Highwood, IL Homes

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  /24

  $775,000

  • 5 Beds
  • 4 Baths

  43 Clay Ave, Highwood, IL 60040

  Exceptional investment opportunity in the heart of downtown ! Perfectly situated on a quiet one-way street within the city's vibrant business district, this beautifully maintained and newly remodeled three-flat has been thoughtfully updated from top to bottom. Each unit showcases stylish new kitchens and baths with modern cabinetry, quartz countertops, updated lighting and fixtures, new tile,

  Jim Abbott Baird & Warner

  43 Clay Ave, Highwood, IL 60040
• Explore Highwood

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  /49

  Starting at $2,248 Per Month

  • 1 - 3 Beds

  440 Green Bay Rd, Highwood, IL 60040

  Welcome 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

  

  440 Green Bay Rd, Highwood, IL 60040
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  /2

  $355,000 Sold Jun 16, 2025

  328 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 $362,839

  Last Listing Agent David Wilkerson eXp Realty

  328 Oak Terrace Ave, Highwood, IL 60040
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  /34

  Est $522,911 Not Listed For Sale

  330 Prairie Ave, Highwood, IL 60040

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

  330 Prairie Ave, Highwood, IL 60040

  Last Sold Summary

  • $372/SF
  • 5 Days On Market

  • Last Sold Price $525,000
  • May 07, 2025

  Last Listing Agent Keith Brand Berkshire Hathaway HomeServices Chicago
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  /20

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  225 Burchell Ave, Highwood, IL 60040

  Discover an incredible opportunity in the heart of downtown Highwood! This 3-bedroom, 2-bath home offers unbeatable location and flexibility, perfect for both investors and owner-occupants. The second floor features 3 spacious bedrooms and a full bath, providing a comfortable and functional living space, while the main level offers great potential to customize or enhance to your vision.

  Jim Abbott Baird & Warner

  225 Burchell Ave, Highwood, IL 60040
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  /35

  Starting at $1,719 Per Month

  • 1 - 3 Beds

  634 Sheridan Rd, Highwood, IL 60040

  Nestled 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

  

  634 Sheridan Rd, Highwood, IL 60040
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  /21

  $285,000 Sold Apr 01, 2026

  330 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 $300,768

  Last Listing Agent Jim Abbott Baird & Warner

  330 Highwood Ave Unit 2B, Highwood, IL 60040
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  /21

  Not Listed For Sale

  114 Michigan Ave, Highwood, IL 60040

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • Built 1933

  114 Michigan Ave, Highwood, IL 60040

  Last Sold Summary

  • $239/SF

  • Last Sold Price $525,000

  Last Listing Agent Derek DiSera Compass
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  /25

  $375,000

  • 3 Beds
  • 1 Bath
  • 1,450 Sq Ft

  239 Sheridan Ave, Highwood, IL 60040

  Charming Home Steps from Downtown Highwood! Welcome to this inviting 3-bedroom, 1-bath home located just steps from vibrant downtown Highwood. Featuring a large kitchen with an attached dining room, this home offers the perfect blend of comfort and convenience. The partially finished basement provides additional living space or room to grow, while the 2-car garage adds valuable storage and

  Carol Santi Coldwell Banker Realty

  239 Sheridan Ave, Highwood, IL 60040
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  /19

  $3,600 Per Month

  • 4 Beds
  • 2 Baths
  • House for Rent

  144 Morgan Place, Highwood, IL 60040

  Property Id: 2434416Renovated 4BR Brick Home in Heart of HighwoodThis solid brick 4-bedroom, 2-bathroom home has been updated and is move-in ready. Located just steps from Highwood’s restaurants, the Metra, and the lake, it offers a great balance of neighborhood charm and modern reliability.The SpaceThe house features a functional layout with a bright living room,

  (224) 360-5364

  144 Morgan Place, Highwood, IL 60040
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  /16

  $700,000 Sold Nov 07, 2025

  738 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 $722,095

  Last Listing Agent Susan Brown Burklin @properties Christie's International Real Estate

  738 Lyster Rd Unit 1, Highwood, IL 60040
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  /20

  Est $483,366 Not Listed For Sale

  32 Michigan Ave, Highwood, IL 60040

  • 4 Beds
  • 2 Baths
  • 1,722 Sq Ft
  • Built 1923

  32 Michigan Ave, Highwood, IL 60040

  Last Sold Summary

  • 9% Below List Price
  • $307/SF
  • 9 Days On Market

  • Last Sold Price $529,000
  • Aug 27, 2024

  Last Listing Agent Beth Alberts Compass
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  /19

  $600,000

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  247 Highwood Ave, Highwood, IL 60040

  TOTALLY UPDATED in 2025 and MOVE IN READY RANCH with a finished basement and two full bathrooms! The main level features an open kitchen with space for a breakfast or dining table and home office desk, a comfortable living room, and two bedrooms served by a full bath with a walk-in shower. The finished lower level offers an additional full bath with tub, laundry area, and a bedroom with an

  Jim Abbott Baird & Warner

  247 Highwood Ave, Highwood, IL 60040
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  /13

  $2,035 Per Month

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

  546 Green Bay Rd Unit 408, Highwood, IL 60040

  Luxury 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.

  546 Green Bay Rd Unit 408, Highwood, IL 60040
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  /36

  $799,000 Sold Sep 19, 2025

  762 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 $798,391

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

  762 Deroo Loop Unit 5, Highwood, IL 60040
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  /26

  Est $432,209 Not Listed For Sale

  102 High St, Highwood, IL 60040

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft
  • Built 1930

  102 High St, Highwood, IL 60040

  Last Sold Summary

  • 6% Above List Price
  • $328/SF
  • 9 Days On Market

  • Last Sold Price $408,000
  • Jul 02, 2024

  Last Listing Agent Joe Tyler Gerber Baird Warner
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  /25

  $899,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,542 Sq Ft

  842 Lyster Rd, Highwood, IL 60040

  Beautifully updated historic 4-bedroom home in sought-after Fort Sheridan, offering the perfect blend of charm and thoughtful updates. Step into an expansive foyer that opens to a spacious great room featuring a gas fireplace and stunning hardwood floors. The eat-in kitchen opens to a lovely patio-ideal for morning coffee while enjoying the scenic surroundings Fort Sheridan is known for. The

  Susan Brown Burklin @properties Christie's International Real Estate

  842 Lyster Rd, Highwood, IL 60040
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  /21

  $1,950

  Total Monthly Price

  • 3 Beds
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  226 North Ave Unit 1, Highwood, IL 60040

  Beautiful unfurnished 3 bedroom (or 2 bedroom + office) apartment in Highwood. 1st floor of 2 unit building. Walk to town and train. Laundry + storage in basement. 1 garage spot + 1 parking spot. Yard and patio. Tenant pays electric and cable. Available June 15th. $1950 per month. $1950 security deposit + 1 month rent required at lease signing. No pets.

  226 North Ave Unit 1, Highwood, IL 60040
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  /2

  $890,000 Sold Oct 01, 2025

  795 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 $890,622

  Last Listing Agent Karen Chien-Rooney Compass

  795 Stables Ct W Unit 4, Highwood, IL 60040
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  /19

  Est $516,402 Not Listed For Sale

  125 Maple Ave, Highwood, IL 60040

  • 3 Beds
  • 2 Baths
  • 1,443 Sq Ft
  • Built 1931

  125 Maple Ave, Highwood, IL 60040

  Last Sold Summary

  • 2% Below List Price
  • $364/SF
  • 18 Days On Market

  • Last Sold Price $525,000
  • Jul 09, 2024

  Last Listing Agent Beth Alberts Compass
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  /38

  $899,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,750 Sq Ft

  44 Westover Rd, Highwood, IL 60040

  Beautiful spacious home for sale in historic Fort Sheridan within easy walking distance to Lake Michigan, lakeshore forest preserve, two Metra stations, and all the incredible restaurants and entertainment of Highwood. Featuring a large open floor plan main floor with vaulted ceiling and large windows allowing plenty of natural light into the living area. The kitchen is a chef's dream with a 60"

  Ryan Cherney Circle One Realty

  44 Westover Rd, Highwood, IL 60040
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  /20

  $2,200 Per Month

  • 2 Beds
  • 1 Bath
  • 1,163 Sq Ft
  • Apartment for Rent

  47 Prairie Ave Unit 1, Highwood, IL 60040

  Charming 1st Floor 2-Bedroom, 1-Bath Apartment Available June 1st. This Sun-Filled, Well-Maintained Unit Offers Spacious Rooms With A Bright & Welcoming Atmosphere. New Refrigerator, Stove, Exhaust Fan, Dishwasher + New Paint Thru (2025). The Large Kitchen Boasts Abundant Cabinet Space & A Walk-In Pantry/Mudroom For Added Convenience. The Full Bath Features A Tub/Shower Combo & Dual Sinks.

  Sandra Locascio RE/MAX Suburban

  47 Prairie Ave Unit 1, Highwood, IL 60040
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  /2

  $190,000 Sold Oct 01, 2025

  307 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 $267,004

  Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago

  307 Prairie Ave, Highwood, IL 60040
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  /19

  Est $384,720 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

  • 17% Above List Price
  • $248/SF
  • 29 Days On Market

  • Last Sold Price $327,500
  • Sep 19, 2023

  Last Listing Agent Carol Santi Coldwell Banker Realty
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  /29

  $800,000

  • 7 Beds
  • 3 Baths

  308 Washington Ave, Highwood, IL 60040

  Fully rehabbed brick 3-flat on an oversized double lot in the heart of Highwood-an exceptional, turn-key investment opportunity with strong, stable income already in place. This property features two expansive 3-bedroom, 1-bath units (Unit 1 rented at $2,950 and Unit 2 at $2,755) plus a 1-bedroom, 1-bath unit (Unit 3 rented at $1,450), all leased through March 2027 for immediate cash flow and

  Jim Abbott Baird & Warner

  308 Washington Ave, Highwood, IL 60040
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  /13

  $2,053 Per Month

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

  546 Green Bay Rd Unit 202, Highwood, IL 60040

  Luxury 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.

  546 Green Bay Rd Unit 202, Highwood, IL 60040
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  /29

  $350,000 Sold Jun 12, 2025

  238 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 $358,850

  Last Listing Agent Frank Rusin Four Seasons Realty, Inc.

  238 Jeffreys Place, Highwood, IL 60040
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  /4

  Est $362,004 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

  • 1% Above List Price
  • $334/SF
  • 17 Days On Market

  • Last Sold Price $359,000
  • Sep 23, 2024

  Last Listing Agent Shara Fata Hashlang, Inc.
• 

  

  /30

  $1,250,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 4,222 Sq Ft

  47 Holabird Cir, Highwood, IL 60040

  Wonderfully Spacious, Sunny, Brick Home with Lovely Yard Space, in Fort Sheridan! Grand 2-Story Entry Opens to a Huge, Light-Filled Great Room with Soaring Ceilings and Walls of Windows, Flowing into the Large Kitchen with Island and Breakfast Bar and a Separate Eating Area Surrounded by Windows and Flooded with Light. The Main Floor also includes a Formal Living Room, Dining Room, Office with

  Janet Borden Compass

  47 Holabird Cir, Highwood, IL 60040
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  /15

  $3,201 Per Month

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

  440 Green Bay Rd Unit 605, 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 605, Highwood, IL 60040
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  /38

  $885,000 Sold Jun 30, 2025

  27 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 $917,699

  Last Listing Agent Alison Wertheimer @properties Christie's International Real Estate

  27 Rienzi Ln, Highwood, IL 60040
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  /20

  Est $489,217 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

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

  • Last Sold Price $500,000
  • Jul 31, 2024

  Last Listing Agent Beth Alberts Compass
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  /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
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  /13

  $2,503 Per Month

  • 1 Bed
  • 1 Bath
  • 1,057 Sq Ft
  • Apartment for Rent

  440 Green Bay Rd Unit 413, 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 413, Highwood, IL 60040
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  /29

  $375,000 Sold Dec 19, 2025

  228 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 $368,756

  Last Listing Agent Sandra Locascio RE/MAX Suburban

  228 Llewellyn Ave, Highwood, IL 60040
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  /2

  Est $500,892 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
  • Aug 09, 2023

  Last Listing Agent Frank Nash Baird Warner
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  /2

  $150,000

  • Land
  • 0 Sq Ft

  0 Wrendale Ave Unit MRD12487576, Highwood, IL 60040

  BUILD YOUR DREAM HOME ON THIS GREAT LOT IN SOUTHEAST HIGHWOOD! LOT HAS A WATER LINE INSTALLED AND AN EASEMENT FOR OTHER UTILITIES. GREAT LOCATION, WALK TO EVERYTHING IN BOOMING HIGHWOOD! ZONED R2 (residential). BUILD UP TO A 2,864 SQUARE FOOT SINGLE FAMILY HOME ON THIS LOT.

  Cory Albiani @properties Christie's International Real Estate

  0 Wrendale Ave Unit MRD12487576, Highwood, IL 60040
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  /15

  $3,075 Per Month

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft
  • Apartment for Rent

  440 Green Bay Rd Unit 608, 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 608, Highwood, IL 60040
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  /2

  $830,000 Sold Jul 07, 2025

  754 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 $812,150

  Last Listing Agent Susan Brown Burklin @properties Christie's International Real Estate

  754 Lyster Rd Unit D, Highwood, IL 60040
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  /17

  Est $554,161 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
  • Sep 06, 2024

  Last Listing Agent Janice Goldblatt @ Properties

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