21846 Trappe Road
Upperville, VA, 20184 $ 19,800,000
Bedrooms11 Baths9.4 Sq 17,000 Monthly Estimate*
$ 123,526
for $19,800,000 with 11 bedrooms and 9 full baths, 4 half baths. This 17,000 square foot home was built in 1912 on a lot size of 571.
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.
See more
FeaturesGeneralLiving Area 17000
Sewer Septic Exists
Heating Forced Air
Cooling Central A/C
Possession Settlement
Zoning SEE ZONING WEBSITE
Architectural Style Colonial Federal Manor
Construction Materials Other
School District LOUDOUN COUNTY PUBLIC SCHOOLS
Year Built 1912
Levels 4
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Accessibility None
County LOUDOUN
New Construction N
Property Type Residential
HOA N
Subdivision Name UPPERVILLE
Garage Y/N N
Water Access Y/N N
Other Structures Above Grade Below Grade
Full Baths 9
Status ACTIVE UNDER CONTRACT
Directions From 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
City UPPERVILLE
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 24872760.00
Tax Annual Amount 48432.0
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Count Main Level 3.00
Price Per Sq Ft Total AG 1164.71
Vacation Rental Y/N N
Virtual Tour https://vimeo.com/1139101359?share=copy&fl=sv&fe=ci
Standard Status Active Under Contract
Year Built Source Estimated
See more
InteriorHeating Fuel Natural Gas
Basement Partially Finished
Total Fireplaces 9
Hot Water Natural Gas
Basement (Y/N) Y
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 17000
Half Baths 4
Central Air Y/N Y
Total Bedrooms 11
Below Grade Finished Area 0
Below Grade Finished Area Unit Type Square Feet
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Estimated
Above Grade Finished Area Unit Type Square Feet
Total Baths 13
See more
ExteriorPool No Pool
Parking Features Circular Driveway Paved Driveway
Water Source Well
Type of Parking Driveway Other
Foundation Details Concrete Perimeter
Water View Y/N N
Lot Size Acres 571.00
Lot Size Source Estimated
Waterfront Y/N N
Land Assessed Value 9485800.00
Navigable Water Y/N N
Water Oriented Y/N N
See more
* Excluded FeaturesList ByTtr Sotheby's International RealtyBroker
daniel@danielheider.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $123,526
- Monthly Property Taxes
- $4,036
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Upperville, VA
Average List Price $6,299,800
Percent of Sale Price 68%
About Upperville, VA 914 Population
22% Since 2002
$ 116,488 Median Income
49.17 Median Age
28% Households with Children
Trends Information provided by ATTOM Data Solutions.
3533481 Elementary School
3533332 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 11/21/2025 | $19,800,000 | | Listed Price |