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343 listings

Homes for Sale in Winchester, VA

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23 of 343 Listings

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23 of 343 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

Price Reduced61

Active

$649,900

3 bd · 2 ba · 2,242 sqft

132 Triangle Ct, Winchester, VA

Kelly Davis · RE/MAX Gateway, LLC

127Active

$3,175,000

6 bd · 7 ba · 8,593 sqft

730 Merrimans Ln, Winchester, VA

Justin Mistretta · Berkshire Hathaway HomeServices PenFed Realty

Price Reduced32Active

$239,000

2 bd · 2 ba · 1,257 sqft

157-6 Brookland Ter #6, Winchester, VA

Kimberly D Hurst · MarketPlace REALTY

Price Reduced58Active

$495,990

4 bd · 4 ba · 2,216 sqft

101 Seminole Dr, Winchester, VA

Victoria Jane Clark · D R Horton Realty of Virginia LLC

Price Reduced25Active

$177,000

2 bd · 2 ba · 896 sqft

313 Avon Ct, Winchester, VA

Sophia Alam · AMN Realty, LLC.

Price Reduced40Active

$289,000

2 bd · 2 ba · 1,173 sqft

110 Brookland Ct #10, Winchester, VA

Traci J. Shoberg · Samson Properties

Price Reduced61Active

$410,000

3 bd · 3 ba · 1,634 sqft

113 Wertland Pl, Winchester, VA

Laura D White · ERA Oakcrest Realty, Inc.

Price Reduced74Active

$624,900

4 bd · 3 ba · 2,904 sqft

104 Bramble Ct, Winchester, VA

Laura D White · ERA Oakcrest Realty, Inc.

17Active

$125,000

1 bd · 1 ba · 624 sqft

415 Puma Trl, Winchester, VA

Kenneth A Evans · RE/MAX Real Estate Connections

Price Reduced34Active

$559,990

6 bd · 4 ba · 3,127 sqft

133 Wappinger Ter, Winchester, VA

Victoria Jane Clark · D R Horton Realty of Virginia LLC

76Active

$989,000

4 bd · 4 ba · 4,152 sqft

137 Old Forest Cir, Winchester, VA

Melissa Joy Perozich · Century 21 Redwood Realty

103Active

$899,000

3 bd · 4 ba · 3,497 sqft

466 Merrimans Ln, Winchester, VA

John B Schroth · Colony Realty

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

Price Reduced54Active

$610,000

4 bd · 4 ba · 4,120 sqft

211 Flanagan Dr, Winchester, VA

Ned S Stock · Berkshire Hathaway HomeServices PenFed Realty

Price Reduced15Active

$289,000

3 bd · 1 ba · 1,056 sqft

211 Fair Ln, Winchester, VA

Kenneth Richard Ritenour · Samson Properties

Price Reduced85Active

$685,000

4 bd · 5 ba · 4,918 sqft

108 Norfolk Ct, Winchester, VA

Nicole Panos Lewis · Coldwell Banker Premier

Price Reduced49Active

$415,000

4 bd · 3 ba · 1,714 sqft

101 Charlton Rd, Winchester, VA

Roxanna D Grimes · RE/MAX Roots

Price Reduced74Active

$647,000

7 bd · 4 ba · 4,116 sqft

256 Skylar Lanes Way, Winchester, VA

Brian Ratliff · Old Dominion Realty

49Active

$320,000

4 bd · 2 ba · 2,034 sqft

410 S Cameron St, Winchester, VA

Heloisa P Amar · Samson Properties

Price Reduced31Active

$499,900

4 bd · 3 ba · 2,068 sqft

110 Russellcroft Rd, Winchester, VA

Grace Mooney · Coldwell Banker Premier

Price Reduced33Active

$348,000

3 bd · 2 ba · 1,554 sqft

302 Wentworth Dr, Winchester, VA

Heloisa P Amar · Samson Properties

47Active

$329,900

3 bd · 2 ba · 1,242 sqft

936 Allen Dr, Winchester, VA

Joanna P Elson · Dream Real Estate

Price Reduced33Active

$379,999

4 bd · 3 ba · 1,904 sqft

123 Etnam St, Winchester, VA

Paul Vincent Sneeringer III · Samson Properties

1…9 10 11…15

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: 2026-09-20 18:08:20 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

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

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Under $700K
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4 beds
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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

By feature

New construction
With a pool

Nearby areas

ZIP codes

22602 (191)
22630 (170)
22601 (91)
22655 (65)
22603 (62)
22664 (47)
22657 (46)
22642 (42)

Cities

Front Royal (145)
Stephens City (65)
Strasburg (47)
Woodstock (47)
Linden (42)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

Nearby areas

ZIP codes

22602 (191)
22630 (170)
22601 (91)
22655 (65)
22603 (62)
22664 (47)
22657 (46)
22642 (42)

Cities

Front Royal (145)
Stephens City (65)
Strasburg (47)
Woodstock (47)
Linden (42)

Berryville (31)

Cross Junction (29)

Lake Frederick (25)

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: 2026-09-20 18:08:20 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.

Winchester, VA Homes for Sale — Page 10 | Realty.com