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575 MADISON AVENUE, NEW YORK, NY 10022. 212.891.7000 © 2026 DOUGLAS ELLIMAN REAL ESTATE. EQUAL EMPLOYMENT OPPORTUNITY PROVIDER. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES, OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS, AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT, OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY. LISTING DATA REFRESHED ON 18 MAR 2026 AT 3:06 AM.

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POWERED BY PURLIN.AI

3252 WINCHESTER RD

delaplane, VA 20144

US$5,000,000

  • 4 BR
    5 BA, 2 HALF BA
    approx. 11,145 SF

Interested? Let's Connect

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.

Details

11,145 Sq Ft

98.01 Private Acres Lot Size

other

US$22,229 Annual Tax

Built in 1845

MLS/Listing ID VAFQ2019664

Amenities & Features

Metal

Terrace

Lot - Private

Lot - Pond

Lot - Partly Wooded

Walk-in Closets

Elevator

Heating - Oil

Stone

Board

Out Buildings

Cooling - Zoned

Construction - Brick

Construction - Stone

Construction - Stucco

Dryer

Washer

Microwave

Dishwasher

Refrigerator

Breakfast Area

Dining Area

Kitchen Island

Heating - Electric

Pets Allowed

Estimate my mortgage

TOTAL MONTHLY COST

US$0

  • PRINCIPAL & INTEREST

    US$0

  • PROPERTY TAXES

    US$0

  • Common Charges

    US$0

HOME PRICE
DOWN PAYMENT
TERM
INTEREST

Interested In 3252 WINCHESTER RD?

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the BrightMLS. Real estate listings held by brokerage firms other than Douglas Elliman of VA are marked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website.

All information deemed reliable but not guaranteed. Last date updated: 03/18/2026.
Source: Bright Multiple Listing Service, Inc.

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