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Showing 37-42 of 79 listings
Property
$1,649,900
5352 Sq Ft
1.71 acres
3D Virtual Tour
2 FREEDOM CT, MECHANICSBURG
Beds: 5
Baths: 6
Lot (acres): 1.71
Price/Sq Ft: no data
Tax Annual: $11,615
Year Built: 2022
Added: 2025-10-27
MLS#: PACB2047840
Property
$1,295,000
5028 Sq Ft
0.39 acres
Virtual Tour
Pending
38 WESTWIND CIR, LITITZ
Beds: 5
Baths: 4
Lot (acres): 0.39
Price/Sq Ft: no data
Tax Annual: $15,604
Year Built: 1993
Added: 2025-10-27
MLS#: PALA2075710
Property
$1,249,900
4956 Sq Ft
5.02 acres
Updated
111 N OLD STONEHOUSE RD, CARLISLE
Beds: 5
Baths: 4
Lot (acres): 5.02
Price/Sq Ft: no data
Tax Annual: $8,359
Year Built: 2003
Added: 2025-10-27
MLS#: PACB2047048
Property
$2,895,000
6699 Sq Ft
2.56 acres
Pending
102 JAMESFIELD PL LOT 4, MANHEIM
Beds: 6
Baths: 7
Lot (acres): 2.56
Price/Sq Ft: no data
Tax Annual: no data
Year Built: 2026
Added: 2025-10-27
MLS#: PALA2076448
Property
$1,875,000
13847 Sq Ft
4.47 acres
Updated
253 BRINDLE RD, MECHANICSBURG
Beds: 6
Baths: 8
Lot (acres): 4.47
Price/Sq Ft: no data
Tax Annual: $11,040
Year Built: 1988
Added: 2025-10-27
MLS#: PACB2047046
Property
$1,998,500
6700 Sq Ft
85.92 acres
Updated
Virtual Tour
5330 LONG CORNER RD, WHITE HALL
Beds: 5
Baths: 5
Lot (acres): 85.92
Price/Sq Ft: no data
Tax Annual: $8,293
Year Built: 2006
Added: 2025-10-27
MLS#: MDHR2047978
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Property Details

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Property Listing
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Address

21846 TRAPPE RD

$19,800,000
City
UPPERVILLE
State
VA
ZIP
20184
Virtual Tour | Pending
MLS#: VALO2111024
11
Bedrooms
13
Bathrooms
17000
Sq Ft
571
Acres
Year Built 1912
Property Type For Sale
Price/Sq Ft $1,165
Tax Annual $48,432
Added 2025-11-23
Cooling
Central A/c
Heating
Forced Air
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 estate’s 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 Farm’s 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 state’s 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 estate’s identity.

The natural setting surrounding the home is as compelling as its history. Upperville’s 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, cafés, 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 Hitchcock’s Topaz was among the works filmed on the estate, a testament to the property’s cinematic presence.

Today, Ayrshire Farm stands as one of the region’s 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.