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Winchester, VA Homes for Sale — Page 14 | Realty.com
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3 beds
345 listings
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New construction
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Homes for Sale in Winchester, VA

Homes for Sale in Winchester, VA

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23 of 345 Listings
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Homes for Sale in Winchester, VA

23 of 345 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. 151 Darby Dr — photoPrice Reduced47Active

    $599,900

    4 bd · 4 ba · 4,419 sqft

    151 Darby Dr, Winchester, VA

    David K Spence · RE/MAX Roots

  2. 805 S Kent St — photo46Active

    $325,000

    4 bd · 2 ba · 1,592 sqft

    805 S Kent St, Winchester, VA

    Carolina M Mosquera · Weichert, REALTORS

  3. 110 Duwamish Trl — photoPrice Reduced26Active

    $295,000

    3 bd · 2 ba · 984 sqft

    110 Duwamish Trl, Winchester, VA

    Tina Marie Jacobin · Main Street Realty

  4. 201 Nathaniel Dr — photo50Active

    $799,000

    3 bd · 4 ba · 3,256 sqft

    201 Nathaniel Dr, Winchester, VA

    Renee L Waymire · Samson Properties

  5. 115 E Monmouth St — photoPrice Reduced28Active

    $400,000

    4 bd · 2 ba · 1,432 sqft

    115 E Monmouth St, Winchester, VA

    Maria Fe Zambrano · Inmobiliaria De Las Casas LLC

  6. 136 Wappinger Ter — photo18Active

    $449,990

    3 bd · 3 ba · 1,657 sqft

    136 Wappinger Ter, Winchester, VA

    Victoria Jane Clark · D R Horton Realty of Virginia LLC

  7. 406 Raccoon Dr — photoPrice Reduced40Active

    $299,900

    3 bd · 2 ba · 1,850 sqft

    406 Raccoon Dr, Winchester, VA

    STEVEN REESE · EXP REALTY LLC - STAFFORD

  8. 251 Rossmann Blvd — photoPrice Reduced58Active

    $474,900

    4 bd · 3 ba · 1,971 sqft

    251 Rossmann Blvd, Winchester, VA

    Marisa L Varley · ERA Oakcrest Realty, Inc.

  9. 619 Farmington Blvd — photoPrice Reduced59Active

    $474,900

    4 bd · 3 ba · 2,023 sqft

    619 Farmington Blvd, Winchester, VA

    Marisa L Varley · ERA Oakcrest Realty, Inc.

  10. Tumble Leaf Lane — photo7Active

    $775,000

    4 bd · 3 ba · 3,150 sqft

    Tumble Leaf Lane, Winchester, VA

    Daniel A. Boris · Pearson Smith Realty, LLC

  11. Tumble Leaf Lane — photo8Active

    $760,000

    3 bd · 4 ba · 2,550 sqft

    Tumble Leaf Lane, Winchester, VA

    Daniel A. Boris · Pearson Smith Realty, LLC

  12. To Be Built-Homesite 209 Duke Ct — photoPrice Reduced13Active

    $598,990

    3 bd · 3 ba · 2,875 sqft

    To Be Built-Homesite 209 Duke Ct, Winchester, VA

    Greta Mirly Fernandez · New Home Star Virginia, LLC

  13. 228 Hydrangea Way — photo47Active

    $646,045

    3 bd · 2 ba · 1,888 sqft

    228 Hydrangea Way, Winchester, VA

    Victoria Jane Clark · D R Horton Realty of Virginia LLC

  14. 227 Hydrangea Way — photo32Active

    $607,990

    3 bd · 2 ba · 1,748 sqft

    227 Hydrangea Way, Winchester, VA

    Victoria Jane Clark · D R Horton Realty of Virginia LLC

  15. To Be Built - Williamson Rd — photoPrice Reduced18Active

    $549,990

    4 bd · 4 ba · 3,747 sqft

    To Be Built - Williamson Rd, Winchester, VA

    Greta Mirly Fernandez · New Home Star Virginia, LLC

  16. 832 Winder Ct — photoPrice Reduced63Active

    $480,000

    3 bd · 2 ba · 1,974 sqft

    832 Winder Ct, Winchester, VA

    Barton Thomas Chasler · Realty ONE Group Old Towne

  17. To Be Built-Homesite 18 Williamson Rd — photo12Active

    $598,990

    3 bd · 2 ba · 3,056 sqft

    To Be Built-Homesite 18 Williamson Rd, Winchester, VA

    Greta Mirly Fernandez · New Home Star Virginia, LLC

  18. To Be Built - Williamson Rd — photoPrice Reduced22Active

    $529,990

    3 bd · 2 ba · 2,658 sqft

    To Be Built - Williamson Rd, Winchester, VA

    Greta Mirly Fernandez · New Home Star Virginia, LLC

  19. Lot 13 Keval Gyan Way — photo46Active

    $950,000

    3 bd · 3 ba · 3,100 sqft

    Lot 13 Keval Gyan Way, Winchester, VA

    Jim Thomson · Realty ONE Group Old Towne

  20. Lot 1 Keval Gyan Way — photo59Active

    $1,150,000

    4 bd · 4 ba · 5,425 sqft

    Lot 1 Keval Gyan Way, Winchester, VA

    Jim Thomson · Realty ONE Group Old Towne

  21. Lot 10 Desant Cir — photoPrice Reduced49Active

    $849,900

    5 bd · 3 ba · 3,057 sqft

    Lot 10 Desant Cir, Winchester, VA

    Jim Thomson · Realty ONE Group Old Towne

  22. Lot 11 Keval Gyan Way — photo5Active

    $899,900

    3 bd · 2 ba · 2,488 sqft

    Lot 11 Keval Gyan Way, Winchester, VA

    Jim Thomson · Realty ONE Group Old Towne

  23. 108 Martin Dr — photoPrice Reduced45Active

    $260,000

    2 bd · 1 ba · 997 sqft

    108 Martin Dr, Winchester, VA

    Heloisa P Amar · Samson Properties

1…131415

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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: 2026-09-15 18:07:56 UTC
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Listing information ©2026 Charlottesville Area AOR®. All Rights Reserved. Last Updated: 2026-07-23 15:44:06 UTC
  • By feature

    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #0225245042

    Call Thomas

    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

    Winchester 12-month median sale price trend

    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.

    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)