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For sale
    • Price cut: $501K (5/3)
    $3,999,000

    3252 Winchester Rd, Delaplane, VA 20144

    4beds
    11,145sqft
    : 
    $25,482/mo
    Get pre-qualified
    Single Family Residence
    Built in 1845
    98.01 Acres Lot
    $3,906,800 Zestimate®
    $359/sqft
    $-- HOA

    What's special

    Heated poolMassive boxwoodsGreek revival manorWisteria-draped pergolaFarm manager apartmentsGrand proportionsDouble drawing room
    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.
    249 days
    |
    1,366
    |
    72
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Carolyn Young 703-261-9190,

    Samson Properties 7033788810,

    Listing Team: The Carolyn Young Team, Co-Listing Team: The Carolyn Young Team,Co-Listing Agent: Mona Botwick 703-691-5405,

    Samson Properties

    Source: Bright MLS,MLS#: VAFQ2019664MLS Logo

      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, Bathroom 2, Bathroom 3, Primary Bathroom, Full Bath, Half Bath
      Primary bedroom
      • Features: Primary Bedroom - Sitting Area, Flooring - HardWood, Fireplace - Wood Burning
      • Level: Upper
      • Area: 450 Square Feet
      • Dimensions: 15 X 30
      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: 15 X 16
      Primary bathroom
      • Level: Upper
      Bathroom 2
      • Level: Upper
      Bathroom 3
      • Level: Upper
      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: 17 X 18
      Foyer
      • Features: Flooring - HardWood
      • Level: Upper
      • Area: 432 Square Feet
      • Dimensions: 12 X 36
      Other
      • Level: Main
      Other
      • Level: Main
      Half bath
      • Level: Upper
      Half bath
      • Level: Main
      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: 20 X 37
      Study
      • Features: Fireplace - Wood Burning
      • Level: Main
      • Area: 270 Square Feet
      • Dimensions: 15 X 18
      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: 11,145
      • Total interior livable area: 11,145 sqft
      • Finished area above ground: 7,789
      • Finished area below ground: 3,356
      Video & virtual tour

      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, Below 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 Exists
      • Water: Well

      Community & HOA

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

      Financial & listing details

      • Price per square foot: $359/sqft
      • Tax assessed value: $3,390,700
      • Annual tax amount: $22,228
      • Date on market: 11/21/2025
      • Listing agreement: Exclusive Agency
      • Exclusions: The 2 Living Room Chandeliers
      • Ownership: Fee Simple
      • Road surface type: Gravel

        Estimated market value

        $3,906,800

        $3.71M - $4.10M

        $5,073/mo

        Price history

        DateEventPrice
        5/3/2026Price change$3,999,000-11.1%$359/sqft
        Source: Bright MLS #VAFQ2019664 Report a problem
        4/21/2026Listed for sale$4,500,000$404/sqft
        Source: Bright MLS #VAFQ2019664 Report a problem
        4/13/2026Contingent$4,500,000$404/sqft
        Source: Bright MLS #VAFQ2019664 Report a problem
        4/10/2026Listed for sale$4,500,000$404/sqft
        Source: Bright MLS #VAFQ2019664 Report a problem
        4/10/2026Contingent$4,500,000$404/sqft
        Source: Bright MLS #VAFQ2019664 Report a problem
        3/30/2026Price change$4,500,000-10%$404/sqft
        Source: Bright MLS #VAFQ2019664 Report a problem
        11/21/2025Listed for sale$5,000,000-13%$449/sqft
        Source: Bright MLS #VAFQ2019664 Report a problem
        10/31/2025Listing removed$5,750,000$516/sqft
        Source: Bright MLS #VAFQ2016254 Report a problem
        8/20/2025Price change$5,750,000-10.2%$516/sqft
        Source: WMLS #BMTVAFQ2016254 Report a problem
        7/24/2025Price change$6,400,000+11.3%$574/sqft
        Source: National Land Realty #VAFQ2016254 Report a problem
        7/21/2025Price change$5,750,000-10.2%$516/sqft
        Source: Bright MLS #VAFQ2016254 Report a problem
        4/18/2025Listed for sale$6,400,000+184.4%$574/sqft
        Source: Bright MLS #VAFQ2016254 Report a problem
        3/1/2017Sold$2,250,000-33.8%$202/sqft
        Source: Public Record Report a problem
        9/6/2005Sold$3,400,000$305/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$33,908 +2.5%$3,506,500
        2024$33,066 +4.4%$3,506,500
        2023$31,664 $3,506,500
        2022$31,664 +21.8%$3,506,500 +34%
        2021$26,007 $2,616,400
        2020-- $2,616,400 -30.4%
        2019$12,755 $3,760,200
        2018$12,755 $3,760,200 +10.9%
        2016-- $3,390,700
        2015-- $3,390,700
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 20144

        Getting around

        1 / 100
        Car-Dependent
        18 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Claude Thompson
        • Middle: Marshall
        • High: Fauquier
        • District: Fauquier County Public Schools

        Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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