3252 Winchester Rd, DELAPLANE, VA

$3,999,000

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4

Beds

6

Baths

11,145

Square feet

98.01

Acres

About 3252 Winchester Rd

VISIT OUR OPEN HOU 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.

Features of 3252 Winchester Rd

MLS® # VAFQ2019664
Price $3,999,000
Bedrooms 4
Bathrooms 6.00
Full Baths 5
Half Baths 2
Square Footage 11,145
Acres 98.01
Year Built 1845
Type Residential
Sub-Type Detached
Style Other
Status Active
HOA/Condo/Coop Fee Amenities None

Community Information

Address 3252 Winchester Rd
Subdivision NONE AVAILABLE
City DELAPLANE
County FAUQUIER-VA
State VA
Zip Code 20144

Amenities

Amenities Primary Bath(s), Built-Ins, Elevator, Crown Moldings, Wood Floors, Bathroom - Soaking Tub, Walk-in Closet(s), Wet/Dry Bar, Wine Storage
Parking Gravel Driveway
# of Garages 1
Garages Garage - Side Entry
View Scenic Vista, Garden/Lawn
Is Waterfront No
Has Pool Yes

Interior

Interior Features Floor Plan - Traditional
Appliances Oven/Range - Electric, Refrigerator, Dishwasher, Microwave, Washer, Dryer
Heating Steam, Heat Pump(s), Zoned
Cooling Heat Pump(s), Zoned
Has Basement No
Fireplace Yes
# of Fireplaces 7
Fireplaces Wood
Stories 2

Exterior

Exterior Stucco, Stone, Brick
Exterior Features Water Fountains,Outbuilding(s),Balconies- Multiple,Terrace,Board
Lot Description Backs to Trees, Partly Wooded, Pond, Private
Roof Metal
Construction Stucco, Stone, Brick
Foundation Stone

School Information

District FAUQUIER COUNTY PUBLIC SCHOOLS
Elementary CLAUDE THOMPSON
Middle MARSHALL
High FAUQUIER

Additional Information

Date Listed November 21st, 2025
Days on Market 279
Zoning RA
Foreclosure No
Short Sale No
RE / Bank Owned No
Listing Ownership Fee Simple

Listing Details

OfficeSamson Properties

Listing Map

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