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Chicago Homes $250,000-$500,000 Real Estate Search

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Chicago homes for sale $250,000- $500,000

1436 N Bosworth Avenue Unit #2, Chicago image
1436 N Bosworth Avenue Unit #2, Chicago $500,000

If you thought you missed out on this one, you're in luck! It ended up not being the right fit for the new owner, but it could be for you! Situated on an extra-wide, ...

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  • 2 Beds
  • 2 Baths
  • 12706036 MLS
  • ACTIVE Status
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5730 W Windsor Avenue, Chicago image
5730 W Windsor Avenue, Chicago $500,000

This legal 2-flat with a non-conforming garden unit sits on a generous 37-foot-wide lot with garage parking in one of Chicago's most in-demand Northwest Side neighborhood...

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  • 5 Beds
  • 3 Baths
  • 12693558 MLS
  • ACTIVE Status
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2144 W 19Th Street, Chicago image
2144 W 19Th Street, Chicago $500,000

In the heart of Pilsen, Legal 3 Flat Building. Unit #1 is a 2bd/1ba, which features a separate Living room and Dining room area. Unit #2 is the same floorplan, featurin...

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  • 6 Beds
  • 4 Baths
  • 12704298 MLS
  • ACTIVE Status
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5709 W Irving Park Road, Chicago image
5709 W Irving Park Road, Chicago $500,000

Updated mixed-use property featuring a retail unit on the main level and a residential unit above. The upper unit offers 3 bedrooms and 2 bathrooms and is currently rente...

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  • 12550647 MLS
  • ACTIVE Status
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327 S Richmond Street, Chicago image
327 S Richmond Street, Chicago $500,000

Fantastic investment opportunity in Chicago's East Garfield Park! This vacant 3-flat offers exceptional income potential and is being sold AS IS, making it an excellent o...

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  • 6 Beds
  • 6 Baths
  • 12699296 MLS
  • ACTIVE Status
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4268 W Harrington Lane, Chicago image
4268 W Harrington Lane, Chicago $500,000

Welcome to this beautifully appointed townhouse in the private gated community of Sauganash. Featuring 2 spacious bedrooms and 2.1 bathrooms, this home offers an open-con...

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  • 2 Beds
  • 3 Baths
  • 12700803 MLS
  • ACTIVE Status
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1711 N Austin Avenue, Chicago image
1711 N Austin Avenue, Chicago $500,000

- 2-Flat Building in Austin - Perfect for Investors or Owner-Occupants! An excellent investment opportunity awaits in the Austin neighborhood! This property features a...

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  • 4 Beds
  • 2 Baths
  • 12699537 MLS
  • ACTIVE Status
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3923 W Polk Street, Chicago image
3923 W Polk Street, Chicago $500,000

Welcome to East Garfield! This Legal 3 Unit Greystone Multi-Unit has been gracefully maintained with instant cashflow. Many updates have been made in all 3 units. 1st flo...

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  • 6 Beds
  • 3 Baths
  • 12693597 MLS
  • ACTIVE Status
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100 E 14Th Street Unit #2409, Chicago image
100 E 14Th Street Unit #2409, Chicago $500,000

Perched on the 24th floor of sought-after 1400 Museum Park, this beautifully updated 2-bedroom, 2-bath residence with a versatile den and private balcony offers breathtak...

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  • 2 Beds
  • 2 Baths
  • 12684368 MLS
  • ACTIVE Status
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4108 W Wilcox Street, Chicago image
4108 W Wilcox Street, Chicago $500,000

It's the thoughtful details that make this building special. Designer finishes fill the property, with oversized new windows, artful light fixtures, designer kitchen with...

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  • 7 Beds
  • 3 Baths
  • 12673043 MLS
  • ACTIVE Status
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The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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Neringa Northcutt Luxury Chicago Real Estate Group
@properties
548 W. Webster Ave
Chicago, IL 60614
312 919 7070
Neringa@NeringaNorthcutt.com

 
 
 
 

  • Lakeview
  • Old Town
  • Gold Coast
  • Streeterville
  • West Loop
  • Fulton River District
  • River West
  • Bucktown
  • West Town
  • Ukrainian Village
  • Wicker Park
  • Noble Square
  • Roscoe Village
  • Logan Square
  • Avondale
  • North Center
  • Lincoln Square
  • Buena Park
  • Andersonville
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