Highland Park, IL Homes for Sale | Gallery Realty Inc.

Living in Highland Park, IL

A North Shore lakefront city known for Ravinia Festival, its beaches and parks, and homes from classic cottages to estate properties.

Below are the newest homes for sale in Highland Park. Want a tour, or curious what your Highland Park home would sell for? Call us at 847-672-8481 or send us a message.

Homes for Sale in Highland Park, IL

$5,975,000

5 Beds ⋅ 9 Baths ⋅ 12455514 MLS ⋅ ACTIVE Status

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

117 Belle Avenue, Highland Park

$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

$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

$4,700,000

5 Beds ⋅ 6 Baths ⋅ 12778380 MLS ⋅ ACTIVE 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

$4,250,000

4 Beds ⋅ 8 Baths ⋅ 12659749 MLS ⋅ ACTIVE Status

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

2665 Bentley Road, Highland Park

$3,900,000

12283503 MLS ⋅ ACTIVE Status

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

660 La Salle Place, Highland Park

2648-2666 Waukegan Avenue, Highland Park

$3,750,000

12320966 MLS ⋅ ACTIVE Status

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

2648-2666 Waukegan Avenue, Highland Park

$3,000,000

12512041 MLS ⋅ ACTIVE Status

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

480 Elm Place, Highland Park

$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

$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

$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

$2,400,000

5 Beds ⋅ 4 Baths ⋅ 12775290 MLS ⋅ ACTIVE Status

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

89 Cary Avenue, Highland Park

$2,250,000

12553280 MLS ⋅ PRICE CHANGE Status

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

1913-15 Sheridan Road, Highland Park

$2,195,000

5 Beds ⋅ 6 Baths ⋅ 12774967 MLS ⋅ ACTIVE Status

1398 Sunnyside Avenue, Highland Park

240 Whistler Road Unit #1E, Highland Park

$2,100,000

5 Beds ⋅ 6 Baths ⋅ 12791592 MLS ⋅ ACTIVE 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

$1,795,000

6 Beds ⋅ 7 Baths ⋅ 12770627 MLS ⋅ ACTIVE 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

$1,780,000

6 Beds ⋅ 6 Baths ⋅ 12553390 MLS ⋅ ACTIVE Status

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

1499 Sheridan Road, Highland Park

$1,699,000

6 Beds ⋅ 5 Baths ⋅ 12803085 MLS ⋅ NEW Status

Welcome to an exceptional Highland Park residence where timeless elegance meets sophisticated modern design. Offering 6 bedrooms, 4.5 bathrooms, and 5,300 square feet of total living space, this extraordinary home is set on an impressive and private .81-acre lot. Meticulously renovated with every detail thoughtfully executed, the home makes an unforgettable first impression from the moment you enter the gracious two-story foyer. Stunning wide-plank white oak floors, charming architectural archways, and beautifully curated contemporary finishes seamlessly blend old-world character with modern luxury. The chef's eat-in kitchen is a true showstopper, featuring custom cabinetry, Bosch and Fisher & Paykel appliances, gorgeous Taj Mahal quartzite, and an oversized walk-in pantry. Open to the expansive family room, which is the perfect gathering space, with soaring ceilings, oversized windows that flood the home with natural light, and breathtaking views of the beautiful grounds. A highly desirable first-floor primary suite option, complete with an attached charming boho-inspired sunroom, offers exceptional flexibility. The fantastic floor plan is equally suited for everyday living and entertaining, with a spacious living room featuring a fireplace that flows effortlessly into the elegant dining room. Two additional first-floor bedrooms, ideal for guests or home offices, and a massive mudroom and laundry room complete this level. Upstairs, the approximately 800-square-foot primary suite is nothing short of spectacular, boasting vaulted ceilings, a fireplace, two fully customized closets with built-in cabinetry, and a private balcony. The spa-inspired bathroom features luxurious finishes and an oversized shower with dual shower heads. Every bathroom throughout the home showcases carefully selected porcelain stone and custom vanities, reflecting the exceptional attention to detail found at every turn. Two additional generously sized bedrooms and a beautifully appointed hall bath complete the second floor. The finished basement provides fantastic additional recreation and entertaining space. Outdoors, enjoy unforgettable summer gatherings on the expansive 600-square-foot deck overlooking the enormous, beautifully landscaped yard. With a new roof, windows, mechanicals, flooring, landscaping, and so much more, this remarkable property offers the luxury, craftsmanship, and peace of mind of new construction-while delivering the character, warmth, and thoughtful design that only a truly exceptional renovation can provide. Ideally located within the highly sought-after Sherwood and Edgewood school districts, this is a rare opportunity to experience better-than-new construction in one of Highland Park's most desirable settings. See additional documents for fact sheet.

1848 Balsam Road, 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

$1,495,000

5 Beds ⋅ 6 Baths ⋅ 12645085 MLS ⋅ RE-ACTIVATED Status

NEW OPPORTUNITY! This stunning Highland Park property is available again! Expanded and renovated in 2008, this two-story prairie-style executive home offers over 9,000 square feet of finished living area across three levels, all easily accessible by a centrally located elevator or stairs, and is situated on over an acre of wooded property along a quiet, private road in Highland Park. The home offers exceptional flexibility with spaces ideal for a variety of lifestyles, hobbies, and extended living arrangements. The home is perfectly centered on over an acre of fully landscaped property with old-growth oak, pine, maple, and a variety of other trees with an endless supply of firewood for the three wood-burning fireplaces with gas starters. The main floor has 10-foot ceilings and was designed for one-floor living. It features a large primary bedroom opening up to a south-facing tropical solarium, a huge walk-in closet, large primary bath with dual sinks, over 10 lineal feet of deep mirrored medicine cabinets, Infinity soaking tub, oversized walk-in shower, and a separate toilet and bidet room. The extra-large kitchen features custom teak cabinetry with full-depth pot drawers, deep upper cabinets, granite tops, and a 6-burner Thermador commercial gas range with griddle, warming trays, and full-size lighted range hood. The kitchen also features a large food-preparation island with granite top, under-counter refrigerator, wine cooler, beverage center, and l teak base cabinets. A second island has counter seating for ten. A large walk-in pantry and a second full kitchen are seamlessly connected to the main kitchen, facilitating large gatherings and specialty cooking. The kitchen and dining area open up onto a large outside concrete deck for outside dining and evening fires overlooking the oversized back yard. The second floor features 9 foot ceilings, a large office and living, study, or hobby area, an ensuite guest room with outside patio, a second guest bedroom with shared bath that has a jacuzzi tub, a large potential second primary suite with an outside patio, a bonus room that is pre-plumbed for an additional bathroom, and an additional bedroom. The expanded lower-level features 8' 6" ceilings, a large, mirrored gym with oak flooring on sleepers, an adjoining full bath and steam room, a separate movie room, and a huge storage area with heavy-duty shelving units. The infrastructure includes 400-amp electrical service, a new 6-inch sewer line, copper water service, three dual sump pumps (120v and 12v with battery backups). The property also features a separate 1,440-square-foot, fully finished building with 10-foot ceilings, an 8-foot-high double garage door with parking for two vehicles, three 8-by-12-foot storage rooms, and a 360-square-foot studio apartment. An additional versatile 12-by-22-foot flex space is ideal for hobbies, projects, a workshop, or extra storage-or could potentially be incorporated into the studio apartment for additional living space. The home features convenient commuting, with access to US Route 41, the Fort Sheridan Metra line, restaurants, shopping, and community events of Highland Park and Highwood. A truly unique home offering privacy, scale, and thoughtful design in a prime Highland Park location.

3464 Old Mill Road, 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

$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

$1,275,000

12797125 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

$1,250,000

3 Beds ⋅ 5 Baths ⋅ 12797748 MLS ⋅ NEW Status

Designed by renowned architect Rick Steven Strusiner, this custom contemporary residence seamlessly blends architectural sophistication with natural beauty. Floor-to-ceiling windows, soaring vaulted ceilings, and hardwood floors create light-filled interiors that connect effortlessly with the outdoors. Expansive front and rear decks and a full-length banquet make entertaining a pleasure. The home features three bedrooms plus a fourth on the lower level, 4 full baths and a powder room, a first-floor den, and a primary suite with a private loft or office. Multiple spacious rooms, custom built-ins, and exceptional storage enhance both comfort and functionality. Beautifully landscaped grounds create a serene setting, just steps from Ravinia Festival, Chicago Botanic Garden, the Ravinia Metra station, and Rosewood Beach. Ravinia Elementary School, Edgewood Middle School and Highland Park High School. A distinctive home offering exceptional design and a desirable North Shore lifestyle. Agent Owned.

495 Hillside Drive, Highland Park

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