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811 Judson Avenue, Highland Park
$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
361 N Deere Park Drive, 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
1470 Ridge Road, 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
1745 Sundrop Circle, 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
41 Scott Loop, 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
475 Burton Avenue, 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
798 Timber Hill Road, 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
1751 Clavey 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
2035 Kipling Court, 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
1520 Oakwood Avenue, Highland Park
$1,650,000
5 Beds ⋅ 6 Baths ⋅ 12790920 MLS ⋅ ACTIVE 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
737 Orleans Drive, 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
1120 Ridgewood 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
155 Whistler Road, 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
1454 Glencoe Avenue, 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
1538 Oakwood 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
1324 Fredrickson Place, 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
86 Prospect Avenue, 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
1440 Concorde Circle, 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
493 Hazel Avenue, 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
271 Whistler Road, 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
1530 Oakwood Avenue, 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 ⋅ ACTIVE 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
1235 Ferndale Avenue, 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
930 Central 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
1466 Concorde Circle, 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
89 Cary Avenue, 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
1398 Sunnyside Avenue, Highland Park
$2,195,000
5 Beds ⋅ 6 Baths ⋅ 12774967 MLS ⋅ ACTIVE Status

1398 Sunnyside Avenue, Highland Park
327 Marshman 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



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