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Homes for sale in Winchester, VA

Figures for Winchester, VA, week ending September 15, 2026.

Paige

watching Winchester · 573 homes for sale

Paige

If you want to see what is active, 102 Forest Valley Road is a 5 bedrooms residential asking $597,000 that was listed 20 days ago and reduced from $615,000. Nearby, 63 Riflemen Lane is a 3 bedrooms residential listed 22 days ago at $394,900, down from its original ask of $409,900. Looking at the wider picture, 37 asking prices were reduced in the last 7 days with a median reduction of 4.9%. Homes currently listed show a median days on market of 37, while 106 homes sold in the last 30 days at a median of 41 days on market before selling. With 106 sales over the past month against 21 new arrivals this week, price adjustments like the ones on Forest Valley Road and Riflemen Lane are keeping the inventory moving. Are you looking to buy or sell a home in Winchester soon?

102 FOREST VALLEY ROAD

For SaleBright MLS

102 FOREST VALLEY ROAD, Winchester

5 bd · 3 ba · House · 21 DOM

VAFV2044454, ERA Oakcrest Realty, Inc.

63 RIFLEMEN LANE

Under ContractBright MLS

63 RIFLEMEN LANE, Winchester

3 bd · 2 ba · House · 23 DOM

VAWI2011452, RE/MAX Roots

131 SHIRLEY STREET

For SaleBright MLS

131 SHIRLEY STREET, Winchester

3 bd · 3 ba · House · 1 DOM

VAWI2011614, Pifer Realty, LLC

902 PANTHER DRIVE

For SaleBright MLS

902 PANTHER DRIVE, Winchester

3 bd · 2.5 ba · House · 2 DOM

VAFV2044744, Coldwell Banker Premier

For SaleBright MLS

610 PUMA TRAIL, Winchester

2 bd · 1 ba · House · 2 DOM

VAFV2044850, EXP Realty, LLC

144 APPLE VALLEY ROAD

For SaleBright MLS

144 APPLE VALLEY ROAD, Winchester

3 bd · 2 ba · House · 2 DOM

VAFV2044840, ERA Oakcrest Realty, Inc.

904 PANTHER DRIVE

For SaleBright MLS

904 PANTHER DRIVE, Winchester

3 bd · 2.5 ba · House · 2 DOM

VAFV2044836, Coldwell Banker Premier

114 NASSAU DRIVE

For SaleBright MLS

114 NASSAU DRIVE, Winchester

4 bd · 4 ba · House · 4 DOM

VAFV2044810, RE/MAX Galaxy

421 LONGVIEW AVENUE

For SaleBright MLS

421 LONGVIEW AVENUE, Winchester

3 bd · 2.5 ba · House · 4 DOM

VAWI2011610, Samson Properties

109 JULEE DRIVE

For SaleBright MLS

109 JULEE DRIVE, Winchester

5 bd · 2.5 ba · House · 4 DOM

VAFV2044802, Realty ONE Group Old Towne

120 COMANCHE TRAIL

For SaleBright MLS

120 COMANCHE TRAIL, Winchester

4 bd · 2 ba · House · 4 DOM

VAFV2044756, NextHome Realty Select

510 CAMERON STREET

For SaleBright MLS

510 CAMERON STREET, Winchester

3 bd · 3 ba · House · 4 DOM

VAWI2011602, Samson Properties

621 WATSON AVENUE

For SaleBright MLS

621 WATSON AVENUE, Winchester

3 bd · 2 ba · Townhouse · 5 DOM

VAWI2011582, Samson Properties

For SaleBright MLS

178 PAYNE ROAD, Winchester

4 bd · 2 ba · House · 5 DOM

VAFV2044446, Century 21 Redwood Realty

314 HUNTERSRIDGE ROAD

For SaleBright MLS

314 HUNTERSRIDGE ROAD, Winchester

5 bd · 4 ba · House · 6 DOM

VAFV2044776, ERA Oakcrest Realty, Inc.

223 ASBURY ROAD

For SaleBright MLS

223 ASBURY ROAD, Winchester

5 bd · 4 ba · House · 6 DOM

VAFV2044748, Real Broker LLC- Winchester

100 WINNS CIRCLE

For SaleBright MLS

100 WINNS CIRCLE, Winchester

4 bd · 3 ba · House · 6 DOM

VAFV2044754, NetRealtyNow.com, LLC

265 MCDONALD ROAD

For SaleBright MLS

265 MCDONALD ROAD, Winchester

3 bd · 2 ba · House · 6 DOM

VAFV2044758, Open Door Brokerage, LLC

1957 CIDERMILL LANE

For SaleBright MLS

1957 CIDERMILL LANE, Winchester

3 bd · 3 ba · Townhouse · 8 DOM

VAWI2011570, Samson Properties

100 GOOSEBERRY DRIVE

For SaleBright MLS

100 GOOSEBERRY DRIVE, Winchester

2 bd · 3 ba · House · 8 DOM

VAFV2044428, Hunt Country Sotheby's International Realty

991 FRONT ROYAL PIKE

For SaleBright MLS

991 FRONT ROYAL PIKE, Winchester

3 bd · 2 ba · House · 8 DOM

VAFV2044768, Re/Max Roots

131 COUNTRY CLUB CIRCLE

For SaleBright MLS

131 COUNTRY CLUB CIRCLE, Winchester

3 bd · 2 ba · House · 9 DOM

VAFV2044502, Berkshire Hathaway HomeServices PenFed Realty

519 VIRGINIA AVENUE

For SaleBright MLS

519 VIRGINIA AVENUE, Winchester

3 bd · 2 ba · House · 30 DOM

VAWI2011358, Colony Realty

424 VALLEY MILL ROAD

For SaleBright MLS

424 VALLEY MILL ROAD, Winchester

4 bd · 3 ba · Townhouse · 30 DOM

VAFV2044272, Burch Real Estate Group, LLC

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