5 Bedroom Homes in Winchester, VA

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3 beds New construction With a pool

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24 of 35 Listings

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5 Bedroom Homes in Winchester, VA

24 of 35 Listings

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Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

83Active
$1,025,000
5 bd · 4 ba · 3,870 sqft
632 Stonymeade Dr, Winchester, VA
Katrina M Smith · Samson Properties
51Active
$615,000
5 bd · 3 ba · 2,515 sqft
102 Forest Valley Rd, Winchester, VA
Julie M Teets · ERA Oakcrest Realty, Inc.
71Active
$1,170,000
5 bd · 6 ba · 3,846 sqft
854 Valley Mill Rd, Winchester, VA
Linden McLean · Samson Properties

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: 2026-09-03 20:24:07 UTC

Winchester housing market

August 2026 · This period is still settling

Selling at 99.0% of asking price

Buyers here are paying below asking. MLS · 78 sales · as of Aug 28, 2026

Homes that sold · County records, as of Aug 12, 2026

Median sale price: $436,660$322,000–$559,900 typical range
Price per sq. ft.: $237
Sales: 33
Paid in cash: 30.3%

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Median list price: $429,450
Homes for sale: 326
Median days on market: 37 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 3.8%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 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

Explore Winchester homes

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: 2026-09-03 20:24:07 UTC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

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

Winchester housing market

August 2026 · This period is still settling

Selling at 99.0% of asking price

Buyers here are paying below asking. MLS · 78 sales · as of Aug 28, 2026

Homes that sold · County records, as of Aug 12, 2026

Median sale price: $436,660$322,000–$559,900 typical range
Price per sq. ft.: $237
Sales: 33
Paid in cash: 30.3%

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Median list price: $429,450
Homes for sale: 326
Median days on market: 37 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 3.8%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,620 sq. ft.

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Your local brokerage

Listing data & MLS disclosures

Winchester housing market

Homes that sold · County records, as of Aug 12, 2026

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 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 Aug 12, 2026

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026