

1534 Mcdaniels Avenue Unit #3E, Highland Park

$429,000

3 Beds ⋅ 2 Baths ⋅ 12697929 MLS ⋅ ACTIVE Status

Exceptional space and value in an in-town Highland Park location! This spacious three-bedroom, two-bath condominium offers generous room sizes, abundant natural light, southern exposure, and an oversized private balcony-an excellent opportunity to bring your own design ideas and create a home that reflects your style. A welcoming foyer leads to spacious living and dining areas, while the kitchen features maple cabinetry, a comfortable eating area, abundant storage, and direct access to the balcony. The privately situated primary suite features hardwood flooring, exceptional closet space, plantation shutters, and an en-suite bath with dual sinks, soaking tub, and separate shower. Two additional generously sized bedrooms, both with hardwood flooring, share a spacious hall bath. One features plantation shutters, while the other offers direct balcony access and flexibility as a guest room, home office, or den. Additional highlights include in-unit laundry, excellent storage, a one-car attached garage, and a convenient main-level storage locker. Walk to downtown Highland Park, Metra transportation, Sunset Park, restaurants, shopping, and Lake Michigan. Property conveyed in as-is condition.

1534 Mcdaniels Avenue Unit #3E, Highland Park

$4,250,000

4 Beds ⋅ 8 Baths ⋅ 12659749 MLS ⋅ PRICE CHANGE Status

Sophisticated new custom built 5 bedroom, 6 full bath & 2 half bath home with guest house, patio, pool & spa located on over 3 acres. This limestone & stucco clad home w/composite terra cotta Spanish roof tiles boasts unsurpassed quality construction by Red Rock Homes & is accompanied w/high-end interior designer finishes by Ilene Chase. Some of the home's highlights include: soaring ceilings, open floor plan, wide plank hardwood floors, custom built-ins, wood-paneled elevator, professional grade appliances, upgraded electrical & Smart home integration system, guest house, 50'x25' outdoor pool & spa. 1st level features a grand foyer w/soaring ceiling, RH brushed brass & crystal tiered chandelier, marble floors & bridal staircase. A formal dining room that is the ideal entertaining space connects to a built-in butler's pantry w/Quartzite counters & antiqued mirror backsplash. Expansive sun-filled great room w/22' ceilings, stone surround wood-burning fireplace that is flanked by custom wood built-ins & French sliders leading to outdoor entertaining areas. The great room leads directly to a gourmet chef's kitchen featuring custom bespoke white cabinetry, Quartzite Iceberg counters & backsplash, professional ss appliances featuring 60" commercial Wolf range w/double ovens, Wolf microwave, Sub-Zero refrigerator/freezer & 2 Bosch dishwashers. A large center island w/Iceberg Quartzite waterfall countertop, prep sink, seating & tons of storage. Wet bar w/custom bespoke dark-stained wood & black cabinetry, Quartzite counter & backsplash, ss hammered bar sink, ice maker, beverage refrigerator plus full-size Sub-Zero designer wine refrigerator. Spacious eat-in area is perfect for large gatherings & opens to a bright 4-season sunroom w/vaulted wood-paneled ceiling & a wall of glass doors that make indoor/outdoor entertaining seamless. Formal powder room w/custom wall covering, vanity w/marble counter & herringbone oval sink & eclectic brass sconces. The private primary wing of the home features a handsome study w/wood & reeded glass French privacy doors, herringbone hardwood floors, wet bar, black marble carved fireplace mantle surround, grass cloth wallcovering & wood coffered ceiling w/smoke eater. The office leads to a secondary formal powder room w/custom wood vanity with double thick block marble countertop, custom wall covering and modern sconces. A luxurious primary suite w/tray ceiling, gas fireplace & sliders that lead to patio & pool areas. Other highlights include a morning bar, dressing area & custom walk-in closet w/ substantial built-ins. Spa-like luxurious primary bath featuring porcelain tile heated floors, double vanities w/quartz countertops, separate make-up vanity, oversized shower w/steam, rain showerhead, wall sprays and sleek touch-style control for Smart bath features, plus Kohler jetted soaking tub w/quartz decking & 2 commode closets, one with urinal. Mudroom w/custom built-ins & back staircase access, plus spacious laundry room is located off the 4 car heated garage w/EV chargers for each space. Completing the 1st level is a full pool bath & changing area w/custom built-in storage, located off the mudroom w/sliders leading directly to rear pool, spa & patio. The 2nd level boasts a catwalk w/magnificent views of the foyer & great room below. 3 additional generous-sized bedrooms all w/en-suite luxurious baths & custom walk-in closets. Plumbed for additional washer/dryer. Lower level features huge rec room, wet bar w/wine fridge, exercise room, dry-sauna, 5th bedroom w/full bath & tons of storage. The ideal outdoor PRIVATE entertaining space features a 9' deep in-ground pool & spa surrounded by expansive 5,000 sq. ft. porcelain tile patio decking, built-in fire-pit & outdoor BBQ grill w/stone surround & honed bluestone countertop. An 1,100 sq ft guest house provides guests privacy with sitting/rec room, full kitchen, bedroom w/en-suite bath, laundry & changing area. A rare opportunity to own this brand-new home!

2665 Bentley Road, Highland Park

$685,000

5 Beds ⋅ 3 Baths ⋅ 12657575 MLS ⋅ ACTIVE Status

Exceptional investment opportunity or owner-occupied two-flat with both units completely remodeled in 2024. Unit 1 offers 3 bedrooms and 2 full baths featuring hardwood floors, a wood-burning fireplace in the spacious living room, updated kitchen with new refrigerator, in-unit washer/dryer, and a side deck off the dining area. The finished lower level adds a family room and brand new full bath - perfect for additional living space. Unit 2 is a bright 2 bed/1 bath with brand new hardwood floors throughout, open-concept living and dining, fully renovated kitchen with quartz countertops, white cabinetry, stainless appliances, new in-unit W/D, and new HVAC. Both units include 1 interior and 1 exterior garage space. Steps to Metra (Highwood Station 0.4 mi), top-rated North Shore District 112 schools, shopping, and dining. A rare chance to own a fully updated, income-producing asset in one of the North Shore's most desirable communities.

2490 Green Bay Road, Highland Park

$799,000

2 Beds ⋅ 2 Baths ⋅ 12624604 MLS ⋅ ACTIVE Status

Modern Parisian-Inspired Carriage House Steps from Downtown Highland Park Fully renovated down to the studs, this unique carriage house blends historic charm with modern design and amenities. The primary living space is located on the second floor and features vaulted ceilings with steel collar ties, exposed brick walls, and an open-concept layout ideal for entertaining. Chef's kitchen includes custom inset cabinetry and Thermador appliances. Loft area provides flexible space for additional sleeping or office use. In-ceiling speakers throughout main living area. Primary suite offers a spa-like bathroom with curb-less walk-in steam shower, dual vanities, and heated floors. Additional features include in-unit washer and dryer and a 2-3 car radiant heated garage. First floor includes a separate studio/office space with private entrance, full bathroom, kitchenette, and radiant heated floors, ideal for home office, guest suite, or potential rental use. Prime location near downtown Highland Park, shopping, dining, and transportation.

1619 Mcgovern Avenue, Highland Park

$5,975,000

5 Beds ⋅ 9 Baths ⋅ 12455514 MLS ⋅ PRICE CHANGE Status

Located in the coveted Belle Avenue Historic District, this extraordinary estate sits on 2.3 acres of manicured grounds with sweeping lake views. Fully renovated and expanded, the residence blends timeless elegance with modern luxury for a truly one-of-a-kind offering. This five-bedroom, eight full and one half bath home showcases craftsmanship of the highest caliber, including a brick exterior, slate tile roof, extensive millwork, crown moldings, built-ins, hardwood floors, expansive windows, soaring ceilings and graciously scaled rooms. No detail was spared in the complete gut renovation and thoughtful addition that restored and elevated this classic beauty. A welcoming foyer leads to a grand living room, perfect for entertaining, with a limestone fireplace, custom built-ins and a wet bar. The living room opens to a light-filled sunroom with three sets of floor-to-ceiling sliders, seamlessly connecting to multiple outdoor entertaining spaces with endless lake views. A formal dining room with herringbone wood floors, custom wallpaper and a crystal chandelier adjoins to a butler's pantry featuring two wine fridges, custom cabinetry and marble counters. The chef's kitchen is a showstopper, with bespoke inset white wood cabinetry, Quartzite counters, decorative marble backsplash, oversized island with prep sink and seating, professional-grade appliances and a walk-in pantry. A spacious eat-in area has 2 sets of sliders that lead to the bluestone patios. The kitchen opens to a large sunken family room that is a perfect gathering spot for family and friends. Additional highlights of the main level include a sophisticated powder room, mudroom with slate flooring and built-ins, full bath, package receiving room and heated three-car garage. Upstairs, the primary suite is a private sanctuary with a cozy sitting area, custom built-ins, dual walk-in closets and a spa-like marble bath featuring vaulted ceilings, a soaking tub, expansive shower, and breathtaking lake views. Four additional bedrooms each include luxury en-suite baths and walk-in closets with custom built-ins. A second-floor laundry with two washer/dryer sets plus a coffee/bar station on the landing outside the family bedrooms add delightful convenience. The third floor, with its vaulted ceiling and abundant natural light, offers a large bonus room with wet bar, office space, home gym/Pilates studio and full bath. The lower level provides flexible living space with a recreation room, game room, sitting area, guest bath and extensive storage. The outdoor spaces are equally impressive, with bluestone patios, a stone fire pit, built-in bar with seating and pristine landscaping overlooking the ravine and lake. This property combines unmatched craftsmanship, spectacular grounds and iconic lakefront vistas-all within close proximity to the lakefront, schools and town. This is a rare opportunity to own a one-of-a-kind stately residence on a stunning property.

117 Belle Avenue, Highland Park

$1,780,000

6 Beds ⋅ 6 Baths ⋅ 12553390 MLS ⋅ ACTIVE Status

Spectacular Historic Queen Anne Revival on Nearly 3/4 Acre in East Highland Park. A rare opportunity to own a magnificent Queen Anne Revival residence, beautifully set on a private lot just under 3/4 of an acre in sought-after East Highland Park. This exceptional home offers the best of all worlds-historic beauty and grandeur paired seamlessly with modern additions and amenities designed for today's living. Meticulously maintained and thoughtfully expanded, the home features two outstanding additions including a dramatic two-story family room, a luxurious primary bedroom and spa-quality bath, a gorgeous paneled library, and a screened porch, creating a home that lives effortlessly while honoring its architectural heritage. This is a historic home that does not feel old. Upon entry through the charming front vestibule with original leaded glass windows, you are welcomed into a grand foyer showcasing a stunning historic staircase, flanked by the formal living and dining rooms. Original oak flooring runs throughout, adding warmth and authenticity. The living room features a beautiful historic mantle and updated double French doors that open to the rear terrace. Beyond lies the richly paneled library, complete with a hidden bar closet and refrigerator, and access to the screened porch-perfect for relaxing or entertaining. On the opposite side of the foyer, the formal dining room flows into the open kitchen, which is exceptionally equipped with a commercial-grade range, double ovens, dual dishwashers, breakfast area, and seamless connection to the two-story family room with a second fireplace and French doors to the terrace-an ideal layout for everyday living and hosting on any scale. The second floor is anchored by a truly extraordinary primary suite, offering space and luxury beyond expectations. The marble-clad primary bath features a double-bowl vanity, whirlpool tub, oversized separate shower, and private water closet. The bedroom boasts a tray ceiling, an expansive walk-in closet with professionally installed organizers, and an additional cedar closet. This level also includes two additional family bedrooms, two full baths, and a dedicated laundry room. The third floor provides three additional bedrooms, a full bath, and an office-ideal for extended-stay guests, a private living suite, or flexible work-from-home needs. The partially finished basement includes heated flooring, exterior access near the mudroom, and generous cubby storage for active lifestyles. An additional unfinished basement area offers abundant storage. The professionally landscaped yard features sprinklered perennial plantings, a fenced garden area, and ample space for outdoor enjoyment. Additional highlights include a second rear staircase, three-car garage, whole-home speaker system, zoned heating and air, excellent insulation, and a highly efficient layout that makes this large home remarkably manageable. Third-floor utilities are zoned separately and can be shut off when not in use. The home's original foundation has been reinforced with structural steel and is exceptionally solid; remaining foundation areas are newer. Original windows are in place. The property is listed on the National Register of Historic Places, built for prominent Highland Park resident Ross J. Beatty. An extraordinary residence combining history, scale, comfort, and location-just minutes to town and train.

1499 Sheridan Road, Highland Park

$3,250,000

12553280 MLS ⋅ ACTIVE Status

This two-story, plus basement commercial building located in downtown Highland Park is available for sale. Completely rehabbed in 2007, this 8,750 square foot property is situated near the corner of Sheridan Road and Central Street. This offering is the perfect opportunity for a user or investor to own a highly visible property on one of the main commercial thoroughfares. Located in the heart of Highland Park's Central Business District, this property benefits from easy access to public transportation, the Metra train station and the Edens Expressway. Highland Park is an affluent suburb located approximately 23 miles north of Chicago in the heart of the North Shore. The suburb is known for its vibrant downtown business district, numerous local boutiques, restaurants, a growing residential community with close to new or recently constructed units and is home to the Ravinia Festival.

1913-15 Sheridan Road, Highland Park

$99,000

12526552 MLS ⋅ ACTIVE Status

Highland Park Tobacco Store - Prime Downtown Location, in the heart of downtown Highland Park, within the vibrant shops and restaurant corridor. Established store offers exceptional visibility and convenience, directly across from the Highland Park Metra Train Station. A true one-stop shop for all tobacco needs provides a wide selection of premium cigars and brand-name products, Tobacco, hookahs, and a full line of accessories, well-appointed cigar room for customers to browse and enjoy, monthly gross sales of $30,000-$35,000, inventory valued at approximately $100,000 (additional). Goodwill, fixtures, features, and equipment included in the sale. A strong opportunity to acquire a well-located, fully equipped tobacco business in a high-traffic downtown setting. Gross monthly rental amount of $3,300.

1621 Saint Johns Avenue, Highland Park

$3,000,000

12512041 MLS ⋅ ACTIVE Status

Available for sale is a 22,727 square foot two-story medical office building in HIghland Park, IL. The property consists of 18 office suites and has multiple long-term tenants. Situated near the corner of Elm Place and St. Johns Avenue in vibrant downtown area, this property benefits from its location just a block away from the the Metra Train Station and public transportation. Additional parking is available from the easement with the adjacent lot to the south. Area features significant barriers to entry, with few available sites for purchase Highland Park is an affluent suburb located in approximately 25 miles north of Chicago in the North Shore. The city has a vibrant downtown with shopping, restaurants and more.

480 Elm Place, Highland Park

$375,000

12402785 MLS ⋅ ACTIVE Status

Beautiful 39,600 SF LOT. NO H.O.A. Build your "Dream Home" on this Wide, Wooded, VACANT Parcel. 132 Foot Frontage by 300 Feet Deep! FAR = 25.04, Max floor area (sf) 9,916. Max FAR 11,166. Choice of Highland Park High School or Deerfield High School.

Highmoor Road, Highland Park

2648-2666 Waukegan Avenue, Highland Park

$3,750,000

12320966 MLS ⋅ ACTIVE Status

Unique Masonry Commercial mixed use, Retail, Office buildings in Highland Park, Extremely rare offering here, 3 Buildings at 2666,2652,2648 Waukegan, in Highland park IL B1-A Zoning, One Auto and Truck repair facility at 2666 Waukegan, Ceiling height of approx. 16FT 4 DID's, Triple catch basins,4959 SQ FT. One Story office Flex warehouse auto body repair building at 2652, Ceiling height 13 FT, 2 DID's, 3, 000 SQ FT and the 2 story mixed use building at 2648 Waukegan 2 DID's, 4608 SQ FT , Upstairs unit is a 3 Bedroom 1 Bath Apartment, and the rear storage yard, - 16,782 SQ FT Prime Location, excellent Exposure Right at the Entrance to the Highwood shopping and entertainment district, The buildings sit between Bloom street and Highwood Ave, 5,500 Cars pass this location a Day On Waukegan Rd (VPD) Full fire alarm Full sprinkler System, Lot Dimensions are 315.04X200105X370X30X570 3 curb cuts on Waukegan road, 200 sq ft OF Frontage on Waukegan, The Buildings have a Great signage area, classic facade, 200 Amp electric, High security Entrance doors, and cameras. The Combined building square footage IS 12,567 FT and the combined Landsite Square footage is 39,232 SQ FT. The property presents the unique opportunity to acquire stand-alone Commercial buildings in Highland Park. Great demographics. Ideal for a variety of commercial uses, Possible Redevelopment to Multifamily or Commercial Mixed use with Zoning Change, Owner user or Investment, Office or professional use, Atty, Architect Accountant, Medical, Podiatrist, Physiatrist, real estate, Mortgage, insurance Possible contractor Use, retail, School, Surrounding Area companies and business include. La Michoacana Bella, Miramar Bistro, Greenwood American Kitchen & Bar, SLYCE Coal Fired Pizza Company, Del Rio Restaurant, Walgreens, La Casa de Isaac Restaurant Longitud315,. Near the Highland Park Metra train stop, and the Highwood Metra train stop, Bus, Close access to area highways, Route 41 and 94 Pin numbers are - 16154140110000 for 2666 Waukegan and 1614311005-0000 for 2652 Waukegan And 16143110060000 for 2648 Waukegan Rear storage lot pin numbers - 1615400001 - 1614300004 Do not bother tenant, Call Listing broker for all showings PLEASE NOTE - OWNER IS NEGOTIABLE ON PRICE AND WILL LOOK AT ALL OFFERS WITHIN REASON.

2648-2666 Waukegan Avenue, Highland Park

$3,900,000

12283503 MLS ⋅ ACTIVE Status

For sale 660 LaSalle place, masonry mixed use loft building in Highland park, Building is 20,301 sq ft, 17,566 sq ft, of land, completely rehabbed, The Zoning is RM1; Current available units measure from 2209 sq ft to 4650 sq ft, open space/units feature exposed brick walls, high end finishes, high ceilings with hardwood oak floors or carpet, very bright, modern lighting, skylights, Wi-Fi access, units typically include kitchen, bathrooms and foyer, office units have privately controlled HVAC, and 24 access, open floor plans for some units an excellent and very rare transit oriented redevelopment opportunity. Building can be left as a loft office building or redeveloped into an apt bldg. or repurposed into high ceiling condos, Parking for 20 cars, building is located walking distance to downtown highland park, shopping, restaurants, parking, Metra train stop. Do not Bother tenants, Call listing broker for showing, 660 Lasalle Parking lot Pin next door 1626201001

660 La Salle Place, Highland Park

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