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240 Whistler Road Unit #1E, Highland Park
$2,100,000
5 Beds ⋅ 6 Baths ⋅ 12791592 MLS ⋅ NEW Status ⋅ Fort Sheridan BLDG.
Built in 1893 and designed by the celebrated Chicago firm Holabird & Roche, this landmark building in the heart of Fort Sheridan began its life as the Infantry Drill Hall and later served as the post gymnasium. Today it holds just 11 distinctive condominiums, and this end unit is one of its most special.With exposures to the east, north, and south, the home is filled with light throughout the day. The building's original wide, arched entrance on the east facade has been reimagined as a dramatic wall of windows, a striking reminder of the building's history. The kitchen pairs clean, contemporary design with serious function, including a Sub-Zero refrigerator and freezer, a Bosch dishwasher, and a six-burner FiveStar range with two ovens. A large marble island with a breakfast bar is the natural gathering spot, and the eating area beside it is surrounded by floor-to-ceiling windows. The kitchen opens to the family room, where 16-foot ceilings and walls of glass lead out to a 38-foot balcony overlooking the meadow and stream, a lovely place to start the morning or unwind at the end of the day. The primary suite has 13-foot ceilings, floor-to-ceiling windows, and its own balcony facing the historic water tower. The primary bath includes a walk-in shower, whirlpool tub, separate Toto toilet room, makeup vanity, and walk-in closet. 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
1520 Oakwood Avenue, Highland Park
$1,650,000
5 Beds ⋅ 6 Baths ⋅ 12790920 MLS ⋅ NEW Status
A rare offering in one of Highland Park's most coveted locations - This stunning custom built all brick residence is beautifully positioned on a private tree filled lot and offers six bedrooms & 5.5 bathrooms. The gracious interior begins with an elegant foyer opening to a spectacular living room, where a striking stone fireplace and windows on two exposures fill the space with natural light. French doors transition seamlessly to the family room, complete with a second fireplace and an open connection to the chef's kitchen. Showcasing an oversized island with breakfast bar, granite countertops, premium stainless steel appliances, beverage refrigerator, breakfast area and generous walk-in pantry this is the perfect space for any home chef. A formal dining room with French doors is just off the kitchen along with a main floor bedroom with en suite, & a spacious mudroom with direct access to the attached three car garage. An elegant powder room completes the main level. Upstairs, the primary suite offers a tranquil private retreat with dual walk-in closets, and a luxurious en suite with separate vanities, soaking tub, oversized walk in shower and private water closet. Three additional bedrooms provide exceptional flexibility, including one with a private en suite bath and walk in closet, while two bedrooms share a beautifully designed Jack and Jill bath with dual vanity. The laundry room is just down the hall and features a utility sink and plenty of additional storage space. The finished basement extends the living space with an expansive recreation room with a bar, media room with screen, billiards room with pool table, sixth bedroom, full bath with walk-in shower and versatile bonus room currently used as a gym. Outside, a lush and beautifully backyard creates a private sanctuary, with mature trees, expansive lawn and a sophisticated paver patio ideal for al fresco dining and entertaining. Perfectly positioned just blocks from the Highland Park Metra, downtown shopping, acclaimed dining and farmers markets, with easy access to Lake Michigan, beaches, lakefront paths and Ravinia. Zoned to highly regarded District 112 schools and Highland Park High School. An exceptional opportunity in one of the most desirable locations on the North Shore.

1520 Oakwood Avenue, Highland Park
737 Orleans Drive, Highland Park
$460,000
3 Beds ⋅ 3 Baths ⋅ 12786236 MLS ⋅ NEW Status
This move-in ready 3 bedroom, 2.5 bath END-UNIT Chantilly townhome is spacious and bright with an ideal floor plan. First level features expansive family room with marble surround fireplace, formal dining room with bar, versatile den with built-ins and sliding doors to a private patio. The kitchen features Shaker wood cabinetry, stainless steel appliances, Corian countertops, pantry and direct patio access. Luxury vinyl flooring throughout first level. Upstairs, the oversized primary suite offers a walk-in closet, cedar closet, built-in cabinetry and beautiful en-suite bath with decorative tile flooring, double sinks plus vanity area and tub/shower. Two additional generously sized bedrooms, a full hall bath and convenient second-floor laundry complete the upper level. Enjoy outdoor entertaining on the oversized private, fenced patio. Additional highlights include a two-car garage with storage. Residents enjoy a community outdoor pool and a fantastic location near Fink Park, walking paths, recreational facilities and Deer Creek Racquet Club. Easy highway access and just minutes to downtown Highland Park.

737 Orleans Drive, Highland Park
1220 Park Avenue Unit #126, Highland Park
$324,900
2 Beds ⋅ 2 Baths ⋅ 12782094 MLS ⋅ ACTIVE Status
Welcome to Brooke Estates! This bright and spacious 2-bedroom, 2-bathroom end-unit condo offers comfortable, move-in-ready living in a beautifully maintained elevator building. Filled with natural light, this inviting home features an updated kitchen with stainless steel appliances, hardwood flooring, and a convenient breakfast bar that opens to the dining area, complete with vaulted ceilings and skylights. The spacious living room features a cozy gas fireplace and direct access to a private balcony, perfect for relaxing or enjoying your morning coffee. The generously sized primary suite offers plenty of space for a king-sized bed, sitting area, and additional furnishings, along with a private full bathroom and walk-in closet with custom built-ins. The second bedroom features an entire wall of closets, providing exceptional storage. Additional storage can be found throughout the home, including a front entry coat closet and linen closets. A generously sized laundry room features a newer stackable washer and dryer, offering both convenience and additional storage space. Completing this exceptional condo are two heated garage parking spaces and a dedicated storage locker (#31). Brooke Estates offers a wonderful selection of amenities, including two outdoor swimming pools, beautifully landscaped grounds, two picturesque ponds with a fountain, scenic walking paths, and ample guest parking. Located in a highly regarded school district, this home offers an ideal combination of comfort, convenience, and community amenities. The association boasts healthy reserves and no special assessments. Enjoy the ease of maintenance-free living in this desirable Highland Park community!

1220 Park Avenue Unit #126, Highland Park
155 Whistler Road, Highland Park
$649,000
2 Beds ⋅ 3 Baths ⋅ 12785449 MLS ⋅ ACTIVE Status ⋅ Fort Sheridan BLDG.
Discover a distinctive blend of historic character and modern sophistication in this exceptional three-story townhome nestled within the storied Fort Sheridan community along Lake Michigan. An open floor plan, two spacious bedrooms, and two and a half bathrooms create an inviting setting for both everyday living and entertaining. The updated kitchen is beautifully appointed with granite countertops, and a center island, while updated bathrooms offer contemporary style and comfort. Architectural appeal shines through in the dramatic ceiling heights, with 10-foot ceilings on the second floor and soaring 11-foot ceilings on the third, featuring arched windows on the top level. A wooden deck extends the living space outdoors, and a two-car garage and dedicated utility room provide added convenience. Enjoy the distinctive Fort Sheridan lifestyle, where historic surroundings meet the natural beauty of Lake Michigan. Explore nearby scenic trails and lakefront vistas, catch the train at the Fort Sheridan Metra station, or stop by Starbucks just moments away. A rare opportunity to enjoy refined, low-maintenance living in one of the North Shore's most distinctive historic communities.

155 Whistler Road, Highland Park
1454 Glencoe Avenue, Highland Park
$575,000
3 Beds ⋅ 3 Baths ⋅ 12786577 MLS ⋅ ACTIVE Status
Set on a serene residential street in the heart of downtown Highland Park, this spacious three-level townhome offers the ideal combination of everyday comfort and easy access to everything the area has to offer. The main level offers a welcoming entry, generous living room with access to a large private fenced patio, separate dining room or den, powder room, and kitchen with stone countertops, subway tile backsplash, abundant cabinetry, and convenient pull-out pantry storage. Hardwood flooring and ample natural light add warmth throughout the space. Upstairs, three bedrooms and two full baths provide a comfortable separation between living and sleeping spaces. The oversized primary bedroom features a walk-in closet and en suite bath with a glass-enclosed walk-in shower. A full-size side-by-side laundry room with additional storage adds everyday convenience. The lower level expands the living space even further with a large family room and direct access to the attached two-car garage, which includes two additional storage rooms. Walk to the Metra, shops, restaurants, coffee, and more, while nearby beaches, Ravinia Festival, country clubs, and golf courses make it easy to enjoy the best of the North Shore.

1454 Glencoe Avenue, Highland Park
23 Rienzi Lane, Highwood
$849,000
3 Beds ⋅ 3 Baths ⋅ 12783212 MLS ⋅ ACTIVE Status
Carefree living in the Fort with LOW HOA fees! This spacious and welcoming 2800 sq ft home is on an extra wide 28' lot. This townhome lives like a large single family home. Rich in History, this site was originally the Military Horse Stables. This open concept home offers a large granite island kitchen for easy cooking & entertaining, featuring updated lighting, cabinet fronts and deluxe pull out drawers. Plenty of space for a crowd, the open layout offers three areas for dining; casual at the island, everyday at the dining room area with chandelier, and along the side of the room that accommodates a table long enough for 8-10 people easily. Great room is the center of easy living with a fireplace hearth and large TV wall, space for a large sectional sofa and chairs, and handsome Plantation shutters gracing the windows overlooking the private patio area and yard with newer wood fence. Beautiful updated first floor powder room, coat closet and roomy 2.5 car attached garage complete the first floor. The stainless steel railings leading to the 2nd floor offers a large loft area, great for a home office or workout area plus 2 bedrooms in addition to the primary bedroom and laundry nook. Enormous light filled primary bedroom has a gorgeous 2025 renovated primary bathroom suite with huge converted WIC. Enjoy daily walks or bike rides by the lakefront and all that vibrant downtown Highwood has to offer with award winning restaurants, bars and entertainment. Close to Metra and just a few minutes drive to downtown Highland Park.

23 Rienzi Lane, Highwood
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
86 Prospect Avenue, Highland Park
$5,495,000
8 Beds ⋅ 12 Baths ⋅ 12781411 MLS ⋅ ACTIVE Status
Stop dreaming, start living. Rarely does a residence of this magnitude and pedigree become available. Nestled just steps from the whispering shores of Lake Michigan, 86 Prospect Avenue is more than a home-it is a masterpiece of architectural significance. Originally commissioned in 2006 by a prominent local builder as his personal sanctuary, this estate has recently emerged from a multi-year, multi-million dollar transformation, championed by Red Rock Custom Homes and Earth Developments, as well as design carefully curated by Kara Mann Interiors, resulting in a seamless fusion of timeless North Shore grandeur and 2026's most sophisticated modern luxuries. Thoughtfully situated on three hand-selected well-located parcels, the land now totals .87 acres of meticulously manicured grounds. Your approach to the home is cinematic, featuring a brand new circular paver drive, adorned by timeless gas lamps and lush potted plants, which leads to a majestic porte-cochere, a private gated motor court, and a heated five-car garage. The rear grounds are anchored by a 45-foot heated pool recently totally redone and resurfaced, complemented by a stone fire pit and sprawling covered patios. The heart of the home is a bespoke Chef's Atelier featuring a striking marble and walnut island, Viking and Wolf ranges, Traulsen refrigeration with a dedicated commercial walk-in refrigerator, and Sub-Zero integrated drawers. This culinary suite transitions effortlessly from a sun-drenched breakfast room complete with a custom eating area with built-in benches to an expansive formal dining room anchored by a stately wood-burning fireplace. With over 14,000 square feet of finished living space, the home offers a versatile floor plan of eight to ten bedrooms, including a primary suite that serves as a bastion of tranquility with a private balcony, seasonal lake views, dual spa-inspired bathrooms, and two expansive custom dressing rooms. Four additional ensuite bedrooms and a hidden play area grace the second floor, while the third floor is dedicated to wellness with a professional gym, massage/yoga room, and recreation room. The walk-out lower level provides a sophisticated retreat with a second kitchen, three guest suites, three full bathrooms, and a large recreation room with a dedicated cabana bath. Built with a "forever" mindset, the estate includes a full-service elevator, two laundry suites, an executive library, a whole-house generator, and an advanced irrigation system. This is not merely an acquisition of real estate, but the acquisition of a lifestyle without compromise. Step into the perfect blend of timeless architecture and luxury north shore living. Welcome home! A few final touches being completed as we speak. Nearly $2.5m was invested in this home since in the last two years, a full list of improvements available upon request.

86 Prospect Avenue, Highland Park
1440 Concorde Circle, Highland Park
$439,000
3 Beds ⋅ 3 Baths ⋅ 12773165 MLS ⋅ ACTIVE Status
Rarely available Chantilly END-UNIT ideally situated overlooking the golf course! Lovingly maintained, this spacious and light-filled 3-bedroom, 2.5-bath townhome offers a wonderful floor plan featuring an expansive family room, formal dining room with wet bar and versatile den/office with sliding doors to a private patio. The kitchen features white cabinetry, granite countertops, ceramic tile flooring, a built-in planning desk area, pantry and direct patio access. Upstairs, the oversized primary suite offers a walk-in closet, cedar closet and en-suite bath. Two additional generously sized bedrooms, a full hall bath and convenient second-floor laundry complete the upper level. Enjoy outdoor entertaining on the private, fenced patio. Additional highlights include a two-car garage with abundant storage. Residents enjoy a community outdoor pool and a fantastic location near Fink Park, walking paths, recreational facilities and Deer Creek Racquet Club. Easy highway access and just minutes to downtown Highland Park. Mechanical ages: Bradford White 50-gallon electric water heater - Sept. 2021, Lennox indoor air handler - Sept. 2023, Maytag washer - Jan. 2021, Maytag electric dryer - older, Maytag side-by-side refrigerator/freezer - Jan. 2009, Maytag 30" electric range and microwave - early 2009, Maytag dishwasher - May 1997

1440 Concorde Circle, Highland Park
493 Hazel Avenue, Highland Park
$2,499,000
6 Beds ⋅ 7 Baths ⋅ 12781765 MLS ⋅ ACTIVE Status
This Beautiful Home on Over an Acre in the Heart of Highland Park Boasts Soaring Barrel Ceilings over 20' High and 5 Fireplaces. Amazing Home for Entertaining with a Magnificent Great Room, a Banquet-Sized Dining Room with a Butlers Pantry, a Wonderful Screened Porch and a Balcony Overlooking the Backyard- which includes Ravines and a Huge Yard, large enough for a tennis/pickleball court, an outdoor pool and more- Accessed by a Bridge! The Double Island Chefs Kitchen has a Fireplace, Walk-in Pantry, Professional Series Appliances, Dumb-waiter and Way Too Many Features to List! The Main Floor has 3 Bedrooms and 3 1/2 Baths and the Entire 2nd Floor is a Romantic Hideaway Primary Suite with its Own Family Room, Fireplace, Huge Walk-in Closet and Spa-like Bath. There is potential to create a 1st Floor Primary if desired. This Home offers over 8000 Sq Ft plus 2330 Sq Ft in the Finished Walkout Basement featuring a 40' Indoor Pool with a Wall of Glass that Open to the Outdoors! 2 Additional Bedrooms and Full Baths, a Massive Workout Room, an Amazing Home Theater, and a Summer Kitchen in the Walkout Basement. 5 Zones of Heat and Air, and a 3+ Car Garage. Located just moments from the Vibrant Shops, Dining, and Cultural Landmarks of Downtown Highland Park, the Metra Train and the Lakefront, this Home offers a Lifestyle of Convenience and Sophisticated Comfort. It's not just a place to live-It's a Place to Thrive. Truly a Must See!

493 Hazel Avenue, Highland Park
271 Whistler Road, Highland Park
$699,999
2 Beds ⋅ 3 Baths ⋅ 12781749 MLS ⋅ ACTIVE Status
Step into this completely renovated (by homeowner) and beautifully appointed Fort Sheridan townhome and prepare to be mesmerized. An unobstructed park view sets the stage for this exceptional home, where 11-foot ceilings, sophisticated design, and state-of-the-art technology come together to create a truly one-of-a-kind living experience. The home has been thoughtfully opened up to create an airy, light-filled floor plan. The first floor features stunning chevron-patterned flooring, a sleek linear modern gas fireplace, and a spectacular custom kitchen. Designed for both everyday living and entertaining, the kitchen showcases 6-foot custom white oak cabinetry, an extra-wide drawer system, a 7-foot island with integrated wine refrigerator and microwave, and gorgeous quartz countertops with a waterfall edge. Additional details include a reverse-osmosis water purification system, under-cabinet toe-kick lighting, and a custom white oak banquette with integrated storage. Even the powder room is gorgeous with hand made cement Moroccan tiles. Smart-home technology is seamlessly integrated throughout, including Lutron Caseta lighting, Sonos surround sound and built-in speakers, and motorized Hunter Douglas window shades. Every detail has been considered, including modern HVAC registers, contemporary outlets with USB-A/C charging ports, and sleek screwless switch plates. Ascend the custom white oak staircase to the second floor, where beautifully appointed bedrooms feature custom wall paneling, spacious closets, extra-wide French doors, and 2 gorgeous bathrooms outfitted with Kohler fixtures. The primary suite offers a generous walk-in closet and a luxurious walk-in shower with floor-to-ceiling tile. The lower level provides exceptional functionality with a new washer and dryer, floating laundry folding cabinet, abundant additional storage, and an epoxy-floored attached two-car garage. Nothing has been overlooked in this extraordinary renovation. Sophisticated, stylish, and exceptionally well executed, this is an effortless way of life in one of the North Shore's most special settings. Living in Fort Sheridan is truly paradise-nestled along Lake Michigan and surrounded by ravines, preserves, and natural beauty. Enjoy beach access, scenic trails, and close proximity to downtown Highwood, Highland Park, and Lake Forest, with an easy commute to Chicago. A rare opportunity to enjoy beautifully designed, completely renovated living in the heart of Fort Sheridan.

271 Whistler Road, Highland Park
1530 Oakwood Avenue, Highland Park
$839,000
4 Beds ⋅ 3 Baths ⋅ 12780388 MLS ⋅ ACTIVE Status
From the dramatic front porch to the bay window off the kitchen and craftsman woodworking throughout, this house is truly a "home". Move right into this classic American foursquare convenient to all the North Shore has to offer? Lovingly maintained and continuously updated by two generations of the same family. Great floor plan too - Kitchen is open to eat-in area, flowing into formal dining space and then into the front living room. Partial finished basement. Craftsman detail in the wood-beam ceilings, staircase and (gas) fireplace mantle. Spacious brick paver patio and large back yard with gorgeous mature landscaping! Plus an UNBEATABLE LOCATION ... On a quiet street lined with historic homes but just a block from downtown Highland Park's restaurants, shops, Metra station, coffee, book stores etc. And just a stone's throw to Ravinia District of Highland Park, Ravinia Festival, Chicago Botanic Garden, schools, parks, beaches and more. No central A/C, but many other recent updates and continuously maintained by owners. See the Improvements List under "additional info" or call listing agent Carolyn Cerf!

1530 Oakwood Avenue, Highland Park
1795 Lake Cook Road Unit #211, Highland Park
$338,900
2 Beds ⋅ 2 Baths ⋅ 12779740 MLS ⋅ PRICE CHANGE Status
Bright and spacious, this rarely available 2-bed, 2-bath condo at the Americana in Highland Park offers a sophisticated retreat in a prime location. The moment you step the attention to detail is evident: New flooring, large living area, updated kitchen and bathrooms. The heart of the home is the reimagined eat-in kitchen, a chef's delight featuring crisp cabinetry, expansive counter space, and new stainless steel appliances. Whether you're prepping a quick breakfast or hosting a dinner party, the direct balcony access makes it easy to step out for some fresh air. The open-concept living and dining area feels incredibly airy, anchored by a fireplace that adds a layer of warmth and ambiance to the contemporary design. The primary suite serves as a true sanctuary, complete with a massive walk-in closet and a private en-suite bathroom. The second bedroom is equally impressive, filled with natural light and offering a large walk-in closet-perfect for a guest room or a dedicated creative space. Living at the Americana means enjoying a suite of amenities, including an outdoor pool, exercise room, and a party room with its own kitchen. This unit includes a dedicated storage space on the same floor and one assigned space in the heated garage. With easy access to parks, shopping, and dining, this home perfectly blends updated style with effortless convenience.

1795 Lake Cook Road Unit #211, Highland Park
930 Central Avenue, Highland Park
$975,000
4 Beds ⋅ 5 Baths ⋅ 12767426 MLS ⋅ ACTIVE Status
Sophisticated, spacious, and beautifully updated, this light-filled luxury townhome offers the ease of maintenance-free living with the space, privacy, and functionality of a single-family home. Ideally located just steps from town and Sunset Foods, the residence features 5 bedrooms-including flexible office space, 4 1/2 baths, and more than $350,000 in thoughtful improvements. The main level is designed for both everyday living and entertainment, with a beautifully updated chef's kitchen featuring Viking appliances, new stone countertops, under cabinet lighting & charging station. Brazilian cherry hardwood floors bring warmth and richness throughout the home. The generous living area is anchored by a striking remote controlled gas fireplace and stunning maple cabinets & shelving, creating a warm and inviting gathering space. Upstairs, the second floor offers three bedrooms, including a serene primary suite and en-suite, spa bath outfitted with a steam shower, heated floors, soaking tub, plus two organized walk-in closets. Two additional bedrooms share a Jack-and-Jill bath, while a conveniently located laundry area and built-in homework station, which can also be used as a display area, provides function and style. The third floor is a private, beautifully finished space ideal for a home office, additional bedroom, studio, or quiet retreat, complete with a stunning Bernhardt built-in office. The finished lower level adds even more versatility, with a bedroom featuring a custom closet, full bath, dedicated gym space, and an updated entertainment area with surround sound-perfect for movie nights, guests, or extended family. Speakers are wired throughout the home, organized closets maximize storage, and thoughtful soundproofing between the primary suite and the neighboring residence provides an added level of privacy. A private heated two-car garage with epoxy flooring offers year-round comfort and convenience, while three furnaces and AC units, Ecobee thermostats & video doorbell and remote garage door openers enhance the home's efficiency and ease of living. The beautifully maintained stone and stucco exterior reflect extensive improvements, including a newer roof, brand new garage door, property grading, outdoor fixtures, front steps, landscaping, and select updated windows. The home has been professionally inspected annually. The landscaping, snowplowing, roof and outdoor lighting remain HOA responsibilities going forward. Outside, enjoy meticulously maintained green space and a new Trex deck just off the main level, complete with a gas grill line and outdoor speakers, an effortless extension of the home for entertaining or relaxing. Guest parking and a sprinkler system add even more convenience. With exceptional space, extensive updates, sophisticated finishes, and an unbeatable walk-to-town location, this is a rare opportunity to enjoy luxury townhome living without compromising on the comforts of a single-family home.

930 Central Avenue, Highland Park
1466 Concorde Circle, Highland Park
$434,000
3 Beds ⋅ 3 Baths ⋅ 12753549 MLS ⋅ ACTIVE Status
Chantilly End Unit on the Golf Course! Bright, sunny, well-loved, and well-maintained, spacious 3-bedroom, 2.1-bath with attached garage, and lovely, fenced private patio facing South and West. The potential and size of the unit and rooms are amazing, with space for entertaining and gatherings, an office, garden room, dining room, or flex space, as well as a living room, dining room, and kitchen, plus a powder room on the first floor. Upstairs, welcome to a huge Primary Suite with year-round views of the golf course, good closets including a separate cedar closet, two more bedrooms with their own substantial closet space, two linen closets, a hall bath, and convenient 2nd-floor laundry. Mechanicals and sliding glass doors updated. Don't miss all that Chantilly has to offer, including parks, a walking path, a dog park nearby, a community pool, and more, plus a great location within the community!

1466 Concorde Circle, Highland Park
1240 Park Avenue Unit #331, Highland Park
$220,000
2 Beds ⋅ 2 Baths ⋅ 12723585 MLS ⋅ PRICE CHANGE Status ⋅ Brooke Estates BLDG.
Bright and spacious second-floor 2-bedroom, 2-bathroom condo in desirable Brooke Estates! Enjoy a private patio overlooking the community pool, creating a pleasant outdoor retreat. Inside, you'll find nicely sized bedrooms, including a primary bedroom with its own private bathroom, along with newer flooring and a newer dishwasher. Enjoy the convenience of an elevator building, one indoor parking space (#19), additional storage, and plenty of guest parking. Brooke Estates offers a beautiful setting with walking paths, a pond, and pool for residents to enjoy. Ideally located just off Route 41 with easy access to expressways, shopping, dining, and downtown Highland Park. A wonderful opportunity to make this condo your own in a convenient and amenity-filled community!

1240 Park Avenue Unit #331, Highland Park
701 Lincoln Avenue, Highland Park
$2,500,000
5 Beds ⋅ 7 Baths ⋅ 12771440 MLS ⋅ ACTIVE Status
AVAILABLE OCTOBER 15, 2026. 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
1230 Park Avenue Unit #210, Highland Park
$339,000
2 Beds ⋅ 2 Baths ⋅ 12765641 MLS ⋅ PRICE CHANGE Status ⋅ Brooke Estates BLDG.
Beautifully renovated and exceptionally spacious, this 1st Floor, two-bedroom, two-bath condominium offers an open, light-filled floor plan designed for comfortable everyday living and entertaining. The gorgeous, updated kitchen features crisp white cabinetry, quartz countertops, a stylish subway tile backsplash, stainless steel appliances, generous workspace, and an easy flow into the dining and living areas. The sunny living room features a fireplace with lovely black marble surround and sliding glass doors that open to a private patio overlooking the lawn, creating a wonderful connection between the indoor and outdoor spaces. The separate dining room area provides the perfect space for casual entertaining or holiday meals. The generously sized primary suite offers a large walk-in closet and beautifully updated private bath. The second bedroom is also nicely proportioned and offers the flexibility to serve as a guest room, home office or combination of both. An updated hall bath and convenient in-unit laundry complete the thoughtfully renovated interior. Located in Highland Park's sought-after Brooke Estates, the residence includes one indoor garage parking space. An additional garage space may be rented through the HOA, subject to availability and association requirements. Residents also enjoy two swimming pools, attractive grounds and a picturesque pond. Easy access to route 41 or downtown Highland Park. Spacious, sunny, renovated and move-in ready, this is an exceptional opportunity to enjoy easy condominium living in Highland Park. This is the one to buy!

1230 Park Avenue Unit #210, Highland Park
1458 Linden Avenue, Highland Park
$393,000
3 Beds ⋅ 1 Baths ⋅ 12756090 MLS ⋅ ACTIVE Status
Alright, thrill-seekers and fearless renovators-here's a unique opportunity on prime Linden Avenue in East Highland Park. This charming 1920s two-bedroom, one-bath cottage has certainly been through its share of challenges. After years of difficult tenants and other issues, the property was cleared out and rehabilitated in 2024. While some improvements have been completed, the home still has some renovation wishlist items, including a new roof, kitchen and bath glow-up, flooring repairs, paint throughout, new decks front and back, French drains, plus full attic and roofing restoration. Priced to reflect the truth, sold strictly as-is. Perfect for the FHA Limited 203(k) program - roll up to $75,000 of those fixes right into your mortgage. Ten-minute walk to town, fifteen to the lake, great schools, quarter-acre lot. Highland Park living, just with... character.

1458 Linden Avenue, Highland Park
1795 Lake Cook Road Unit #110, Highland Park
$359,000
2 Beds ⋅ 2 Baths ⋅ 12729689 MLS ⋅ PRICE CHANGE Status
TWO PARKING SPACES! Beautifully updated 2-bedroom, 2-bathroom condo offering modern style, comfort, and convenience. The inviting living room features a gorgeous stone fireplace, creating a warm and welcoming space for relaxing or entertaining. The stylish kitchen boasts crisp white cabinetry, stainless steel appliances, stunning white quart countertops and a clean, contemporary design. Pella windows with integrated blinds for a easy and updated feel. Gorgeous engineered wood throughout the unit.The spacious primary bedroom features a huge walk-in closet and beautifully updated private bath. Both bathrooms have been thoughtfully renovated with gorgeous tilework and modern finishes. A private balcony provides the perfect spot to enjoy your morning coffee or unwind at the end of the day. With two dedicated parking spaces and beautiful updates throughout, this move-in-ready condo is the perfect combination of style and convenience! *50K in Pella windows and doors have been updated in this unit!*

1795 Lake Cook Road Unit #110, Highland Park
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
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
117 Belle Avenue, Highland Park
$6,750,000
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
1499 Sheridan Road, 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



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