Highwood, IL Homes

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  $800,000

  • 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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  /3

  $2,468 per month

  • 2 Beds
  • 2 Baths
  • 975 Sq Ft
  • Condo for Rent

  542 Green Bay Rd Unit 209, Highwood, IL 60040

  542 Green Bay Rd Unit 209, 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 $368,637

  Last Listing Agent David Wilkerson eXp Realty

  328 Oak Terrace Ave, Highwood, IL 60040
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  /13

  Est $419,457 Not Listed For Sale

  536 N Central Ave, Highwood, IL 60040

  • 3 Beds
  • 3 Baths
  • 2,347 Sq Ft
  • Built 1961

  536 N Central Ave, Highwood, IL 60040

  Last Sold Summary

  • 17% Above List Price
  • $153/SF

  Last Sold Price $360,000

  Last Listing Agent Carolyn Cerf @ Properties
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  /11

  $779,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,400 Sq Ft

  535 Lockard Ln, Highwood, IL 60040

  Detached single family with over 2,400 square ft with a once in a lifetime layout. 45 foot backyard that lays out directly from the kitchen. 4 bedrooms or an office. Open layout. Pre-construction pricing. Pictures are architectural renderings of possibilities and potential options to be decided with builder. - $15,000 of free options if under contract by 2/15/2026

  Jorge Zea Jorge Zea Managing Broker

  535 Lockard Ln, Highwood, IL 60040
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  /30

  $4,249 per month

  • 3 Beds
  • 2.5 Baths
  • 1,759 Sq Ft
  • Townhouse for Rent

  25 Clay Ave Unit D, Highwood, IL 60040

  Rarely 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

  25 Clay Ave Unit D, 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 $709,423

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

  738 Lyster Rd Unit 1, Highwood, IL 60040
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  /19

  Est $382,840 Not Listed For Sale

  340 Ashland Ave Unit 108, Highwood, IL 60040

  • 2 Beds
  • 2.5 Baths
  • 1,543 Sq Ft
  • Built 1979

  340 Ashland Ave Unit 108, Highwood, IL 60040

  Last Sold Summary

  • 5% Above List Price
  • $237/SF
  • 2 Days On Market

  Last Sold Price $366,000

  Last Listing Agent Shannon Towson Coldwell Banker Realty
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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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  /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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  /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 $797,793

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

  762 Deroo Loop Unit 5, Highwood, IL 60040
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  /24

  Est $680,568 Not Listed For Sale

  705 Lyster Rd, Highwood, IL 60040

  • 3 Beds
  • 2.5 Baths
  • 2,560 Sq Ft
  • Built 2002

  705 Lyster Rd, Highwood, IL 60040

  Last Sold Summary

  • 9% Above List Price
  • $244/SF
  • 4 Days On Market

  Last Sold Price $625,000

  Last Listing Agent Susan Brown Burklin @ Properties
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  /19

  $600,000 Open Sun 1PM - 3PM

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

  247 Highwood Ave, Highwood, IL 60040

  Totally updated ranch 2025 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 attached bonus room-ideal

  Jim Abbott Baird & Warner

  247 Highwood Ave, Highwood, IL 60040
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  /13

  $2,400 per month

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

  440 Green Bay Rd Unit 506, 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 506, 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 $901,496

  Last Listing Agent Karen Chien-Rooney Compass

  795 Stables Ct W Unit 4, Highwood, IL 60040
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  /2

  Est $728,156 Not Listed For Sale

  740 Deroo Loop, Highwood, IL 60040

  • 3 Beds
  • 2.5 Baths
  • 2,708 Sq Ft
  • Built 2000

  740 Deroo Loop, Highwood, IL 60040

  Last Sold Summary

  • 7% Above List Price
  • $251/SF
  • 27 Days On Market

  Last Sold Price $680,000

  Last Listing Agent Mona Hellinga @ Properties
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  /20

  $400,000 Open Sun 10:30AM - 12:30PM

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

  225 Burchell Ave, Highwood, IL 60040

  Great unit for investors, there is already a tenant in there month to month that would like to stay. Walk out unfinished basement with bathroom. PLEASE NOTE MANY PHOTOS ARE VIRTUALLY STAGED. Original is first photo, followed by the staged version of it.

  Jim Abbott Baird & Warner

  225 Burchell Ave, Highwood, IL 60040
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  $3,100 per month

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Apartment for Rent

  440 Green Bay Rd Unit 309, 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 309, 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 $265,234

  Last Listing Agent Jeannine Viti Berkshire Hathaway HomeServices Chicago

  307 Prairie Ave, Highwood, IL 60040
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  /40

  Not Listed For Sale

  114 Michigan Ave, Highwood, IL 60040

  • 3 Beds
  • 1 Bath
  • 2,200 Sq Ft
  • Built 1933

  114 Michigan Ave, Highwood, IL 60040

  Last Sold Summary

  • $239/SF
  • 255 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Mada Hitchmough Compass
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  /3

  $149,000

  • Land
  • 0 Acre

  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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  /16

  $3,759 per month

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Apartment for Rent

  440 Green Bay Rd Unit 305, Highwood, IL 60040

  This three-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 305, 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 $363,335

  Last Listing Agent Frank Rusin Four Seasons Realty, Inc.

  238 Jeffreys Place, Highwood, IL 60040
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  /33

  Est $630,576 Not Listed For Sale

  338 Burchell Ave, Highwood, IL 60040

  • 3 Beds
  • 3.5 Baths
  • 4,002 Sq Ft
  • Built 1971

  338 Burchell Ave, Highwood, IL 60040

  Last Sold Summary

  • 20% Above List Price
  • $131/SF
  • 26 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Anthony Maione @ Properties
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  /28

  $799,900 New Construction

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

  525 Lockard Ln, Highwood, IL 60040

  Proposed custom home well below market value for a limited time. First floor owners suites and ranch plans now available. Won't last long.

  Jorge Zea Jorge Zea Managing Broker

  525 Lockard Ln, Highwood, IL 60040
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  /15

  $2,975 per month

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

  546 Green Bay Rd Unit 506, 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 506, 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 $898,835

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

  27 Rienzi Ln, Highwood, IL 60040
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  /20

  Est $490,556 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

  • 7% Below List Price
  • $307/SF
  • 9 Days On Market

  Last Sold Price $529,000

  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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  /14

  $3,200 per month

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

  440 Green Bay Rd Unit 508, 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 508, 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 $368,934

  Last Listing Agent Sandra Locascio RE/MAX Suburban

  228 Llewellyn Ave, Highwood, IL 60040
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  /26

  Est $432,137 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

  Last Listing Agent Joe Tyler Gerber Baird Warner
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  /29

  $800,000

  • 7 Beds
  • 3 Baths

  308 Washington Ave, Highwood, IL 60040

  Great investment property in Highwood. Unit 1 is 6 rooms, 3 bed, 1 bath rented at $2,950. Unit 2 is 6 rooms, 3 bed, 1 bath rented at $2,755. Unit 3 a 3 room 1 bath 1 bath rented at $1,450. Garage houses 4 cars, two spaces double deep. ALL LEASES THROUGH MARCH 2027. Currently tenant only responsible for wifi/internet. Landlord charges $50 a month for all other utilities. PHOTOS ARE VIRTUALLY

  Jim Abbott Baird & Warner

  308 Washington Ave, Highwood, IL 60040
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  /13

  $2,200 per month

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

  246 Green Bay Rd Unit 202, 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 202, 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 $836,700

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

  754 Lyster Rd Unit D, Highwood, IL 60040
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  /19

  Est $517,508 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

  • 1% Below List Price
  • $364/SF
  • 18 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Beth Alberts Compass
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  /2

  $150,000

  • Land
  • 0 Acre

  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

  $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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  /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 $278,371

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

  330 Highwood Ave Unit 2A, Highwood, IL 60040
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  /15

  Est $403,763 Not Listed For Sale

  144 Morgan Place, Highwood, IL 60040

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft
  • Built 1955

  144 Morgan Place, Highwood, IL 60040

  Last Sold Summary

  • 4% Above List Price
  • $318/SF
  • 18 Days On Market

  Last Sold Price $389,000

  Last Listing Agent Darren Allen Real Broker LLC

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