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Start here

Homes for sale by state
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Before you start looking
The buying timeline

Afford it

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Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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Rentals
Commercial

348 listings

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Get an instant cash offer
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3 beds New construction

348 listings

Homes for Sale in Winchester, VA

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24 of 348 Listings

Map

24 of 348 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

New23

Active

$299,000

3 bd · 4 ba · 1,979 sqft

219 Tudor Dr, Winchester, VA

James Cox Sr. · Weichert Realtors - Blue Ribbon

New37Active

$349,999

3 bd · 3 ba · 2,250 sqft

Homesite 60 Shuoner Ct, Winchester, VA

James Thomas · New Home Star Virginia, LLC

New37Active

$389,990

4 bd · 4 ba · 2,250 sqft

Homesite 61 Shuoner Ct, Winchester, VA

James Thomas · New Home Star Virginia, LLC

New18Active

$142,240

3 bd · 2 ba · 1,248 sqft

102 Chamberlain Ct, Winchester, VA

Lydia A Zache · Long & Foster Real Estate, Inc.

New24Active

$200,000

3 bd · 2 ba · 1,050 sqft

23 E Germain St, Winchester, VA

Laura Lea Fields · Exit Success Realty

NewActive

$319,900

2 bd · 2 ba · 1,154 sqft

151 McCormick Circle #105, Winchester, VA

Michael S Campbell · EXP Realty, LLC

New37Active

$389,990

4 bd · 4 ba · 2,250 sqft

Homesite 52 Shuoner Ct, Winchester, VA

James Thomas · New Home Star Virginia, LLC

42Active

$394,900

3 bd · 3 ba · 1,251 sqft

709 Ross St, Winchester, VA

Angela R. Duncan · MarketPlace REALTY

21Active

$399,000

4 bd · 2 ba · 1,800 sqft

317 S Kent St, Winchester, VA

Sharon Farinholt · Realty ONE Group Old Towne

66Active

$673,000

6 bd · 4 ba · 4,472 sqft

718 Academy Cir, Winchester, VA

Elizabeth Gaines Kerns · Realty ONE Group Old Towne

48Active

$439,900

3 bd · 1 ba · 1,247 sqft

411 Mosby St, Winchester, VA

Lisa S Gill · ERA Oakcrest Realty, Inc.

1Active

$399,900

3 bd · 2 ba · 1,626 sqft

115 Ware Pl, Winchester, VA

Dawn E Billow · Compass West Realty, LLC

52Active

$249,000

2 bd · 1 ba · 756 sqft

133 Blackfeet Trl, Winchester, VA

Stephanie Feltner · Realty ONE Group Old Towne

52Active

$572,990

4 bd · 3 ba · 3,038 sqft

1 Plaid Hill Dr #Sheldon 40-F2, Winchester, VA

Shannon Lynn Bray · Pearson Smith Realty, LLC

33Active

$399,990

3 bd · 4 ba · 2,382 sqft

1 Swansong Pl #Teagan 24-F2, Winchester, VA

Shannon Lynn Bray · Pearson Smith Realty, LLC

59Active

$320,000

3 bd · 1 ba · 1,040 sqft

2310 Senseny Rd, Winchester, VA

Roxane Morrison · NextHome Realty Select

34Active

$299,900

2 bd · 2 ba · 1,254 sqft

121 Lighthouse Ln, Winchester, VA

Daniel J Whitacre · Colony Realty

Active

$859,000

3 bd · 3 ba · 2,408 sqft

115 Garnett Ct, Winchester, VA

Lindsey Richardson · ERA Oakcrest Realty, Inc.

33Active

$699,000

4 bd · 3 ba · 2,802 sqft

432 N Loudoun St, Winchester, VA

Derek J. Greene · The Greene Realty Group

21Active

$229,000

2 bd · 2 ba · 1,160 sqft

23 Jigsaw Pl, Winchester, VA

Wendy R Longerbeam · Coldwell Banker Elite

26Active

$374,990

3 bd · 3 ba · 2,000 sqft

Lot 5 Shuoner Ct, Winchester, VA

James Thomas · New Home Star Virginia, LLC

50Active

$524,990

5 bd · 3 ba · 3,414 sqft

3336 Hunting Ridge Rd, Winchester, VA

Leslie O Carter · Carter Real Estate, Inc.

17Active

$439,000

3 bd · 3 ba · 2,500 sqft

999 Dicks Hollow Rd, Winchester, VA

Collin Sediqi · Real Broker, LLC

99Active

$575,000

4 bd · 4 ba · 4,368 sqft

105 Okeefe Dr, Winchester, VA

Deborah Matthews · ERA Oakcrest Realty, Inc.

1 2…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: 2026-10-14 14:32:42 UTC

Winchester housing market

September 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 91 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 23, 2026

Median sale price: $400,000$304,350–$606,625 typical range
Price per sq. ft.: $254
Sales: 87
Paid in cash: 36.8%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $422,495

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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2 Bedroom Homes
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Nearby areas

ZIP codes

22602 (186)
22630 (160)
22601 (100)
22603 (64)
22655 (64)
22642 (49)
22657 (45)
22664 (39)

Cities

Front Royal (137)
Stephens City (64)
Linden (49)
Strasburg (45)
Woodstock (39)
Berryville (34)
Cross Junction (32)
Stephenson (28)

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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

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: 2026-10-14 14:32:42 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

September 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 91 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 23, 2026

Median sale price: $400,000$304,350–$606,625 typical range
Price per sq. ft.: $254
Sales: 87
Paid in cash: 36.8%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $422,495

Homes for sale

334

Median days on market

33 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -5.4%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

Median home size: 1,620 sq. ft.

Winchester, VA Homes for Sale | Realty.com

Nearby areas

ZIP codes

22602 (186)
22630 (160)
22601 (100)
22603 (64)
22655 (64)
22642 (49)
22657 (45)
22664 (39)

Cities

Front Royal (137)
Stephens City (64)
Linden (49)
Strasburg (45)
Woodstock (39)
Berryville (34)
Cross Junction (32)
Stephenson (28)