5 Bedroom Homes in Winchester, VA

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3 beds New construction With a pool

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24 of 40 Listings

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5 Bedroom Homes in Winchester, VA

24 of 40 Listings

57Active

40 listings

5 Bedroom Homes in Winchester, VA

Show Map

24 of 40 Listings

Map

5 Bedroom Homes in Winchester, VA

24 of 40 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

57Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

$599,990

5 bd · 5 ba · 3,386 sqft

112 Wappinger Ter, Winchester, VA

Victoria Jane Clark · D R Horton Realty of Virginia LLC

30Active

$530,345

5 bd · 3 ba · 2,415 sqft

138 Wappinger Ter, Winchester, VA

Victoria Jane Clark · D R Horton Realty of Virginia LLC

34Active

$512,990

5 bd · 4 ba · 2,446 sqft

130 Seminole Dr, Winchester, VA

Victoria Jane Clark · D R Horton Realty of Virginia LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

76Active

$539,900

5 bd · 4 ba · 3,290 sqft

114 Settlers Cir, Winchester, VA

Daniel J Whitacre · Colony Realty

58Active

$748,900

5 bd · 3 ba · 5,430 sqft

416 Briarmont Dr, Winchester, VA

John B Schroth · Colony Realty

43Active

$340,000

5 bd · 1 ba · 1,200 sqft

199 Dicks Hollow Rd, Winchester, VA

Cynthia Lee · RE/MAX Roots

49Active

$479,900

5 bd · 3 ba · 3,276 sqft

109 Julee Dr, Winchester, VA

Josh W Feltner · Realty ONE Group Old Towne

75Active

$634,900

5 bd · 4 ba · 3,856 sqft

314 Huntersridge Rd, Winchester, VA

Laura D White · ERA Oakcrest Realty, Inc.

48Active

$439,000

5 bd · 3 ba · 2,508 sqft

300 Pembridge Dr, Winchester, VA

Magnolia L Halkowitz · ERA Oakcrest Realty, Inc.

16Active

$759,900

5 bd · 5 ba · 2,383 sqft

174 Williamson Rd, Winchester, VA

Brenda Mangum Miller · Berkshire Hathaway HomeServices PenFed Realty

70Active

$674,000

5 bd · 4 ba · 4,623 sqft

337 Canyon Rd, Winchester, VA

Sharon Farinholt · Realty ONE Group Old Towne

83Active

$1,025,000

5 bd · 4 ba · 3,870 sqft

632 Stonymeade Dr, Winchester, VA

Katrina M Smith · Samson Properties

Price Reduced51Active

$597,000

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

73Active

$615,000

5 bd · 4 ba · 3,626 sqft

922 Wayne Dr, Winchester, VA

Katrina M Smith · Samson Properties

25Active

$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

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 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 Reduced90Active

$625,000

5 bd · 3 ba · 4,030 sqft

146 Stonebrook Rd, Winchester, VA

Bradley Comstock · ERA Oakcrest Realty, Inc.

Price Reduced32Active

$614,999

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

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: 2026-09-22 00:22:10 UTC

Winchester housing market

August 2026

Selling at 99.0% of asking price

Buyers here are paying below asking. MLS · 86 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $382,500$283,750–$562,175 typical range
Price per sq. ft.: $234
Sales: 112
Paid in cash: 30.4%

Homes on the market · MLS, as of 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: 2026-09-22 00:22:10 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

Selling at 99.0% of asking price

Buyers here are paying below asking. MLS · 86 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $382,500$283,750–$562,175 typical range
Price per sq. ft.: $234
Sales: 112
Paid in cash: 30.4%

Homes on the market · MLS, as of 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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Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winchester housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of 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 31, 2026

Homes on the market · MLS, as of 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