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3252 Winchester RoadDelaplane, VA 20144Price: $3,999,000

  • Price: $3,999,000
  • Est. Mortgage of $/month
  • 236 Days on Market
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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jul 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $3,999,000List Price
  • 4Bedrooms
  • 7Bathrooms
  • 11,145Square Feet
VISIT OUR OPEN HOUSES!!! SUN. JULY 12, 2026 - 11AM to 2PM SUN. JULY 19, 2026 - 11AM to 2PM SUN. JULY 26, 2026 - 11AM to 2PM 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.
Listed by Carolyn Young of Samson Properties

Open Houses

July 19th
Starts: 11:00am
Ends: 2:00pm
July 26th
Starts: 11:00am
Ends: 2:00pm

Driving Directions

Railey Vacations
Railey Vacations
Office: 301-387-2124
5 Vacation Way
McHenry, MD 21541

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More Info

Location Information

  • Date Listed11/21/2025
  • ZoningRA
  • UsmAreaDelaplane

School Information

  • Junior HighMarshall
  • High SchoolFauquier
  • Elementary SchoolClaude Thompson

Parking

  • Parking FeaturesGravel Driveway
  • Parking TypesAttached Garage
  • Total Garage And Parking Spaces1

Property

  • Road ResponsibilityPrivate
  • Road Surface TypeGravel
  • New Construction YNN
  • Lot DescriptionBacks to Trees, Partly Wooded, Pond, Private
  • FencingBoard

Exterior

  • RoofMetal
  • FoundationStone
  • Exterior FeaturesWater Fountains, Outbuilding(s)

Property Information

  • Lot Size Square Feet4,269,481
  • Above Grade Finished Area7789
  • Below Grade Area Total3,356
  • Below Grade Finished Area3356

Other

  • Other Structures List
    • Cabana/Pool House
    • Guest House
    • Horse Stable
    • Machine Shed
    • Run-in Shed
    • Shed Shop
    • Tenant House
  • Additional Parcels YNN
  • Historic YNYes
  • ExclusionsThe 2 Living Room chandeliers

Basic Information

  • MLS NumberVAFQ2019664
  • Ownership InterestFee Simple
  • List Price$3,999,000
  • Square Feet11,145
  • Acreage98.01
  • Year Built1845
  • MLS Property TypeResidential
  • StatusACT

Basic Information

Building

  • ViewScenic Vista, Garden/Lawn
  • Rooms
    • Bathroom 2
    • Bathroom 3
    • Bedroom 2
    • Bedroom 3
    • Bedroom 4
    • Breakfast Room
    • Dining Room
    • Foyer
    • Full Bath
    • Half Bath
    • Kitchen
    • Library
    • Living Room
    • Primary Bathroom
    • Primary Bedroom
    • Study
  • Walls CeilingsPlaster Walls
  • Interior FeaturesKitchen - 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, Other
  • Association Fee IncludesNone
  • Security FeaturesSecurity Gate
  • High School DistrictFauquier County Public Schools
  • LocationTypeRural
  • Broker NameSamson Properties
  • Building Number3252
  • DirectionsGPS
  • Num Attached Garage Spaces1
  • Main Level Total Baths3
  • Main Level Bedrooms1
  • Main Level Half Baths1
  • Main Level Full Baths2
  • Upper Levels Total Full Baths3
  • Upper Levels Total Bedrooms3
  • Upper Levels Total Baths4
  • Upper Level1 Bedrooms3
  • Upper Level1 Full Baths3
  • Upper Level1 Total Baths4
  • Upper Level1 Half Baths1
  • Upper Levels Total Half Baths1
  • Story ListMain, Upper 1
  • Structure Design TypeDetached
  • Construction MaterialsStucco, Stone, Brick
  • Property StyleOther
  • Bedrooms4
  • Full Bath5
  • Bathroom7
  • Half Baths2
  • Levels2
  • Fireplace FeaturesWood
  • Fireplace YNYes
  • Fireplace7
  • Garage TypeGarage - Side Entry
  • Garage Spaces1
  • GarageYes
  • Patio And Porch FeaturesBalconies- Multiple, Terrace

Tax Information

  • Total Taxes Payment FrequencyAnnually
  • Tax Total Finished Sq Ft8,150
  • Tax Assessment Amount3390700
  • Tax Year2015
  • Taxes$22,228
  • County Tax$21,093.95
  • County Tax Payment FrequencyAnnually
  • Assessment Year2025

Location

  • Address3252 Winchester Road
  • Area Total11,145
  • SubdivisionNone Available
  • TownDelaplane
  • StateVA
  • Zip20144
  • CountyFauquier

Interior

  • Appliances Included
    • Dishwasher
    • Dryer
    • Microwave
    • Oven/Range - Electric
    • Refrigerator
    • Washer
  • Heating YNYes
  • CoolingHeat Pump(s), Zoned

Utilities

  • Water SourceWell
  • SewerSeptic Exists
  • Cooling FuelElectric
  • Water HeaterElectric
  • Heating FuelOil, Electric
  • Heat SystemSteam, Heat Pump(s), Zoned

Amenities

  • PoolYes - Personal
  • AmenitiesNone
  • PricePerSqFt513
  • Other AmenitiesFireplace, Pool

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Railey Vacations participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated July 14, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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