Highwood, IL Homes

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  /12

  $325,000

  • 2 Beds
  • 2 Baths

  249 Evolution Ave, Highwood, IL 60040

  This is an excellent flip or great for an end user who doesn't mind doing work but wants a fantastic location! Located on a beautiful street that's quiet and close to everything Highwood has to offer. Two large bedrooms on 2nd floor with a full bath. There are a few updates including a newer furnace and water heater as well as some hardwood floors on the first floor. This home has tremendous

  Kim Kelley Baird & Warner

  249 Evolution Ave, Highwood, IL 60040
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  /15

  $2,900 per month

  • 2 Beds
  • 2 Baths
  • 966 Sq Ft
  • Apartment for Rent

  546 Green Bay Rd Unit 305, Highwood, IL 60040

  Luxury Living in the Heart of Highwood! This stunning 2-bedroom, 2-bathroom apartment offers modern elegance with a private terrace and generous closet space. Nestled in Highwood's vibrant historic downtown, you're just steps from premier shopping, fine dining, and the Metra station for effortless commuting. The building features a selection of 1, 2, and 3-bedroom residences, each thoughtfully

  Christopher Dumitru Crosstown Realtors, Inc.

  546 Green Bay Rd Unit 305, 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 $375,810

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

  306 Ashland Ave, Highwood, IL 60040
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  /18

  Est $430,305 Not Listed For Sale

  116 High St, Highwood, IL 60040

  • 2 Beds
  • 1.5 Baths
  • 1,202 Sq Ft
  • Built 1923

  116 High St, Highwood, IL 60040

  Last Sold Summary

  • 1% Above List Price
  • $354/SF
  • 5 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Beth Alberts Compass
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  /13

  $3,300 per month

  • 3 Beds
  • 1 Bath
  • Apartment for Rent

  423 Funston Ave Unit 2F, Highwood, IL 60040

  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

  423 Funston Ave Unit 2F, Highwood, IL 60040
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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 $396,199

  Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago

  137 Highwood Ave, Highwood, IL 60040
• 

  

  /19

  Est $388,175 Not Listed For Sale

  217 Prairie Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,321 Sq Ft
  • Built 1930

  217 Prairie Ave, Highwood, IL 60040

  Last Sold Summary

  • 19% Above List Price
  • $248/SF
  • 29 Days On Market

  Last Sold Price $327,500

  Last Listing Agent Carol Santi Coldwell Banker Realty
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  /13

  $2,250 per month

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

  246 Green Bay Rd Unit 308, Highwood, IL 60040

  Luxurious apartments feature high-end kitchens with 42-inch cabinets, stone countertops, breakfast bars, over-the-stove microwaves, and dishwashers. They also offer nine-foot ceilings, outdoor spaces, spacious closets, and in-unit washer and dryers. This modern rental community is situated in the heart of Highwood's historic downtown entertainment center, providing easy access to shopping, fine

  Christopher Dumitru Crosstown Realtors, Inc.

  246 Green Bay Rd Unit 308, 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 $450,977

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

  44 Prairie Ave, Highwood, IL 60040
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  /4

  Est $368,799 Not Listed For Sale

  239 Prairie Ave, Highwood, IL 60040

  • 3 Beds
  • 2.5 Baths
  • 1,075 Sq Ft
  • Built 1938

  239 Prairie Ave, Highwood, IL 60040

  Last Sold Summary

  • 3% Above List Price
  • $334/SF
  • 17 Days On Market

  Last Sold Price $359,000

  Last Listing Agent Shara Fata Hashlang, Inc.
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  /15

  $3,050 per month

  • 2 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Apartment for Rent

  246 Green Bay Rd Unit 211, Highwood, IL 60040

  Luxurious apartments feature high-end kitchens with 42-inch cabinets, stone countertops, breakfast bars, over-the-stove microwaves, and dishwashers. They also offer nine-foot ceilings, outdoor spaces, spacious closets, and in-unit washer and dryers. This modern rental community is situated in the heart of Highwood's historic downtown entertainment center, providing easy access to shopping, fine

  Christopher Dumitru Crosstown Realtors, Inc.

  246 Green Bay Rd Unit 211, 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 $374,384

  Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago

  311 Prairie Ave, Highwood, IL 60040
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  /20

  Est $487,353 Not Listed For Sale

  102 S Central Ave, Highwood, IL 60040

  • 3 Beds
  • 1.5 Baths
  • 1,530 Sq Ft
  • Built 1929

  102 S Central Ave, Highwood, IL 60040

  Last Sold Summary

  • 3% Below List Price
  • $327/SF
  • 2 Days On Market

  Last Sold Price $500,000

  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 $604,497

  Last Listing Agent Carol Santi Coldwell Banker Realty

  336 Burchell Ave, Highwood, IL 60040
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  /2

  Est $498,214 Not Listed For Sale

  52 S Central Ave, Highwood, IL 60040

  • 4 Beds
  • 2.5 Baths
  • 2,260 Sq Ft
  • Built 1928

  52 S Central Ave, Highwood, IL 60040

  Last Sold Summary

  • 20% Above List Price
  • $184/SF
  • 42 Days On Market

  Last Sold Price $416,000

  Last Listing Agent Frank Nash Baird Warner
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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 $515,795

  Last Listing Agent Carol Santi Coldwell Banker Realty

  221 Burchell Ave, Highwood, IL 60040
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  /17

  Est $554,957 Not Listed For Sale

  63 Western Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 2,117 Sq Ft
  • Built 1955

  63 Western Ave, Highwood, IL 60040

  Last Sold Summary

  • 7% Above List Price
  • $246/SF
  • 4 Days On Market

  Last Sold Price $520,000

  Last Listing Agent Janice Goldblatt @ Properties
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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 $348,425

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

  334 Ashland Ave Unit 103, Highwood, IL 60040
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  /35

  Est $477,368 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

  • 11% Above List Price
  • $345/SF
  • 1 Day On Market

  Last Sold Price $430,000

  Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago
• 

  /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 $556,672

  Last Listing Agent Anna Klarck AK Homes

  317 Highwood Ave, Highwood, IL 60040
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  /24

  Est $517,262 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

  • 3% Above List Price
  • $256/SF
  • 24 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Beth Alberts Compass
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  /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 $1,338,942

  Last Listing Agent John Barry Mc Naughton Realty Group

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

  

  /22

  Est $457,061 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

  • 19% Above List Price
  • $247/SF
  • 0 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Janet Borden Compass
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  /4

  $141,000 Sold Mar 17, 2025

  0 N Central Ave, Highwood, IL 60040

  • Land
  • 0.18 Acre
  • $783,333 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 23 Days On Market

  Current Estimated Value $297,487

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

  0 N Central Ave, Highwood, IL 60040
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  /20

  Est $466,768 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

  • 7% Above List Price
  • $160/SF
  • 20 Days On Market

  Last Sold Price $435,000

  Last Listing Agent Beth Alberts Compass
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  /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 $380,326

  Last Listing Agent Thomas Hood Riverside Management

  218 S Central Ave, Highwood, IL 60040
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  /14

  Est $344,898 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

  • 25% Above List Price
  • $277/SF
  • 5 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Susan Brown Burklin @ 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 $666,000

  Last Listing Agent Alissa Morton Compass

  25 Webster Ave, Highwood, IL 60040
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  /13

  Est $392,984 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

  Last Listing Agent Mary Caselli Indian Creek Enterprises, Inc.
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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 $965,992

  Last Listing Agent Beth Alberts Compass

  281 Michigan Ave, Highwood, IL 60040
• 

  

  /10

  Est $490,342 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

  • 11% Above List Price
  • $116/SF
  • 92 Days On Market

  Last Sold Price $440,000

  Last Listing Agent Beth Alberts Compass
• 

  

  /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 $356,047

  Last Listing Agent Janet Borden Compass

  500 Lake View Ave Unit 2A, Highwood, IL 60040
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  /4

  Est $219,237 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

  • 19% Above List Price
  • $237/SF
  • 6 Days On Market

  Last Sold Price $185,000

  Last Listing Agent Beth Alberts Compass
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  /16

  $535,000 Sold Apr 09, 2025

  321 Prairie Ave, Highwood, IL 60040

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

  Last Sold Summary

  • 8% Below List Price
  • $239/SF
  • 16 Days On Market

  Current Estimated Value $551,246

  Last Listing Agent Beth Alberts Compass

  321 Prairie Ave, Highwood, IL 60040
• 

  

  /3

  Est $274,305 Not Listed For Sale

  232 Evolution Ave, Highwood, IL 60040

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

  232 Evolution Ave, Highwood, IL 60040

  Last Sold Summary

  • 61% Above List Price
  • $220/SF
  • 2 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Pedro Porcayo Porcayo & Associates Realty
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  /34

  $525,000 Sold May 07, 2025

  330 Prairie Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,412 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Above List Price
  • $372/SF
  • 5 Days On Market

  Current Estimated Value $534,345

  Last Listing Agent Keith Brand Berkshire Hathaway HomeServices Chicago

  330 Prairie Ave, Highwood, IL 60040
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  /27

  Est $534,782 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

  • 22% Above List Price
  • $161/SF
  • 4 Days On Market

  Last Sold Price $440,000

  Last Listing Agent Sandra Soldano @ Properties
• 

  

  /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 $418,365

  Last Listing Agent Benjamin Lissner Baird & Warner

  134 Pleasant Ave, Highwood, IL 60040
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  /21

  Est $285,019 Not Listed For Sale

  330 Highwood Ave Unit 2D, Highwood, IL 60040

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

  330 Highwood Ave Unit 2D, Highwood, IL 60040

  Last Sold Summary

  • 24% Above List Price
  • $153/SF
  • 77 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Jim Abbott Baird Warner
• 

  

  /37

  $287,500 Sold Aug 27, 2025

  540 Green Bay Rd, Highwood, IL 60040

  • 3 Beds
  • 1.5 Baths
  • 1,350 Sq Ft
  • Built 1890

  Last Sold Summary

  • $213/SF
  • 13 Days On Market

  Current Estimated Value $403,333

  Last Listing Agent Rafay Qamar Real Broker LLC

  540 Green Bay Rd, Highwood, IL 60040

Showing Results 41 - 80, Page 2 of 18