3252 Winchester Road Delaplane, VA 20144

$3,999,000
4
Beds
6
Baths
98.01
Acres
11,145
SQFT
359
$/SQFT
$3,999,000
4
Beds
6
Baths
11,145   sf
$359 / sf
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VISIT OUR OPEN HOUSES!!! SUN. JULY 12, 2026 - 11AM to 2PM SUN. JULY 19, 2026 - 11AM to 2PMSUN. JULY 26, 2026 - 11AM to 2PMIntroducing 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 cottage near the main house.Perfectly positioned at the intersection of Route 17 and Route 55, with quick access to I-66, Ashleigh offers unmatched beauty, privacy, and historic pedigree—an extraordinary Delaplane opportunity rarely available.

VISIT OUR OPEN HOUSES!!! SUN. JULY 12, 2026 - 11AM to 2PM SUN. JULY 19, 2026 - 11AM to 2PMSUN. JULY 26, 2026 - 11AM to 2PMIntroducing 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 cottage near the main house.Perfectly positioned at the intersection of Route 17 and Route 55, with quick access to I-66, Ashleigh offers unmatched beauty, privacy, and historic pedigree—an extraordinary Delaplane opportunity rarely available.

  • Neighborhood
  • Type
  • Total Baths
  • 1/2 Baths
  • County
    Fauquier
  • Tax Amount
    $22,229
  • Status
    Active
  • Listing #
    VAFQ2019664
  • Built
    1845
  • Lot Size
    98.01
  • Listed on site
    242 days
  • Listing Agent Id
    121135101593
  • Co Listing Agent Id
    121137260113

Listed by:
Samson Properties

Source:
BRIGHT MLS

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Property details

Community Features

  • No HOA
  • No Adult Community

Property Features

  • No Builder Restrictions
  • Historic Property

Exterior features

  • Balcony
  • Fence
  • Has garage
  • Pool

Interior Features

  • Fire Place
  • Main Floor Bedroom
  • Study
  • Wet Bar

Property History

DateDays AgoEventNew Price
May 3, 20262 mos agoPrice decreased501,000 (11%)$3,999,000
Apr 13, 20263 mos agoPrice increased600,000 (13%)$4,500,000
Apr 12, 20263 mos agoPrice decreased600,000 (13%)$3,900,000
Mar 30, 20264 mos agoPrice decreased500,000 (10%)$4,500,000
Nov 13, 20258 mos agoNew on market$5,000,000
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