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3252 WINCHESTER RD
DELAPLANE VA 20144 US

$5,000,000

Active Listing ID VAFQ2019664
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4 bed
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7.00 Bath (5 Full , 2 Half)
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Lot: 98.01 Acres
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Other

$5,000,000

Active Listing ID VAFQ2019664
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3252 WINCHESTER RD 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.

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Property Features

  • Facts
  • Lot Size: 98.01 Acres
  • Property Type: Residential
  • Property Sub-type: Other
  • Features
  • Full Bathrooms: 5
  • 1/2 Bathrooms: 2
  • Cooling System: Zoned, Heat Pump
  • Heating Fuels: Steam, Zoned, Heat Pump (Heating)
  • Additional Features
  • Fireplace
  • Pool

School Information

  • School
  • CLAUDE THOMPSON(Elementary)
  • MARSHALL(MiddleSchool)
  • FAUQUIER(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Other
  • listprice: 5000000
  • unparsedaddress: 3252 WINCHESTER RD
  • postalcity: DELAPLANE
  • stateorprovince: VA
  • country: US
  • postalcode: 20144
  • bathroomsfull: 5
  • bathroomshalf: 2
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 98.01
  • lotsizeunits: Acres
  • lotsizearea: 98.01
  • livingarea: 11145
  • livingareaunits: Square Feet
  • latitude: 38.90209
  • longitude: -77.91869
  • listagentfullname: Carolyn Young
  • listagentemail: carolyn@carolynyoungteam.com
  • listagentkey: 3yd-TRENDPA-12089
  • listagentmlsid: 12089
  • listagentpreferredphone: 7032619190
  • listagentofficephone: 7032619190
  • listofficekey: 3yd-TRENDPA-SAMP8
  • listagentstatelicense: 0225023781
  • listofficemlsid: SAMP8
  • disclaimer: Copyright © 2025 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: TRENDPA
  • yearbuilt: 1845
  • listingcontractdate: 2025-11-21
  • listagenturl: http://www.samsonproperties.net
  • countyorparish: FAUQUIER
  • elementaryschool: CLAUDE THOMPSON
  • highschool: FAUQUIER
  • elementaryschooldistrict: FAUQUIER COUNTY PUBLIC SCHOOLS
  • middleorjuniorschooldistrict: FAUQUIER COUNTY PUBLIC SCHOOLS
  • highschooldistrict: FAUQUIER COUNTY PUBLIC SCHOOLS
  • appliances: Oven/Range - Electric, Refrigerator, Dishwasher, Microwave, Washer, Dryer
  • cooling: Zoned, Heat Pump
  • constructionmaterials: Stucco, Stone, Brick
  • heating: Steam, Zoned, Heat Pump (Heating)
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 1
  • parkingfeatures: Driveway, Garage - Attached
  • waterfrontyn: False
  • franchiseaffiliation: Independent
  • interiorfeatures: Kitchen - Island, Dining Area, Breakfast Area, Primary Bath(s), Built-Ins, Elevator, Crown Moldings, Wood Floors, Bathroom - Soaking Tub, Floor Plan - Traditional, Walk-in Closet(s), Wet/Dry Bar, Wine Storage
  • rooms: Dining Room, Bathroom 3, Bathroom 6, Bathroom 7, Bathroom 1, Bedroom 1, Bedroom 4, Bathroom 5, Bedroom 3, Bathroom 2, Bathroom 4, Bedroom 2
  • otherstructures: Storage
  • accessibilityfeatures: Accessible Elevator Installed
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -77.91869, 38.90209
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Samson Properties", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"carolyn@carolynyoungteam.com", "ListBrokerageCity":"Chantilly", "ListBrokerageCountry":"US", "ListBrokerageEmail":"dsamson@samsonproperties.net", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/190/361431/20171013193508700.png", "ListBrokerageName":"Samson Properties", "ListBrokeragePhone":"(703) 378-8810", "ListBrokeragePostalCode":"20151", "ListBrokerageStateOrProvince":"VA", "ListBrokerageUnitNumber":"Suite 100", "ListBrokerageUnparsedAddress":"14526 Lee Road", "ListBrokerageWebsiteUrl":"http://www.samsonproperties.net", "ListOfficeAddress1":"1602 Village Market Boulevard unit: 255 ", "ListOfficeAddress2":"Suite 100", "ListOfficeBrokerMlsId":"SAMP8", "ListOfficeCity":"Leesburg", "ListOfficeCountry":"USA", "ListOfficeEmail":"dsamson@samsonproperties.net", "ListOfficePostalCode":"20175", "ListOfficeStateOrProvince":"VA", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - DELAPLANE, VA", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/3252-Winchester-Rd_Delaplane_VA_20144_M68102-18933?f=listhub&s=TRENDPA&m=VAFQ2019664&c=rexren", "MLSModificationTimestamp":"2025-11-21 17:47:30", "Neighborhoods":[{"Description":null, "Name":"NONE AVAILABLE"}], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":22229, "TaxDescription":null, "TaxYear":null}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 11/21/2025 6:34:19 PM GMT
Source Updated Date: 12/15/2025 6:54:16 AM GMT

Courtesy of: Carolyn Young, Samson Properties, carolyn@carolynyoungteam.com

Copyright © 2025 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.