$3,999,000

3252 WINCHESTER RD, Delaplane, VA 20144

  • 4 beds |
  • 7 baths |
  • 11,145 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1845
  • Property Lot Size Icon98.01acre lot
  • Property Parking Icon 1 car garage
  • Property Price Per Square Feet Icon $359/sqft
  • Property List Date Icon Listed 5 months ago

Property Description

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 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.

Listing Status:
Active
Date Added:
November 21, 2025
Data Last Updated:
May 7, 2026 at 3:22PM
Listing Office:
Samson Properties : 7033788810
Listing Agent:
Carolyn Young : 7032619190
MLS ID:
VAFQ2019664
  • General: Kitchen - IslandDining AreaBreakfast AreaPrimary Bath(s)Built-InsElevatorCrown MoldingsWood FloorsBathroom - Soaking TubFloor Plan - TraditionalWalk-in Closet(s)Wet/Dry BarWine StorageOther
  • Rooms: Living RoomDining RoomPrimary BedroomBedroom 2Bedroom 3Bedroom 4KitchenLibraryFoyerBreakfast RoomStudyBathroom 2Bathroom 3Primary BathroomFull BathHalf Bath
  • Appliances: Oven/Range - ElectricRefrigeratorDishwasherMicrowaveWasherDryer
  • A/C: Heat Pump(s)Zoned
  • Heating: SteamHeat Pump(s)ZonedOilElectric
  • Fireplace: WoodFireplaceFireplaces: 7
  • Disability Feature: None
  • General: Water FountainsOutbuilding(s)Above GradeBelow Grade
  • Style: Other
  • Other Structures: TerraceBalconies- Multiple
  • Parking: Gravel Driveway
  • Roofing: Metal
  • General: StuccoStoneBrick2Stone
  • HOA Amenities: None
  • Originating MLS: BRIGHT_MAIN
  • School District: FAUQUIER COUNTY PUBLIC SCHOOLS
  • County: FAUQUIER-VA
  • Zoning: RA6041-82-2210
  • View: Scenic VistaGarden/Lawn
  • Fencing: Board
  • Water: Well
  • Sewer: Septic Exists
  • Source: BRIGHT_MAIN
  • Exclusions: The 2 Living Room chandeliers

This listing courtesy of Carolyn Young , Samson Properties

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

Ready to Start a VA Loan?

Get Started Veterans United Home LoansNMLS #1907  †
Get Prequalified »
Interest rates used in the VA mortgage calculator are shown for illustrative purposes only. Your rate may differ based on a variety of factors, including your credit score and the current market conditions. To get your personalized interest rate, start your quote online.

Location