$775,000
$25K PRICE DROP
- 5 Beds
- 4 Baths
43 Clay Ave, Highwood, IL 60040
Jim Abbott Baird & Warner
1,547
Homes in ZIP Code 60040
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43 Clay Ave, Highwood, IL 60040
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Starting at $2,248 Per Month
- 1 - 3 Beds
440 Green Bay Rd, Highwood, IL 60040
440 Green Bay Rd, Highwood, IL 60040Welcome to Highpoint Highwood Station 440 — modern 1, 2 & 3-bedroom apartments for rent in Highwood, IL. Enjoy updated kitchens, in-unit laundry, and walkable access to downtown Highwood, Green Bay Road, and Fort Sheridan. Our pet-friendly community offers convenient living near Highland Park, boutique dining, and local shops. Schedule your tour today.
HIGHPOINT Highwood Station 440
(224) 258-0628
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$355,000
Sold Jun 16, 2025328 Oak Terrace Ave, Highwood, IL 60040
- 2 Beds
- 2 Baths
- 1,397 Sq Ft
- Built 1956
Last Sold Summary
- 1% Above List Price
- $254/SF
- 1 Day On Market
Current Estimated Value $379,028
Last Listing Agent David Wilkerson eXp Realty
328 Oak Terrace Ave, Highwood, IL 60040 -
Not Listed For Sale114 Michigan Ave, Highwood, IL 60040
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
- Built 1933
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$650,000
Pending- 4 Beds
- 2 Baths
- 2,260 Sq Ft
52 S Central Ave, Highwood, IL 60040
52 S Central Ave, Highwood, IL 60040Laura McCain Compass
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Starting at $1,759 Per Month
- 1 - 3 Beds
634 Sheridan Rd, Highwood, IL 60040
634 Sheridan Rd, Highwood, IL 60040Nestled between affluent Lake Forest and Highland Park, Arrive North Shore® is located in vibrant downtown Highwood and offers a unique opportunity to live on Chicago's scenic North Shore, just minutes away from Downtown Highwood shops and restaurants and Fort Sheridan Metra Stations. Our newly restyled apartment homes are equipped with deluxe kitchens, generous living spaces, and private patios.
Arrive North Shore
(224) 328-2900
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$285,000
Sold Apr 01, 2026330 Highwood Ave Unit 2B, Highwood, IL 60040
- 2 Beds
- 2 Baths
- 1,364 Sq Ft
- Built 1984
Last Sold Summary
- $209/SF
Current Estimated Value $294,756
Last Listing Agent Jim Abbott Baird & Warner
330 Highwood Ave Unit 2B, Highwood, IL 60040 -
Est $497,437
Not Listed For Sale32 Michigan Ave, Highwood, IL 60040
- 4 Beds
- 2 Baths
- 1,722 Sq Ft
- Built 1923
Last Sold Summary
- 9 Days On Market
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$375,000
$7K PRICE DROP Pending- 3 Beds
- 2 Baths
- 1,428 Sq Ft
225 Burchell Ave, Highwood, IL 60040
225 Burchell Ave, Highwood, IL 60040Jim Abbott Baird & Warner
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$1,650
Total Monthly Price
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
124 S Central Ave Unit First Floor Apartment, Highwood, IL 60040
124 S Central Ave Unit First Floor Apartment, Highwood, IL 60040Beautiful 1 Bedroom 1 Bath apartment in a quiet neighborhood in Highwood. 1st floor of 2 unit building. Walking distance to Highwood's business district, train station and the Preserve of Highland Park. Located right off Half Day Rd/Rte 22 making it very close to Highway 41.Large, eat-in updated kitchen with new refrigerator and gas range. Newly renovated bathroom with a full shower
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$700,000
Sold Nov 07, 2025738 Lyster Rd Unit 1, Highwood, IL 60040
- 2 Beds
- 2.5 Baths
- 2,552 Sq Ft
- Built 1885
Last Sold Summary
- 7% Below List Price
- $274/SF
- 48 Days On Market
Current Estimated Value $731,000
Last Listing Agent Susan Brown Burklin @properties Christie's International Real Estate
738 Lyster Rd Unit 1, Highwood, IL 60040 -
Est $425,981
Not Listed For Sale102 High St, Highwood, IL 60040
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Built 1930
Last Sold Summary
- 9 Days On Market
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$563,000
Pending- 3 Beds
- 2 Baths
- 1,108 Sq Ft
328 Ashland Ave, Highwood, IL 60040
328 Ashland Ave, Highwood, IL 60040Mada Hitchmough Compass
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$2,100
Total Monthly Price
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
- Condo for Rent
350 Prairie Ave Unit A, Highwood, IL 60040
350 Prairie Ave Unit A, Highwood, IL 60040Spacious and charming 3-bedroom apartment available in Highwood, IL, located in a brick duplex (upstairs unit in a 2-unit building). Just a short stroll to downtown Highwood and the Highwood Train Station, with easy access to Highway 41 right around the corner. This unit features a generous kitchen and dining area, along with a large living room ideal for relaxation. The apartment includes one
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$799,000
Sold Sep 19, 2025762 Deroo Loop Unit 5, Highwood, IL 60040
- 3 Beds
- 2.5 Baths
- 3,173 Sq Ft
- Built 1885
Last Sold Summary
- $252/SF
- 18 Days On Market
Current Estimated Value $812,825
Last Listing Agent Michael Mitchell @properties Christie's International Real Estate
762 Deroo Loop Unit 5, Highwood, IL 60040 -
Est $526,312
Not Listed For Sale125 Maple Ave, Highwood, IL 60040
- 3 Beds
- 2 Baths
- 1,443 Sq Ft
- Built 1931
Last Sold Summary
- 18 Days On Market
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$350,000
$25K PRICE DROP- 3 Beds
- 1 Bath
- 1,450 Sq Ft
239 Sheridan Ave, Highwood, IL 60040
239 Sheridan Ave, Highwood, IL 60040Carol Santi Coldwell Banker Realty
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$2,035 Per Month
- 1 Bed
- 1 Bath
- 699 Sq Ft
- Apartment for Rent
546 Green Bay Rd Unit 408, Highwood, IL 60040
546 Green Bay Rd Unit 408, Highwood, IL 60040Luxury Living in the Heart of Highwood! This stunning 1-bedroom, 1-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.
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$890,000
Sold Oct 01, 2025795 Stables Ct W Unit 4, Highwood, IL 60040
- 3 Beds
- 2.5 Baths
- 2,617 Sq Ft
- Built 1895
Last Sold Summary
- 4% Below List Price
- $340/SF
- 11 Days On Market
Current Estimated Value $913,479
Last Listing Agent Karen Chien-Rooney Compass
795 Stables Ct W Unit 4, Highwood, IL 60040 -
Est $414,669
Not Listed For Sale144 Morgan Place, Highwood, IL 60040
- 2 Beds
- 2 Baths
- 1,224 Sq Ft
- Built 1955
Last Sold Summary
- 18 Days On Market
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$599,000
- 4 Beds
- 2 Baths
124 S Central Ave, Highwood, IL 60040
124 S Central Ave, Highwood, IL 60040Mada Hitchmough Compass
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$2,550 Per Month
- 3 Beds
- 1 Bath
- Apartment for Rent
522 N Central Ave Unit 1, Highwood, IL 60040
522 N Central Ave Unit 1, Highwood, IL 60040Beautifully updated 2-flat featuring a spacious first-floor apartment with 3 bedrooms and 1 bath. The well-designed open floor plan offers abundant natural light, an updated kitchen and bath, custom closet organizers, and window treatments throughout. Enjoy the convenience of a large private bonus room with washer and dryer. The property also includes access to a wonderful yard and 1 garage
Diana Martinez Realty of America, LLC
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$190,000
Sold Oct 01, 2025307 Prairie Ave, Highwood, IL 60040
- 2 Beds
- 1 Bath
- 988 Sq Ft
- Built 1923
Last Sold Summary
- 12% Below List Price
- $192/SF
- 3 Days On Market
Current Estimated Value $268,481
Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago
307 Prairie Ave, Highwood, IL 60040 -
Est $465,181
Not Listed For Sale116 High St, Highwood, IL 60040
- 2 Beds
- 1.5 Baths
- 1,202 Sq Ft
- Built 1923
Last Sold Summary
- 5 Days On Market
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$989,000
Pending- 3 Beds
- 2.5 Baths
- 2,153 Sq Ft
824 Stables Ct W Unit D, Highwood, IL 60040
824 Stables Ct W Unit D, Highwood, IL 60040Alison Wertheimer @properties Christie's International Real Estate
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$4,249 Per Month
- 3 Beds
- 2.5 Baths
- 1,791 Sq Ft
- Townhouse for Rent
20 Webster Ave Unit C, Highwood, IL 60040
20 Webster Ave Unit C, Highwood, IL 60040Rarely available Highwood 3 bedroom, 2.5 bathroom townhome is now available. This listing boasts hardwood floors throughout each floor, central air conditioning and heat, and washer / dryer in the unit. Granite countertops and stainless steel appliances (incl. dishwasher) in massive kitchen. More than ample countertop and cabinet space to enjoy. Large & sunny living area with separate dining
Daniel Management Group Daniel Management Group Inc
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$350,000
Sold Jun 12, 2025238 Jeffreys Place, Highwood, IL 60040
- 4 Beds
- 3 Baths
- 1,638 Sq Ft
- Built 1950
Last Sold Summary
- $214/SF
- 16 Days On Market
Current Estimated Value $393,354
Last Listing Agent Frank Rusin Four Seasons Realty, Inc.
238 Jeffreys Place, Highwood, IL 60040 -
Est $412,512
Not Listed For Sale217 Prairie Ave, Highwood, IL 60040
- 3 Beds
- 2 Baths
- 1,321 Sq Ft
- Built 1930
Last Sold Summary
- 29 Days On Market
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$775,000
$25K PRICE DROP- 7 Beds
- 3 Baths
308 Washington Ave, Highwood, IL 60040
308 Washington Ave, Highwood, IL 60040Jim Abbott Baird & Warner
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$1,500 Per Month
- 1 Bed
- 1 Bath
- Apartment for Rent
131 Pleasant Ave Unit 1E, Highwood, IL 60040
131 Pleasant Ave Unit 1E, Highwood, IL 60040The perfect Highwood location-just blocks away from downtown Highwood with all its fabulous restaurants and shopping!! This 1 bed, 1 bath condo close to everything you need. It's been freshly painted, professionally cleaned with new luxury vinyl plank flooring throughout and new quartz countertop! Ready for new tenants and available immediately. It's also close to the Metra station, Lake
Marco Amidei RE/MAX Suburban
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$885,000
Sold Jun 30, 202527 Rienzi Ln, Highwood, IL 60040
- 4 Beds
- 3.5 Baths
- 3,500 Sq Ft
- Built 2005
Last Sold Summary
- 2% Below List Price
- $253/SF
- 11 Days On Market
Current Estimated Value $945,145
Last Listing Agent Alison Wertheimer @properties Christie's International Real Estate
27 Rienzi Ln, Highwood, IL 60040 -
Est $427,017
Not Listed For Sale134 Pleasant Ave, Highwood, IL 60040
- 3 Beds
- 2 Baths
- 987 Sq Ft
- Built 1956
Last Sold Summary
- 5 Days On Market
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$1,250,000
- 4 Beds
- 3.5 Baths
- 4,222 Sq Ft
47 Holabird Cir, Highwood, IL 60040
47 Holabird Cir, Highwood, IL 60040Janet Borden Compass
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$2,995 Per Month
- 3 Beds
- 1 Bath
- Apartment for Rent
423 Funston Ave Unit 2F, Highwood, IL 60040
423 Funston Ave Unit 2F, Highwood, IL 60040Lovely 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
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$375,000
Sold Dec 19, 2025228 Llewellyn Ave, Highwood, IL 60040
- 3 Beds
- 2.5 Baths
- 1,480 Sq Ft
- Built 1920
Last Sold Summary
- $253/SF
- 43 Days On Market
Current Estimated Value $379,632
Last Listing Agent Sandra Locascio RE/MAX Suburban
228 Llewellyn Ave, Highwood, IL 60040 -
Est $366,394
Not Listed For Sale239 Prairie Ave, Highwood, IL 60040
- 3 Beds
- 2.5 Baths
- 1,075 Sq Ft
- Built 1938
Last Sold Summary
- 17 Days On Market
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$1,850,000
- 3 Beds
- 5 Baths
- 3,488 Sq Ft
260 Whistler Rd Unit 2B-C, Highland Park, IL 60035
260 Whistler Rd Unit 2B-C, Highland Park, IL 60035Judy Weiss @properties Christie's International Real Estate
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$2,409 Per Month
- 1 Bed
- 1 Bath
- 862 Sq Ft
- Apartment for Rent
440 Green Bay Rd Unit 401, Highwood, IL 60040
440 Green Bay Rd Unit 401, Highwood, IL 60040This 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.
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$830,000
Sold Jul 07, 2025754 Lyster Rd Unit D, Highwood, IL 60040
- 3 Beds
- 3 Baths
- 2,405 Sq Ft
- Built 1895
Last Sold Summary
- 11% Above List Price
- $345/SF
- 3 Days On Market
Current Estimated Value $835,013
Last Listing Agent Susan Brown Burklin @properties Christie's International Real Estate
754 Lyster Rd Unit D, Highwood, IL 60040 -
Est $494,049
Not Listed For Sale102 S Central Ave, Highwood, IL 60040
- 3 Beds
- 1.5 Baths
- 1,530 Sq Ft
- Built 1929
Last Sold Summary
- 2 Days On Market
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