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For sale
  • Price increase: $650K (7/24)
    $5,750,000

    3252 Winchester Rd, Delaplane, VA 20144

    4beds
    7,789sqft
    : 
    Single Family Residence
    Built in 1845
    98.01 Acres Lot
    $5,477,500 Zestimate®
    $738/sqft
    $-- HOA

    What's special

    Heated poolGuest cottageWood-paneled elevatorHorse facilitiesLarge stone terraceStone terrace with fountainRun-in sheds
    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 which 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 sculpture 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.
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    Zillow last checked: 7 hours ago

    Listing updated: July 21, 2025 at 03:04am

    Listed by:

    Will Driskill 540-454-7522,

    Thomas and Talbot Estate Properties, Inc.

    Source: Bright MLS,MLS#: VAFQ2016254MLS Logo
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    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 7
    • Full bathrooms: 5
    • 1/2 bathrooms: 2
    • Main level bathrooms: 3
    • Main level bedrooms: 1
    Rooms
    • Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Library, Foyer, Breakfast Room, Study
    Primary bedroom
    • Features: Primary Bedroom - Sitting Area, Flooring - HardWood, Fireplace - Wood Burning
    • Level: Upper
    • Area: 450 Square Feet
    • Dimensions: 30 X 15
    Bedroom 2
    • Features: Flooring - HardWood, Fireplace - Wood Burning
    • Level: Upper
    • Area: 225 Square Feet
    • Dimensions: 15 X 15
    Bedroom 3
    • Features: Flooring - HardWood, Fireplace - Wood Burning
    • Level: Upper
    • Area: 225 Square Feet
    • Dimensions: 15 X 15
    Bedroom 4
    • Level: Main
    • Area: 240 Square Feet
    • Dimensions: 16 X 15
    Breakfast room
    • Features: Flooring - Other
    • Level: Main
    • Area: 144 Square Feet
    • Dimensions: 12 X 12
    Dining room
    • Features: Flooring - HardWood, Fireplace - Wood Burning
    • Level: Main
    • Area: 306 Square Feet
    • Dimensions: 18 X 17
    Foyer
    • Features: Flooring - HardWood
    • Level: Upper
    • Area: 432 Square Feet
    • Dimensions: 36 X 12
    Kitchen
    • Level: Unspecified
    Library
    • Features: Flooring - HardWood
    • Level: Upper
    • Area: 784 Square Feet
    • Dimensions: 28 X 28
    Living room
    • Features: Flooring - HardWood, Fireplace - Wood Burning
    • Level: Upper
    • Area: 740 Square Feet
    • Dimensions: 37 X 20
    Study
    • Features: Fireplace - Wood Burning
    • Level: Main
    • Area: 270 Square Feet
    • Dimensions: 18 X 15
    Heating
    • Steam, Heat Pump, Zoned, Oil, Electric
    Cooling
    • Heat Pump, Zoned, Electric
    Appliances
    • Included: Oven/Range - Electric, Refrigerator, Dishwasher, Microwave, Washer, Dryer, Electric Water Heater
    Features
    • Kitchen Island, Dining Area, Breakfast Area, Primary Bath(s), Built-in Features, Elevator, Crown Molding, Soaking Tub, Floor Plan - Traditional, Walk-In Closet(s), Bar, Wine Storage, Other, Plaster Walls
    • Flooring: Wood
    • Has basement: No
    • Number of fireplaces: 7
    • Fireplace features: Wood Burning
    Interior area
    • Total structure area: 7,789
    • Total interior livable area: 7,789 sqft
    • Finished area above ground: 7,789
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    Property

    Parking
    • Total spaces: 1
    • Parking features: Garage Faces Side, Gravel, Attached
    • Attached garage spaces: 1
    • Has uncovered spaces: Yes
    Accessibility
    • Accessibility features: None
    Features
    • Levels: Two
    • Stories: 2
    • Patio & porch: Terrace
    • Exterior features: Water Fountains, Balcony
    • Has private pool: Yes
    • Pool features: Private
    • Fencing: Board
    • Has view: Yes
    • View description: Scenic Vista, Garden
    Lot
    • Size: 98.01 Acres
    • Features: Backs to Trees, Wooded, Pond, Private, Rural
    Details
    • Additional structures: Above Grade, Outbuilding
    • Parcel number: 6041822210
    • Zoning: RA
    • Special conditions: Standard

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Other
    • Property subtype: Single Family Residence
    Materials
    • Stucco, Stone, Brick
    • Foundation: Stone
    • Roof: Metal
    Condition
    • New construction: No
    • Year built: 1845

    Utilities & green energy

    • Sewer: Septic = # of BR
    • Water: Well

    Community & HOA

    Community
    • Security: Security Gate
    • Subdivision: None Available
    HOA
    • Has HOA: No
    Location
    • Region: Delaplane

    Financial & listing details

    • Price per square foot: $738/sqft
    • Tax assessed value: $3,390,700
    • Annual tax amount: $22,228
    • Date on market: 4/18/2025
    • Listing agreement: Exclusive Right To Sell
    • Listing terms: Cash
    • Ownership: Fee Simple
    • Road surface type: Gravel
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