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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
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
1751 Clavey Road, Highland Park
$525,000
3 Beds ⋅ 3 Baths ⋅ 12790006 MLS ⋅ ACTIVE 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
2035 Kipling Court, Highland Park
$2,250,000
4 Beds ⋅ 5 Baths ⋅ 12791828 MLS ⋅ ACTIVE 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
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
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
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
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
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
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
1326 Cavell Avenue, 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
701 Lincoln 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
211 Blackhawk Road, 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
327 Marshman Avenue, 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
822 Timber Hill Road, 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
1320 Deerfield Place, 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
1630 Ridge Road, 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
22 Lakeview Terrace, 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
215 Prospect Avenue, 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
552 Burton Avenue, Highland Park
$545,000
4 Beds ⋅ 2 Baths ⋅ 12728137 MLS ⋅ RE-ACTIVATED Status

552 Burton Avenue, Highland Park
3107 Dato 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
2441 Woodbridge Lane, 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
2009 Skyelar Court, 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



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