3252 WINCHESTER RD — primary listing photo
    ActiveFarm & Estate· 187 days on market

    3252 WINCHESTER RD

    Delaplane, VA

    List price

    $3,999,000

    Originally listed at $5,000,000

    3252 WINCHESTER RD — featured photo
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    30 listing photos · scroll down for the full gallery

    4

    Bedrooms

    Bathrooms

    11,145

    Square feet

    98.01

    Acres

    1845

    Year built

    About this property

    Introducing Ashleigh, a storied 98-acre estate with sweeping views of the Delaplane countryside. Originally part of Chief Justice John Marshall's Oak Hill holdings, this Greek Revival manor was built for his granddaughter and remains one of Virginia's most admired historic properties. Ashleigh is listed on both the National Register of Historic Places and the Virginia Landmarks Register, and is further protected by a conservation easement with The Land Trust of Virginia. The main residence showcases grand proportions, 12' ceilings, heart pine floors, triple-sash windows, and elegant entertaining spaces including a double drawing room, formal dining room, paneled study, and a sun-filled gallery entry. The east wing features an extraordinary octagonal library added in 2001, while the west wing hosts a private and refined owner's suite. The grounds are truly exceptional””renowned gardens with three outdoor garden rooms, curated plantings, wisteria-draped pergola, massive boxwoods, sculptures, a 100' fountain, heated pool, and a pool/guest house with full kitchen and two bedrooms. Additional structures include three stables (17 stalls combined), run-in sheds, machine shed, farm manager apartments, and a charming 2-bedroom guest cottag

    Property details

    Type
    SingleFamilyResidence
    Style
    Other
    Subdivision
    NONE
    County
    Fauquier
    Garage
    1 space
    Stories
    2
    Pool
    Pool,Private
    Annual tax (2015)
    $22,228
    Interior
    Wet Bar · Walk-In Closet(s) · Breakfast Area · Kitchen Island
    Cooling
    Heat Pump
    Heating
    Dual System · Electric · Heat Pump · Oil
    View
    Garden · Panoramic

    Schools

    Elementary
    C. Thompson
    Middle
    Marshall
    High
    Fauquier

    Gallery (30 photos)

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    Listing courtesy of: Samson Properties — Carolyn Young

    MLS #235447737 · CAAR · Updated May 19, 2026

    This information is believed to be accurate, but without warranty.