12,678

Highland Park, IL Homes

Section Image
    • /4

      Est $585,029

      Not Listed For Sale

      427 Broadview Ave, Highland Park, IL 60035

      • 3 Beds
      • 1.5 Baths
      • 2,078 Sq Ft
      • Built 1968
      427 Broadview Ave, Highland Park, IL 60035

      Last Sold Summary

      Last Listing Agent Jonathan Self Compass

  • /17

    $349,000

    • 2 Beds
    • 2 Baths
    • 1,410 Sq Ft

    Unlisted Address

    Welcome home to this beautifully updated 2-bedroom condominium featuring one of the most desirable views in the building. Enjoy peaceful views overlooking the expansive rear grounds with mature trees and lush green space, all backing directly to a City of Highland Park public park, creating a serene and private setting.The spacious living room and dining room flow seamlessly together, offering an

    Ted Pickus @properties Christie's International Real Estate

    Unlisted Address
  • /15

    $1,081,000

    Sold Jan 22, 2026

    2035 Kipling Ct, Highland Park, IL 60035

    • 4 Beds
    • 2.5 Baths
    • 3,408 Sq Ft
    • Built 1976

    Last Sold Summary

    • 1% Above List Price
    • $317/SF
    • 3 Days On Market

    Current Estimated Value $1,095,556

    Last Listing Agent Jacqueline Lotzof Compass

    2035 Kipling Ct, Highland Park, IL 60035
    • /30

      Est $693,337

      Not Listed For Sale

      498 Burton Ave, Highland Park, IL 60035

      • 3 Beds
      • 2 Baths
      • 2,522 Sq Ft
      • Built 1955
      498 Burton Ave, Highland Park, IL 60035

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Cory Albiani @properties Christie's International Real Estate

  • /34

    $1,679,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 4,374 Sq Ft

    955 Wildwood Ln, Highland Park, IL 60035

    Rare opportunity to own a fully renovated 4-bedroom, 4.1 bathroom home set on a stunning East Highland Park ravine lot with nearly one acre of land at the end of a private cul-de-sac. Combining timeless elegance with extensive modern updates designed for today's lifestyle, this home features spacious living areas, hardwood floors throughout and magnificent views from every window. The beautifully

    Margie Brooks Baird & Warner

    955 Wildwood Ln, Highland Park, IL 60035
  • /30

    $1,050,000

    Sold Jun 05, 2026

    144 Oak Knoll Terrace, Highland Park, IL 60035

    • 4 Beds
    • 3.5 Baths
    • 3,191 Sq Ft
    • Built 1953

    Last Sold Summary

    • $329/SF
    • 0 Days On Market

    Current Estimated Value $1,064,143

    Last Listing Agent Lindsey Kaplan @properties Christie's International Real Estate

    144 Oak Knoll Terrace, Highland Park, IL 60035
    • /18

      Est $664,299

      Not Listed For Sale

      512 Burton Ave, Highland Park, IL 60035

      • 3 Beds
      • 2.5 Baths
      • 1,948 Sq Ft
      • Built 1928
      512 Burton Ave, Highland Park, IL 60035

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Susan Brown Burklin @properties Christie's International Real Estate

  • /72

    $3,800,000

    • 7 Beds
    • 6.5 Baths
    • 7,891 Sq Ft

    34 Logan Loop Unit 242, Highland Park, IL 60035

    Historic lakefront Queen Anne mansion on Lake Michigan! Set on a private 3/4 acre, surrounded on three sides by park, ravine, and Lake, adding "borrowed landscape". Premier location within the "Fort Sheridan" neighborhood of Highland Park, with parks, nearby restaurants, walking trails, beach, and many cultural activities. NuHaus kitchen overlooks Lake. Gorgeous views everywhere. Master Bedroom

    Eileen Campbell Jameson Sotheby's International Realty

    34 Logan Loop Unit 242, Highland Park, IL 60035
  • /35

    $686,000

    Sold May 27, 2026

    1380 Glencoe Ave, Highland Park, IL 60035

    • 3 Beds
    • 1.5 Baths
    • 1,189 Sq Ft
    • Built 1955

    Last Sold Summary

    • 15% Above List Price
    • $577/SF
    • 4 Days On Market

    Current Estimated Value $651,474

    Last Listing Agent Cory Albiani @properties Christie's International Real Estate

    1380 Glencoe Ave, Highland Park, IL 60035
    • /33

      Est $729,895

      Not Listed For Sale

      485 Pleasant Ave, Highland Park, IL 60035

      • 3 Beds
      • 2.5 Baths
      • 1,976 Sq Ft
      • Built 1942
      485 Pleasant Ave, Highland Park, IL 60035

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Cory Albiani @properties Christie's International Real Estate

  • /71

    $6,750,000

    • 5 Beds
    • 8.5 Baths
    • 8,186 Sq Ft

    117 Belle Ave, Highland Park, IL 60035

    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,

    Beth Wexler @properties Christie's International Real Estate

    117 Belle Ave, Highland Park, IL 60035
  • /42

    $1,562,500

    Sold Sep 18, 2025

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

    • 5 Beds
    • 4.5 Baths
    • 3,117 Sq Ft
    • Built 1929

    Last Sold Summary

    • 2% Below List Price
    • $501/SF
    • 13 Days On Market

    Current Estimated Value $1,622,419

    Last Listing Agent Ted Pickus @properties Christie's International Real Estate

    350 N Deere Park Dr W, Highland Park, IL 60035
    • /20

      Est $708,845

      Not Listed For Sale

      525 Pleasant Ave, Highland Park, IL 60035

      • 3 Beds
      • 3 Baths
      • 2,054 Sq Ft
      • Built 1951
      525 Pleasant Ave, Highland Park, IL 60035

      Last Sold Summary

      • 93 Days On Market

      Last Listing Agent Patricia Denenberg @properties Christie's International Real Estate

  • /56

    $4,399,900

    $250K PRICE DROP
    • 5 Beds
    • 8 Baths
    • 9,437 Sq Ft

    2665 Bentley Rd, Highland Park, IL 60035

    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,

    Beth Wexler @properties Christie's International Real Estate

    2665 Bentley Rd, Highland Park, IL 60035
  • /7

    $520,000

    Sold Aug 15, 2025

    1780 Rosemary Rd, Highland Park, IL 60035

    • 3 Beds
    • 3 Baths
    • 1,400 Sq Ft
    • Built 1955

    Last Sold Summary

    • 5% Below List Price
    • $371/SF
    • 53 Days On Market

    Current Estimated Value $541,285

    Last Listing Agent Amaliia Baturina Your House Realty

    1780 Rosemary Rd, Highland Park, IL 60035
    • /34

      Est $1,290,083

      Not Listed For Sale

      478 Hillside Dr, Highland Park, IL 60035

      • 4 Beds
      • 5 Baths
      • 4,174 Sq Ft
      • Built 1967
      478 Hillside Dr, Highland Park, IL 60035

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Beth Wexler @properties Christie's International Real Estate

  • /29

    $949,500

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,292 Sq Ft

    905 Villas Ct, Highland Park, IL 60035

    MAIN-FLOOR PRIMARY SUITE! Rarely available and beautifully updated, this exceptional residence in The Villas of Highland Park offers sophisticated living with an ideal floor plan and impeccable finishes throughout. The stunning kitchen (2019) features abundant white cabinetry, stainless steel appliances, quartz countertops, a classic subway tile backsplash, and a sun-filled breakfast area. The

    Stephanie Hofman @properties Christie's International Real Estate

    905 Villas Ct, Highland Park, IL 60035
  • /37

    $530,000

    Sold Apr 17, 2026

    566 Bellevue Place, Highland Park, IL 60035

    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft
    • Built 1928

    Last Sold Summary

    • 3% Below List Price
    • $348/SF
    • 19 Days On Market

    Current Estimated Value $562,343

    Last Listing Agent Cory Albiani @properties Christie's International Real Estate

    566 Bellevue Place, Highland Park, IL 60035
    • /35

      Est $1,363,489

      Not Listed For Sale

      730 Highland Place, Highland Park, IL 60035

      • 5 Beds
      • 4.5 Baths
      • 5,226 Sq Ft
      • Built 1963
      730 Highland Place, Highland Park, IL 60035

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Ryan Pavey Baird & Warner

  • /32

    $525,000

    $14K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 2,751 Sq Ft

    1958 Castlewood Rd, Highland Park, IL 60035

    New roof and freshly painted inside and out! Opportunity knocks on coveted Castlewood Road! This 3-bedroom, 2-bathroom home features a private office/den ideal for remote work, a study, traditional living space and sits on a generous 1/3-acre lot in one of Highland Park's most established neighborhoods. Built in 1956 with the solid bones of mid-century construction, this 2,751 sq ft property

    Scott Rose Baird & Warner

    1958 Castlewood Rd, Highland Park, IL 60035
  • /2

    $1,400,000

    Sold Oct 24, 2025

    155 S Deere Park Dr, Highland Park, IL 60035

    • 3 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • Built 1950

    Last Sold Summary

    • 8% Above List Price
    • $400/SF
    • 0 Days On Market

    Current Estimated Value $1,483,269

    Last Listing Agent Jacqueline Lotzof Compass

    155 S Deere Park Dr, Highland Park, IL 60035
    • /30

      Est $939,948

      Not Listed For Sale

      545 Green Bay Rd, Highland Park, IL 60035

      • 4 Beds
      • 3 Baths
      • 3,472 Sq Ft
      • Built 1938
      545 Green Bay Rd, Highland Park, IL 60035

      Last Sold Summary

      • 92 Days On Market

      Last Listing Agent Patricia Denenberg @properties Christie's International Real Estate

  • /28

    $550,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 2,528 Sq Ft

    1491 Chantilly Ct, Highland Park, IL 60035

    Welcome to this one-of-a-kind, renovated end-unit townhome in sought-after Chantilly. Perfectly positioned overlooking Chantilly's beautifully landscaped pool, this coveted location offers a resort-like lifestyle just steps from your front door within East Highland Park Ravinia Neighborhood. Completely reimagined by its owner, a professional interior designer, the home showcases exceptional

    Debbie Croft @properties Christie's International Real Estate

    1491 Chantilly Ct, Highland Park, IL 60035
  • /2

    $589,000

    Sold Oct 30, 2025

    1633 2nd St Unit 204, Highland Park, IL 60035

    • 2 Beds
    • 2 Baths
    • 1,904 Sq Ft
    • Built 2001

    Last Sold Summary

    • $309/SF
    • 0 Days On Market

    Current Estimated Value $628,872

    Last Listing Agent Jacqueline Lotzof Compass

    1633 2nd St Unit 204, Highland Park, IL 60035
    • /2

      Est $676,886

      Not Listed For Sale

      546 Broadview Ave, Highland Park, IL 60035

      • 3 Beds
      • 2.5 Baths
      • 1,913 Sq Ft
      • Built 1985
      546 Broadview Ave, Highland Park, IL 60035

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Cory Albiani @properties Christie's International Real Estate

  • /52

    $2,599,000

    • 6 Beds
    • 6.5 Baths
    • 8,256 Sq Ft

    493 Hazel Ave, Highland Park, IL 60035

    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

    Janet Borden Compass

    493 Hazel Ave, Highland Park, IL 60035
  • /45

    $1,250,000

    Sold Sep 29, 2025

    130 Sheridan Rd, Highland Park, IL 60035

    • 5 Beds
    • 3.5 Baths
    • 3,915 Sq Ft
    • Built 1941

    Last Sold Summary

    • 5% Above List Price
    • $319/SF
    • 0 Days On Market

    Current Estimated Value $1,329,953

    Last Listing Agent Ted Pickus @properties Christie's International Real Estate

    130 Sheridan Rd, Highland Park, IL 60035
    • /18

      Est $567,695

      Not Listed For Sale

      554 Broadview Ave, Highland Park, IL 60035

      • 3 Beds
      • 1.5 Baths
      • 1,226 Sq Ft
      • Built 1951
      554 Broadview Ave, Highland Park, IL 60035

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Linda Levin Jameson Sotheby's Intl Realty

  • /65

    $799,000

    Pending
    • 5 Beds
    • 3 Baths
    • 2,787 Sq Ft

    1860 Eastwood Ave, Highland Park, IL 60035

    Beautifully updated and refreshed 5-bedroom home which includes a first-floor bedroom/office/flex room and 3 full bathrooms in Highland Park's highly sought-after Sherwood Forest neighborhood. A dramatic two-story foyer welcomes you into bright, inviting living spaces featuring hardwood floors, a wood-burning fireplace, and an exceptional floor plan designed for comfortable everyday living and

    Aaron Masliansky Compass

    1860 Eastwood Ave, Highland Park, IL 60035
  • /18

    $592,500

    Sold Oct 16, 2025

    1491 Deerfield Place, Highland Park, IL 60035

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Below List Price
    • $374/SF
    • 12 Days On Market

    Current Estimated Value $616,789

    Last Listing Agent Tammy VanKrevelen Compass

    1491 Deerfield Place, Highland Park, IL 60035
    • /19

      Est $621,311

      Not Listed For Sale

      523 Green Bay Rd, Highland Park, IL 60035

      • 3 Beds
      • 2 Baths
      • 1,690 Sq Ft
      • Built 1961
      523 Green Bay Rd, Highland Park, IL 60035

      Last Sold Summary

      Last Listing Agent David Miller Redfin Corporation

  • /51

    $1,900,000

    • 6 Beds
    • 4.5 Baths
    • 5,300 Sq Ft

    1848 Balsam Rd, Highland Park, IL 60035

    This exceptional Highland Park residence offers nearly 5,300 square feet of impeccably designed living space, including a beautifully finished lower level, on an expansive lot just shy of an acre. Featuring 6 bedrooms and 4.5 baths across three finished levels, the home blends timeless elegance with modern sophistication. Sun-drenched interiors showcase wide-plank hardwood flooring, designer

    Melissa Siegal @properties Christie's International Real Estate

    1848 Balsam Rd, Highland Park, IL 60035
  • /29

    $925,000

    Sold Jun 05, 2026

    1145 Melvin Dr, Highland Park, IL 60035

    • 4 Beds
    • 2.5 Baths
    • 3,676 Sq Ft
    • Built 1977

    Last Sold Summary

    • 12% Above List Price
    • $252/SF
    • 5 Days On Market

    Current Estimated Value $1,053,333

    Last Listing Agent Marcia Lyman Engel & Voelkers Chicago North Shore

    1145 Melvin Dr, Highland Park, IL 60035
    • /28

      Est $780,071

      Not Listed For Sale

      580 Pleasant Ave, Highland Park, IL 60035

      • 3 Beds
      • 2.5 Baths
      • 2,645 Sq Ft
      • Built 1938
      580 Pleasant Ave, Highland Park, IL 60035

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Laurie Field Engel & Voelkers Chicago North Shore

  • /45

    $1,900,000

    • 5 Beds
    • 3.5 Baths
    • 3,884 Sq Ft

    1620 Ravine Terrace, Highland Park, IL 60035

    Perched on one of the prettiest streets in east Highland Park, this beautiful all brick and stucco home is set on a gorgeous, nearly half-acre property with stunning fully-fenced and professionally landscaped backyard. Start your day with a morning stroll to That Little French Guy for coffee and a croissant, see what's new at the Highland Park Library, then enjoy your walk to enchanting Ravine

    Cheryl Waldstein @properties Christie's International Real Estate

    1620 Ravine Terrace, Highland Park, IL 60035
  • /40

    $842,000

    Sold Jun 04, 2026

    105 Lakeside Place, Highland Park, IL 60035

    • 3 Beds
    • 1.5 Baths
    • 1,913 Sq Ft
    • Built 1941

    Last Sold Summary

    • 9% Above List Price
    • $440/SF
    • 3 Days On Market

    Current Estimated Value $826,323

    Last Listing Agent Julie Schultz @properties Christie's International Real Estate

    105 Lakeside Place, Highland Park, IL 60035
    • /42

      Est $751,200

      Not Listed For Sale

      555 Broadview Ave, Highland Park, IL 60035

      • 3 Beds
      • 3 Baths
      • 2,355 Sq Ft
      • Built 1927
      555 Broadview Ave, Highland Park, IL 60035

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Cory Albiani @properties Christie's International Real Estate

  • /29

    $700,000

    $49K PRICE DROP
    • 5 Beds
    • 3 Baths

    2490 Green Bay Rd, Highland Park, IL 60035

    Exceptional investment opportunity or owner-occupied two-flat with both units completely remodeled in 2024. Unit 1 offers 3 bedrooms and 2 full baths featuring hardwood floors, a wood-burning fireplace in the spacious living room, updated kitchen with new refrigerator, in-unit washer/dryer, and a side deck off the dining area. The finished lower level adds a family room and brand new full bath -

    Jacqueline Lotzof Compass

    2490 Green Bay Rd, Highland Park, IL 60035
  • /49

    $1,595,000

    Sold Jun 22, 2026

    124 Ravinoaks Ln, Highland Park, IL 60035

    • 5 Beds
    • 4.5 Baths
    • 3,908 Sq Ft
    • Built 1954

    Last Sold Summary

    • 6% Below List Price
    • $408/SF
    • 5 Days On Market

    Current Estimated Value $1,585,238

    Last Listing Agent Patricia Denenberg @properties Christie's International Real Estate

    124 Ravinoaks Ln, Highland Park, IL 60035
    • /24

      Est $864,798

      Not Listed For Sale

      588 Burton Ave, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 2,510 Sq Ft
      • Built 1951
      588 Burton Ave, Highland Park, IL 60035

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jodi Taub @properties Christie's International Real Estate

Showing Results 321 - 360, Page 9 of 18

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