Peace and Plenty at Bollingbrook, circa 1809, presents an outstanding property in the history of Virginia. Originally part of a 9,600-acre land patent from Lord Fairfax in 1731 it later became a wedding present of 790 acres in 1809 whereas the one-story, Federal brick house of four rooms was constructed. Later in 1830, Robert Bolling added 21 rooms creating an ornate and classic Jeffersonian design with 15 ft. ceilings, beautiful fireplace mantels, intricate cornices and columns, a glorious staircase, beautiful hand-blown glass windows, decorative door handles and hinges and gorgeous, white oak floors. All original seventeen (17) structures remain: The Manor House, The Pool House, The Guest Cottage, The Gate House, The Chapel, The Overseer's House, The 12-stall Barn, The Old Silo barn (oldest in the State of Virginia), The Cannery, The Scale House, The Blacksmith Shop, A Wood Shed, The Schoolhouse, A Smokehouse, A Summer Kitchen, A Barn Apartment and The Hilleary House. The main house offers four generous entertaining rooms upon entry; a Music room, Living room, Meeting room and a Library. The expansive Dining room can accommodate two dozen friends and family. A Primary Suite with adjoining sitting room, opens to the deck sunroom and a stroll on the wrap around balcony. Of course, a luxurious bath leading to an expansive closet of 27 ft. x 18ft. outfits the suite. In addition, there are two, luxurious bedrooms with fireplaces and private baths, a back staircase, full basement, a three-car garage, and a lovely mudroom entry to the Kitchen with enclosed porch. The Pool House flanks a saltwater pool with a wide lounging ledge and overlooks the Blue Ridge displaying spectacular sunset views! Among the pristinely manicured grounds is the notable 250-year-old Cedar of Lebanon tree, largest in Virginia. Preserved in Easement with the Land Trust of Virginia and in the Piedmont Hunt territory, this 365-acre retreat offers unparalleled tranquility and privacy for All to enjoy!
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.
Rare village offering with acreage and views! Tucked away on a quiet dead-end street on the southern edge of historic Upperville, this beautifully updated brick home offers the best of country living—peaceful, private, and within walking distance to a village favorite - the Hunter’s Head Tavern. Set on 1.8 acres and offered with an adjacent 2+ acre buildable parcel, this is a unique opportunity for expanded living or future investment. Thoughtfully renovated, this split-foyer home features an open main-level layout ideal for modern living. The living and dining areas flow seamlessly into a bright, eat-in kitchen with a new oversized island, quartz countertops, LVT flooring and updated lighting. Also on the main level are the primary bedroom suite, a guest bedroom, and a stylishly renovated full bath. The lower level is designed for comfort and versatility. It includes a cozy family room with a wood-burning fireplace, two additional bedrooms (one currently used as a fitness room), a second updated full bath, and a dedicated home office complete with custom built-ins and wet bar. The laundry/mudroom includes a new built-in cubby area and ample storage with direct access to the detached garage. Outdoor living is just as special: a fenced-in pool with a charming pool house (shower + half bath), two open decks, a covered front porch, and sweeping views of neighboring protected farmland and open lawn. An oversized two-car brick garage and a separate storage shed provide additional functionality. The property is fully fenced and offers ample room to relax, entertain, or explore future possibilities. Just minutes to Route 50, this home is perfectly located for commuters yet feels worlds away. Live in the heart of Upperville, but with privacy, space, and the bonus of an extra lot. A must-see!
Tucked away on a quiet dead-end street on the southern edge of historic Upperville is this beautifully updated contemporary brick home offering the best of country living—peaceful, private and within walking distance to a village favorite - the Hunter’s Head Tavern. Set on 1.8 open acres, this thoughtfully renovated home features an open main-level layout ideal for modern living. The living and dining areas flow seamlessly into a bright, eat-in kitchen with a new oversized island, quartz countertops, LVT flooring and updated lighting. Also on the main level are the primary bedroom suite, a guest bedroom and a stylishly renovated full bath. The lower level is designed for comfort and versatility. It includes a cozy family room with a wood-burning fireplace, two additional bedrooms (one currently used as a fitness room), a second updated full bath and a dedicated home office complete with custom built-ins and a wet bar. The laundry/mudroom includes a new built-in custom cubby area and ample storage with direct access to the detached garage. Outdoor living is just as special: a fenced-in pool with a charming pool house (shower + half bath), two open decks, a covered front porch, and sweeping views of neighboring farmland and open lawn. An oversized two-car brick garage and a separate storage shed provide additional functionality. The property is partially fenced and offers ample room to relax and entertain. Just minutes to Route 50, this home is perfectly located for commuters yet feels worlds away. Live in the heart of Upperville, but with privacy and space. A must-see! (Separate lot available together with this parcel. See MLS#:VAFQ2018374).
Peace and Plenty at Bollingbrook, circa 1809, presents an outstanding property in the history of Virginia. Originally part of a 9,600-acre land patent from Lord Fairfax in 1731 it later became a wedding present of 790 acres in 1809 whereas the one-story, Federal brick house of four rooms was constructed. Later in 1830, Robert Bolling added 21 rooms creating an ornate and classic Jeffersonian design with 15 ft. ceilings, beautiful fireplace mantels, intricate cornices and columns, a glorious staircase, beautiful hand-blown glass windows, decorative door handles and hinges and gorgeous, white oak floors. All original seventeen (17) structures remain: The Manor House, The Pool House, The Guest Cottage, The Gate House, The Chapel, The Overseer's House, The 12-stall Barn, The Old Silo barn (oldest in the State of Virginia), The Cannery, The Scale House, The Blacksmith Shop, A Wood Shed, The Schoolhouse, A Smokehouse, A Summer Kitchen, A Barn Apartment and The Hilleary House. The main house offers four generous entertaining rooms upon entry; a Music room, Living room, Meeting room and a Library. The expansive Dining room can accommodate two dozen friends and family. A Primary Suite with adjoining sitting room, opens to the deck sunroom and a stroll on the wrap around balcony. Of course, a luxurious bath leading to an expansive closet of 27 ft. x 18ft. outfits the suite. In addition, there are two, luxurious bedrooms with fireplaces and private baths, a back staircase, full basement, a three-car garage, and a lovely mudroom entry to the Kitchen with enclosed porch. The Pool House flanks a saltwater pool with a wide lounging ledge and overlooks the Blue Ridge displaying spectacular sunset views! Among the pristinely manicured grounds is the notable 250-year-old Cedar of Lebanon tree, largest in Virginia. Preserved in Easement with the Land Trust of Virginia and in the Piedmont Hunt territory, this 365-acre retreat offers unparalleled tranquility and privacy for All to enjoy!
Courtesy: Hunt Country Sotheby's International Realty
540-687-8500
Welcome to Slate Hill, an exquisite country estate on almost 10 acres. Fully renovated interior and exterior in 2021 with all original features retained, including wide heart pine flooring throughout and detailed woodwork. This elegant c. 1700’s property has 4 bedrooms, 2.5 full baths and combines a wonderful mix of old and new. The property was originally a portion of the 2,000 acre land patent granted to George Washington by Lord Fairfax in 1768. The original house and cabin structures date from 1770s with additions to the house built in the 1820s. A stone entrance bridge with stone pillars crosses a small spring-fed stream, flanked by ancient boxwoods and wrought iron gates. A large parking area and driveway provides ease of access. Towering trees ring the property, providing a sense of your this beautifully private glen. The perfect country lifestyle awaits inside the house. A gourmet kitchen offers soapstone counters, custom cabinetry, farmhouse sink, imported AGA appliances and a casual dining area. The formal dining room retains its exposed original stone walls, restored beams, original fireplace and antique lighting. Living Room has expansive windows allowing the natural light to flood in, 9ft ceiling beams, and the original fireplace mantle. The master bedroom has a fireplace, cedar closets and a luxury bath with custom slate shower walls and Hansgrohe Raindance showerhead and fittings. Of the three guest bedrooms, one includes an en-suite bathroom and two walk-in wardrobes. Other features include new standing seam metal roofs on the main house and cabin, a new two-zone HVAC system, and a new washing machine and dryer (2024). A large stone patio is reached through the kithcen. Extensive mature landscaping and gardens surround the house. George Washington's original log cabin has been fully restored with a repointed chimney & two fireplaces, a loft bedroom and new full bath. Horse amenities include a center aisle barn by renowned builders King Construction (2021), with four oversized stalls, tack room, bathroom, wash stall and feed/laundry room. A breezeway with carriage doors provides beautiful airflow and views. Behind the barn, are four fenced paddocks and a 120x70 EquiSand riding arena that suits all riding disciplines.
Virginia’ s renowned “Hunt Country” provides the fabulous setting for this exquisite country estate, encompassing over 51.7 acres of verdant pastures, lush woodlands. and towering trees. A long and picturesque driveway, alongside a sparkling, meandering stream, winds through the woods and leads to the entrance of this stunning three level English manor home. Boasting a total of 7 spacious Bedrooms, 7 ½ Baths, and over 6,935 square feet of spectacular living space, this stately home is private, secluded and ideally located in prestigious Greystone. The historic villages of Upperville and Middleburg are just minutes away, offering fine shops, wonderful restaurants, bucolic vineyards, sporting clubs and excellent schools. The breathtaking views of the magnificent Blue Ridge Mountains serve as a backdrop and create a simply magical setting. Upon entering the main residence, the extraordinary architectural design and uncompromising quality of workmanship is immediately evident. The dramatic Center Hall offers a warm and gracious reception and extends to the rear façade, with French doors accessing an absolutely gorgeous courtyard. A beautiful gunite Pool, bordered by field stone terraces and brilliant gardens, create a magical and serene setting. Showcasing some of the outstanding features of this impeccable property are spacious rooms, 11’ high ceilings, vaulted and beamed ceilings, multiple French doors and walls of windows, bathing the rooms in natural sunlight. The Main House features handsome crown moldings, gleaming hardwood floors, and three beautiful wood burning fireplaces, adding warmth and charm to the ambiance of the rooms. The Kitchen, which is highlighted by premium appliances (Viking and SubZero), opens to the Great Room. The Primary Bedroom was completely remodeled, and the luxurious Bath includes heated flooring, stone counter tops and a fantastic soaking tub. The second level features three spacious Bedrooms, one of which is currently used as an additional office. Two more lovely, tiled full Bathrooms are located here. The stunning lower “Walk Out Level” is ideal for many uses. There is an additional Bedroom, a crafts room, a Family Room and two additional full Baths. A fabulous new wing / Pool House/ Guest Quarters, was added to the main residence. It greatly expanded the living space and includes a gorgeous Great Room, a paneled Library, a second Kitchen, two additional Bedrooms and two additional full Baths, plus a wonderful, screened Porch, overlooking the Pool and courtyard. This entire wing is tastefully designed and beautifully appointed, creating a marvelous area for the enjoyment of both family and friends. This wing is perfect as an in-law suite, guest suite, private office or separate living quarters for extended family. Huge windows grace every wall and capture scenic vistas of the open fields and paddock, perfect for the equestrian, with a four-board fenced paddock and run-in shed. Westfield is a splendid country estate, beautifully appointed and built with extraordinary quality, offering the utmost in a gracious and luxurious lifestyle. Highlights of Westfield: Whole House Generator / Heated gunite inground pool / Pool and cover completely rebuilt in 2021 / Exterior of stucco and stone / Wood and tiled flooring / 11-foot-high ceilings, vaulted, coffered and tray ceilings / Three bay attached garage / Beautiful stone fountain serves as centerpiece of the courtyard / An addition of a new wing overlooking the Pool and courtyard / Mature Orchard includes: Peaches, Apples & Plums / Shooting Range for Target practice/Window treatments in Living Room, Foyer, Kitchen, new in 2023/Water treatment system was upgraded and replaced in April 2025/Home Alarm System was fully replaced in 2024/Whole House Sound System upgraded in early 2023/Pool Heater replaced in 2024/Pool and Automatic Cover completely rebuilt in 2021/Pool motor replaced in April 2025.
Welcome to Slate Hill, an exquisite country estate on almost 10 acres. Fully renovated interior and exterior in 2021 with all original features retained, including wide heart pine flooring throughout and detailed woodwork. This elegant c. 1700’s property has 4 bedrooms, 2.5 full baths and combines a wonderful mix of old and new. The property was originally a portion of the 2,000 acre land patent granted to George Washington by Lord Fairfax in 1768. The original house and cabin structures date from 1770s with additions to the house built in the 1820s. A stone entrance bridge with stone pillars crosses a small spring-fed stream, flanked by ancient boxwoods and wrought iron gates. A large parking area and driveway provides ease of access. Towering trees ring the property, providing a sense of your this beautifully private glen. The perfect country lifestyle awaits inside the house. A gourmet kitchen offers soapstone counters, custom cabinetry, farmhouse sink, imported AGA appliances and a casual dining area. The formal dining room retains its exposed original stone walls, restored beams, original fireplace and antique lighting. Living Room has expansive windows allowing t
Courtesy: Thomas and Talbot Estate Properties, Inc.
540-687-6500
Welcome to Slate Hill, an exquisite country estate on almost 10 acres. Fully renovated interior and exterior in 2021 with all original features retained, including wide heart pine flooring throughout and detailed woodwork. This elegant c. 1700's property has 4 bedrooms, 2.5 full baths and combines a wonderful mix of old and new. The property was originally a portion of the 2,000 acre land patent granted to George Washington by Lord Fairfax in 1768. The original house and cabin structures date from 1770s with additions to the house built in the 1820s. A stone entrance bridge with stone pillars crosses a small spring-fed stream, flanked by ancient boxwoods and wrought iron gates. A large parking area and driveway provides ease of access. Towering trees ring the property, providing a sense of your this beautifully private glen. The perfect country lifestyle awaits inside the house. A gourmet kitchen offers soapstone counters, custom cabinetry, farmhouse sink, imported AGA appliances and a casual dining area. The formal dining room retains its exposed original stone walls, restored beams, original fireplace and antique lighting. Living Room has expansive windows allowing the natural light to flood in, 9ft ceiling beams, and the origin
Opportunity to to own a charming historic church building in the heart of Upperville. A perfect location and opportunity to live in the heart of the historic village of Upperville just west of Middleburg. The church and the studio have been both renovated and connected to offer more living space and a seamless home in excellent condition. Beautiful Mountain views from the large back yard. Close to Sky Meadows State Park, the Appalachian Trail and many local Vineyards.
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Upperville is located in Virginia. Upperville, Virginia has a population of 118. Upperville is more family-centric than the surrounding county with 100% of the households containing married families with children. The county average for households married with children is 35.08%.
The median household income in Upperville, Virginia is $78,987. The median household income for the surrounding county is $111,368 compared to the national median of $69,021. The median age of people living in Upperville is 59.3 years.
The average high temperature in July is 86.6 degrees, with an average low temperature in January of 23.3 degrees. The average rainfall is approximately 43.7 inches per year, with 19.1 inches of snow per year.
