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3 beds New construction With a pool

340 listings

Homes for Sale in Winchester, VA

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24 of 340 Listings

Map

24 of 340 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

44Active

$585,659

3 bd · 3 ba · 3,200 sqft

108 Magpie Ln #Homesite 1035, Winchester, VA

Shannon Lynn Bray · Pearson Smith Realty, LLC

52Active

$369,990

3 bd · 4 ba · 1,756 sqft

229 Monteith Dr, Winchester, VA

Brittany Newman · DRB Group Realty, LLC

33Active

$599,500

3 bd · 2 ba · 1,350 sqft

479 Perry Rd, Winchester, VA

Thomas A Dawe · Winchester Real Estate Connection

38Active

$370,000

3 bd · 3 ba · 1,772 sqft

100 Stribling Way, Winchester, VA

Raven Nicole Staub · Samson Properties

25Active

$250,000

2 bd · 1 ba · 870 sqft

1125 Conway St, Winchester, VA

Curtis W Siever · NextHome Realty Select

40Active

$359,990

3 bd · 4 ba · 1,756 sqft

237 Monteith Dr, Winchester, VA

Brittany Newman · DRB Group Realty, LLC

70Active

$659,900

4 bd · 5 ba · 4,271 sqft

291 Huntersridge Rd, Winchester, VA

Laura D White · 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

42Active

$175,000

1 bd · 1 ba · 384 sqft

305 Raccoon Dr, Winchester, VA

William Fitzgerald Dixon · Dandridge Realty Group, LLC

33Active

$429,000

3 bd · 2 ba · 1,544 sqft

1412 S Loudoun St, Winchester, VA

Leslie A. Webb · Long & Foster Real Estate, Inc.

17Active

$240,000

2 bd · 1 ba · 997 sqft

187 Valley Mill Rd, Winchester, VA

Heloisa P Amar · Samson Properties

Price Reduced28Active

$354,900

3 bd · 2 ba · 1,791 sqft

1077 Carpers Dr, Winchester, VA

William Curtise Howard III · Burch Real Estate Group, LLC

Price Reduced17Active

$344,000

3 bd · 4 ba · 1,740 sqft

108 Monticello Sq, Winchester, VA

Donald A Butler · Virginia Property Group, Inc.

51Active

$364,900

3 bd · 3 ba · 2,064 sqft

802 Appleseed Ct, Winchester, VA

D'Arcy D Amburn · Colony Realty

29Active

$385,490

4 bd · 4 ba · 1,889 sqft

648 Arden Ct, Winchester, VA

Victoria Jane Clark · D R Horton Realty of Virginia LLC

62Active

$575,000

3 bd · 2 ba · 2,205 sqft

123 Harvest Ridge Dr, Winchester, VA

Brian Keith Yoder · Realty ONE Group Old Towne

Price Reduced39Active

$425,000

3 bd · 3 ba · 2,277 sqft

422 S Loudoun St, Winchester, VA

Dana L Cloud · Realty ONE Group Old Towne

73Active

$615,000

5 bd · 4 ba · 3,626 sqft

922 Wayne Dr, Winchester, VA

Katrina M Smith · Samson Properties

29Active

$381,690

4 bd · 4 ba · 1,889 sqft

652 Arden Ct, Winchester, VA

Victoria Jane Clark · D R Horton Realty of Virginia LLC

8Active

$289,900

2 bd · 2 ba · 1,024 sqft

2640 Limestone Ct, Winchester, VA

Meridee A Powars · Link Realty Services LLC

9Active

$308,000

2 bd · 2 ba · 800 sqft

2519 Hockman Ave, Winchester, VA

Meridee A Powars · Link Realty Services LLC

29Active

$385,690

4 bd · 4 ba · 1,889 sqft

660 Arden Ct, Winchester, VA

Victoria Jane Clark · D R Horton Realty of Virginia LLC

54Active

$340,000

3 bd · 2 ba · 1,092 sqft

197 Denny Ln, Winchester, VA

Stephanie Nicole Ambrogi · Realty ONE Group Old Towne

42Active

$456,639

3 bd · 3 ba · 2,181 sqft

100 Keystone Ln #Homesite 1090, Winchester, VA

Shannon Lynn Bray · Pearson Smith Realty, LLC

1…3 4 5…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: 2026-09-22 15:53:07 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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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

Co-ops

By feature

New construction
With a pool

Nearby areas

ZIP codes

22602 (189)
22630 (167)
22601 (90)
22655 (63)
22603 (61)
22664 (49)
22657 (45)
22642 (42)

Cities

Front Royal (143)
Stephens City (63)
Woodstock (49)
Strasburg (46)
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 (189)
22630 (167)
22601 (90)
22655 (63)
22603 (61)
22664 (49)
22657 (45)
22642 (42)

Cities

Front Royal (143)
Stephens City (63)
Woodstock (49)
Strasburg (46)
Linden (42)

Berryville (30)

Cross Junction (29)

Lake Frederick (24)

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 15:53:07 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 4 | Realty.com