$1,495,000
New Construction
- 4 Beds
- 3.5 Baths
- 3,281 Sq Ft
251 High St, Highwood, IL 60040
Margie Brooks Baird & Warner
1,507
Highwood, IL Homes
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251 High St, 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
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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 $298,606
Last Listing Agent Jim Abbott Baird & Warner
330 Highwood Ave Unit 2B, Highwood, IL 60040 -
Not Listed For Sale114 Michigan Ave, Highwood, IL 60040
- 3 Beds
- 1 Bath
- 2,200 Sq Ft
- Built 1933
Last Sold Summary
- 255 Days On Market
Last Listing Agent Mirella Caputo @properties Christie's International Real Estate
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$775,000
$25K PRICE DROP Pending- 5 Beds
- 4 Baths
43 Clay Ave, Highwood, IL 60040
43 Clay Ave, Highwood, IL 60040Jim Abbott Baird & Warner
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Starting at $1,819 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
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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 $740,392
Last Listing Agent Susan Brown Burklin @properties Christie's International Real Estate
738 Lyster Rd Unit 1, Highwood, IL 60040 -
Est $352,365
Not Listed For Sale3 Burtis Ave, Highwood, IL 60040
- 2 Beds
- 1.5 Baths
- 864 Sq Ft
- Built 1920
Last Sold Summary
- 25 Days On Market
Last Listing Agent Erin Kahn @properties Christie's International Real Estate
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$1,199,000
- 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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Starting at $4,072 Per Month
- 3 Beds
25 Clay Ave, Highwood, IL 60040
25 Clay Ave, Highwood, IL 60040Webster Place
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$636,000
Sold Aug 13, 202652 S Central Ave, Highwood, IL 60040
- 4 Beds
- 2 Baths
- 2,260 Sq Ft
- Built 1928
Last Sold Summary
- 2% Below List Price
- $281/SF
- 0 Days On Market
Current Estimated Value $636,977
Last Listing Agent Laura McCain Compass
52 S Central Ave, Highwood, IL 60040 -
Est $496,679
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
Last Listing Agent Beth Alberts Compass
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$549,000
$50K PRICE DROP- 4 Beds
- 2 Baths
124 S Central Ave, Highwood, IL 60040
124 S Central Ave, Highwood, IL 60040Mada Hitchmough Compass
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$1,980
Total Monthly Price
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
- Condo for Rent
113 Burtis Ave Unit A, Highwood, IL 60040
113 Burtis Ave Unit A, Highwood, IL 60040**PLEASE READ CAREFULLY & THOROUGHLY**We are renting a perfect 2-bedroom 1-bath apartment in a wonderfully quiet neighborhood in Highwood. Just renovated in May 2026. It's also within walking distance to Highwood's bustling business district and train station. Located right off Half Day Rd/Rte 22, making it very close to Highway 41.This first-floor apartment is composed of a large
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$310,000
Sold Jul 07, 2026225 Burchell Ave, Highwood, IL 60040
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
- Built 1933
Last Sold Summary
- 19% Below List Price
- $217/SF
- 66 Days On Market
Current Estimated Value $427,103
Last Listing Agent Jim Abbott Baird & Warner
225 Burchell Ave, Highwood, IL 60040 -
Est $431,210
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
Last Listing Agent Joe Tyler Gerber Baird & Warner
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$1,249,000
Pending- 4 Beds
- 4 Baths
- 3,485 Sq Ft
88 Holabird Cir, Highwood, IL 60040
88 Holabird Cir, Highwood, IL 60040Alison Wertheimer @properties Christie's International Real Estate
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$1,900
Total Monthly Price
- 2 Beds
- 1 Bath
- 800 Sq Ft
- Condo for Rent
30 Michigan Ave Unit 2, Highwood, IL 60040
30 Michigan Ave Unit 2, Highwood, IL 6004030 Michigan ave is a two flat house in which the second floor is available for rent. Utilities are $150 additional to rent price. This 2 bedroom 1 bath is 800 square ft with a personal deck that is 300 square ft. This space has been completely renovated with brand new wood floors, new appliances, new cabinets, new bathroom and brand new patio ready for furniture. Parking spot available in
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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 $824,609
Last Listing Agent Michael Mitchell @properties Christie's International Real Estate
762 Deroo Loop Unit 5, Highwood, IL 60040 -
Est $527,460
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
Last Listing Agent Beth Alberts Compass
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$699,000
Open Sun 12PM - 2PM- 6 Beds
- 6 Baths
240 & 242 Highwood Ave, Highwood, IL 60040
240 & 242 Highwood Ave, Highwood, IL 60040Cory Albiani @properties Christie's International Real Estate
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$4,072 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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$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 $855,820
Last Listing Agent Karen Chien-Rooney Compass
795 Stables Ct W Unit 4, Highwood, IL 60040 -
Est $418,456
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
Last Listing Agent Darren Allen Real Broker LLC
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$548,000
$15K PRICE DROP Pending- 3 Beds
- 2 Baths
- 1,108 Sq Ft
Unlisted Address
Unlisted AddressMada Hitchmough Compass
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$2,800 Per Month
- 3 Beds
- 2 Baths
- 1,736 Sq Ft
- Townhouse for Rent
322 Euclid Ave, Highwood, IL 60040
322 Euclid Ave, Highwood, IL 60040Beautifully remodeled 3 bedroom 2 bath duplex is fabulous Highwood location. Lovely updated kitchen, gorgeous hardwood floors throughout much of the home. Parking includes one garage space and one exterior space in the driveway. Close to all the amazing Highwood businesses, train, festivals and schools. Dogs and cats considered at owners discretion. No other pets considered. More photos coming
Mada Hitchmough Compass
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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 $314,522
Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago
307 Prairie Ave, Highwood, IL 60040 -
Est $527,007
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
Last Listing Agent Beth Alberts Compass
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$899,000
Pending- 4 Beds
- 2.5 Baths
- 2,542 Sq Ft
842 Lyster Rd, Highwood, IL 60040
842 Lyster Rd, Highwood, IL 60040Susan Brown Burklin @properties Christie's International Real Estate
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$2,900 Per Month
- 3 Beds
- 2.5 Baths
- 1,680 Sq Ft
- Townhouse for Rent
334 Euclid Ave, Highwood, IL 60040
334 Euclid Ave, Highwood, IL 60040Welcome Home To This Beautifully Maintained 3-Bedroom, 2.5-Bath Half Duplex, Nestled On A Quiet Dead-End Street In A Prime Location. Filled With Natural Light, The Spacious Living & Dining Rooms Offer The Perfect Space For Everyday Living & Entertaining. The Generously Sized Kitchen Features A Cozy Breakfast Area, While All Three Bedrooms Provide Comfortable Living Space & Ample Closet Storage,
Sandra Locascio RE/MAX Suburban
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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 $383,206
Last Listing Agent Sandra Locascio RE/MAX Suburban
228 Llewellyn Ave, Highwood, IL 60040 -
Est $419,881
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
Last Listing Agent Carol Santi Coldwell Banker Realty
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$600,000
- 4 Beds
- 2 Baths
- 1,500 Sq Ft
247 Highwood Ave, Highwood, IL 60040
247 Highwood Ave, Highwood, IL 60040Jim Abbott Baird & Warner
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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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$255,000
Sold Jan 09, 2026330 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 $278,188
Last Listing Agent Andrew Langer @properties Christie's International Real Estate
330 Highwood Ave Unit 2A, Highwood, IL 60040 -
Est $410,610
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
Last Listing Agent Benjamin Lissner Baird & Warner
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$775,000
$25K PRICE DROP Pending- 7 Beds
- 3 Baths
308 Washington Ave, Highwood, IL 60040
308 Washington Ave, Highwood, IL 60040Jim Abbott Baird & Warner
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$2,995 Per Month
- 3 Beds
- 1.5 Baths
- 2,204 Sq Ft
- House for Rent
111 Pleasant Ave, Highwood, IL 60040
111 Pleasant Ave, Highwood, IL 60040Charming single family home with beautiful hardwood floors, new windows and freshly painted throughout! Main level features living room with wood burning fireplace, built-ins and french doors. Separate dining room, and kitchen with all new appliances. Second floor has 3 nice sized bedrooms and a full bath. Lower level has half bath, laundry and plenty of space for storage. Outdoor spaces include
Lane Klein Compass
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$430,000
Sold Feb 24, 2026137 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 $427,483
Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago
137 Highwood Ave, Highwood, IL 60040 -
Est $363,178
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
Last Listing Agent Shara Fata Hashlang, Inc.
Showing Results 1 - 40, Page 1 of 18
Home Prices in Highwood, IL
The median home sale price in Highwood, IL is $550,000, up 11% year-over-year. Homes in Highwood sell in 13 days on average, compared to the national average of 56 days.
Home Price Trends
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Median Sale Price
$550,000
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Median Single Family Sale Price
$600,000
|
|
Median 2 Bedroom Sale Price
$287,500
|
Average Price Per Sq Ft
$288
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|
Number of Homes for Sale
3
|
Last 12 months Home Sales
24
|
|
Months of Supply
1.50
|
Median List Price
$615,000
|
|
Median Change From 1st List Price
0%
|
Median Home Sale Price YoY Change
11%
|
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