Highland Park, IL Homes

/82
$5,995,000 Open Sun 1AM - 3PM
- 5 Beds
- 8 Baths
- 9,000 Sq Ft
55 Prospect Ave, Highland Park, IL 60035

Welcome to 55 Prospect Avenue-where every day feels like a seaside escape. Perfectly sited on 1.5 acres with an extraordinary 175 feet of private Lake Michigan beachfront, this coastal-inspired estate offers a rare blend of architectural elegance, resort-style living, and timeless design. Evoking the relaxed sophistication of the Hamptons, this is Highland Park's crown jewel. Designed and built

Carrie McCormick @properties Christie's International Real Estate

55 Prospect Ave, Highland Park, IL 60035
/9
$2,095 per month
- 1 Bed
- 1 Bath
- Condo for Rent
447 Roger Williams Ave Unit 730-16, Highland Park, IL 60035

Must see renovated 1 bedroom apartment! Features hardwood floors, updated kitchen & bath, spacious living area, laundry in-unit. Pet friendly building. Steps to Jens Jensen Park. Close to Metra, restaurants and more! Presented by Fulton Grace, Chicago IL.*Pictures may be of a similar unit in building.

447 Roger Williams Ave Unit 730-16, Highland Park, IL 60035
/7
$520,000 Sold Aug 15, 2025
- 1,400 Sq Ft
- $371/SF
- 53 Days On Market
- 3 Beds
- 3 Baths
- Built 1955
1780 Rosemary Rd, Highland Park, IL 60035

Welcome to this beautifully renovated 3-bedroom, 3-bathroom home in the heart of Highland Park! This move-in ready property blends modern upgrades with a prime location near top-rated schools and local parks. Step inside to find a spacious, light-filled layout featuring brand-new windows, updated flooring throughout, and stylish lighting fixtures. The main level showcases a bright living and

Amaliia Baturina Your House Realty

1780 Rosemary Rd, Highland Park, IL 60035

/36
Est $1,314,125 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,483 Sq Ft
171 Indian Tree Dr, Highland Park, IL 60035

171 Indian Tree Dr, Highland Park, IL 60035

/37
$599,000 Open Sun 11AM - 1PM
- 3 Beds
- 2 Baths
- 1,524 Sq Ft
566 Bellevue Place, Highland Park, IL 60035

Ravinia! Charming 3 bedroom brick bungalow! Freshly painted interior & refinished hardwood floors. Features include: 3 bedrooms on the main floor with a full bathroom, inviting living room with wood burning fireplace, sunroom, kitchen with walk in pantry, detached 2 car garage, full finished basement with additional full bathroom. There is a pull down stairs to a large attic space for extra

Cory Albiani @properties Christie's International Real Estate

566 Bellevue Place, Highland Park, IL 60035
/19
$3,200 per month
- 3 Beds
- 2 Baths
- Condo for Rent
2490 Green Bay Rd Unit 1, Highland Park, IL 60035

Completely remodeled 3 bed/2 bath within walking distance to Schools, metra, shopping and more. Bright and spacious living room with wood burning fire place. Wood floors throughout. Updated kitchen with brand new refrigerator and plenty of storage. New W/D on main level. Dining area with access to side deck. Bedrooms share modern and brand new hallway bath. Back entry area provides access to

Jacqueline Lotzof Compass

2490 Green Bay Rd Unit 1, Highland Park, IL 60035
/22
$815,000 Sold Aug 15, 2025
- 2,463 Sq Ft
- $331/SF
- 5 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1996
1700 2nd St Unit 509A, Highland Park, IL 60035

Rarely available top-floor corner unit lives like a single-family home! Nearly 2,500 sq ft of light-filled living space featuring 3 private balconies, enormous eat-in kitchen with granite countertops, double ovens, and new stainless steel refrigerator. Spacious separate dining room and oversized family room perfect for entertaining. Expansive primary en suite with sitting area and desk, large

Lauren Rabin @properties Christie's International Real Estate

1700 2nd St Unit 509A, Highland Park, IL 60035

/35
Est $739,491 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,982 Sq Ft
145 Blackhawk Rd, Highland Park, IL 60035

145 Blackhawk Rd, Highland Park, IL 60035

/18
$740,000
- 6 Beds
- 6 Baths
2500 Green Bay Rd, Highland Park, IL 60035

Attention Investors or End Users! Discover this fantastic turnkey 2-family Townhome. Ideal for living in one unit while renting out the other, this beautifully updated duplex offers a perfect blend of comfort and functionality. Each unit features a kitchen with lovely white cabinetry and granite countertops, complemented by an adjacent dining area. Enjoy the cozy ambiance of the living room's

Ellen Chukerman Compass

2500 Green Bay Rd, Highland Park, IL 60035
/9
$1,695 per month
- Studio
- 1 Bath
- Condo for Rent
447 Roger Williams Ave Unit 730-20, Highland Park, IL 60035

Must see renovated Studio apartment! Features hardwood floors, updated kitchen & bath, spacious living area, laundry in-unit. Pet friendly building. Steps to Jens Jensen Park. Close to Metra, restaurants and more! Presented by Fulton Grace, Chicago IL.*Pictures may be of a similar unit in building.

447 Roger Williams Ave Unit 730-20, Highland Park, IL 60035
/44
$1,485,000 Sold Aug 15, 2025
- 7,567 Sq Ft
- $196/SF
- 59 Days On Market
- 6 Beds
- 4.5 Baths
- Built 1988
2333 Tennyson Ln, Highland Park, IL 60035

Dramatic Custom Contemporary (over 7500SF Above Grade) with a 3-Car Heated Garage and Circular Drive, set on a Gorgeous, Close to an Acre Property! The Big Ticket Items have been Done for You: Brand New Pella Windows, New DaVinci Roof, 4 Newer Furnaces and 3 Newer Air Conditioners. Enter into the Grand Foyer and Fall in Love with the Expansive, Open Floor Plan Featuring a Gourmet Chef's Kitchen

Janet Borden Compass

2333 Tennyson Ln, Highland Park, IL 60035

/38
Est $708,965 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,082 Sq Ft
103 Green Bay Rd, Highland Park, IL 60035

103 Green Bay Rd, Highland Park, IL 60035

/20
$499,000
- 3 Beds
- 2 Baths
- 1,080 Sq Ft
927 Half Day Rd, Highland Park, IL 60035

$50,000 price reduction! Sunny and inviting ranch home filled with natural light. Large 73' X 231' lot (nearly a half acre). 3 bedrooms, 2 baths total with 2 bedrooms and one bath on the main level and one bedroom and one bath on the fully finished lower level. Extra large 2+ car detached garage with attached workshop area. Concrete driveway. Spacious back patio. Easy access to Rt. 41 and

Greg Weissman @properties Christie's International Real Estate

927 Half Day Rd, Highland Park, IL 60035
/23
$2,670 per month
- 1 Bed
- 1 Bath
- 1,047 Sq Ft
- Apartment for Rent
833 Laurel Ave Unit 103, Highland Park, IL 60035

Newer construction apartment has it all! 1-bedroom residence offers luxury living in the heart of downtown Highland Park. Located in an elevator building, the unit features a gourmet kitchen with quartz countertops, stainless steel appliances, Italian cabinetry, breakfast bar, and dishwasher. The open-concept layout includes a spacious living area with sliding glass doors that lead to a large

Shari Saratovsky Diplomat Realty, Inc.

833 Laurel Ave Unit 103, Highland Park, IL 60035
/38
$455,000 Sold Aug 15, 2025
- 2,154 Sq Ft
- $211/SF
- 248 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1978
704 Lorraine Cir, Highland Park, IL 60035

Nestled in the best location of the subdivision on the Park, this townhome offers luxury and convenience in every detail. The main floor boasts a high-end gourmet kitchen, fully equipped with top-of-the-appliances for anyone who loves to cook or entertain. Adjoining the kitchen is a large, sunlit living and dining area, along with an inviting reading nook or extra sitting space, all flowing out

Grace Martinez Exit Grace Realty

704 Lorraine Cir, Highland Park, IL 60035

/31
Est $1,169,284 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,535 Sq Ft
580 Rambler Ln, Highland Park, IL 60035

580 Rambler Ln, Highland Park, IL 60035

/21
$240,000
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
2046 Saint Johns Ave Unit 2A, Highland Park, IL 60035

Bright and spacious 2-bedroom, 2-bathroom northeast corner unit in a prime downtown Highland Park location. This freshly painted home is filled with natural light and features a large living room that opens to a private balcony overlooking the landscaped front grounds-ideal for relaxing or entertaining. A separate dining area, eat-in kitchen, and generously sized primary suite with excellent

Tedi Smola @properties Christie's International Real Estate

2046 Saint Johns Ave Unit 2A, Highland Park, IL 60035
/8
$1,895 per month
- 1 Bed
- 1 Bath
- Condo for Rent
725 St Johns Ave Unit 21, Highland Park, IL 60035

UNIT FEATURES:* Hardwood Floors* Large Updated Kitchen* Separate Dining Area* Updated Bathroom* Miniblinds* Ceiling Fans* Plenty of Closet Space* Laundry on site* Pet-Friendly BuildingDisclaimer: The Apartment SourceCall or text:

725 St Johns Ave Unit 21, Highland Park, IL 60035
/2
$1,398,150 Sold Aug 14, 2025
- 4,630 Sq Ft
- $302/SF
- 12 Days On Market
- 5 Beds
- 5.5 Baths
- Built 1977
2143 Tennyson Ln, Highland Park, IL 60035

Welcome to this exceptional 5 bedroom, 5.5 bath luxury residence set on nearly an acre of beautifully landscaped grounds. Designed for refined living and grand-scale entertaining, this home offers a true resort-style backyard featuring a sparkling pool, outdoor kitchen and bar, elegant fireplace lounge, and multiple sitting areas that evoke the ambiance of a five-star hotel. Inside, the

Beth Wexler @properties Christie's International Real Estate

2143 Tennyson Ln, Highland Park, IL 60035

/40
Est $1,032,398 Not Listed For Sale
- 5 Beds
- 5 Baths
- 3,019 Sq Ft
377 Delta Rd, Highland Park, IL 60035

377 Delta Rd, Highland Park, IL 60035

/43
$2,699,999
- 6 Beds
- 6 Baths
- 6,239 Sq Ft
1144 Green Bay Rd, Highland Park, IL 60035

1144 Green Bay Road is a unique and unparalleled French Country estate originally built in 1937 by prominent architect, William Mann and meticulously restored in 1996 to resemble a French chateau. The exterior of the home was built with limestone and concrete base, and the interior was designed with steel supports and steel girder throughout, with most interior walls of plaster. Situated on 1.37

Melissa Lipschultz Baird & Warner

1144 Green Bay Rd, Highland Park, IL 60035
/19
$3,000 per month
- 5 Beds
- 2 Baths
- 1,271 Sq Ft
- House for Rent
1014 Half Day Rd, Highland Park, IL 60035

Conveniently located and nicely updated Highland Park single family 5 bedroom home. The first floor features a large eat-in kitchen, living room, 2 bedrooms and a newly remodeled full bathroom with bathtub. On the second floor, there are 3 additional bedrooms and a recently refinished full bathroom with shower. There is additional storage and laundry in the unfinished basement. There is garage

Cory Albiani @properties Christie's International Real Estate

1014 Half Day Rd, Highland Park, IL 60035
/16
$280,000 Sold Aug 12, 2025
- 1,269 Sq Ft
- $221/SF
- 2 Days On Market
- 2 Beds
- 2 Baths
- Built 1987
2020 St Johns Ave Unit 309, Highland Park, IL 60035

Extraordinary opportunity to make this in-town 2-bedroom/2-bath condo with walls of windows and lovely exposed brick in the entry and kitchen your own. Laminate wood floors throughout. Includes two tandem parking spaces and a storage locker in the underground garage. Free shared laundry down the hall. Desirable building with beautiful outdoor courtyards and a shared roof terrace. Fabulously

Debbie Croft @properties Christie's International Real Estate

2020 St Johns Ave Unit 309, Highland Park, IL 60035

/21
Est $695,682 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,814 Sq Ft
238 Pierce Rd, Highland Park, IL 60035

238 Pierce Rd, Highland Park, IL 60035

/43
$1,899,000
- 3 Beds
- 4.5 Baths
- 4,610 Sq Ft
2021 Saint Johns Ave Unit 4C, Highland Park, IL 60035

Simply striking & palatial condo ripped right from the pages of Architectural Digest located in-town just blocks from Lake Michigan in one of Highland Park's most prestigious concierge buildings. Designed by renowned architects Powel/Kleinschmidt this unique and timeless unit is like living inside of a masterpiece. A grand foyer leads into the sunny & sleek living room featuring floating frosted

Patricia Denenberg @properties Christie's International Real Estate

2021 Saint Johns Ave Unit 4C, Highland Park, IL 60035
/64
$1,650 per month
- Studio
- 1 Bath
- 500 Sq Ft
- Condo for Rent
730 Judson Ave Unit 1, Highland Park, IL 60035

Live in this beautiful building in an amazing part of Highland Park! This building is located near the Metra! Also nearby is a food center, plenty of restaurants and great nightlife. This apartment is a studio with in unit laundry. It is a gut rehab apartment which features stainless steel appliances, granite counter tops and amazing cabinets in the kitchen. The bathroom features a tiled shower,

730 Judson Ave Unit 1, Highland Park, IL 60035
/14
$311,000 Sold Aug 11, 2025
- 1,344 Sq Ft
- $231/SF
- 3 Days On Market
- 3 Beds
- 3 Baths
- Built 1964
2110 Saint Johns Ave Unit B, Highland Park, IL 60035

Great space in this three bedroom townhouse, two blocks to downtown Highland Park and Metra station! The all brick unit features one full and two half baths. Spacious living room 20 x 15, which can be used as a combination dining room space, if you so choose! Kitchen appliances recently updated in 2024 (refrigerator, oven/range and dishwasher) and granite counters complete the cooking area, as

Susan Ringel Segal @properties Christie's International Real Estate

2110 Saint Johns Ave Unit B, Highland Park, IL 60035

/31
Est $880,383 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,737 Sq Ft
260 Lakeside Place, Highland Park, IL 60035

260 Lakeside Place, Highland Park, IL 60035

/42
$1,499,000
- 5 Beds
- 5.5 Baths
- 5,900 Sq Ft
2005 Keats Ln, Highland Park, IL 60035

Welcome to 2005 Keats Lane! Tucked away on a serene, quiet lane lined with towering trees and dappled sunlight, this expansive home sits on nearly a full acre of land. Located in sought-after Highland Park, within the award winning Wayne Thomas and Deerfield school districts, this home offers the perfect balance of original and new. Lovingly maintained and impeccably remodeled from top to bottom,

Daniel Cartalucca Coldwell Banker Realty

2005 Keats Ln, Highland Park, IL 60035
/12
$3,310 per month
- 2 Beds
- 2 Baths
- 1,142 Sq Ft
- Apartment for Rent
555 Roger Williams Ave Unit 303, Highland Park, IL 60035

Welcome to Ravinia Crossing, Highland Park's newest boutique rental building in the heart of the Ravinia Business District. This intimate four story 30-unit building consists of a variety of one and two-bedroom unit floor plans with luxury high-end finishes. open great room with walls of windows- the north facing units have balconies and overlook the ravines, the south and east facing units have

Larry Klairmont Twins Realty LLC

555 Roger Williams Ave Unit 303, Highland Park, IL 60035
/13
$450,000 Sold Aug 08, 2025
- 1,981 Sq Ft
- $227/SF
- 13 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1965
626 Barberry Rd, Highland Park, IL 60035

Well maintained and well loved 4BR/2.5BA split-level home in desirable West Highland Park. Built in 1966, this home features an updated kitchen, enclosed rear porch, and spacious layout with multiple living areas. Hardwood floors in bedrooms . Large backyard offers great outdoor space for entertaining or relaxing. Attached 2-car garage. High-speed AT&T 1 Gb fiber optic internet ideal for work or

Sonia Cohen Coldwell Banker Realty

626 Barberry Rd, Highland Park, IL 60035

/34
Est $1,269,977 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,216 Sq Ft
340 Carol Ct, Highland Park, IL 60035

340 Carol Ct, Highland Park, IL 60035

/36
$685,000
- 4 Beds
- 1.5 Baths
- 2,350 Sq Ft
847 Marion Ave, Highland Park, IL 60035

Lovely and completely updated home nestled in the highly sought-after Braeside community and located on one of Highland Park's most desirable streets. This elegant Colonial home offers a delightful blend of sophistication and family-friendly features, creating an ideal setting for lasting memories. Boasting 2350 square feet of living space, the residence features 4+ bedrooms and 1.5 bathrooms,

Sharon Rizzo Compass

847 Marion Ave, Highland Park, IL 60035
/17
$1,750 per month
- Studio
- 1 Bath
- 400 Sq Ft
- Condo for Rent
730 Judson Ave Unit A05C, Highland Park, IL 60035

730 JudsonJudson + Roger WilliamsHighland Park$1750 per MonthAvailable: 9/1/2025AVAILABLE SEPTEMBER! Terrific studio in the heart of downtown Highland Park features brand new kitchen with espresso cabinets, stainless steel appliances, dishwasher, spacious living area with ceiling fan, great closet space, brand new bathroom, hardwood floors throughout, laundry in unit, and

730 Judson Ave Unit A05C, Highland Park, IL 60035
/158
$1,300,000 Sold Aug 08, 2025
- 8,176 Sq Ft
- $159/SF
- 10 Days On Market
- 4 Beds
- 6 Baths
- Built 1994
1424 Glencoe Ave, Highland Park, IL 60035

A Timeless Masterpiece in East Highland Park, nestled on one of the area's most coveted double lots, this opulent residence combines exceptional luxury with modern sophistication for today's most desired lifestyle. Impeccable design + details combined with an expansive floorplan offer a luxurious living experience. As you approach the home, you will appreciate the full brick and stone quality

Maria Etling Berkshire Hathaway HomeServices Chicago

1424 Glencoe Ave, Highland Park, IL 60035

/28
Est $1,096,700 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,743 Sq Ft
46 Insignia Ct, Highland Park, IL 60035

46 Insignia Ct, Highland Park, IL 60035

/42
$750,000
- 4 Beds
- 2.5 Baths
- 2,522 Sq Ft
1239 Cambridge Ct, Highland Park, IL 60035

Welcome to this light filled 4 / 2.1 Mid-Century Modern Multi-Level home in the Highlands. The open Foyer greets you with gleaming oak hardwood floors and a short staircase up to the Living Room, featuring huge Pella picture windows, oak hardwood floors and shares a spacious vaulted ceiling with the Dining Room. The vaulted ceiling in the updated Kitchen gives the sensation of the Canadian

Becky Dolin @properties Christie's International Real Estate

1239 Cambridge Ct, Highland Park, IL 60035
/22
$89,000 per month
- 9 Beds
- 19 Baths
- 37,706 Sq Ft
- House for Rent
2700 Point Ln, Highland Park, IL 60035

A once-in-a-lifetime opportunity to rent this gated, world-class estate, meticulously designed for those who live and breathe sports. This custom-built masterpiece blends luxury, recreation, and privacy in an unparalleled setting, offering nine bedrooms, 19 bathrooms, and parking for 14 cars. Whether you're hosting an exclusive event, entertaining distinguished guests, or planning a high-level

Carrie McCormick @properties Christie's International Real Estate

2700 Point Ln, Highland Park, IL 60035
/45
$850,000 Sold Aug 07, 2025
- 2,517 Sq Ft
- $338/SF
- 2 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1926
653 Blackstone Place, Highland Park, IL 60035

Ravinia Story Book Charm Hansel & Gretel Tudor! Completely gutted to the studs in 2012 and added on to with a two story kitchen, primary suite, and basement addition. Features a large eat-in kitchen with island, stainless appliances, leather finished granite countertops, and abundant white cabinetry. Entering through the front door, you are greeted by the classic charm of the living room with

Cory Albiani @properties Christie's International Real Estate

653 Blackstone Place, Highland Park, IL 60035

/27
Est $1,155,794 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,192 Sq Ft
50 Barnard Ln, Highland Park, IL 60035

50 Barnard Ln, Highland Park, IL 60035

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