5 Bedroom Homes in Winchester, VA

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3 beds New construction With a pool

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24 of 36 Listings

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5 Bedroom Homes in Winchester, VA

24 of 36 Listings

83Active

36 listings

5 Bedroom Homes in Winchester, VA

Hide Map

24 of 36 Listings

Map

5 Bedroom Homes in Winchester, VA

24 of 36 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

83Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

$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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

73Active

$615,000

5 bd · 4 ba · 3,626 sqft

922 Wayne Dr, Winchester, VA

Katrina M Smith · Samson Properties

42Active

$499,900

5 bd · 3 ba · 2,528 sqft

102 Primrose Pl, Winchester, VA

Nestor D Gotay · Corcoran McEnearney

Price Reduced77Active

$710,000

5 bd · 4 ba · 4,542 sqft

103 Renee Ln, Winchester, VA

Leila Smith · Pearson Smith Realty, LLC

21Active

$519,990

5 bd · 4 ba · 2,297 sqft

139 Wappinger Ter, Winchester, VA

Matt Boyer · Keller Williams Realty

142Active

$760,000

5 bd · 5 ba · 4,438 sqft

769 Seldon Dr, Winchester, VA

Amanda Slate · Keller Williams Realty

51Active

$530,000

5 bd · 4 ba · 2,417 sqft

1605 Fort Braddock Ct, Winchester, VA

Timothy R Kotlowski · Long & Foster Real Estate, Inc.

Price Reduced80Active

$699,000

5 bd · 5 ba · 3,767 sqft

199 Meeting House Dr, Winchester, VA

Katie Anne Deskins · Century 21 Redwood Realty

Price Reduced26Active

$749,900

5 bd · 4 ba · 4,220 sqft

175 Shields Dr, Winchester, VA

Sheila R Pack · RE/MAX Roots

85Active

$725,000

5 bd · 4 ba · 4,408 sqft

223 Fairfield Dr, Winchester, VA

Antonella Costa · Samson Properties

Price Reduced60Active

$935,000

5 bd · 3 ba · 3,278 sqft

218 Babbs Mountain Rd, Winchester, VA

John Ginty · Samson Properties

Price Reduced90Active

$649,900

5 bd · 3 ba · 4,030 sqft

146 Stonebrook Rd, Winchester, VA

Bradley Comstock · ERA Oakcrest Realty, Inc.

1Active

$625,000

5 bd · 3 ba · 3,093 sqft

139 Darby Dr, Winchester, VA

Ally Goldwater · Coldwell Banker Realty

32Active

$630,000

5 bd · 4 ba · 3,135 sqft

313 Lehigh Dr, Winchester, VA

Maqsood A Khan · Golston Real Estate Inc.

81Active

$969,000

5 bd · 4 ba · 3,932 sqft

485 Lake Serene Dr, Winchester, VA

Angela R. Duncan · MarketPlace REALTY

Price Reduced43Active

$499,000

5 bd · 4 ba · 2,288 sqft

144 Morning Glory, Winchester, VA

James Michael Powell · RE/MAX Supercenter

Price Reduced93Active

$714,000

5 bd · 4 ba · 4,264 sqft

342 Canyon Rd, Winchester, VA

Michele L Gibson · Samson Properties

Price Reduced101Active

$849,900

5 bd · 5 ba · 5,226 sqft

102 Julie Ct, Winchester, VA

Charles Witt · Nova Home Hunters Realty

103Active

$750,000

5 bd · 5 ba · 4,731 sqft

136 Cahille Dr, Winchester, VA

Victoria Davis · Century 21 Redwood Realty

Price Reduced52Active

$559,000

5 bd · 3 ba · 2,368 sqft

440 Canyon Rd, Winchester, VA

Tami Rene' Woerl · ERA Oakcrest Realty, Inc.

Price Reduced31Active

$489,990

5 bd · 3 ba · 2,415 sqft

130 Wappinger Ter, Winchester, VA

Victoria Jane Clark · D R Horton Realty of Virginia LLC

Price Reduced57Active

$784,900

5 bd · 5 ba · 5,310 sqft

118 Aulee Ct, Winchester, VA

George W Glaize Jr. · George W. Glaize, Jr., Inc. REALTOR

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: 2026-09-04 16:41:08 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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

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: 2026-09-04 16:41:08 UTC

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

Your local brokerage

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

Your local brokerage

Listing data & MLS disclosures

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