12,678

Highland Park, IL Homes

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  • /29

    $799,000

    Sold Jan 30, 2026

    368 Woodland Rd, Highland Park, IL 60035

    • 3 Beds
    • 2.5 Baths
    • 1,912 Sq Ft
    • Built 1924

    Last Sold Summary

    • $418/SF
    • 6 Days On Market

    Current Estimated Value $815,561

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

    368 Woodland Rd, Highland Park, IL 60035
    • /44

      Est $918,636

      Not Listed For Sale

      505 Groveland Ave, Highland Park, IL 60035

      • 4 Beds
      • 2.5 Baths
      • 2,986 Sq Ft
      • Built 1962
      505 Groveland Ave, Highland Park, IL 60035

      Last Sold Summary

      • 5 Days On Market

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

  • /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
  • /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 $1,114,226

    Last Listing Agent Donna Mancuso Jameson Sotheby's International Realty

    3760 Gilgare Ln, Highland Park, IL 60035
    • /26

      Est $797,821

      Not Listed For Sale

      419 Sheridan Rd, Highland Park, IL 60035

      • 2 Beds
      • 1.5 Baths
      • 2,067 Sq Ft
      • Built 1948
      419 Sheridan Rd, Highland Park, IL 60035

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Karen Skurie Baird & Warner

  • /3

    $135,000

    Pending
    • Land
    • 0 Sq Ft

    1 Burtis Ave, Highland Park, IL 60035

    Builder's Dream Opportunity! Seize this prime Highland Park lot - a 7,900 sq. ft. blank canvas ready for a stunning 3,085 sq. ft. home! Perfectly located near Highland Park and Highwood's vibrant festivals, top-rated restaurants, and thriving businesses, this property offers the best location. With utilities already in place from a previous home, you can hit the ground running on your next

    Melissa Newman @properties Christie's International Real Estate

    1 Burtis Ave, Highland Park, IL 60035
  • /38

    $659,000

    Sold Sep 11, 2025

    1802 Winthrop Rd, Highland Park, IL 60035

    • 4 Beds
    • 2.5 Baths
    • 2,491 Sq Ft
    • Built 1961

    Last Sold Summary

    • 1% Below List Price
    • $265/SF
    • 3 Days On Market

    Current Estimated Value $686,687

    Last Listing Agent Jill Okun Berkshire Hathaway HomeServices Chicago

    1802 Winthrop Rd, Highland Park, IL 60035
    • /45

      Est $1,027,447

      Not Listed For Sale

      487 Sheridan Rd, Highland Park, IL 60035

      • 4 Beds
      • 3.5 Baths
      • 2,056 Sq Ft
      • Built 1956
      487 Sheridan Rd, Highland Park, IL 60035

      Last Sold Summary

      • 14 Days On Market

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

  • /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
  • /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 $341,553

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

    1795 Lake Cook Rd Unit 107, Highland Park, IL 60035
    • /48

      Est $1,574,852

      Not Listed For Sale

      110 Lakewood Place, Highland Park, IL 60035

      • 6 Beds
      • 4.5 Baths
      • 4,972 Sq Ft
      • Built 1939
      110 Lakewood Place, Highland Park, IL 60035

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent William Platt Jameson Sotheby's International Realty

  • /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
  • /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 $1,593,207

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

    800 Deerfield Rd Unit 306, Highland Park, IL 60035
    • /45

      Est $2,189,215

      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

  • /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
  • /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 $963,346

    Last Listing Agent Paul Lopata Mark Allen Realty ERA Powered

    370 Charal Ln, Highland Park, IL 60035
    • /56

      Est $1,987,404

      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

  • /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
  • /28

    $400,000

    Sold Sep 08, 2025

    1223 Cavell Ave, Highland Park, IL 60035

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft
    • Built 1952

    Last Sold Summary

    • $250/SF
    • 14 Days On Market

    Current Estimated Value $440,586

    Last Listing Agent Janet Borden Compass

    1223 Cavell Ave, Highland Park, IL 60035
    • /31

      Est $1,514,700

      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

  • /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
  • /17

    $250,000

    Sold Sep 12, 2025

    2086 Saint Johns Ave Unit 306, Highland Park, IL 60035

    • 2 Beds
    • 2 Baths
    • 1,532 Sq Ft
    • Built 1979

    Last Sold Summary

    • $163/SF
    • 10 Days On Market

    Current Estimated Value $348,474

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

    2086 Saint Johns Ave Unit 306, Highland Park, IL 60035
    • /39

      Est $1,011,625

      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

  • /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
  • /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 $741,481

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

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

      Est $1,523,161

      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

  • /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
  • /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 $694,040

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

    1140 Ridge Rd, Highland Park, IL 60035
    • /26

      Est $2,039,764

      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

  • /39

    $2,300,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 4,575 Sq Ft

    990 Sheridan Rd, Highland Park, IL 60035

    Experience the height of North Shore sophistication at 990 Sheridan Road -- an impressive ranch offering 4575 square feet of refined living space. Located down a long driveway, this exceptionally pristine ranch is set among towering trees. Three car heated garage, motor court, and circular drive awaits you. From the moment you enter, the home's grand scale is revealed through the Foyer's soaring

    Merle Kirsner-Styer Engel & Voelkers Chicago North Shore

    990 Sheridan Rd, 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 $1,521,934

    Last Listing Agent Aimee Glovsky Compass

    995 Harvard Ct, Highland Park, IL 60035
    • /29

      Est $1,336,245

      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

  • /6

    $749,990

    New Construction
    • 3 Beds
    • 2.5 - 3.5 Baths
    • 1,747 Sq Ft

    Crosby Plan at The Bowery of Highland Park, Highland Park, IL 60035

    The Crosby townhome combines flexible living spaces, an open-concept main floor, and a private balcony for effortless everyday living. With room to work, relax, and entertain across three thoughtfully designed levels, this home adapts to your lifestyle.

    M/I Homes Builder
    1700 Old Deerfield Rd Unit 41174121, 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 $1,401,652

    Last Listing Agent Janet Borden Compass

    2372 Tennyson Ln, Highland Park, IL 60035
    • /44

      Est $2,465,762

      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

  • /15

    $2,500,000

    New Construction Pending
    • 6 Beds
    • 5.5 Baths
    • 4,968 Sq Ft

    1350 Glencoe Ave, Highland Park, IL 60035

    Introducing The Lincoln Collection - an exclusive offering of nine new construction residences on the former Lincoln School site. Currently under construction and available July 2026. Perfectly positioned on a professionally landscaped .31-acre homesite, this exceptional 6-bedroom, 5.1-bath home offers approximately 5,400 square feet of curated living space across three impeccably finished

    Beth Wexler @properties Christie's International Real Estate

    1350 Glencoe 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 $1,049,178

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

    Unlisted Address
    • /81

      Est $2,700,041

      Not Listed For Sale

      750 Sheridan Rd, Highland Park, IL 60035

      • 6 Beds
      • 9 Baths
      • 8,430 Sq Ft
      • Built 1966
      750 Sheridan Rd, Highland Park, IL 60035

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Jane Goldman Gold & Azen Realty

  • /36

    $675,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,063 Sq Ft

    1633 2nd St Unit 503, Highland Park, IL 60035

    Enjoy penthouse living in the heart of downtown Highland Park! Rarely available this beautifully updated 3-bedroom, 2-bath condo with an office offers an expansive open floor plan filled with natural light from walls of windows and multiple skylights. The spacious living and dining areas feature a fireplace and open to a private balcony with beautiful downtown views. Extensively renovated in 2020

    Nicholas Manfredini @properties Christie's International Real Estate

    1633 2nd St Unit 503, 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 $763,793

    Last Listing Agent David Chung Compass

    590 Broadview Ave, Highland Park, IL 60035

Showing Results 281 - 320, Page 8 of 18

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