12,663

Highland Park, IL Homes

Section Image
  • /80

    $1,780,000

    $700K 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
  • /65

    $1,025,000

    Sold Dec 16, 2025

    3760 Gilgare Ln, Highland Park, IL 60035

    • 6 Beds
    • 6 Baths
    • 5,004 Sq Ft
    • Built 1890

    Last Sold Summary

    • 18% Below List Price
    • $205/SF
    • 55 Days On Market

    Current Estimated Value $1,135,341

    Last Listing Agent Donna Mancuso Jameson Sotheby's International Realty

    3760 Gilgare Ln, Highland Park, IL 60035
    • /45

      Est $2,208,464

      Not Listed For Sale

      124 Lakewood Place, Highland Park, IL 60035

      • 5 Beds
      • 5.5 Baths
      • 7,200 Sq Ft
      • Built 1999
      124 Lakewood Place, Highland Park, IL 60035

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Natasha Motev Jameson Sotheby's Intl Realty

  • /44

    $750,000

    $15K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 3,861 Sq Ft

    1645 Sherwood Rd, Highland Park, IL 60035

    New Price! 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

    Lynn Kosner Baird & Warner

    1645 Sherwood Rd, Highland Park, IL 60035
  • /26

    $321,500

    Sold Jul 30, 2026

    1795 Lake Cook Rd Unit 107, Highland Park, IL 60035

    • 2 Beds
    • 2 Baths
    • 1,418 Sq Ft
    • Built 1985

    Last Sold Summary

    • 12% Below List Price
    • $227/SF
    • 35 Days On Market

    Current Estimated Value $344,713

    Last Listing Agent Michael Maggio @properties Christie's International Real Estate

    1795 Lake Cook Rd Unit 107, Highland Park, IL 60035
    • /56

      Est $2,101,032

      Not Listed For Sale

      136 Lakewood Place, Highland Park, IL 60035

      • 2 Beds
      • 4.5 Baths
      • 4,339 Sq Ft
      • Built 1957
      136 Lakewood Place, Highland Park, IL 60035

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jacqueline Colando Redfin Corporation

  • /2

    $299,900

    • Land
    • 0 Sq Ft

    550 Skokie Ave, Highland Park, IL 60035

    Rare opportunity to build your dream home on a beautiful wooded lot in an exceptional North Shore location. Surrounded by mature trees and situated on a quiet residential street, this property offers a peaceful setting while remaining just minutes from the vibrant downtown districts of both Highwood and Highland Park. Perfect for homeowners seeking to build a one-of-a-kind dream home or

    Alex Panek American International Realty

    550 Skokie Ave, Highland Park, IL 60035
  • /2

    $1,700,000

    Sold Oct 15, 2025

    800 Deerfield Rd Unit 306, Highland Park, IL 60035

    • 3 Beds
    • 4.5 Baths
    • 3,268 Sq Ft
    • Built 1991

    Last Sold Summary

    • $520/SF
    • 3 Days On Market

    Current Estimated Value $1,783,376

    Last Listing Agent Alex Entratter @properties Christie's International Real Estate

    800 Deerfield Rd Unit 306, Highland Park, IL 60035
    • /31

      Est $1,475,061

      Not Listed For Sale

      168 Lakewood Place, Highland Park, IL 60035

      • 5 Beds
      • 4.5 Baths
      • 3,465 Sq Ft
      • Built 1949
      168 Lakewood Place, Highland Park, IL 60035

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Linda Levin Jameson Sotheby's Intl Realty

  • /49

    $1,695,000

    Pending
    • 5 Beds
    • 7 Baths
    • 5,074 Sq Ft

    395 Cedar Ave, Highland Park, IL 60035

    A rare opportunity to own this beautifully Updated Contemporary Home with over 5000 sq feet of Living Space in one of East Highland Park's most sought-after neighborhoods. Featuring TWO LARGE PRIMARY BEDROOMS with EN-SUITE BATHROOMS, one on the MAIN LEVEL and one on the SECOND LEVEL. This exceptional 5-bedroom, 5 full bath, 2 half bath residence offers an Ideal Layout for today's lifestyle and is

    Brooke Bakalar Sloane @properties Christie's International Real Estate

    395 Cedar Ave, Highland Park, IL 60035
  • /19

    $930,000

    Sold Jul 14, 2026

    370 Charal Ln, Highland Park, IL 60035

    • 3 Beds
    • 2.5 Baths
    • 2,588 Sq Ft
    • Built 1961

    Last Sold Summary

    • 5% Below List Price
    • $359/SF
    • 21 Days On Market

    Current Estimated Value $931,549

    Last Listing Agent Paul Lopata Mark Allen Realty ERA Powered

    370 Charal Ln, Highland Park, IL 60035
    • /39

      Est $1,011,281

      Not Listed For Sale

      355 Oakland Dr, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 3,146 Sq Ft
      • Built 1923
      355 Oakland Dr, Highland Park, IL 60035

      Last Sold Summary

      • 6 Days On Market

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

  • /41

    $899,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 2,496 Sq Ft

    650 Green Bay Rd, Highland Park, IL 60035

    Classic Dutch Colonial elegance meets thoughtful modern updates in this exceptional Ravinia home. Built with the character and craftsmanship of the 1930's, this 5-bedroom, 3.1-bath home has been carefully and thoughtfully refreshed while retaining its timeless charm. The welcoming and bright main level offers a spacious living room with limestone fireplace, sophisticated cook's kitchen, formal

    Marlene Rubenstein Baird & Warner

    650 Green Bay Rd, Highland Park, IL 60035
  • /29

    $760,000

    Sold Jul 13, 2026

    1433 Glencoe Ave, Highland Park, IL 60035

    • 3 Beds
    • 2.5 Baths
    • 1,812 Sq Ft
    • Built 1932

    Last Sold Summary

    • 1% Above List Price
    • $419/SF
    • 15 Days On Market

    Current Estimated Value $742,242

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

    1433 Glencoe Ave, Highland Park, IL 60035
    • /2

      Est $1,517,029

      Not Listed For Sale

      451 Oakland Dr, Highland Park, IL 60035

      • 4 Beds
      • 4.5 Baths
      • 3,300 Sq Ft
      • Built 2006
      451 Oakland Dr, Highland Park, IL 60035

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Noah Levy Compass

  • /16

    $4,399,000

    New Construction
    • 6 Beds
    • 5.5 Baths

    966 Wade St, Highland Park, IL 60035

    NEW CONSTRUCTION luxury single-family home coming soon to Highland Park within sought after Ravinia Elementary School boundaries. Designed for both everyday living and elevated entertaining, the main level features a private home office with striking glass and iron doors, a formal dining room framed by oversized windows, two powder rooms, and an expansive living room that seamlessly opens to the

    William Goldberg Fulton Grace Realty

    966 Wade St, Highland Park, IL 60035
  • /31

    $658,800

    Sold Jan 05, 2026

    1140 Ridge Rd, Highland Park, IL 60035

    • 3 Beds
    • 2.5 Baths
    • 2,248 Sq Ft
    • Built 1955

    Last Sold Summary

    • 2% Above List Price
    • $293/SF
    • 4 Days On Market

    Current Estimated Value $710,102

    Last Listing Agent Peggy Glickman @properties Christie's International Real Estate

    1140 Ridge Rd, Highland Park, IL 60035
    • /41

      Est $1,172,028

      Not Listed For Sale

      441 Oakland Dr, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 3,335 Sq Ft
      • Built 1992
      441 Oakland Dr, Highland Park, IL 60035

      Last Sold Summary

      • 10 Days On Market

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

  • /31

    $885,000

    Pending
    • 6 Beds
    • 3.5 Baths
    • 3,392 Sq Ft

    770 North Ave, Highland Park, IL 60035

    Built by experienced Marco Homes and ideally situated on a quiet cul-de-sac in the highly sought-after Highland Park Highlands, this exceptional residence offers the perfect blend of timeless elegance, generous living space, and thoughtful design. Featuring four spacious bedrooms on the second level and two additional bedrooms in the beautifully finished lower level, this home is perfectly suited

    Maxine Goldberg Engel & Voelkers Chicago North Shore

    770 North Ave, Highland Park, IL 60035
  • /25

    $1,525,000

    Sold Apr 17, 2026

    995 Harvard Ct, Highland Park, IL 60035

    • 5 Beds
    • 4.5 Baths
    • 3,238 Sq Ft
    • Built 2016

    Last Sold Summary

    • 2% Above List Price
    • $471/SF
    • 5 Days On Market

    Current Estimated Value $1,551,013

    Last Listing Agent Aimee Glovsky Compass

    995 Harvard Ct, Highland Park, IL 60035
    • /26

      Est $2,068,740

      Not Listed For Sale

      666 Rice St, Highland Park, IL 60035

      • 6 Beds
      • 6 Baths
      • 4,000 Sq Ft
      • Built 1919
      666 Rice St, Highland Park, IL 60035

      Last Sold Summary

      Last Listing Agent Ila Coretti @properties Christie's International Real Estate

  • /35

    $4,995,000

    • 9 Beds
    • 14 Baths
    • 10,777 Sq Ft

    2441 Woodbridge Ln, Highland Park, IL 60035

    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

    Rebecca Gilberg Compass

    2441 Woodbridge Ln, Highland Park, IL 60035
  • /27

    $1,350,000

    Sold May 15, 2026

    2372 Tennyson Ln, Highland Park, IL 60035

    • 7 Beds
    • 6.5 Baths
    • 6,306 Sq Ft
    • Built 1986

    Last Sold Summary

    • 10% Below List Price
    • $214/SF
    • 1 Day On Market

    Current Estimated Value $1,406,575

    Last Listing Agent Janet Borden Compass

    2372 Tennyson Ln, Highland Park, IL 60035
    • /29

      Est $1,349,047

      Not Listed For Sale

      687 Kincaid St, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 2,984 Sq Ft
      • Built 1920
      687 Kincaid St, Highland Park, IL 60035

      Last Sold Summary

      • 3 Days On Market

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

  • /35

    $1,499,000

    Pending
    • 5 Beds
    • 7 Baths
    • 5,026 Sq Ft

    390 Hazel Ave, Highland Park, IL 60035

    Sip lemonade on your veranda and enjoy the classic Georgian charm of this stunning residence, nestled on nearly an acre in the heart of East Highland Park. This beautiful and gracious home spans three stories plus a huge finished basement, offering unparalleled living space. Experience stunning views from every window and tranquil living from porches and a gazebo. The first floor features a

    Ila Coretti @properties Christie's International Real Estate

    390 Hazel Ave, Highland Park, IL 60035
  • /31

    $1,100,000

    Sold Jun 18, 2026

    Unlisted Address

    • 5 Beds
    • 3 Baths
    • 3,410 Sq Ft
    • Built 1923

    Last Sold Summary

    • 14% Above List Price
    • $323/SF

    Current Estimated Value $1,069,967

    Last Listing Agent Debbie B. Glickman @properties Christie's International Real Estate

    Unlisted Address
    • /44

      Est $2,534,791

      Not Listed For Sale

      99 Roger Williams Ave, Highland Park, IL 60035

      • 4 Beds
      • 7 Baths
      • 5,935 Sq Ft
      • Built 2000
      99 Roger Williams Ave, Highland Park, IL 60035

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Lyn Wise @properties Christie's International Real Estate

  • /29

    $595,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,744 Sq Ft

    1353 Golf Ave, Highland Park, IL 60035

    Move right into this quality updated, solid built brick ranch. A fabulous one story alternative to condo/townhouse living set on a third of an acre, located in a private subdivision near Sunset Valley golf course and Highland Park's Hidden Creek Aqua Park. Two bedrooms and two newer bathrooms offer private spaces to the wide-open floor plan which is wonderful for entertaining. Front entrance

    Susan Ringel Segal @properties Christie's International Real Estate

    1353 Golf Ave, Highland Park, IL 60035
  • /2

    $742,000

    Sold Oct 08, 2025

    590 Broadview Ave, Highland Park, IL 60035

    • 3 Beds
    • 1.5 Baths
    • 2,151 Sq Ft
    • Built 1928

    Last Sold Summary

    • 10% Above List Price
    • $345/SF
    • 5 Days On Market

    Current Estimated Value $776,325

    Last Listing Agent David Chung Compass

    590 Broadview Ave, Highland Park, IL 60035
    • /45

      Est $885,571

      Not Listed For Sale

      653 Blackstone Place, Highland Park, IL 60035

      • 3 Beds
      • 2.5 Baths
      • 2,517 Sq Ft
      • Built 1926
      653 Blackstone Place, Highland Park, IL 60035

      Last Sold Summary

      • 2 Days On Market

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

  • /78

    $2,500,000

    Pending
    • 5 Beds
    • 7 Baths
    • 5,467 Sq Ft

    1418 Waverly Rd, Highland Park, IL 60035

    RARE OPPORTUNITY ON COVETED WAVERLY ROAD IN EAST HIGHLAND PARK, DIRECTLY ACROSS FROM LAKE MICHIGAN. Set on approximately 1.3 acres, this stately 1933 brick and limestone estate combines an exceptional location, substantial existing residence and the flexibility to create something truly extraordinary. Offering approximately 5,510 square feet, the home is livable as it stands while presenting

    Shannan Maxwell eXp Realty

    1418 Waverly Rd, Highland Park, IL 60035
  • /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 $1,151,131

    Last Listing Agent Jacqueline Lotzof Compass

    2035 Kipling Ct, Highland Park, IL 60035
    • /28

      Est $756,767

      Not Listed For Sale

      454 Broadview Ave, Highland Park, IL 60035

      • 3 Beds
      • 3 Baths
      • 2,289 Sq Ft
      • Built 1957
      454 Broadview Ave, Highland Park, IL 60035

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Julia Podedworny HomeSmart Connect LLC

  • /29

    $1,950,000

    Pending
    • 3 Beds
    • 4.5 Baths
    • 4,750 Sq Ft

    775 Stonegate Dr, Highland Park, IL 60035

    Rarely available 4,700 sqft ranch set on an expansive, meticulously landscaped property offering exceptional privacy and presence. This elegant 3 bedroom, 4.1-bath residence is thoughtfully designed and rich in architectural detail, unfolding in a refined yet understated and unexpected manner. The expansive foyer creates a gracious sense of arrival, immediately drawing the eye toward the stunning

    Margie Brooks Baird & Warner

    775 Stonegate Dr, 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 $1,078,237

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

    144 Oak Knoll Terrace, Highland Park, IL 60035
    • /4

      Est $656,719

      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

  • /29

    $1,175,000

    $123K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 2,769 Sq Ft

    881 Marion Ave, Highland Park, IL 60035

    Some homes just feel right the moment you walk in - and 881 Marion is one of them. Tucked on a beautiful stretch of Marion Avenue in Highland Park's beloved Braeside neighborhood, this 4-bedroom, 2.5-bathroom home has been thoughtfully transformed from the inside out, with carefully considered improvements that make everyday living feel effortless. The layout was reimagined with real life in mind

    Jacqueline Lotzof Compass

    881 Marion Ave, 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 $680,594

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

    1380 Glencoe Ave, Highland Park, IL 60035
    • /30

      Est $748,048

      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

  • /58

    $3,900,000

    • 4 Beds
    • 5.5 Baths
    • 5,500 Sq Ft

    22 Lakeview Terrace, Highland Park, IL 60035

    Amazing lakefront property on end Cul De Sac street!!! This home has been totally REMODELED and meticulously curated for modern living with impeccable design. The expansive floor plan features four generous bedrooms, each with its own en-suite bathroom, including a refined primary retreat complete with 12 foot ceiling, a private balcony overlooking iconic Lake Michigan and 2 lavish walk-in

    Ted Pickus @properties Christie's International Real Estate

    22 Lakeview Terrace, Highland Park, IL 60035

Showing Results 281 - 320, Page 8 of 18

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