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Luxury Homes in Winchester, VA
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15 listings
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3 bedsNew constructionWith a pool

Luxury Homes in Winchester, VA

Luxury Homes in Winchester, VA

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15 Listings
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Luxury Homes in Winchester, VA

15 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. 632 Stonymeade Dr — photo83Active

    $1,025,000

    5 bd · 4 ba · 3,870 sqft

    632 Stonymeade Dr, Winchester, VA

    Katrina M Smith · Samson Properties

  2. 1030 Breckinridge Ln — photo97Active

    $1,100,000

    6 bd · 6 ba · 6,789 sqft

    1030 Breckinridge Ln, Winchester, VA

    Joleen Ritter Haymaker · Samson Properties

  3. 144 Robinson Dr — photo111Active

    $2,599,000

    4 bd · 6 ba · 4,753 sqft

    144 Robinson Dr, Winchester, VA

    Daniel J Whitacre · Colony Realty

  4. 2216 Laurel Grove Rd — photo107Active

    $1,300,000

    4 bd · 3 ba · 3,922 sqft

    2216 Laurel Grove Rd, Winchester, VA

    Jennifer Nichole Burn · Real Broker, LLC

  5. 450 Green Spring Rd — photo67Active

    $3,500,000

    3 bd · 4 ba · 4,421 sqft

    450 Green Spring Rd, Winchester, VA

    Phyllis Guthrie · Keller Williams Realty

  6. 582 Miller Rd — photo76Active

    $1,650,000

    4 bd · 5 ba · 6,183 sqft

    582 Miller Rd, Winchester, VA

    Elizabeth Anne Cossette · ERA Oakcrest Realty, Inc.

  7. 1022 Heth Pl — photo83Active

    $1,239,000

    4 bd · 8 ba · 5,662 sqft

    1022 Heth Pl, Winchester, VA

    Cynthia Butler · Samson Properties

  8. 730 Merrimans Ln — photo127Active

    $3,175,000

    6 bd · 7 ba · 8,593 sqft

    730 Merrimans Ln, Winchester, VA

    Justin Mistretta · Berkshire Hathaway HomeServices PenFed Realty

  9. 1116 Woodstock Ln — photoPrice Reduced14Active

    $4,900,000

    1 bd · 1 ba · 44,000 sqft

    1116 Woodstock Ln, Winchester, VA

    Meridee A Powars · Link Realty Services LLC

  10. 801 Armistead St — photo46Active

    $1,150,000

    5 bd · 5 ba · 5,695 sqft

    801 Armistead St, Winchester, VA

    Donna Chong · Samson Properties

  11. 2230 Jones Rd — photo83Active

    $2,200,000

    5 bd · 5 ba · 5,884 sqft

    2230 Jones Rd, Winchester, VA

    Jennifer Sacco · RE/MAX Roots

  12. 1015 Redbud Rd — photoPrice Reduced88Active

    $1,050,000

    4 bd · 5 ba · 4,188 sqft

    1015 Redbud Rd, Winchester, VA

    Ryan Rice · Keller Williams Capital Properties

  13. 1004 Heth Pl — photo50Active

    $1,179,000

    4 bd · 5 ba · 4,970 sqft

    1004 Heth Pl, Winchester, VA

    Kathryn R Hallett · Long & Foster Real Estate, Inc.

  14. 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

  15. Lot 60 Gravenstein Ct — photo7Active

    $1,150,000

    3 bd · 3 ba · 2,947 sqft

    Lot 60 Gravenstein Ct, Winchester, VA

    Daniel A. Boris · Pearson Smith Realty, LLC

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

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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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Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-08-31 16:33:49 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 · This period is still settling

    Winchester 12-month median sale price trend

    Selling at 99.0% of asking price

    Buyers here are paying below asking. MLS · 78 sales · as of Aug 28, 2026

    Homes that sold · County records, as of Aug 12, 2026

    Median sale price
    $436,660$322,000–$559,900 typical range
    Price per sq. ft.
    $237
    Sales
    33
    Paid in cash
    30.3%

    Homes on the market · MLS, as of Aug 28, 2026–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.