1795 Colonial Revival Home On 1,100 Acres Listed In Upperville, Virginia

21515 Trappe Rd, Upperville, VA 20184

There are properties that impress, and then there are properties that define a landscape. Llangollen, the legendary estate at 21515 Trappe Road in Upperville, Virginia, is one of the latter—a 1,100-acre expanse of rolling pastures, forests, and heritage that stands as a living monument to America’s agricultural and architectural past. Built in 1795, this remarkable Colonial Revival home sits at the heart of the Middleburg and Upperville hunt country, one of the most storied regions in the United States, long celebrated for its equestrian traditions, its natural beauty, and its deep historical roots. Now listed for sale at $25,000,000, this property represents not only one of the finest pieces of real estate in Virginia, but also one of the most complete and enduring private estates in the nation.

To approach Llangollen is to step back through centuries of American life. The mile-long driveway, bordered by mature trees and sweeping fields, offers a slow reveal—a procession through time and space that culminates in the sight of the grand house itself, perfectly positioned at the center of a vast pastoral canvas. The main residence rises with an understated confidence, its symmetrical facade and white-painted columns echoing the enduring ideals of early American architecture. With nine bedrooms, eleven bathrooms, and 12,500 square feet of living space, the mansion combines historical authenticity with modern comfort, blending the charm of its 18th-century origins with the refinement of later Colonial Revival influences.

This is not merely a home; it is an institution. From the moment of its creation, Llangollen was envisioned as a working estate, a place where architecture and agriculture would coexist in harmony. Its founders understood that beauty could be both functional and profound, that land could nurture not only crops and horses but also heritage. For over two centuries, the property has done just that—sheltering families, welcoming guests, and shaping the cultural identity of Virginia’s countryside. Every field, fence line, and outbuilding carries the weight of that continuity.

The setting of Llangollen is unparalleled. With 700 acres of level, open pasture and 400 acres of forested land, the estate stretches beyond the eye’s horizon. This vast sweep of private terrain ensures both complete seclusion and a sense of limitless freedom—qualities that have made the region so beloved by horsemen, conservationists, and dreamers alike. The estate’s topography is as varied as it is beautiful: gently undulating hills, glassy ponds reflecting the sky, and ancient trees that have stood as silent witnesses to the passing of empires and generations.

Equestrian life has always been at the core of Llangollen’s identity. Today, it remains one of the finest equestrian estates in the country, complete with a best-in-class polo facility, seven meticulously maintained barns, and extensive turnout options. The fields are crisscrossed with post-and-rail fencing, perfectly suited for breeding, training, and recreation. There are eight ponds across the property, each one adding not only beauty but also function—watering livestock, supporting wildlife, and enhancing the sense of peace that pervades the landscape. For horse enthusiasts, this is not just a home for sale; it is the ultimate expression of equestrian excellence, where every detail has been shaped by centuries of passion for the sport.

The main house itself is a study in refinement and restraint, its Colonial Revival architecture evoking an era when proportion, balance, and natural materials defined domestic grandeur. The original section, built in 1795, remains intact, bearing the marks of early craftsmanship: thick stone walls, hand-hewn beams, and fireplaces built to endure the centuries. Later expansions and restorations respected these foundations, introducing higher ceilings, broader windows, and elegant moldings that align with the evolving tastes of the 19th and early 20th centuries.

The grand entrance hall, with its sweeping staircase and gleaming wood floors, serves as the axis around which the home unfolds. From here, the rooms extend with the kind of grace only found in historic estates—spacious yet intimate, formal yet welcoming. The drawing rooms are bright and stately, their fireplaces framed in marble and their windows opening toward the rolling hills beyond. Each room tells a story, layered with centuries of design and care.

The dining room, with its generous proportions and traditional detailing, has likely hosted gatherings that span the history of Virginia’s gentry. It is easy to imagine the soft glow of candlelight across polished silver and linen, the murmur of conversation echoing beneath high ceilings. Even now, the house exudes a sense of timeless hospitality—of belonging to a tradition that values both grace and generosity.

Modern comforts have been introduced with discretion, ensuring that the mansion remains livable without losing its authenticity. The kitchen, for example, has been designed for contemporary use, offering high-end appliances and ample space for entertaining, yet its cabinetry and finishes harmonize with the home’s architectural lineage. Each of the nine bedrooms offers a view—of the gardens, the pastures, or the distant Blue Ridge Mountains—and each of the eleven bathrooms combines classic style with quiet luxury.

Throughout, craftsmanship takes precedence over ostentation. The woodwork is detailed but never excessive, the colors neutral yet warm. Sunlight filters through original windowpanes, and the sound of the countryside—a distant bird call, the whisper of wind through the trees—remains part of the experience. This is architecture that respects both its occupants and its environment, an approach that feels increasingly rare in today’s real estate landscape.

Yet what truly sets Llangollen apart is not simply its scale or architecture, but its continuity. The estate has survived wars, economic upheavals, and countless transitions of ownership, each era leaving its quiet imprint without disturbing the essence of the place. Its 1,100 acres are protected under a conservation easement, ensuring that its scenic beauty and agricultural character will endure for generations to come. To own this property is to participate in that stewardship—to assume the responsibility of preserving one of Virginia’s great rural estates.

Beyond the main house, the property unfolds like a private village. There are eight tenant cottages, each with its own story and architectural charm, providing accommodations for guests, staff, or extended family. Numerous outbuildings—including barns, workshops, garages, and storage structures—attest to the estate’s working nature. Every component has been maintained or restored with an eye toward authenticity, ensuring that the farm remains not just picturesque but fully functional.

The polo fields, meticulously groomed and maintained, reflect the estate’s long association with sport and tradition. Riders and horses have trained here for generations, and the fields continue to embody the same dedication to excellence that defines the entire property. For equestrians, few homes for sale in America can compare to this level of facility and setting—a rare combination of heritage and practicality that elevates Llangollen beyond mere luxury to something enduring and cultural.

As one walks the grounds, it becomes clear that this is more than a house or farm—it is a landscape of meaning. The forests, spanning approximately 400 acres, offer sanctuary to wildlife and serenity to those who wander beneath their canopy. The open pastures, stretching across 700 acres, glimmer with the subtle variations of light that only Virginia’s hunt country can produce. Every vista feels deliberate, composed as if by the hand of a painter. This interplay of nature and architecture defines the estate’s character: cultivated yet wild, vast yet personal.

The property’s proximity to Washington, D.C.—only about an hour away—adds to its rarity. It offers complete privacy without isolation, combining the peace of rural life with the accessibility of the nation’s capital. Meanwhile, the nearby town of Middleburg, just fifteen minutes from the gates, provides a charming blend of boutiques, restaurants, and cultural life that complements the tranquility of the estate. For those seeking to balance retreat and connection, Llangollen offers an ideal harmony.

It is easy to understand why this estate is regarded as a generational asset. Its sheer scale, its architectural integrity, and its location within one of America’s most iconic landscapes make it more than an investment—it is a legacy. Few properties embody so completely the ideals of preservation, beauty, and purpose. For collectors of historic real estate, for equestrian professionals, or for families seeking a permanent anchor in the countryside, Llangollen represents an opportunity that will not soon be replicated.

This home for sale stands as both a monument to the past and a promise for the future. Its roots reach back to 1795, when the United States itself was still defining its identity, and yet it continues to evolve, adapting gracefully to the needs of modern life. The architectural language of the Colonial Revival—symmetry, proportion, and craftsmanship—has allowed the house to remain timeless. Unlike so many estates that fade into obsolescence, Llangollen has never lost relevance. It is as captivating now as it was two centuries ago.

For the realtor entrusted with presenting this property, there is no need for embellishment. The facts themselves carry their own poetry: 1,100 acres of private land, a nine-bedroom mansion, seven barns, eight cottages, and a mile-long drive that leads to serenity. In a market where luxury is often defined by excess, Llangollen defines it through authenticity—through the quiet confidence of history and the enduring beauty of land and architecture in perfect balance.

Standing on the front steps, looking out over the vast fields that stretch toward the horizon, one cannot help but feel the weight of time and the promise of continuity. The same sun that warmed these stones in 1795 still illuminates them today. The same breezes that stirred the trees centuries ago still move through the air with calm familiarity. This is not merely a house—it is a living chronicle, a space where generations have come and gone, leaving their imprints in the land, the walls, and the stories that still echo through its halls.

For the next owner, the acquisition of Llangollen will mean more than the possession of extraordinary real estate. It will mean joining the lineage of caretakers who have protected and cherished this place. It will mean walking in the footsteps of history, tending to the same fields, and drawing inspiration from the same timeless views. Most of all, it will mean the chance to experience what so few can claim: the ownership of one of Virginia’s true historic estates—an architectural masterpiece, a pastoral sanctuary, and a lasting testament to the artistry of both human hands and the natural world.

Photos: