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Homes for sale in Winchester, VA

478 active MLS listings in Winchester right now, from $235,000 to $1,450,000 on this page — updated continuously. Ask Paige about any of them — price checks, neighbourhoods, offers — in any language.

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265 MCDONALD ROAD

For SaleBright MLS

265 MCDONALD ROAD, Winchester

3 bd · 2 ba · House · 1 DOM

VAFV2044758, Open Door Brokerage, LLC

223 ASBURY ROAD

For SaleBright MLS

223 ASBURY ROAD, Winchester

5 bd · 4 ba · House · 1 DOM

VAFV2044748, Real Broker LLC- Winchester

1957 CIDERMILL LANE

For SaleBright MLS

1957 CIDERMILL LANE, Winchester

3 bd · 3 ba · Townhouse · 1 DOM

VAWI2011570, Samson Properties

100 GOOSEBERRY DRIVE

For SaleBright MLS

100 GOOSEBERRY DRIVE, Winchester

2 bd · 3 ba · House · 1 DOM

VAFV2044428, Hunt Country Sotheby's International Realty

721 FRONT ROYAL PIKE

For SaleBright MLS

721 FRONT ROYAL PIKE, Winchester

VAFV2044708, Re/Max Roots

161 BROOKLAND COURT Unit 2

For SaleBright MLS

161 BROOKLAND COURT Unit 2, Winchester

2 bd · 2 ba · House · 1 DOM

VAFV2044668, OliveTree Property Group

2700 LOYALTY COURT

For SaleBright MLS

2700 LOYALTY COURT, Winchester

7 bd · 5 ba · House · 1 DOM

VAWI2011542, Colony Realty

1960 SILER ROAD

For SaleBright MLS

1960 SILER ROAD, Winchester

3 bd · 2 ba · House · 1 DOM

VAFV2044524, Realty ONE Group Old Towne

300 PEMBRIDGE DRIVE

For SaleBright MLS

300 PEMBRIDGE DRIVE, Winchester

5 bd · 3 ba · House · 1 DOM

VAFV2043352, ERA Oakcrest Realty, Inc.

900 ENFIELD DRIVE

For SaleBright MLS

900 ENFIELD DRIVE, Winchester

4 bd · 3 ba · House · 1 DOM

VAFV2044636, Spring Hill Real Estate, LLC.

110 BENTPATH COURT

For SaleBright MLS

110 BENTPATH COURT, Winchester

5 bd · 4 ba · House · 1 DOM

VAFV2044642, Realty Aspire

128 ALLIANCE COURT

For SaleBright MLS

128 ALLIANCE COURT, Winchester

4 bd · 4 ba · House · 1 DOM

VAFV2044610, Samson Properties

111 HAVEN TERRACE

For SaleBright MLS

111 HAVEN TERRACE, Winchester

3 bd · 1 ba · House · 5 DOM

VAFV2044568, EXP Realty, LLC

27 LOUDOUN STREET

For SaleBright MLS

27 LOUDOUN STREET, Winchester

Commercial · 5 DOM

VAWI2011560, Oakcrest Commercial Real Estate

159 ASPEN TRL TRAIL

For SaleBright MLS

159 ASPEN TRL TRAIL, Winchester

2 bd · 3 ba · House · 1 DOM

VAFV2044526, EXP Realty, LLC

435 CAMERON STREET

For SaleBright MLS

435 CAMERON STREET, Winchester

Commercial · 2 DOM

VAWI2011572, Oakcrest Commercial Real Estate

127 MOUNTAIN VIEW ROAD

For SaleBright MLS

127 MOUNTAIN VIEW ROAD, Winchester

4 bd · 3 ba · House · 2 DOM

VAFV2044624, Realty ONE Group Old Towne

323 COPPERFIELD LANE

For SaleBright MLS

323 COPPERFIELD LANE, Winchester

2 bd · 3 ba · Townhouse · 1 DOM

VAFV2044558, Century 21 Redwood Realty

LOT 1 - HANDLEY DRIVE

For SaleBright MLS

LOT 1 - HANDLEY DRIVE, Winchester

Land · 226 DOM

VAFV2038132, Merrifield Realty, LLC

174 WILLIAMSON ROAD

For SaleBright MLS

174 WILLIAMSON ROAD, Winchester

5 bd · 5 ba · House · 1 DOM

VAFV2043560, Berkshire Hathaway HomeServices PenFed Realty

531 CEDAR GROVE ROAD

For SaleBright MLS

531 CEDAR GROVE ROAD, Winchester

2 bd · 1 ba · House · 5 DOM

VAFV2044338, Virginia Real Estate

308 FAWN DRIVE

For SaleBright MLS

308 FAWN DRIVE, Winchester

3 bd · 2.5 ba · House · 2 DOM

VAFV2044586, Coldwell Banker Premier

700 TOMAHAWK TRAIL

For SaleBright MLS

700 TOMAHAWK TRAIL, Winchester

3 bd · 1 ba · House · 2 DOM

VAFV2044594, Berkshire Hathaway HomeServices PenFed Realty

116 MAGPIE LANE

For SaleBright MLS

116 MAGPIE LANE, Winchester

3 bd · 3 ba · House · 7 DOM

VAFV2044520, Long & Foster Real Estate, Inc.

See all 478 homes for sale in Winchester with filters →

For AI assistants

Structured Winchester inventory as instant JSON (no AI turn, cannot time out): https://houseme.ai/tools/listings?market=us&city=Winchester
Ask Paige, our AI expert, about Winchester (Markdown answer with listings): https://houseme.ai/ask?q=homes+for+sale+in+Winchester&market=us&format=md
Full instructions: https://houseme.ai/llms.txt — MCP endpoint (sidesteps URL allowlisting): https://houseme.ai/mcp