Upperville, VA 20184 21846 Trappe Road

21846 Trappe Road Upperville, VA - Image 121846 Trappe Road Upperville, VA - Image 221846 Trappe Road Upperville, VA - Image 3
45 more
21846 Trappe Road Upperville, VA - Image 421846 Trappe Road Upperville, VA - Image 521846 Trappe Road Upperville, VA - Image 621846 Trappe Road Upperville, VA - Image 721846 Trappe Road Upperville, VA - Image 821846 Trappe Road Upperville, VA - Image 921846 Trappe Road Upperville, VA - Image 1021846 Trappe Road Upperville, VA - Image 1121846 Trappe Road Upperville, VA - Image 1221846 Trappe Road Upperville, VA - Image 1321846 Trappe Road Upperville, VA - Image 1421846 Trappe Road Upperville, VA - Image 1521846 Trappe Road Upperville, VA - Image 1621846 Trappe Road Upperville, VA - Image 1721846 Trappe Road Upperville, VA - Image 1821846 Trappe Road Upperville, VA - Image 1921846 Trappe Road Upperville, VA - Image 2021846 Trappe Road Upperville, VA - Image 2121846 Trappe Road Upperville, VA - Image 2221846 Trappe Road Upperville, VA - Image 2321846 Trappe Road Upperville, VA - Image 2421846 Trappe Road Upperville, VA - Image 2521846 Trappe Road Upperville, VA - Image 2621846 Trappe Road Upperville, VA - Image 2721846 Trappe Road Upperville, VA - Image 2821846 Trappe Road Upperville, VA - Image 2921846 Trappe Road Upperville, VA - Image 3021846 Trappe Road Upperville, VA - Image 3121846 Trappe Road Upperville, VA - Image 3221846 Trappe Road Upperville, VA - Image 3321846 Trappe Road Upperville, VA - Image 3421846 Trappe Road Upperville, VA - Image 3521846 Trappe Road Upperville, VA - Image 3621846 Trappe Road Upperville, VA - Image 3721846 Trappe Road Upperville, VA - Image 3821846 Trappe Road Upperville, VA - Image 3921846 Trappe Road Upperville, VA - Image 4021846 Trappe Road Upperville, VA - Image 4121846 Trappe Road Upperville, VA - Image 4221846 Trappe Road Upperville, VA - Image 4321846 Trappe Road Upperville, VA - Image 4421846 Trappe Road Upperville, VA - Image 4521846 Trappe Road Upperville, VA - Image 4621846 Trappe Road Upperville, VA - Image 4721846 Trappe Road Upperville, VA - Image 4821846 Trappe Road Upperville, VA - Image 49
Presented By: TTR Sotheby's International Realty
  • MLS# VALO2111024
  • 11/21/2025
  • Request Tour
  • Request Info
  • Beds • 11
  • Full/Half Baths • 9 / 4
  • SQFT • 17,000

Home Details

Set amid the picturesque countryside of Upperville, Virginia, Ayrshire Farm rises from the landscape with a presence that feels both timeless and stately. Encompassing 571 acres in the heart of the Virginia Piedmont, the estate is rich in heritage, design, and purposeful land stewardship. Few properties in the region balance these elements with such ease or at this scale. The manor house, completed in 1912, stands as the estates architectural anchor. Constructed of fieldstone quarried from the property, its four-foot-thick walls and steel-reinforced structure were bold innovations in their day. The residence carried the rare distinction of offering electricity, indoor plumbing, and central heating at a time when such comforts were little more than distant ideas for most of the country. More than a century later, its original cypress windows, beams, and intricate masonry speak to a standard of craftsmanship that endures with remarkable clarity. In recent years, the home has undergone a careful and comprehensive restoration, bringing modern performance and convenience to its historic framework. Its 17,000-square-foot interiors have been methodically rewired and re-plumbed, outfitted with three-phase power, central air, underground utilities, and a sophisticated security and communication system. Twelve restored fireplaces, finely calibrated lighting, locally crafted cabinetry, and an English conservatory designed by Glass Houses of England reflect a discerning approach to preservation. The materials, textures, and architectural details that define the residence create an atmosphere of quiet grandeur, grounded in authenticity rather than overt opulence. Ayrshire Farms influence extends far beyond the manor. The property became the first in Virginia to achieve both Certified Humane and USDA Certified Organic status, marking a defining moment in the states agricultural landscape. Its fields, orchards, and pastures continue to support working organic operations, helping shape regional standards for sustainable and ethical farming. This commitment to the land is not ornamental; it is foundational to the estates identity. The natural setting surrounding the home is as compelling as its history. Uppervilles storied equestrian traditions blanket the landscape with a quiet sophistication unique to the Virginia Piedmont. Located just 65 miles from the heart of Washington, DC, and 35 miles from Dulles International Airport, Ayrshire offers a sense of escape without isolation. The charming village of Middleburg, with its boutiques, cafs, and equestrian heritage, lies only a short drive away, placing everyday conveniences and refined country life within effortless reach. To the west, the ridgelines of the Blue Ridge Mountains and the expanse of Shenandoah National Park form a dramatic horizon. Artists and filmmakers have long been drawn to this terrain, captivated by its pastoral simplicity and sense of permanence. Alfred Hitchcocks Topaz was among the works filmed on the estate, a testament to the propertys cinematic presence. Today, Ayrshire Farm stands as one of the regions most significant estate holdings, a rare convergence of architectural provenance, ecological leadership, and natural beauty. It is a property defined not only by its past, but by the clarity of its vision. In an area known for remarkable estates, Ayrshire remains singular, offering a balance of history, purpose, and place that feels both beautifully rooted and unmistakably relevant.
Presented By: TTR Sotheby's International Realty

Interior Features for 21846 Trappe Road

Bedrooms

Bedrooms Count All Upper Levels11
Bedrooms Count Upper Level 18
Bedrooms Count Upper Level 23
Total Bedrooms11

Bathrooms

Bathrooms Half Upper Level 11
Bathrooms Half Main Level3
Bathrooms Half All Upper Levels1
Bathrooms Full Upper Level 23
Bathrooms Full Upper Level 16
Bathrooms Full All Upper Levels9
Bathrooms Count Upper Level 23.00
Bathrooms Count Upper Level 17.00
Bathrooms Count All Upper Levels10
Half Baths4
Total Baths13

Other Interior Features

LivingAreaSourceEstimated
Below Grade Unfin Area UnitsSquare Feet
Below Grade Unfin SQFT0
Below Grade Unfin SQFT SourceAssessor
Above Grade Finished Area17000
Above Grade Finished Area SourceEstimated
Above Grade Finished Area Unit TypeSquare Feet
BasementPartially Finished
Basement (Y/N)Yes
Below Grade Finished Area
Below Grade Finished Area SourceAssessor
Below Grade Finished Area Unit TypeSquare Feet
Central Air Y/NYes
Fireplace Y/NYes
Heating FuelNatural Gas
Heating Y/NYes
Hot WaterNatural Gas
Total Fireplaces9

General for 21846 Trappe Road

AccessibilityNone
Architectural StyleColonial, Federal, Manor
Bathrooms Count Main Level3.00
CityUPPERVILLE
Condo/Coop Association fee Y/NNo
Construction MaterialsOther
Cool FuelElectric
CoolingCentral A/C
CountyLOUDOUN
DirectionsFrom I-66, take Exit 23 toward US-17 North (Delaplane); Continue on US-17 to US-50 West; Turn left onto US-50 West toward Upperville; Turn right onto Trappe Road; Follow Trappe Road to the 21846 on th
Full Baths9
Garage Y/NNo
HOANo
HeatingForced Air
Levels4
Living Area17000
Lot Size Square Feet24872760.00
Lot Size UnitsSquare Feet
New ConstructionNo
Other StructuresAbove Grade, Below Grade
OwnershipFee Simple
PossessionSettlement
Price Per Sq Ft Total AG1164.71
Property TypeResidential
School DistrictLOUDOUN COUNTY PUBLIC SCHOOLS
Senior Community Y/NNo
SewerSeptic Exists
Standard StatusActive Under Contract
StatusACTIVE UNDER CONTRACT
Structure TypeDetached
Subdivision NameUPPERVILLE
Tax Annual Amount48432.0
Tax Assessed Value6016440.0
Tax Year2025
Total SQFT17000
Vacation Rental Y/NNo
Virtual TourClick here
Water Access Y/NNo
Year Built1912
Year Built SourceEstimated
ZoningSEE ZONING WEBSITE

Exterior for 21846 Trappe Road

Foundation DetailsConcrete Perimeter
Land Assessed Value9485800.00
Lot Size Acres571.00
Lot Size SourceEstimated
Navigable Water Y/NNo
Parking FeaturesCircular Driveway, Paved Driveway
PoolNo Pool
Type of ParkingDriveway, Other
Water Oriented Y/NNo
Water SourceWell
Water View Y/NNo
Waterfront Y/NNo

Additional Details

Price History

Rachel Shepherd

Price $19,800,000
MLS#VALO2111024
List Date 11/21/2025
Property Type Contingent
Phone 703.929.4729
Request Tour
Request Info
Visit My Website

Similar Properties to 21846 Trappe Road

Skip to content