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3252 Winchester Rd

Delaplane, VA
  • $5,000,000
  • STATUS: Active
  • ON SITE: 61 Days
  • MLS #: VAFQ2019664
UPDATED: 40 min ago
$5,000,000
  • 4
    BEDS
  • 98.01
    ACRES
  • 5
    BATHS
  • 2
    1/2 BATHS
  • 11,145
    SQFT
  • $449
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1845
Area:

School Information

Elementary School:
Middle School:
High School:

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 cottag

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Listing information © 2026 Charlottesville Area Association of Realtors Multiple Listing Service. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS or Kline & Co Real Estate. Data last updated 2026-01-14T15:12:37.973.
www.klineandcorealestate.com/homes/169910034
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3252 Winchester Rd Delaplane, VA

  • Price: $5,000,000
  • Status: Active
  • On Site: 61 Days
  • Updated: 40 min ago
  • MLS #: VAFQ2019664
4
Beds
5
Baths
2
½ Baths
98.01
Acres
11,145
SQFT
$449
$/SQFT
1845
Built
Neighborhood:
None
Area:
Fauquier
Elementary School:
C. Thompson
Middle School:
Marshall
High School:
Fauquier
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 cottag
Exterior Features

Architectural Style Other Attached Garage YN Yes Construction Materials Brick Stone Stucco Fencing Wood Foundation Details Stone Garage YN Yes Lot Features Private Wooded Other Structures Other Parking Features Attached Garage Gravel Garage Faces Side Pool Features Pool Private Pool Private YN Yes Roof Metal Other View Garden Panoramic View YN Yes

Interior Features

Above Grade Finished Area 7789 Appliances Dishwasher Electric Range Microwave Refrigerator Wine Cooler Dryer Washer Basement YN No Below Grade Finished Area 3356 Cooling Heat Pump Cooling YN Yes Fireplace Features Wood Burning Fireplace YN Yes Flooring Wood Heating Dual System Electric Heat Pump Oil Heating YN Yes Interior Features Wet Bar Walk- In Closet(s) Breakfast Area Kitchen Island Levels Two Main Level Bathrooms 3 Main Level Bedrooms 1 Room Type Living Room

Property Features

Accessibility Features Accessible Elevator Installed Association YN No Building Area Total 11145 Community Features Pond Gated Lease Amount Frequency Monthly Lease Considered YN No New Construction YN No Possession Close Of Escrow Property Attached YN No Property Sub Type Detached Property Sub Type Additional Detached Sale Or Lease Indicator For Sale Security Features Gated Community Sewer Septic Tank Tax Annual Amount 22228.75 Tax Year 2015 Water Source Private Well Zoning Description RA Rural Area

Listing provided courtesy of Samson Properties: 703-378-8810.


Listing information © 2026 Charlottesville Area Association of Realtors Multiple Listing Service. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS or Kline & Co Real Estate. Data last updated 2026-01-14T15:12:37.973.
 
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2503 Jefferson Highway
Waynesboro VA, 22980