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Winchester, VA Homes for Sale — Page 8 | Realty.com
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3 bedsNew construction

Homes for Sale in Winchester, VA

Homes for Sale in Winchester, VA

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24 of 347 Listings
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Homes for Sale in Winchester, VA

24 of 347 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. 111 Haven Ter — photoPrice Reduced17Active

    $279,900

    3 bd · 1 ba · 1,008 sqft

    111 Haven Ter, Winchester, VA

    Erin M Kavanagh · EXP Realty, LLC

  2. 127 Mountain View Rd — photoPrice Reduced58Active

    $539,900

    4 bd · 3 ba · 2,208 sqft

    127 Mountain View Rd, Winchester, VA

    Josh W Feltner · Realty ONE Group Old Towne

  3. 236 Delmas Trl — photoPrice Reduced55Active

    $959,900

    4 bd · 4 ba · 3,317 sqft

    236 Delmas Trl, Winchester, VA

    Kathrin Donovan · Keller Williams Realty

  4. 159 Aspen Trl — photo51Active

    $295,000

    2 bd · 3 ba · 2,148 sqft

    159 Aspen Trl, Winchester, VA

    Kimberly C Baggett · EXP Realty, LLC

  5. 308 Fawn Dr — photoPrice Reduced22Active

    $300,600

    3 bd · 3 ba · 1,680 sqft

    308 Fawn Dr, Winchester, VA

    Steve A DuBrueler · Coldwell Banker Premier

  6. 531 Cedar Grove Rd — photoPrice Reduced83Active

    $659,900

    2 bd · 1 ba · 1,540 sqft

    531 Cedar Grove Rd, Winchester, VA

    Tyler Franklin Hazelwood · Virginia Real Estate

  7. 700 Tomahawk Trl — photoPrice Reduced19Active

    $280,000

    3 bd · 1 ba · 1,104 sqft

    700 Tomahawk Trl, Winchester, VA

    Stacy Priddy · Berkshire Hathaway HomeServices PenFed Realty

  8. 812 Appleseed Ct — photo40Active

    $359,000

    3 bd · 2 ba · 1,710 sqft

    812 Appleseed Ct, Winchester, VA

    Feletia Van Valkenburg Sharples · Realty FC

  9. 148 Doe Trl — photoPrice Reduced43Active

    $311,265

    3 bd · 2 ba · 1,550 sqft

    148 Doe Trl, Winchester, VA

    Pamela Jean Dors · Keller Williams Realty Advantage

  10. 1847 Melvor Ln — photoPrice Reduced98Active

    $339,900

    2 bd · 2 ba · 1,234 sqft

    1847 Melvor Ln, Winchester, VA

    Lisette B. Turner · Century 21 Redwood Realty

  11. 322 E Piccadilly — photoPrice Reduced30Active

    $400,000

    4 bd · 1 ba · 1,768 sqft

    322 E Piccadilly, Winchester, VA

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

  12. Tumble Leaf Lane — photo11Active

    $805,000

    4 bd · 4 ba · 3,050 sqft

    Tumble Leaf Lane, Winchester, VA

    Daniel A. Boris · Pearson Smith Realty, LLC

  13. 200 Fairfield Dr — photo72Active

    $645,000

    4 bd · 4 ba · 3,582 sqft

    200 Fairfield Dr, Winchester, VA

    Angela R. Duncan · MarketPlace REALTY

  14. 337 Canyon Rd — photoPrice Reduced69Active

    $639,000

    5 bd · 4 ba · 4,623 sqft

    337 Canyon Rd, Winchester, VA

    Sharon Farinholt · Realty ONE Group Old Towne

  15. 109 Marlow Ct — photoPrice Reduced51Active

    $410,000

    4 bd · 4 ba · 2,004 sqft

    109 Marlow Ct, Winchester, VA

    Crystal Dudurich · ERA Liberty Realty

  16. 182 Mason St — photoPrice Reduced23Active

    $319,990

    3 bd · 2 ba · 1,024 sqft

    182 Mason St, Winchester, VA

    Samantha Young · Young & Associates

  17. 142 Sequoia Dr — photoPrice Reduced86Active

    $434,900

    3 bd · 4 ba · 2,239 sqft

    142 Sequoia Dr, Winchester, VA

    Michele L Gibson · Samson Properties

  18. 102 Forest Valley Rd — photoPrice Reduced51Active

    $597,000

    5 bd · 3 ba · 2,515 sqft

    102 Forest Valley Rd, Winchester, VA

    Julie M Teets · ERA Oakcrest Realty, Inc.

  19. 229 Monteith Dr — photo52Active

    $369,990

    3 bd · 4 ba · 1,756 sqft

    229 Monteith Dr, Winchester, VA

    Brittany Newman · DRB Group Realty, LLC

  20. 100 Stribling Way — photoPrice Reduced38Active

    $363,999

    3 bd · 3 ba · 1,772 sqft

    100 Stribling Way, Winchester, VA

    Raven Nicole Staub · Samson Properties

  21. 1125 Conway St — photo25Active

    $250,000

    2 bd · 1 ba · 870 sqft

    1125 Conway St, Winchester, VA

    Curtis W Siever · NextHome Realty Select

  22. 291 Huntersridge Rd — photo70Active

    $659,900

    4 bd · 5 ba · 4,271 sqft

    291 Huntersridge Rd, Winchester, VA

    Laura D White · ERA Oakcrest Realty, Inc.

  23. 305 Raccoon Dr — photoPrice Reduced42Active

    $169,900

    1 bd · 1 ba · 384 sqft

    305 Raccoon Dr, Winchester, VA

    William Fitzgerald Dixon · Dandridge Realty Group, LLC

  24. 1077 Carpers Dr — photoPrice Reduced28Active

    $340,000

    3 bd · 2 ba · 1,791 sqft

    1077 Carpers Dr, Winchester, VA

    James W Watson · Burch Real Estate Group, LLC

1…789…15

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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.

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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: 2026-11-03 14:44:42 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #0225245042

    Call Thomas

    Nearby areas

    ZIP codes

    • 22602 (181)
    • 22630 (172)
    • 22601 (93)
    • 22603 (73)
    • 22655 (69)
    • 22642 (47)
    • 22657 (40)
    • 22664 (40)

    Cities

    • Front Royal (146)
    • Stephens City (69)
    • Linden (47)
    • Strasburg (40)
    • Woodstock (40)
    • Berryville (35)
    • Cross Junction (30)
    • Stephenson (23)

    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

    October 2026 · This period is still settling

    Winchester 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 76 sales · as of Oct 30, 2026

    Homes that sold · County records, as of Oct 13, 2026

    Median sale price
    $508,579$325,000–$720,000 typical range
    Price per sq. ft.
    $242
    Sales
    41
    Paid in cash
    48.8%

    Homes on the market · MLS, as of Oct 25, 2026–Oct 30, 2026

    Median list price
    $425,000
    Homes for sale
    343
    Median days on market
    29 days

    Price trend · Assessor repeat sales, as of Oct 31, 2026

    Year-over-year
    29.4%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,620 sq. ft.