3252 Winchester Rd Delaplane, VA 20144
Estimated payment $38,240/month
About This Lot
The stunning and historic estate of Ashleigh, ca. 1840, is rich in history and beautifully sited to enjoy the magnificent gardens as well as grand views of the Delaplane countryside. These 98 acres were once part of Oak Hill, Chief Justice John Marshall’s estate, and the stone and stucco Greek Revival Manor house was designed and built for his granddaughter, Margaret Marshall Smith, and her husband. Ashleigh is listed on both the National Register of Historic Places and Virginia Historic Landmarks. To further protect the estate, the current owners put Ashleigh into a conservation easement with The Land Trust of Virginia. Wide stairs ascend to the columned front portico, from there one enters the grand front hall. Some exquisite details of the hall include beautiful heart pine flooring and wide moldings, large, deep-set windows, and a ceiling height of over 12’. Through deep-set, heart pine doorways, one then enters the elegant double drawing room adorned with a fireplace at each end of the room, a wet bar, and floor-to-ceiling triple sash windows which open onto decorative iron balconies. From the windows, one overlooks the lower-level stone terrace with fountain, gardens, and lawn. The upper level of the east wing, in addition to bedrooms and baths, features an impressive octagonal library, built in 2001 to house an extensive collection of books and art. The wide hallway leading to the library features a wood-paneled elevator and a full bath. The upper level of the west wing features the very private and elegant owner’s suite. The foyer of the suite offers a wall of closets and a powder room. The lovely bedroom features a 10’ ceiling height, heart pine flooring, a fireplace, and stately deep-set windows. From the bedroom one then enters the spacious walk-in closet, and adjacent marble bath. The ground level, light filled gallery is the entrance most used and features a tile mural by local artist Joan Gardiner. The gallery opens into a gracious sitting room from which one has access to the formal dining room and study. The study’s handsome pine paneling was removed from the White House during the Hoover Administration and installed at Ashleigh by then-owner Dr. Edmund Horgan. The very inviting formal dining room features French doors that open out to a large stone terrace, perfect for al fresco dining and entertaining. From the dining room, one passes through the butler’s pantry to the recently remodeled kitchen equipped with beautiful white cabinetry and marble countertops. GARDENS, FOUNTAINS, AND POOL: Featured in several Garden Tours, and most recently in 2021, the three garden rooms invite and encourage one to relax and breathe. When the current owners purchased Ashleigh, the gardens had been established and maintained; however, they took them to a new level. In 2019, they installed an impressive 100’ long fountain within an existing garden room and added a new pergola to support the established wisteria. The gardens are beautiful year-round, but it is the springtime when they come alive with thousands of perennials, including a gorgeous allee of peonies. Adjacent to the gardens is the heated pool and stunning pool/guest house with gathering room, full kitchen, and 2 bedrooms. The gardens of Ashleigh are further enhanced by massive boxwoods trimmed bi-annually by the Boxwood Society and by sculptures which remain from when Sandra Whitney Payson owned Ashleigh. HORSE FACILITIES AND DEPENDENCIES: Three stables: 10-stall, 4-stall, and 3-stall, run-in sheds and a large machine shed. Attached to the10-stall stable are two separate living quarters designed for farm managers. Close to the main home is a 2 bedroom, 2 bath guest cottage. Ashleigh is a beautiful and historically significant property, which provides the most perfect setting for an elegant lifestyle and for grand entertaining. Located at the SW intersection of Winchester Road, (Rt. 17) and Rt. 55, it is very convenient to I-66.
Listing provided by: Thomas and Talbot

Property Details
Property Type
- Land
Est. Annual Taxes
- $33,908
Horse Facilities and Amenities
- Horses Allowed On Property
Map
Home Values in the Area
Average Home Value in this Area
Tax History
Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
---|---|---|---|---|
2025 | $33,908 | $3,506,500 | $634,800 | $2,871,700 |
2024 | $33,080 | $3,506,500 | $634,800 | $2,871,700 |
2023 | $31,677 | $3,506,500 | $634,800 | $2,871,700 |
2022 | $31,677 | $3,506,500 | $634,800 | $2,871,700 |
2021 | $13,011 | $2,616,400 | $480,100 | $2,136,300 |
2020 | $26,021 | $2,616,400 | $480,100 | $2,136,300 |
2019 | $25,822 | $3,760,200 | $1,643,900 | $2,116,300 |
2018 | $25,510 | $3,760,200 | $1,643,900 | $2,116,300 |
2016 | $23,132 | $3,390,700 | $1,593,900 | $1,796,800 |
2015 | -- | $3,390,700 | $1,593,900 | $1,796,800 |
2014 | -- | $3,390,700 | $1,593,900 | $1,796,800 |
Property History
Date | Event | Price | Change | Sq Ft Price |
---|---|---|---|---|
07/21/2025 07/21/25 | Price Changed | $5,750,000 | -10.2% | $738 / Sq Ft |
04/18/2025 04/18/25 | For Sale | $6,400,000 | -- | $822 / Sq Ft |
Purchase History
Date | Type | Sale Price | Title Company |
---|---|---|---|
Deed | -- | None Listed On Document | |
Deed | -- | None Listed On Document | |
Deed | -- | None Listed On Document | |
Warranty Deed | $2,250,000 | Title Solutions Inc | |
Warranty Deed | $3,400,000 | -- |
Mortgage History
Date | Status | Loan Amount | Loan Type |
---|---|---|---|
Open | $1,500,000 | Credit Line Revolving | |
Previous Owner | $1,600,000 | New Conventional | |
Previous Owner | $1,250,000 | Adjustable Rate Mortgage/ARM | |
Previous Owner | $1,330,000 | New Conventional | |
Previous Owner | $1,400,000 | New Conventional |
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