The agencies at Upperville
These agencies offer a selection of luxury properties vente at Upperville. Feel free to contact them for personalized assistance.
Peace and Plenty at Bollingbrook, circa 1809, is a remarkable Virginia estate with breathtaking sunset views and a history reaching back to the earliest years of the Commonwealth. The property was originally part of a 9,600-acre land patent granted by Lord Fairfax in 1731. In 1809, 790 acres were given as a wedding present, upon which the original one-story Federal brick house was constructed. In 1830, Robert Bolling expanded the residence to 21 rooms, creating the handsome Jeffersonian house that remains today, distinguished by 14-foot ceilings, finely carved fireplace mantels, intricate cornices and columns, a graceful staircase, hand-blown glass walk-through windows, original decorative hardware and white oak floors. The estate retains all 17 of its historic structures, creating an unusually complete record of life on a Virginia country estate: the Manor House (4BR/3.5BA), Pool House (2BR/1.5BA), Stone Guest Cottage (1BR/1BA), Gate House Cottage (1BR/1BA), Chapel, Estate Manager’s House (2BR/2.5BA), 12-stall Barn, Broodmare Barn, Underground Silo—the oldest in the State of Virginia, the Cannery, Scale House, Blacksmith Shop, Wood Shed, Schoolhouse, Smokehouse, Summer Kitchen, Barn Apartment (2BR/1BA), and the Hilleary House. This amazing property could serve as a multi-generational compound, thriving equine business, showplace for entertaining, private luxury escape or all of the above. The first-floor of the Manor House opens to a grand foyer and four magnificent entertaining rooms—a Music Room, Living Room, Meeting Room, and Library. Beyond is an expansive Dining Room suited to large gatherings. The second-floor hallway leads to the Primary Suite which includes an adjoining sitting room that opens to the sunroom and wraparound upper balcony. The primary bath leads to an exceptional 27-by-18-foot closet and dressing room. There are two additional bedrooms, each with a fireplace and private bath. A wrought-iron spiral staircases lead to a cupola with spectacular 360-degree views. The Manor House also includes a back staircase, full basement, three-car garage, and mudroom entry adjoining the kitchen and enclosed porch. The Pool House overlooks the saltwater, heated pool surrounded by French cast iron statues and long views of the Blue Ridge, particularly beautiful at sunset. Across the grounds are open lawns, historic outbuildings, horse pastures and fields, and magnificent mature trees including the notable 250-year-old Cedar of Lebanon, recognized as one of the largest in Virginia. Preserved in easement with the Land Trust of Virginia and within the Piedmont Hunt territory, the 365-acre Bollingbrook estate remains a rare example of a Virginia estate preserved in both character and setting.
…By Hunt Country Sotheby's International Realty
CHAMBLIN MILL | CIRCA 1792 — HISTORY, PRIVACY & A LIFESTYLE LIKE NO OTHER 2,75% Assumable Mortgage/Separate Guesthouse with rental income Set on 3.21 private and scenic acres with approximately 1,000 feet of Beaver Dam Creek frontage, this extraordinary historic property offers something increasingly difficult to find in Northern Virginia: genuine character, remarkable privacy, natural beauty and a story more than two centuries in the making — all just 10 minutes from the charming village of Middleburg. Originally built in 1792 as a working grist mill, the surviving Miller's home now forms the heart of a beautifully restored and expanded residence where centuries-old character blends comfortably with modern living. With more than 4,700 square feet of total living space, 5 bedrooms, 3.5 baths and five wood-burning fireplaces, Chamblin Mill is a home meant to be experienced rather than simply viewed. Outside, the property becomes its own private retreat. Listen to the creek from the porch, watch wildlife move through the grounds, catch a glimpse of the resident blue heron, or spend summer afternoons beside the in-ground pool and spa. Here, privacy is not created by fences or landscaping — it comes naturally. Adding exceptional versatility is a fully independent guest house with its own entrance, driveway and utilities. Featuring 2 bedrooms, a full bath, kitchen, dining room, family room and full front porch, it offers wonderful possibilities for extended family, guests, a private office or continued income-producing use. (MLS Lower Level 2 reflects finished living spaces within the guest house.) An assumable loan at 2.75% provides an additional opportunity for qualified buyers. And for the buyer who falls in love not only with the home but with the way it has been furnished, with an acceptable offer, the furniture is included, creating the possibility of stepping into Chamblin Mill and simply beginning the next chapter. This is not a cookie-cutter luxury home, and it was never meant to be. It is a 234-year-old piece of Virginia history with a creek, pool, guest house, privacy and a personality entirely its own. If you have been waiting for a property that feels different from everything else you have seen, come experience Chamblin Mill in person. Schedule your private showing and discover why some homes are not merely purchased — they are passed from one caretaker to the next.
…By Hunt Country Sotheby's International Realty
A masterful expression of French château-inspired elegance, this extraordinary estate is a private sanctuary where timeless architecture, resort-style living, and refined craftsmanship converge across 5.16 breathtaking acres in the heart of Grenata. Beyond stately gas lanterns, a flowing fountain, and lush woodland surroundings, a refined breezeway and hand-carved entry introduce interiors spanning more than 11,500 square feet, thoughtfully curated with bespoke millwork, rich hardwoods, soaring coffered ceilings, and geothermal comfort throughout. Designed for both grand entertaining and everyday living, the home blends sophistication with warmth, as a dramatic floating staircase anchors elegant gathering spaces illuminated by sparkling chandeliers and centered around a striking dual-sided fireplace. The chef’s kitchen features custom cabinetry, professional-grade appliances, intricate detailing, and a fully appointed butler’s pantry, while adjacent indoor and outdoor living spaces flow seamlessly onto an enclosed deck with retractable screens, outdoor kitchen, and fireside lounge overlooking the estate grounds. The resort-caliber pool setting serves as the centerpiece of the outdoor experience, complete with a concealed winding waterslide and dedicated pool bath with double showers. The expansive lower level was designed for elevated entertaining, offering spaces for wine tastings, game nights, cinematic screenings, catered gatherings, and a custom bar crafted for effortless hosting. A spectacular primary suite offers dual dressing rooms and a spa-inspired steam shower sanctuary, complemented by two additional bedrooms with private en suite baths and two generously sized bedrooms connected by a shared bath. A dedicated upper-level executive office suite with private entrance and welcoming lobby creates an exceptional environment for private consultations, remote business operations, wellness services,inspired creative pursuits or au-pair/in-law suite, while additional highlights include a home gym, Victorian-style conservatory greenhouse, spacious mudroom, main-level bedroom suite with full bath, and attached four-car garage. Perfectly positioned moments from shopping, dining, wineries, and the equestrian lifestyle of Leesburg’s celebrated Hunt and Wine Country, this exceptional estate delivers a luxury lifestyle defined by privacy, beauty, and timeless distinction.
…By Hunt Country Sotheby's International Realty
This is the one you have been waiting for!! Well cared for home, one story living in desirable Briarwood Estates...east side location convenient to commuter routes, shopping and Old Towne Winchester. Open floor plan with close to 1700 square feet. Three bedrooms, two full baths with hardwood floors in living/family room and dining area. Gas fireplace in family room, two walk in closets in master suite. Two car garage, two decks (enjoy your morning coffee on deck off of master bedroom!!) and large fenced backyard with storage shed.
…By Hunt Country Sotheby's International Realty
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These agencies offer a selection of luxury properties vente at Upperville. Feel free to contact them for personalized assistance.