12,678

Highland Park, IL Homes

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  • /47

    $799,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,394 Sq Ft

    985 Coventry Ln, Highland Park, IL 60035

    Rarely available and beautifully maintained Tudor-style home in the sought-after Highland Park Club! First-floor primary bedroom suite with large walk-in closet, and a bright ensuite bath with double vanities, soaking tub, and separate shower. The dramatic great room with soaring ceilings and fireplace, inviting space for relaxing or entertaining, seamlessly connected to a dining area. Updated

    Marina Jacobson Berkshire Hathaway HomeServices Chicago

    985 Coventry Ln, Highland Park, IL 60035
  • /28

    $825,000

    Sold Nov 04, 2025

    590 Rambler Ln, Highland Park, IL 60035

    • 4 Beds
    • 3 Baths
    • 2,800 Sq Ft
    • Built 1954

    Last Sold Summary

    • 3% Above List Price
    • $295/SF
    • 3 Days On Market

    Current Estimated Value $834,827

    Last Listing Agent Eve Del Monte Coldwell Banker Realty

    590 Rambler Ln, Highland Park, IL 60035
    • /16

      Est $865,856

      Not Listed For Sale

      267 Charal Ln, Highland Park, IL 60035

      • 4 Beds
      • 2.5 Baths
      • 2,288 Sq Ft
      • Built 1961
      267 Charal Ln, Highland Park, IL 60035

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Lisa Davis @properties Christie's International Real Estate

  • /20

    $225,000

    • 1 Bed
    • 1 Bath
    • 747 Sq Ft

    2020 St Johns Ave Unit 207, Highland Park, IL 60035

    Welcome to this bright and inviting condo perfectly situated in a fabulous in-town Highland Park location! Set within a beautifully maintained building featuring an updated, modern lobby, this home offers the ideal combination of style, comfort, and convenience. Step inside to discover a thoughtfully designed interior with a modern kitchen featuring sleek granite countertops, exposed brick walls,

    Peggy Glickman @properties Christie's International Real Estate

    2020 St Johns Ave Unit 207, Highland Park, IL 60035
  • /2

    $718,000

    Sold Dec 19, 2025

    32 Valley Rd, Highland Park, IL 60035

    • 3 Beds
    • 2.5 Baths
    • 2,663 Sq Ft
    • Built 1936

    Last Sold Summary

    • 3% Below List Price
    • $270/SF
    • 48 Days On Market

    Current Estimated Value $747,811

    Last Listing Agent Courtney Cook @properties Christie's International Real Estate

    32 Valley Rd, Highland Park, IL 60035
    • /26

      Est $946,451

      Not Listed For Sale

      295 Charal Ln, Highland Park, IL 60035

      • 4 Beds
      • 2.5 Baths
      • 2,260 Sq Ft
      • Built 1962
      295 Charal Ln, Highland Park, IL 60035

      Last Sold Summary

      • 6 Days On Market

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

  • /9

    $375,000

    • Land
    • 39,204 Sq Ft
    • $416,667 per Acre

    0 Highmoor Rd Unit MRD12402785, Highland Park, IL 60035

    Beautiful 39,600 SF LOT. NO H.O.A. Build your "Dream Home" on this Wide, Wooded, VACANT Parcel. 132 Foot Frontage by 300 Feet Deep! FAR = 25.04, Max floor area (sf) 9,916. Max FAR 11,166. Choice of Highland Park High School or Deerfield High School.

    Carol Santi Coldwell Banker Realty

    0 Highmoor Rd Unit MRD12402785, Highland Park, IL 60035
  • /25

    $659,000

    Sold Sep 22, 2025

    611 Hillside Dr, Highland Park, IL 60035

    • 4 Beds
    • 3 Baths
    • 2,732 Sq Ft
    • Built 1958

    Last Sold Summary

    • $241/SF
    • 60 Days On Market

    Current Estimated Value $738,219

    Last Listing Agent Maxine Goldberg Engel & Voelkers Chicago North Shore

    611 Hillside Dr, Highland Park, IL 60035
    • /20

      Est $883,283

      Not Listed For Sale

      312 Charal Ln, Highland Park, IL 60035

      • 4 Beds
      • 5 Baths
      • 3,254 Sq Ft
      • Built 1963
      312 Charal Ln, Highland Park, IL 60035

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Lisa Rome Jameson Sotheby's International Realty

  • /31

    $899,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,918 Sq Ft

    264 Central Ave, Highland Park, IL 60035

    You will fall in love with this beautifully improved home, perfectly located within easy walking distance to town, train, and Central Park overlooking the beach, move-in ready, inside, outside and all around. Homeowners have made all the right improvements since purchasing their home ten years ago, new Marvin windows, new roof, new two and a half car garage and driveway, new bluestone walkway and

    Cheryl Waldstein @properties Christie's International Real Estate

    264 Central Ave, Highland Park, IL 60035
  • /16

    $305,000

    Sold Jan 09, 2026

    2066 Saint Johns Ave Unit 404, Highland Park, IL 60035

    • 2 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Below List Price
    • $210/SF
    • 39 Days On Market

    Current Estimated Value $318,303

    Last Listing Agent Bill Bommarito Norshore Realty, LLC.

    2066 Saint Johns Ave Unit 404, Highland Park, IL 60035
    • /22

      Est $971,963

      Not Listed For Sale

      322 Charal Ln, Highland Park, IL 60035

      • 4 Beds
      • 2.5 Baths
      • 3,150 Sq Ft
      • Built 1961
      322 Charal Ln, Highland Park, IL 60035

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Geri Emalfarb @properties Christie's International Real Estate

  • /25

    $495,000

    • 2 Beds
    • 2 Baths
    • 1,926 Sq Ft

    1000 Deerfield Rd Unit 303, Highland Park, IL 60035

    Beautifully renovated, designer's own corner penthouse with balcony and southwest treetop views in a pet-friendly, boutique 12-unit elevator building, near vibrant downtown Highland Park and Sunset Valley Golf Club. Two bedrooms plus Den, 2 baths, 2 car heated garage parking. Bright & open concept condo is a rare find at over 1,900 sf, with a spacious covered balcony. Originally designed as a

    Deborah Fischer Berkshire Hathaway HomeServices Chicago

    1000 Deerfield Rd Unit 303, Highland Park, IL 60035
  • /37

    $660,000

    Sold Apr 20, 2026

    627 Pleasant Ave, Highland Park, IL 60035

    • 3 Beds
    • 1.5 Baths
    • 1,352 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Above List Price
    • $488/SF
    • 11 Days On Market

    Current Estimated Value $654,648

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

    627 Pleasant Ave, Highland Park, IL 60035
    • /35

      Est $998,738

      Not Listed For Sale

      360 Charal Ln, Highland Park, IL 60035

      • 5 Beds
      • 3.5 Baths
      • 2,911 Sq Ft
      • Built 1970
      360 Charal Ln, Highland Park, IL 60035

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Janet Borden Compass

  • /40

    $2,999,999

    Open Sun 11AM - 1PM $499K PRICE DROP
    • 6 Beds
    • 7 Baths
    • 6,325 Sq Ft

    282 Linden Park Place, Highland Park, IL 60035

    Stunning Custom Contemporary on Coveted Double Lot in Highland Park designed, built and meticulously maintained by the current owners. This one-of-a-kind home sits on over an acre on a beautiful ravine on one of Highland Park's most sought after streets - just steps from town, top-rated schools, the Lake, parks, and more. With soaring ceilings and expansive open living spaces, the home offers an

    Linda Levin Jameson Sotheby's Intl Realty

    282 Linden Park Place, Highland Park, IL 60035
  • /14

    $190,000

    Sold Sep 26, 2025

    1950 Sheridan Rd Unit 105, Highland Park, IL 60035

    • 2 Beds
    • 1.5 Baths
    • 1,136 Sq Ft
    • Built 2025

    Last Sold Summary

    • $167/SF
    • 39 Days On Market

    Last Listing Agent Shari Saratovsky Diplomat Realty, Inc.

    1950 Sheridan Rd Unit 105, Highland Park, IL 60035
    • /25

      Est $875,702

      Not Listed For Sale

      798 Timber Hill Rd, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 2,624 Sq Ft
      • Built 1964
      798 Timber Hill Rd, Highland Park, IL 60035

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Tami Leviton @properties Christie's International Real Estate

  • /20

    $440,000

    • 3 Beds
    • 2 Baths
    • 2,049 Sq Ft

    1534 Mcdaniels Ave Unit 3E, Highland Park, IL 60035

    Rarely available three-bedroom, two-bath condominium offering an exceptional combination of space, natural light, and value. Enjoying a desirable southern exposure, this inviting residence features a thoughtfully designed split-bedroom floor plan, generous room sizes, and an oversized private balcony. A welcoming foyer leads to spacious living and dining areas, creating an ideal setting for

    Noah Levy Compass

    1534 Mcdaniels Ave Unit 3E, Highland Park, IL 60035
  • /37

    $1,130,000

    Sold Jul 20, 2026

    423 Pleasant Ave, Highland Park, IL 60035

    • 4 Beds
    • 2.5 Baths
    • 2,276 Sq Ft
    • Built 1938

    Last Sold Summary

    • 5% Above List Price
    • $496/SF
    • 7 Days On Market

    Current Estimated Value $1,047,332

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

    423 Pleasant Ave, Highland Park, IL 60035
    • /25

      Est $925,612

      Not Listed For Sale

      766 Timber Hill Rd, Highland Park, IL 60035

      • 4 Beds
      • 2.5 Baths
      • 3,567 Sq Ft
      • Built 1963
      766 Timber Hill Rd, Highland Park, IL 60035

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Monica Childs @properties Christie's International Real Estate

  • /20

    $469,000

    • 3 Beds
    • 2.5 Baths
    • 2,528 Sq Ft

    1470 Saint Tropez Ct, Highland Park, IL 60035

    Come see this bright and light 3 bdrm 2.5 bath end-unit home in Chantilly! This favorite and larger floor plan faces an interior courtyard (no road in front of your windows) with serene and lovely garden views.The entry leads to the living room, dining room and powder room. The spacious family room with wet bar, adjoins the living room, dining room and kitchen offering flexibilty and great flow.

    Susan Zeller Jennings Realty,Inc.

    1470 Saint Tropez Ct, Highland Park, IL 60035
  • /28

    $670,000

    Sold Jun 15, 2026

    601 Mulberry Place Unit 3B, Highland Park, IL 60035

    • 3 Beds
    • 3 Baths
    • 2,792 Sq Ft
    • Built 1991

    Last Sold Summary

    • 3% Above List Price
    • $240/SF
    • 7 Days On Market

    Current Estimated Value $672,301

    Last Listing Agent Greg Desmond @properties Christie's International Real Estate

    601 Mulberry Place Unit 3B, Highland Park, IL 60035
    • /40

      Est $953,604

      Not Listed For Sale

      383 Hastings Ave, Highland Park, IL 60035

      • 4 Beds
      • 4 Baths
      • 3,200 Sq Ft
      • Built 1968
      383 Hastings Ave, Highland Park, IL 60035

      Last Sold Summary

      Last Listing Agent Philip Skowron Compass

  • /80

    $1,900,000

    $580K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 6,908 Sq Ft

    1499 Sheridan Rd, Highland Park, IL 60035

    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

    Vince Dinh HomeSmart Connect LLC

    1499 Sheridan Rd, Highland Park, IL 60035
  • /33

    $1,495,000

    Sold Apr 09, 2026

    2005 Keats Ln, Highland Park, IL 60035

    • 6 Beds
    • 5.5 Baths
    • 5,900 Sq Ft
    • Built 1981

    Last Sold Summary

    • $253/SF

    Current Estimated Value $1,494,952

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

    2005 Keats Ln, Highland Park, IL 60035
    • /27

      Est $1,017,501

      Not Listed For Sale

      240 Hastings Ave, Highland Park, IL 60035

      • 5 Beds
      • 3 Baths
      • 2,887 Sq Ft
      • Built 1964
      240 Hastings Ave, Highland Park, IL 60035

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Philip Skowron Compass

  • /29

    $1,250,000

    • 5 Beds
    • 6 Baths
    • 6,360 Sq Ft

    201 Aspen Ln Unit 2, Highland Park, IL 60035

    Nestled on a private property this residence stands as a testament to sophisticated design and timeless elegance. This custom-built residence is poised on a lush, wooded lot, offering a serene backdrop that feels worlds away while remaining moments from the very best of North Shore living. Spanning three finished levels of meticulously curated space, the home features five expansive bedrooms and

    Gloria Matlin Compass

    201 Aspen Ln Unit 2, Highland Park, IL 60035
  • /2

    $540,000

    Sold Jul 15, 2026

    1227 Lynn Terrace, Highland Park, IL 60035

    • 4 Beds
    • 3 Baths
    • 2,768 Sq Ft
    • Built 1963

    Last Sold Summary

    • 2% Below List Price
    • $195/SF
    • 4 Days On Market

    Current Estimated Value $754,498

    Last Listing Agent Christopher Lobrillo Grandview Realty, LLC

    1227 Lynn Terrace, Highland Park, IL 60035
    • /18

      Est $894,845

      Not Listed For Sale

      344 Hastings Ave, Highland Park, IL 60035

      • 4 Beds
      • 2.5 Baths
      • 2,377 Sq Ft
      • Built 1962
      344 Hastings Ave, Highland Park, IL 60035

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Bridgett McKenzie Engel & Voelkers Chicago North Shore

  • /35

    $895,000

    Pending
    • 4 Beds
    • 2 Baths
    • 2,652 Sq Ft

    983 Harvard Ct, Highland Park, IL 60035

    Beautifully updated 4 bedroom, 2 bath home in the highly sought-after Sunset Woods neighborhood. Ideally situated near Sunset Park, downtown Highland Park, shopping, dining, and everyday conveniences, this move-in-ready home offers the perfect blend of comfort, style, and location. The renovated kitchen features elegant quartz countertops, stainless steel appliances, and contemporary finishes,

    Margie Brooks Baird & Warner

    983 Harvard Ct, Highland Park, IL 60035
  • /31

    $703,000

    Sold Feb 27, 2026

    643 Broadview Ave, Highland Park, IL 60035

    • 3 Beds
    • 1.5 Baths
    • 1,349 Sq Ft
    • Built 1933

    Last Sold Summary

    • 41% Above List Price
    • $521/SF
    • 5 Days On Market

    Current Estimated Value $659,320

    Last Listing Agent Nancy Gibson @properties Christie's International Real Estate

    643 Broadview Ave, Highland Park, IL 60035
    • /2

      Est $1,250,078

      Not Listed For Sale

      415 Dell Ln, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 3,974 Sq Ft
      • Built 1949
      415 Dell Ln, Highland Park, IL 60035

      Last Sold Summary

      • 52 Days On Market

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

  • /30

    $1,750,000

    $100K PRICE DROP Pending
    • 3 Beds
    • 5 Baths
    • 3,488 Sq Ft

    260 Whistler Rd Unit 2B-C, Highland Park, IL 60035

    Experience unparalleled scale and sophistication in this one-of-a-kind Drill Hall residence within a boutique, luxury Fort Sheridan elevator building. Two units, offering an alternative to ranch inspired living, were expertly combined to create this 3 bedroom, 3.2 bath gallery style condominium with the added features of 3 spacious, private balconies overlooking the Meadow and the Pond, 2 loft

    Judy Weiss @properties Christie's International Real Estate

    260 Whistler Rd Unit 2B-C, Highland Park, IL 60035
  • /31

    $690,000

    Sold Dec 15, 2025

    325 Lincolnwood Rd, Highland Park, IL 60035

    • 4 Beds
    • 2.5 Baths
    • 2,134 Sq Ft
    • Built 1928

    Last Sold Summary

    • 8% Below List Price
    • $323/SF
    • 19 Days On Market

    Current Estimated Value $734,148

    Last Listing Agent Janet Borden Compass

    325 Lincolnwood Rd, Highland Park, IL 60035
    • /21

      Est $1,311,825

      Not Listed For Sale

      429 Groveland Ave, Highland Park, IL 60035

      • 5 Beds
      • 4.5 Baths
      • 4,332 Sq Ft
      • Built 1951
      429 Groveland Ave, Highland Park, IL 60035

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Linda Fink @properties Christie's International Real Estate

  • /17

    $475,000

    Pending
    • 1 Bed
    • 1 Bath
    • 1,430 Sq Ft

    154 Leonard Wood S Unit 213, Highland Park, IL 60035

    Experience the perfect blend of elegance and contemporary living in this exceptional 1 bedroom + loft condo located in the coveted Tower Barracks East at Historic Fort Sheridan. Overlooking the iconic Parade Grounds, this open and airy second-floor unit is filled with natural light and showcases the architectural details that make Fort Sheridan so distinctive. Inside, you'll find soaring vaulted

    Susan Brown Burklin @properties Christie's International Real Estate

    154 Leonard Wood S Unit 213, Highland Park, IL 60035
  • /6

    $272,000

    Sold Oct 03, 2025

    2066 Saint Johns Ave Unit 304, Highland Park, IL 60035

    • 2 Beds
    • 2 Baths
    • 1,420 Sq Ft
    • Built 1984

    Last Sold Summary

    • 6% Below List Price
    • $192/SF
    • 33 Days On Market

    Current Estimated Value $299,903

    Last Listing Agent Bill Bommarito Norshore Realty, LLC.

    2066 Saint Johns Ave Unit 304, Highland Park, IL 60035
    • /41

      Est $2,343,960

      Not Listed For Sale

      508 Sheridan Rd, Highland Park, IL 60035

      • 6 Beds
      • 9 Baths
      • 6,890 Sq Ft
      • Built 2005
      508 Sheridan Rd, Highland Park, IL 60035

      Last Sold Summary

      • 23 Days On Market

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

  • /44

    $765,000

    Open Sun 12PM - 2PM
    • 4 Beds
    • 2.5 Baths
    • 3,861 Sq Ft

    1645 Sherwood Rd, Highland Park, IL 60035

    Nestled in tree-lined Sherwood Forest, near parks and transportation, is this welcoming, updated, and well-maintained 2-story Colonial home ready for you! Total Kitchen remodel 2015 with all the bells and whistles and Bath remodels - Primary, Hall and Powder Room - in 2017. Bright two-story entry with an exceptionally striking staircase, inviting Living Room with full-length Bay window, spacious

    Lynn Kosner Baird & Warner

    1645 Sherwood Rd, Highland Park, IL 60035

Showing Results 241 - 280, Page 7 of 18

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