Homes Under $500K in Winchester, VA

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24 of 218 Listings

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Thomas O'Leary

Realty.com

Lic. #0225245042

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New26Active
$374,990
3 bd · 3 ba · 2,000 sqft
Lot 9 Shuoner Ct, Winchester, VA
James Thomas · New Home Star Virginia, LLC
New11Active
$429,990
4 bd · 4 ba · 2,094 sqft
116 Coriander Way, Winchester, VA
Elizabeth Ellis · Brookfield Mid-Atlantic Brokerage, LLC
New24Active
$359,990
3 bd · 3 ba · 1,651 sqft
675 Arden Ct, Winchester, VA
Victoria Jane Clark · D R Horton Realty of Virginia LLC

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-10-18 18:47:54 UTC

About Homes Under $500K in Winchester, VA

Homes Under $500K in Winchester, VA: 218 active listings as of October 18, 2026, 23:10 UTC.

Property types among these 218 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property type	Listings	Share
Single Family Residence	124	56.9%
Townhouse	58	26.6%
Condominium	14	6.4%

Winchester housing market

September 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 91 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 30, 2026

Median sale price: $399,000$306,725–$581,250 typical range
Price per sq. ft.: $252
Sales: 119
Paid in cash: 36.1%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $422,495
Homes for sale: 334
Median days on market: 33 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -6.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

Median home size: 1,620 sq. ft.

Winchester, VA community profile

Population: 27,805
Median income: $66,091
Housing units: 12,270
People per sq. mi.: 128.8
Area: 215.8 sq. mi.

Source: HJN community data

Homes Under $500K in Winchester, VA

Your local brokerage

Listing data & MLS disclosures

About Homes Under $500K in Winchester, VA

Winchester housing market

Homes that sold · County records, as of Sep 30, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

Winchester, VA community profile

Explore Winchester homes

Listing data & MLS disclosures

Your local brokerage

Your local brokerage

Winchester, VA community profile

Winchester housing market

Homes that sold · County records, as of Sep 30, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026