Highland Park, IL Homes

/52
$2,999,000
- 6 Beds
- 6.5 Baths
- 8,256 Sq Ft
493 Hazel Ave, Highland Park, IL 60035

Why Would You Want Ordinary When You Can Have Extraordinary! This Stunning and Majestic Brick Home Sits on Over an Acre in the Heart of Highland Park and Features a 40' Indoor Pool with a Wall of Glass that Opens to the Outdoors! Over 8000 Sq Ft plus 2330 Sq Ft in the Finished Walkout Basement, It Boasts Barrel Ceilings over 20' High and 5 Fireplaces. The Double Island Chefs Kitchen has a

Janet Borden Compass

493 Hazel Ave, Highland Park, IL 60035
/9
$2,250 per month
- 1 Bed
- 1 Bath
- Condo for Rent
447 Roger Williams Ave Unit 730-04, 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 730-04, Highland Park, IL 60035
/18
$170,000 Sold Oct 14, 2025

891 Central Ave Unit 331, Highland Park, IL 60035
- 2 Beds
- 2 Baths
- 1,089 Sq Ft
- Built 2002
Last Sold Summary
- $156/SF
- 30 Days On Market
Current Estimated Value $170,354

Last Listing Agent Carolyn Cerf @properties Christie's International Real Estate

891 Central Ave Unit 331, Highland Park, IL 60035

/65
Est $1,343,254 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,705 Sq Ft
41 Sheridan Rd, Highland Park, IL 60035

41 Sheridan Rd, Highland Park, IL 60035

/53
$5,999,000
- 9 Beds
- 12 Baths
- 10,777 Sq Ft
2441 Woodbridge Ln, Highland Park, IL 60035

Introducing an exceptional lakefront residence on one of Highland Park's most coveted private lanes. Set on a masterfully landscaped 1.85-acre parcel, 2441 Woodbridge Lane offers a rare combination of privacy, scale, and sophistication-backed by unobstructed, panoramic views of Lake Michigan. This architecturally striking, contemporary home spans approximately 10,000 square feet and has been

Patrick Milhaupt Jameson Sotheby's International Realty

2441 Woodbridge Ln, Highland Park, IL 60035
/12
$3,330 per month
- 2 Beds
- 2 Baths
- 1,142 Sq Ft
- Apartment for Rent
555 Roger Williams Ave Unit 203, Highland Park, IL 60035

Remarks: 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

Larry Klairmont Twins Realty LLC

555 Roger Williams Ave Unit 203, Highland Park, IL 60035
/32
$840,000 Sold Mar 24, 2025

588 Chicago Ave, Highland Park, IL 60035
- 3 Beds
- 3.5 Baths
- 2,940 Sq Ft
- Built 2011
Last Sold Summary
- 7% Below List Price
- $286/SF
- 48 Days On Market
Current Estimated Value $900,878

Last Listing Agent Carolyn Cerf @properties Christie's International Real Estate

588 Chicago Ave, Highland Park, IL 60035

/65
Est $3,702,996 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 6,950 Sq Ft
33 Sheridan Rd, Highland Park, IL 60035

33 Sheridan Rd, Highland Park, IL 60035

/29
$780,000 Pending
- 3 Beds
- 2.5 Baths
- 2,300 Sq Ft
945 Villas Ct, Highland Park, IL 60035

Enjoy maintenance-free living in this spacious 3-bedroom, 2.1-bath single-family home. The open floor plan features vaulted ceilings, recessed lighting, and abundant natural light throughout. The main-floor primary suite offers a large private bath with a whirlpool tub, separate shower, and walk-in closet. The updated kitchen boasts granite countertops, stainless steel appliances and a generous

Deb Baker Compass

945 Villas Ct, Highland Park, IL 60035
/12
$1,850 per month
- 1 Bed
- 1 Bath
- Condo for Rent
725 St Johns Ave Unit 21, Highland Park, IL 60035

Welcome to this beautifully updated condo, perfectly situated in the heart of Highland Park. Located just across from the Ravinia Metra station, this home offers unparalleled convenience with top-rated schools, parks, and all the amenities you need right at your door. Sunset Woods Park, only half a block away, features expansive green spaces, playgrounds, and local shops. Plus, enjoy a wide

725 St Johns Ave Unit 21, Highland Park, IL 60035
/23
$550,000 Sold Dec 22, 2025

940 Augusta Way Unit 304, Highland Park, IL 60035
- 2 Beds
- 2 Baths
- 1,926 Sq Ft
- Built 2001
Last Sold Summary
- $286/SF
- 9 Days On Market
Last Listing Agent Dan Timm Baird & Warner

940 Augusta Way Unit 304, Highland Park, IL 60035

/24
Est $1,725,015 Not Listed For Sale
- 4 Beds
- 7 Baths
- 4,171 Sq Ft
218 Ivy Ln, Highland Park, IL 60035

218 Ivy Ln, Highland Park, IL 60035

/20
$449,000 Pending
- 3 Beds
- 2 Baths
- 1,080 Sq Ft
927 Half Day Rd, Highland Park, IL 60035

ANOTHER $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

Greg Weissman @properties Christie's International Real Estate

927 Half Day Rd, Highland Park, IL 60035
/16
$5,950 per month
- 5 Beds
- 4.5 Baths
- 2,489 Sq Ft
- House for Rent
2078 Linden Ave, Highland Park, IL 60035

Fabulous 4 bed 3.2 bath beautiful colonial in superb East Highland Park location. Gracious living room with wood burning fireplace. Separate formal dining room with leaded glass windows. Wonderful sunny kitchen with 42" wood cabinets and granite countertops. Three bedrooms on the 2nd floor including the primary bedroom suite with walk-in closet. Third floor suite and full bath, office or play

Linda Levin Jameson Sotheby's Intl Realty

2078 Linden Ave, Highland Park, IL 60035
/16
$280,000 Sold Aug 12, 2025

2020 St Johns Ave Unit 309, Highland Park, IL 60035
- 2 Beds
- 2 Baths
- 1,269 Sq Ft
- Built 1987
Last Sold Summary
- 2% Above List Price
- $221/SF
- 2 Days On Market
Current Estimated Value $285,239

Last Listing Agent Debbie Croft @properties Christie's International Real Estate

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

/53
Est $1,458,155 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,452 Sq Ft
59 Sheridan Rd, Highland Park, IL 60035

59 Sheridan Rd, Highland Park, IL 60035

/10
$1,490,000 Pending
- Land
- 1.33 Acres
- $1,120,301 per Acre
0 Patten Rd, Highland Park, IL 60035

Amazing opportunity for a developer to build condos or possibly executive rental condos. The panoramic views alone would make it a highly desirable location for luxury living. Developers could capitalize on the serene surroundings, access to Lake Michigan, walkability to the Fort Sheridan Forest Preserve, proximity to downtown Highland Park, and breathtaking vistas. Crafting condos or executive

Michael Lafido LPT Realty

0 Patten Rd, Highland Park, IL 60035
/10
$1,895 per month
- 1 Bed
- 1 Bath
- 1,394 Sq Ft
- Condo for Rent
696 Elm Place, Highland Park, IL 60035

Welcome to this charming rental opportunity in the heart of Highland Park, Illinois. This inviting property offers comfortable living in a vibrant community, perfect for anyone seeking convenience and a warm neighborhood atmosphere.One of the highlights of this home is its close proximity to fantastic dining options, several department stores for your shopping needs, and the peaceful

696 Elm Place, Highland Park, IL 60035
/8
$480,000 Sold Feb 28, 2025

56 Country Ln, Highland Park, IL 60035
- Land
- 0.57 Acre
- $842,105 per Acre
Last Sold Summary
- 17% Below List Price
- 25 Days On Market
Current Estimated Value $527,492

Last Listing Agent Aleksandr Katsman Barr Agency, Inc

56 Country Ln, Highland Park, IL 60035

/53
Est $1,014,073 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,500 Sq Ft
227 Ivy Ln, Highland Park, IL 60035

227 Ivy Ln, Highland Park, IL 60035

/5
$2,840,000 Pending
- 3 Beds
- 3.5 Baths
- 4,105 Sq Ft
650 Walnut St Unit 301, Highland Park, IL 60035

Introducing the North Shore's most exquisite luxury residences, The Wolbright. Occupancy Winter 2025/2026. This exclusive residential building exemplifies a modern and sophisticated design. No detail is overlooked in this 3 bedroom 3.5-bathroom home with a library and family room. 10' ceilings flooded with natural light, designer finishes, and two covered terraces create a new standard of

Shari Saratovsky Diplomat Realty, Inc.

650 Walnut St Unit 301, Highland Park, IL 60035
/12
$3,400 per month
- 2 Beds
- 2 Baths
- 1,142 Sq Ft
- Apartment for Rent
555 Roger Williams Ave Unit 405, 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 405, Highland Park, IL 60035
/2
$635,000 Sold Mar 14, 2025

943 Pleasant Ave, Highland Park, IL 60035
- 4 Beds
- 2 Baths
- 2,028 Sq Ft
- Built 1924
Last Sold Summary
- 1% Below List Price
- $313/SF
- 0 Days On Market
Current Estimated Value $653,391

Last Listing Agent Joe Gozun Midwest America Realty, Inc.

943 Pleasant Ave, Highland Park, IL 60035

/30
Est $1,463,984 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 4,362 Sq Ft
149 Oak Knoll Terrace, Highland Park, IL 60035

149 Oak Knoll Terrace, Highland Park, IL 60035

/59
$8,750,000
- 5 Beds
- 9 Baths
- 9,749 Sq Ft
55 S Deere Park Dr, Highland Park, IL 60035

This extraordinary lakefront residence is the ultimate blend of luxury, comfort, breathtaking views and private beach. This sophisticated contemporary home boasts 9,749 square feet above-grade and an additional 4,434 square feet of finished lower-level space, all of which has been thoughtfully redesigned during a comprehensive renovation from 2006 to 2008. Every aspect of this dream property was

Erin Smith @properties Christie's International Real Estate

55 S Deere Park Dr, Highland Park, IL 60035
/12
$1,850 per month
- 1 Bed
- 1 Bath
- Condo for Rent
725 St Johns Ave Unit 18, Highland Park, IL 60035

Welcome to this beautifully updated condo, perfectly situated in the heart of Highland Park. Located just across from the Ravinia Metra station, this home offers unparalleled convenience with top-rated schools, parks, and all the amenities you need right at your door. Sunset Woods Park, only half a block away, features expansive green spaces, playgrounds, and local shops. Plus, enjoy a wide

725 St Johns Ave Unit 18, Highland Park, IL 60035
/13
$835,000 Sold Jan 14, 2026

378 Oakland Dr, Highland Park, IL 60035
- 5 Beds
- 3 Baths
- 2,845 Sq Ft
- Built 1925
Last Sold Summary
- 7% Below List Price
- $293/SF
- 14 Days On Market
Last Listing Agent Ted Pickus @properties Christie's International Real Estate

378 Oakland Dr, Highland Park, IL 60035

/44
Est $1,888,244 Not Listed For Sale
- 3 Beds
- 5.5 Baths
- 4,721 Sq Ft
15 S Deere Park Dr, Highland Park, IL 60035

15 S Deere Park Dr, Highland Park, IL 60035

/16
$649,000
- 3 Beds
- 3 Baths
- 1,387 Sq Ft
2325 Shady Ln, Highland Park, IL 60035

Charming brick bungalow sitting on almost an acre of lush, wooded private property in the Northshore acres neighborhood. Home features 3 Bedrooms, 3 full Baths with the master BR having its own master BT. Hardwood floors and newer appliances throughout. Large unfinished basement. Oversized 2+ car detached garage with large driveway. Paved brick patio and walkway, new roof 2024.

Rony Khezeran American International Realty

2325 Shady Ln, Highland Park, IL 60035
/12
$3,340 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
/79
$2,200,000 Sold May 19, 2025

388 N Deere Park Dr E, Highland Park, IL 60035
- 5 Beds
- 7.5 Baths
- 14,000 Sq Ft
- Built 2007
Last Sold Summary
- 27% Below List Price
- $157/SF
- 119 Days On Market
Current Estimated Value $3,231,736

Last Listing Agent Julianne Conroy Core Realty & Investments, Inc

388 N Deere Park Dr E, Highland Park, IL 60035

/32
Est $1,433,185 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,410 Sq Ft
294 N Deere Park Dr W, Highland Park, IL 60035

294 N Deere Park Dr W, Highland Park, IL 60035

/46
$775,000 Open Sun 11AM - 2PM
- 4 Beds
- 2.5 Baths
50 Red Oak Ln, Highland Park, IL 60035

This beautiful spacious home has a great open floorplan and wonderful natural light in every room. As you enter there is a big foyer that leads to the huge LIVING ROOM which has wide crown molding and bay windows. The updated KITCHEN has new quartz counters, all stainless appliances, tile backsplash, deep stainless sink, new flooring & light fixtures, and has a bright eating area overlooking the

John Nash Jameson Sotheby's International Realty

50 Red Oak Ln, Highland Park, IL 60035
/4
$3,400 per month
- 3 Beds
- 2.5 Baths
- 1,500 Sq Ft
- Townhouse for Rent
432 Elm Place, Highland Park, IL 60035

Property Id: 2144650Stop by and take a look at this RehabNew Imported Kitchen CabinetsQuartz CountertopsBeautiful Hardwood Floors ThroughoutNew Lighting3 Bedrooms -- 1 has a Master bathMaster bathroom is brand new with new tiling and vanitiesThe other 1.5 baths are completely new with tiling and vanities alsoSpacious Townhome All new Stainless Steel

432 Elm Place, Highland Park, IL 60035
/2
$1,400,000 Sold Dec 09, 2025

1375 Sheridan Rd, Highland Park, IL 60035
- 4 Beds
- 3.5 Baths
- 3,568 Sq Ft
- Built 1919
Last Sold Summary
- $392/SF
Last Listing Agent Brandy Simon Engel & Voelkers Chicago North Shore

1375 Sheridan Rd, Highland Park, IL 60035

/30
Est $1,752,973 Not Listed For Sale
- 6 Beds
- 5.5 Baths
- 5,444 Sq Ft
340 N Deere Park Dr W, Highland Park, IL 60035

340 N Deere Park Dr W, Highland Park, IL 60035

/31
$499,900
- 3 Beds
- 1.5 Baths
- 1,349 Sq Ft
643 Broadview Ave, Highland Park, IL 60035

***MULTIPLE OFFERS HAVE BEEN RECEIVED*** Best and Final Due Sunday 2/8/26 via email by 12 noon--No Escalation Clauses. LOCATION! LOCATION! LOCATION! This 3 bedroom, 1.5 bath picturesque charmer with enviable 2.5 car garage enjoys a PRIME and sought after location right around the corner from Highland Park's FUN downtown RAVINIA!!! Truly a commuter's dream come true--imagine being just 2 blocks

Nancy Gibson @properties Christie's International Real Estate

643 Broadview Ave, 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
/24
$467,000 Sold Aug 22, 2025

1660 1st St Unit 303, Highland Park, IL 60035
- 2 Beds
- 2 Baths
- 1,810 Sq Ft
- Built 1998
Last Sold Summary
- 4% Below List Price
- $258/SF
- 12 Days On Market
Current Estimated Value $479,768

Last Listing Agent Annette Blumberg Baird & Warner

1660 1st St Unit 303, Highland Park, IL 60035

/49
Est $1,605,063 Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 4,516 Sq Ft
333 Lakeside Place, Highland Park, IL 60035

333 Lakeside Place, Highland Park, IL 60035

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