Highwood, IL Homes

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  /24

  $525,000

  • 2 Beds
  • 1.5 Baths
  • 1,202 Sq Ft

  116 High St, Highwood, IL 60040

  This fully renovated ranch in Highwood blends clean design with thoughtful upgrades throughout, including a newly finished basement and major 2024-2025 improvements. A bright four-season front porch sets the tone on entry, offering flexible space for a sitting room, office, or mudroom. Inside, the open living and dining area flows naturally into a crisp white kitchen with quartz countertops,

  Joshua Black eXp Realty

  116 High St, Highwood, IL 60040
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  /10

  $2,200 Per Month

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Apartment for Rent

  328 Green Bay Rd Unit 1, Highwood, IL 60040

  Amazing and large Vintage 3 Bedroom apartment, in-Town Highwood. Nicely updated, beautiful Hardwood flooring, on site parking, large eat-in Kitchen. Feels like a home! Move to Highwood where all the action is! Walk to the restaurants and shopping. Walk to Train.

  Jeannine Viti Berkshire Hathaway HomeServices Chicago

  328 Green Bay Rd Unit 1, Highwood, IL 60040
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  /26

  $255,000 Sold Jan 09, 2026

  330 Highwood Ave Unit 2A, Highwood, IL 60040

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1984

  Last Sold Summary

  • 9% Below List Price
  • $170/SF
  • 7 Days On Market

  Current Estimated Value $262,111

  Last Listing Agent Andrew Langer @properties Christie's International Real Estate

  330 Highwood Ave Unit 2A, Highwood, IL 60040
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  /16

  Est $542,749 Not Listed For Sale

  321 Prairie Ave, Highwood, IL 60040

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • Built 1928

  321 Prairie Ave, Highwood, IL 60040

  Last Sold Summary

  • 1% Above List Price
  • $239/SF
  • 16 Days On Market

  • Last Sold Price $535,000
  • Apr 09, 2025

  Last Listing Agent Beth Alberts Compass
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  /45

  $649,000 Pending

  • 6 Beds
  • 3 Baths
  • 3,967 Sq Ft

  250 High St, Highwood, IL 60040

  FIRST TIME on the market, this single-owner property has been meticulously maintained and presents an exceptional opportunity in Highwood's most desirable location. Situated on a quiet residential street just steps from vibrant downtown, this property offers the perfect blend of privacy and walkability. This well-maintained single-family home offers exceptional flexibility with a thoughtfully

  Nicholas Manfredini @properties Christie's International Real Estate

  250 High St, Highwood, IL 60040
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  /13

  $2,375 Per Month

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft
  • Apartment for Rent

  440 Green Bay Rd Unit 503, Highwood, IL 60040

  This one-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,

  Christopher Dumitru Crosstown Realtors, Inc.

  440 Green Bay Rd Unit 503, Highwood, IL 60040
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  /17

  $335,000 Sold Jul 01, 2025

  306 Ashland Ave, Highwood, IL 60040

  • 2 Beds
  • 1 Bath
  • 1,005 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Above List Price
  • $333/SF
  • 6 Days On Market

  Current Estimated Value $364,565

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

  306 Ashland Ave, Highwood, IL 60040
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  /35

  Est $468,401 Not Listed For Sale

  337 Prairie Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1942

  337 Prairie Ave, Highwood, IL 60040

  Last Sold Summary

  • 9% Above List Price
  • $345/SF
  • 1 Day On Market

  • Last Sold Price $430,000
  • Aug 18, 2023

  Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago
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  /13

  $3,100 Per Month

  • 3 Beds
  • 1 Bath
  • Apartment for Rent

  Unlisted Address

  Lovely rehabbed 3 bedroom apartment ideally located close to all the action in the vibrant village of Highwood. This inviting home features a modern kitchen with granite countertops, gas cooking, and ample storage. Both bedrooms are generously sized and offer flexibility for a variety of needs, while the bonus space is perfect for a dedicated home office.The beautifully updated bathroom features

  Axel Cohen Compass

  Unlisted Address
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  /34

  $430,000 Sold Feb 24, 2026

  137 Highwood Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1930

  Last Sold Summary

  • 4% Above List Price
  • $375/SF
  • 5 Days On Market

  Current Estimated Value $420,152

  Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago

  137 Highwood Ave, Highwood, IL 60040
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  /24

  Est $536,755 Not Listed For Sale

  129 Highwood Ave, Highwood, IL 60040

  • 2 Beds
  • 3.5 Baths
  • 1,954 Sq Ft
  • Built 1925

  129 Highwood Ave, Highwood, IL 60040

  Last Sold Summary

  • 7% Above List Price
  • $256/SF
  • 24 Days On Market

  • Last Sold Price $500,000
  • Jul 28, 2023

  Last Listing Agent Beth Alberts Compass
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  /13

  $2,409 Per Month

  • 1 Bed
  • 1 Bath
  • 862 Sq Ft
  • Apartment for Rent

  440 Green Bay Rd Unit 401, Highwood, IL 60040

  This one-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,

  Christopher Dumitru Crosstown Realtors, Inc.

  440 Green Bay Rd Unit 401, Highwood, IL 60040
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  /27

  $430,000 Sold Jun 03, 2025

  44 Prairie Ave, Highwood, IL 60040

  • 5 Beds
  • 2 Baths
  • 2,201 Sq Ft
  • Built 1930

  Last Sold Summary

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

  Current Estimated Value $450,548

  Last Listing Agent Jason Giambarberee @properties Christie's International Real Estate

  44 Prairie Ave, Highwood, IL 60040
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  /22

  Est $465,522 Not Listed For Sale

  238 High St, Highwood, IL 60040

  • 3 Beds
  • 3 Baths
  • 1,560 Sq Ft
  • Built 1929

  238 High St, Highwood, IL 60040

  Last Sold Summary

  • 21% Above List Price
  • $247/SF
  • 0 Days On Market

  • Last Sold Price $385,000
  • Jan 04, 2024

  Last Listing Agent Janet Borden Compass
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  /15

  $2,995 Per Month

  • 2 Beds
  • 2 Baths
  • 1,077 Sq Ft
  • Apartment for Rent

  440 Green Bay Rd Unit 405, Highwood, IL 60040

  This two-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,

  Christopher Dumitru Crosstown Realtors, Inc.

  440 Green Bay Rd Unit 405, Highwood, IL 60040
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  /2

  $310,000 Sold Oct 01, 2025

  311 Prairie Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1946

  Last Sold Summary

  • 5% Below List Price
  • $208/SF
  • 2 Days On Market

  Current Estimated Value $322,854

  Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago

  311 Prairie Ave, Highwood, IL 60040
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  /20

  Est $462,747 Not Listed For Sale

  230 Oakridge Ave, Highwood, IL 60040

  • 2 Beds
  • 2 Baths
  • 2,720 Sq Ft
  • Built 1924

  230 Oakridge Ave, Highwood, IL 60040

  Last Sold Summary

  • 6% Above List Price
  • $160/SF
  • 20 Days On Market

  • Last Sold Price $435,000
  • Jun 10, 2024

  Last Listing Agent Beth Alberts Compass
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  /2

  $600,000 Sold Aug 29, 2025

  336 Burchell Ave, Highwood, IL 60040

  • 2 Beds
  • 2 Baths
  • 1,923 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Above List Price
  • $312/SF

  Current Estimated Value $603,277

  Last Listing Agent Carol Santi Coldwell Banker Realty

  336 Burchell Ave, Highwood, IL 60040
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  /14

  Est $345,978 Not Listed For Sale

  320 Prairie Ave, Highwood, IL 60040

  • 3 Beds
  • 1.5 Baths
  • 994 Sq Ft
  • Built 1939

  320 Prairie Ave, Highwood, IL 60040

  Last Sold Summary

  • 26% Above List Price
  • $277/SF
  • 5 Days On Market

  • Last Sold Price $275,000
  • Aug 02, 2023

  Last Listing Agent Susan Brown Burklin @ Properties
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  /22

  $500,000 Sold Dec 31, 2025

  221 Burchell Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 2,101 Sq Ft
  • Built 1923

  Last Sold Summary

  • 12% Below List Price
  • $238/SF
  • 21 Days On Market

  Current Estimated Value $502,869

  Last Listing Agent Carol Santi Coldwell Banker Realty

  221 Burchell Ave, Highwood, IL 60040
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  /13

  Est $392,897 Not Listed For Sale

  214 S Central Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1955

  214 S Central Ave, Highwood, IL 60040

  Last Sold Summary

  • 19% Above List Price
  • $278/SF
  • 23 Days On Market

  • Last Sold Price $330,000
  • Aug 30, 2023

  Last Listing Agent Mary Caselli Indian Creek Enterprises, Inc.
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  /19

  $349,900 Sold Jul 30, 2025

  334 Ashland Ave Unit 103, Highwood, IL 60040

  • 2 Beds
  • 2.5 Baths
  • 1,818 Sq Ft
  • Built 1979

  Last Sold Summary

  • 5% Below List Price
  • $192/SF
  • 38 Days On Market

  Current Estimated Value $350,279

  Last Listing Agent Ivan Santos O'Neil Property Group, LLC

  334 Ashland Ave Unit 103, Highwood, IL 60040
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  /10

  Est $475,908 Not Listed For Sale

  334 Prairie Ave, Highwood, IL 60040

  • 4 Beds
  • 2 Baths
  • 3,808 Sq Ft
  • Built 1958

  334 Prairie Ave, Highwood, IL 60040

  Last Sold Summary

  • 8% Above List Price
  • $116/SF
  • 92 Days On Market

  • Last Sold Price $440,000
  • May 13, 2024

  Last Listing Agent Beth Alberts Compass
• 

  /2

  $565,000 Sold Jun 27, 2025

  317 Highwood Ave, Highwood, IL 60040

  • 2 Beds
  • 2 Baths
  • 1,922 Sq Ft
  • Built 1984

  Last Sold Summary

  • 5% Below List Price
  • $294/SF
  • 39 Days On Market

  Current Estimated Value $539,702

  Last Listing Agent Anna Klarck AK Homes

  317 Highwood Ave, Highwood, IL 60040
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  /4

  Est $218,337 Not Listed For Sale

  338 Prairie Ave, Highwood, IL 60040

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • Built 1930

  338 Prairie Ave, Highwood, IL 60040

  Last Sold Summary

  • 18% Above List Price
  • $237/SF
  • 6 Days On Market

  • Last Sold Price $185,000
  • Dec 01, 2023

  Last Listing Agent Beth Alberts Compass
• 

  

  /23

  $1,307,500 Sold Jul 10, 2025

  2528 Hidden Oak (Lot 6) Cir, Highland Park, IL 60035

  • 3 Beds
  • 2.5 Baths
  • 2,900 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Above List Price
  • $451/SF
  • 640 Days On Market

  Current Estimated Value $1,305,568

  Last Listing Agent John Barry Mc Naughton Realty Group

  2528 Hidden Oak (Lot 6) Cir, Highland Park, IL 60035
• 

  

  /23

  Est $504,245 Not Listed For Sale

  236 Evolution Ave, Highwood, IL 60040

  • 3 Beds
  • 3 Baths
  • 1,700 Sq Ft
  • Built 1930

  236 Evolution Ave, Highwood, IL 60040

  Last Sold Summary

  • 1% Above List Price
  • $293/SF
  • 24 Days On Market

  • Last Sold Price $497,500
  • Apr 04, 2025

  Last Listing Agent Ila Coretti @ Properties
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  /36

  $861,000 Sold Apr 01, 2026

  263 Michigan Ave, Highwood, IL 60040

  • 3 Beds
  • 2.5 Baths
  • 2,483 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $347/SF
  • 7 Days On Market

  Current Estimated Value $712,688

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

  263 Michigan Ave, Highwood, IL 60040
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  /27

  Est $542,582 Not Listed For Sale

  209 North Ave, Highwood, IL 60040

  • 6 Beds
  • 2 Baths
  • 2,736 Sq Ft
  • Built 1945

  209 North Ave, Highwood, IL 60040

  Last Sold Summary

  • 23% Above List Price
  • $161/SF
  • 4 Days On Market

  • Last Sold Price $440,000
  • Sep 18, 2023

  Last Listing Agent Sandra Soldano @ Properties
• 

  /2

  $275,000 Sold Apr 09, 2026

  500 Lakeview Ave Unit 1C, Highwood, IL 60040

  • 2 Beds
  • 2 Baths
  • 1,013 Sq Ft
  • Built 1986

  Last Sold Summary

  • 10% Above List Price
  • $271/SF

  Current Estimated Value $313,348

  Last Listing Agent Carol Santi Coldwell Banker Realty

  500 Lakeview Ave Unit 1C, Highwood, IL 60040
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  /10

  Est $1,082,449 Not Listed For Sale

  423 Funston Ave, Highwood, IL 60040

  • 8 Beds
  • 4 Baths
  • 4,268 Sq Ft
  • Built 1929

  423 Funston Ave, Highwood, IL 60040

  Last Sold Summary

  • 195% Above List Price
  • $86/SF
  • 47 Days On Market

  • Last Sold Price $367,000
  • Jul 01, 2014

  Last Listing Agent Erik Gimbel Compass
• 

  

  /26

  $370,000 Sold Jun 26, 2025

  218 S Central Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,093 Sq Ft
  • Built 1956

  Last Sold Summary

  • 7% Above List Price
  • $339/SF
  • 3 Days On Market

  Current Estimated Value $369,288

  Last Listing Agent Thomas Hood Riverside Management

  218 S Central Ave, Highwood, IL 60040
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  /26

  Est $512,305 Not Listed For Sale

  334 North Ave, Highwood, IL 60040

  • 5 Beds
  • 2 Baths
  • 2,271 Sq Ft
  • Built 1929

  334 North Ave, Highwood, IL 60040

  Last Sold Summary

  • 13% Above List Price
  • $200/SF
  • 3 Days On Market

  • Last Sold Price $455,000
  • Jul 17, 2023

  Last Listing Agent Peggy Glickman @ Properties
• 

  

  /25

  $655,000 Sold Feb 26, 2026

  25 Webster Ave, Highwood, IL 60040

  • 6 Beds
  • 4 Baths
  • 3,504 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Below List Price
  • $187/SF
  • 7 Days On Market

  Current Estimated Value $643,000

  Last Listing Agent Alissa Morton Compass

  25 Webster Ave, Highwood, IL 60040
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  /35

  Est $690,272 Not Listed For Sale

  43 Clay Ave, Highwood, IL 60040

  • 5 Beds
  • 4 Baths
  • 3,082 Sq Ft
  • Built 1933

  43 Clay Ave, Highwood, IL 60040

  Last Sold Summary

  • 6% Above List Price
  • $211/SF
  • 13 Days On Market

  • Last Sold Price $649,000
  • Dec 03, 2024

  Last Listing Agent Sandra Locascio RE/MAX Suburban
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  /30

  $935,000 Sold Sep 30, 2025

  281 Michigan Ave, Highwood, IL 60040

  • 3 Beds
  • 4 Baths
  • 3,600 Sq Ft
  • Built 1978

  Last Sold Summary

  • 9% Below List Price
  • $260/SF
  • 21 Days On Market

  Current Estimated Value $957,661

  Last Listing Agent Beth Alberts Compass

  281 Michigan Ave, Highwood, IL 60040
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  /29

  Est $407,437 Not Listed For Sale

  247 Sheridan Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft
  • Built 1928

  247 Sheridan Ave, Highwood, IL 60040

  Last Sold Summary

  • 18% Below List Price
  • $314/SF
  • 3 Days On Market

  • Last Sold Price $495,000
  • Dec 27, 2024

  Last Listing Agent Lily Hosseini Baird Warner
• 

  

  /17

  $349,900 Sold Aug 29, 2025

  500 Lake View Ave Unit 2A, Highwood, IL 60040

  • 2 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Built 1986

  Last Sold Summary

  • $305/SF
  • 6 Days On Market

  Current Estimated Value $345,644

  Last Listing Agent Janet Borden Compass

  500 Lake View Ave Unit 2A, Highwood, IL 60040
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  /11

  Est $328,879 Not Listed For Sale

  246 Sheridan Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,955 Sq Ft
  • Built 1919

  246 Sheridan Ave, Highwood, IL 60040

  Last Sold Summary

  • 22% Above List Price
  • $138/SF
  • 257 Days On Market

  • Last Sold Price $270,000
  • Jul 01, 2024

  Last Listing Agent Paula Avenaim Baird Warner
• 

  

  /20

  $410,000 Sold Jun 09, 2025

  134 Pleasant Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 987 Sq Ft
  • Built 1956

  Last Sold Summary

  • 6% Above List Price
  • $415/SF
  • 5 Days On Market

  Current Estimated Value $407,262

  Last Listing Agent Benjamin Lissner Baird & Warner

  134 Pleasant Ave, Highwood, IL 60040

Showing Results 41 - 80, Page 2 of 18