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262 Rokeby Rd, Delaplane
$2,400,000
4 Beds ⋅ 5 Baths
Along the gravel stretch of Rokeby Road, across the bridge at Gap Run, Brookside Farm unfolds as it has for nearly two centuries—a timeless property in the heart of Piedmont Hunt Country. Its historic 1840s residence, outbuildings, and approximately 100 acres belong to a landscape that feels not arranged, but inherited—shaped over generations and remarkably intact. Hayfields rise toward long views of the Blue Ridge Mountains, streams flow beneath mature trees, and the house and outbuildings rest naturally within the countryside. At the heart of the property stands the stately yet unpretentious 1840s residence, built of stone and stuccoed brick. It has been thoughtfully updated over the years while retaining its historic character. Originally two separate structures—a main house and stone cook house—the two were joined in the 1960s by a fieldstone kitchen. A broad screened porch provides entry into the kitchen’s breakfast area. From there, one step rises into the old cook house, now an informal den, while an original swinging service door leads into the spacious dining room with a fireplace. Beyond the dining room, the back hall serves as the home’s informal crossroads. Stairs lead to the rooms above and the basement below. A main door provides additional entry from outside, while another opens onto a rear terrace beside the brook. Two steps descend into the library, a favorite gathering place, with its fireplace and floor-to-ceiling bookcases framing the entrance to the front hall. The original formal entrance, framed by sidelights and a transom, opens onto a stone landing flanked by mature boxwood and lawn. A broad doorway leads into the generously proportioned living room, with tall windows, original woodwork, and a fireplace. From the front hall, the staircase rises gracefully to the second floor, with its walnut handrail and turned balusters. At the top of the front staircase, the spacious primary bedroom, one of three with fireplaces, overlooks the grounds through tall windows. It allows ample room for both sleeping and sitting. The upper hall leads past two full bathrooms to another bedroom overlooking the brook. At the top of the back staircase are a sitting room and an adjoining bedroom, currently used as an office. This bedroom, as well as the hall landing, gives access to a large second-story screened “sleeping porch.” Built directly above the porch below, with exposed rafters and wood floors, it remains a wonderfully intact expression of an earlier way of summer living. Behind the house, a footbridge crosses the brook to the swimming pool. Across the gravel drive, beneath old persimmon, dogwood, and cherry trees, the carriage house remains part of the working fabric of the farm. Three large bays provide storage, while a fourth serves as a run-in shed for the adjoining paddock. An expansive hayloft above offers further possibilities. Approaching the barn, the history of Holland’s Mill becomes tangible. Its foundation incorporates surviving stonework from the former woolen factory, destroyed by fire in 1864. Built into the hillside, the barn’s immense hayloft remains accessible at grade through large double doors. West of the barn, behind the silo and partly concealed by vines, stands a largely intact, imposing dry-laid stone structure. It remains a remarkable surviving feature thought to have served the mill’s operations. The approximately 100 acres surrounding the historic house and outbuildings rise and fall through hayfields, pasture, wooded slopes, and winding streams. A hayfield near the house climbs alongside Gap Run, offering views over its wide bends below, while pastures above the barn look unimpeded toward the Blue Ridge Mountains. The land is protected under a conservation easement.

262 Rokeby Rd, Delaplane

Listing courtesy of Thomas and Talbot Estate Properties, Inc.. Contact:

2697 Rokeby Rd, Delaplane
$2,225,000
Along the gravel stretch of Rokeby Road, approximately 85 acres of Brookside Farm unfold in rolling hayfields, mature woods, and the winding waters of Gap Run. An 1840s log cabin stands within this breathtaking landscape, while some 30 acres of woods shelter old trails and secluded stretches of stream. The property’s elevated ground offers the possibility of a new homesite amid the enduring beauty of Piedmont Hunt Country. The old log cabin retains its early character, with a large living room, fireplace, and stairs to a second floor. Beside the kitchen entrance, a spring still runs clear and cold, its edges thick with watercress. Behind the cabin, a tractor path climbs through the hayfield, with stunning views across the farm below. Large stands of oaks rise along the hilltop, and the ground levels to a shaded corridor along the woodland edge. Here, an opening leads into mature woods identified on early surveys as “Jacob’s Ladder.” Well-worn trails are maintained throughout by the Piedmont Hunt, preserving the old network of travel through this extraordinary forest. The wooded ground falls away to the south and east toward the deep water and wide bends of Gap Run, while to the north and west it rises along a ridge behind the vast hayfield beside the cabin. Here, at Brookside’s highest elevation, the land commands sweeping views across the countryside to the Cobbler and the Blue Ridge Mountains. The land is conscientiously protected under a conservation easement held by the Virginia Outdoors Foundation.

2697 Rokeby Rd, Delaplane

Listing courtesy of Thomas and Talbot Estate Properties, Inc.. Contact:

10257 Stillhouse Rd, Delaplane
$1,300,000
3 Beds ⋅ 3 Baths
Nestled on a secluded cul-de-sac in the rolling hills of Fauquier County, this property has been transformed over two decades into a one-of-a-kind mountain retreat. With over 3,000 square feet of living space, breathtaking mountain views, a picturesque creek, a resort-style pool and basketball court, and hundreds of thousands of dollars in hardscaping, this is truly a property unlike any other. Step through the custom 36-inch front doors into a family room with soaring 14-foot ceilings, a stone fireplace with gas insert, and stone veneer pillars and accent walls. The entire interior has been freshly painted. A few steps up leads to the expansive kitchen with hickory cabinetry, granite countertops, a gas stove, and custom oak crown molding with inlays. Recent appliance upgrades include a new dishwasher (2023), microwave (2023), refrigerator (2025), and washer and dryer (2026). Ascending the custom oak staircase with curved railing and oak trim, you enter the upper level where soaring 12-foot vaulted cathedral ceilings with knotty pine tongue-and-groove boards flow above premium 6-inch hickory hardwood floors. Four dramatic doghouse dormers add tremendous living space and natural light throughout. Three bedrooms, a bonus room off the primary serving as a sitting room or home office, and a spa-like primary bathroom featuring a 65-inch soaking tub, Ariel Cambridge 72-inch dual-sink marble vanity, marble wall tile, and LED lighted mirror complete the upper level. All bathrooms feature new Kohler toilets installed in 2025. Step outside to a resort-style complex where a second-story deck overlooks a 20x40 foot, 10-foot-deep saltwater pool with diving board, outdoor shower, and 24-foot waterfall fountain. A concrete basketball court with commercial-grade hoop, bluestone hardscaping, multiple retaining walls, and low-voltage landscape lighting complete the outdoor experience. Major infrastructure upgrades include a new 275-foot well with pump, pressure tank, and whole house filtration (2025), a Fauquier County permitted septic system with 1,500-gallon holding tank (2026), a whole house 16kW generator, new A coil (2023), new ejector pump with alarm (2023), radon mitigation system, whole house propane manifold, and an extensive underground drainage system. The detached two-car garage is fully wired and received a brand new roof in 2025. This is a legacy property, expertly crafted, endlessly upgraded, and ready for its next chapter.

10257 Stillhouse Rd, Delaplane

Listing courtesy of Samson Properties. Contact:

2626 Rokeby Rd, Delaplane
$4,625,000
4 Beds ⋅ 5 Baths
Along the gravel stretch of Rokeby Road, across the bridge at Gap Run, Brookside Farm unfolds as it has for nearly two centuries—a timeless property in the heart of Piedmont Hunt Country. Its 1840s house, historic outbuildings, and 185 acres form a remarkably intact landscape shaped over generations. Hayfields rise toward sweeping views of the Blue Ridge Mountains, streams wind beneath mature trees, and historic structures rest naturally within the countryside. At the heart of the farm stands the stately yet unpretentious 1840s residence, built of stone and stuccoed brick. Originally two structures—a main house and stone cook house—they were joined in the 1960s by a fieldstone kitchen. Thoughtfully updated over time, the house retains its original character. A broad screened porch welcomes visitors, while the former cook house now serves as an informal den. An original swinging service door opens to the spacious dining room, and the back hall connects the upper rooms, basement, front landing, and rear stone terrace beside the brook. The library features a fireplace and floor-to-ceiling bookcases framing the front hall. The original formal entrance retains its sidelights and transom, and a graceful staircase features a walnut handrail and turned balusters. The generous living room offers tall windows, original woodwork, and a fireplace. Upstairs, the spacious primary bedroom, one of three bedrooms with fireplaces, overlooks the grounds and accommodates both sleeping and sitting areas. The upper hall leads past two full bathrooms to another bedroom overlooking the brook. A second staircase opens to a sitting room and adjoining bedroom, currently used as an office. Both access a large second-story screened sleeping porch, with exposed rafters and wood floors—a wonderfully preserved reminder of an earlier era of summer living. Across the gravel drive, beneath mature persimmon, dogwood, and cherry trees, the carriage house offers three large storage bays and a fourth bay serving as a paddock run-in shed. An expansive hayloft above offers further possibilities. The barn incorporates stonework from Holland’s Mill, a former woolen factory destroyed by fire in 1864. Its immense hayloft, built into the hillside, remains accessible at grade through large double doors. West of the barn, behind the silo and partly concealed by vines, stands a largely intact, imposing dry-laid stone structure believed to have served the mill’s operations. Across the road, an 1840s log cabin retains its early character, with a large living room, fireplace, and stairs to the second floor. A spring beside the kitchen entrance still runs clear and cold, bordered by watercress. Behind the cabin, a tractor path climbs through the fields to expansive views across the farm. Mature oaks line the hilltop, where the land transitions into a shaded woodland corridor. Some 35 acres of mature forest, historically identified on early surveys as “Jacob’s Ladder,” preserve a network of worn trails. The woods descend toward the broad bends of Gap Run and rise along a ridge behind the hayfield. At Brookside’s highest elevation, the ridge commands sweeping views of the countryside, the Cobbler, and the Blue Ridge Mountains. The land is protected by a conservation easement held by the Virginia Outdoors Foundation.

2626 Rokeby Rd, Delaplane

Listing courtesy of Thomas and Talbot Estate Properties, Inc.. Contact:

5000 Lilac Ln, Delaplane
$3,165,000
5 Beds ⋅ 5 Baths
Lost Corner Farm features a beautiful custom-built country home on 50 open acres with spectacular Blue Ridge Mountain views. This property is ideally located just 15 minutes from Middleburg and convenient to I-66. Designed for both gracious entertaining and comfortable everyday living, this 5-bedroom, 4.5-bath residence offers over 5,300 square feet on three levels. The main level features a bright, open living space with soaring 12-foot ceilings, oversized windows, custom hardwood floors and a fireplace. The well-appointed kitchen offers high-end appliances, double ovens, an oversized refrigerator and a large quartz island with seating for six. The main-level primary suite includes a sitting area, custom walk-in closet, luxurious glass shower and direct access to the pool and terrace. A private office and beautifully renovated mudroom/laundry room complete the main level. Upstairs are four additional bedrooms, including two spacious luxury suites, each with beautifully renovated baths, plus two guest bedrooms sharing a Jack-and-Jill bath. The finished lower level provides flexible space for a recreation room, gym or storage. Outdoor living is equally appealing with a large pool, flagstone terrace, English gardens, raised beds, a small creek and an extensive fenced garden with water and electricity. The open acreage offers tremendous flexibility for equestrian improvements with excellent ride-out in the Orange County Hunt territory. Additional highlights include a slate roof, generator, Waterworks bathroom fixtures, security system, Starlink, 60-gallon-per-minute well, new pool cover, paved parking area and equipment shed. A rare combination of sophisticated country living, exceptional views and manageable acreage in one of Virginia’s most sought-after horse and wine country locations. (See documents for full list of upgrades and more. And don't miss the video!)

5000 Lilac Ln, Delaplane

Listing courtesy of Thomas and Talbot Estate Properties, Inc.. Contact:

10210 Possum Hollow Dr, Delaplane
$1,995,000
5 Beds ⋅ 5 Baths
A Million-Dollar View. Perched atop Lost Mountain with sweeping views across the Virginia Piedmont, Greencrest is a private 25-acre retreat where European inspiration meets the romance of Virginia Hunt and Wine Country. A quiet private road winds through mature woodland before arriving at the three-level residence, seemingly suspended above the world below. Yet Greencrest is remarkably convenient: I-66 is just minutes away, while the charming towns of Middleburg and Upperville are equally close, putting the best of Virginia’s Hunt Country, wineries and country life within easy reach. Washington, D.C., is approximately 50 miles from the property. It is a rare juxtaposition: privacy without remoteness, country life without compromise. Designed as beautifully for a weekend escape as it is for a full-time homestead, Greencrest offers five bedrooms and four-and-a-half baths, with interiors that feel cozy, sophisticated and effortlessly beautiful. Clean lines are softened by warm, inviting spaces, while windows throughout the home draw the landscape inside. At the heart of the house, the stately Great Room is anchored by an impressive stone fireplace. The sleek, newly renovated kitchen is both efficient and luxurious, with the landscape providing perhaps its most memorable feature: a view that turns even morning coffee into an occasion. Multiple sitting areas, a charming breakfast nook and a second fireplace create an easy flow between gathering and retreating, entertaining and simply being home. Three upper-level bedrooms enjoy ensuite baths, while additional bedrooms and a newly renovated spa-like bathroom occupy the walkout lower level. Far from feeling like a traditional basement, this beautifully finished level feels like a natural extension of the home, with warm, heated ceramic tile floors designed to resemble distressed wood, creating an especially comfortable and inviting space for family and guests. But at Greencrest, the house is only the beginning. Expansive front and rear decks and a screened porch blur the boundaries between indoors and out, offering multiple places from which to enjoy the mountain. In summer, life gravitates toward the private pool and its dramatic diving stone. As temperatures fall, the six-person hot tub becomes the perfect place to watch the sun disappear, the stars emerge and the valley settle into darkness below. The 25 acres offer a thoughtful balance of open ground, mature woods and a thoughtfully designed peach and cherry orchard, with additional fruit and nut trees woven throughout the property. There is room to wander, garden, explore and disappear for a while, with abundant wildlife as frequent company. And then there is the view. It changes by the hour and by the season: morning mist settling into the valley, summer greens stretching toward the horizon, brilliant fall color and expansive winter skies. From the mountain, the Piedmont unfolds in every direction, with 360-degree vistas that seem to go on forever. At Greencrest, the landscape isn’t simply something you look at. It becomes part of the way you live. Beyond the property lies one of Virginia’s most treasured landscapes. Middleburg and Upperville, celebrated for their equestrian traditions, historic villages and protected countryside, are both within easy reach. Vineyards and tasting rooms dot the surrounding hills, while Sky Meadows State Park and the Appalachian Trail offer miles of hiking nearby. Horseback riding, cycling, wineries, farm markets and the Blue Ridge are all part of life here. There is a lovely rhythm to life at Greencrest: pick fruit from your own trees, disappear into the woods for a morning walk, spend a summer afternoon by the pool, gather for dinner on the screened porch and watch the last light fall across the Piedmont.

10210 Possum Hollow Dr, Delaplane

Listing courtesy of Compass. Contact:

9565 Briar Ln, Delaplane
$1,699,000
4 Beds ⋅ 5 Baths
A Distinguished Virginia Hunt Country Estate: 4 Bedrooms | 5 Baths | 4,000+ Sq. Ft. | Classic Brick Colonial | Built 2001 Set amid the rolling hills and sweeping vistas of Delaplane, Virginia, this distinguished brick Colonial embodies the timeless beauty and refined country lifestyle of Virginia’s renowned Hunt Country. Surrounded by pastoral views and a collection of equestrian and recreational amenities, the estate offers privacy, elegance, and a remarkable connection to the land, all while remaining convenient to the region’s finest destinations. Located in the heart of Fauquier County, Delaplane is celebrated for its rolling countryside, picturesque horse farms, vineyards, craft breweries, and relaxed sophistication. Nearby Middleburg and Marshall offer acclaimed restaurants, boutique shopping, galleries, equestrian events, and charming local gathering places. The nearby Shenandoah Region provides opportunities for hiking, fishing, kayaking, canoeing, and outdoor recreation. Washington, D.C. is approximately one hour away, with Dulles International Airport just 45 minutes from the property. Classic brick architecture creates an elegant first impression, complemented by thoughtful updates and exceptional craftsmanship throughout. Gracious interiors feature custom floor-to-ceiling built-ins, including beautifully crafted bookshelves and an entertainment center in the main living room, hardwood floors, Pella windows and doors. A striking marble foyer and crystal chandelier welcome you, while Swarovski crystal chandeliers and coordinating sconces add glamour and sophistication to the principal rooms. The kitchen was completely gutted and renovated in 2021 with refined finishes and KitchenAid appliances. Bathrooms have been thoughtfully updated, including the luxurious primary bath renovated in 2020 with a new tub and shower, tile, vanities, shadowboxing, custom closet shelving, a spectacular Swarovski crystal chandelier and stunning Mountain views. A remarkable list of improvements includes a new roof (2017), Pella windows (2018), Pella rear entry and storm doors (2019), two Lennox Elite heat pump systems (2020), updated plumbing and electrical components, a water softener and whole-house filtration system, new septic pump and hatch, custom garage doors and openers, and new ceramic tile flooring in the finished basement. Beyond the residence, the property truly distinguishes itself as a private Hunt Country retreat. Equestrian amenities include horse paddocks, small barn with three stalls, shed (as-is) and heated water feeders. A private tennis court (as-is) and fenced rear yard provide exceptional opportunities for recreation, entertaining, and relaxation. From its beautiful Hunt Country setting and classic architecture to its elegant interiors, equestrian amenities, tennis court, and extensive improvements, this exceptional estate captures the enduring appeal of Delaplane living at its finest. Sophisticated yet welcoming, it is a remarkable country estate designed to be enjoyed for generations.

9565 Briar Ln, Delaplane

Listing courtesy of TTR Sotheby's International Realty. Contact:

3608 N Red Oak Ln, Delaplane
$789,999
4 Beds ⋅ 5 Baths
This home solves unique problems for homebuyers. Looking to bring in family or friends but worry about space. Well, this home has the solution for that with the distinct living spaces. Have pets that cannot get a long, with the 3 "separated" privacy fenced backyards solves this problem. Want to avoid having an HOA telling you what you can and cannot do, then this home solves this issue. Space to spread out. Privacy to unwind. Virginia wine country to explore. Set on 1.76 acres with peaceful views, meaningful updates, and a highly adaptable layout, 3608 N Red Oak Ln brings together country living and everyday flexibility in the heart of Delaplane. This home as a 5.5% assumable loan and feautures 4 bedrooms, 4 full bathrooms, 1 half bath, multiple living areas, two full kitchens, and a finished lower level with its own rear entrance. The layout offers excellent flexibility for guests, extended stays, work-from-home needs, recreation, multigenerational living, or simply enjoying more space and privacy. Recent improvements add value and peace of mind. The bathrooms have been renovated, and major system updates include new water heater, and new water filtration system. Hardwood floors, generous gathering spaces, walk-in closets, recessed lighting, a pantry, and a stone fireplace add warmth and function throughout the home. Outside, multiple fenced sections create separate areas for entertaining, pets, gardening, play, or quiet relaxation. Pasture and wooded views provide a peaceful backdrop for morning coffee, outdoor gatherings, and evenings spent unwinding at home. The lifestyle extends well beyond the property. Spend an afternoon exploring six nearby wineries and vineyards—Delaplane Cellars, Barrel Oak Winery & Brewery, Three Fox Vineyards & Brewery, Arterra Wines, Lost Mountain Vineyards, and Naked Mountain Winery. Pair a weekend tasting with a hike at Sky Meadows State Park or an outing to Marshall or Middleburg, then return to your own private retreat. Access to major commuter routes keeps Northern Virginia within reach while home feels a world away. For buyers seeking additional flexibility, the home’s layout may also support income-producing potential. A third-party short-term rental analysis is available for review; buyers should independently verify all use, permitting, occupancy, tax, and zoning requirements. With renovated bathrooms, two full kitchens, flexible living areas, and nearly two acres to enjoy, 3608 N Red Oak Ln offers room to live, work, host, and embrace the Delaplane lifestyle.

3608 N Red Oak Ln, Delaplane

Listing courtesy of Signature Move Real Estate. Contact:

2525 Gibson Ct, Delaplane
$7,900,000
4 Beds ⋅ 5 Baths
Piccola Toscana | Elegantly designed Italian Tuscan villa where rustic charm meets refined country estate living. Defined by earthy tones, natural materials, and seamless indoor-outdoor connections, this extraordinary residence was thoughtfully created to exist in harmony with its surrounding landscape. Set amidst the breathtaking rolling countryside of Delaplane, the property embraces its natural setting through extensive landscaping, gardens, hardscaping, and carefully designed outdoor living spaces. Authentic materials are featured throughout, including terracotta tiles, stone walls, wrought iron accents, exposed timber beams, and richly textured plaster finishes, creating a timeless sense of warmth and character. The main residence offers exceptional architectural detail at every turn, highlighted by five gas fireplaces, a gracious formal dining room, a wine room, an enclosed porch, and a luxurious primary suite conveniently located on the main level. Expansive windows frame picturesque views of the surrounding gardens and rolling hills, while outdoor patios, fire pits, and walking paths extend the living experience into nature. Complementing the main residence is a separate guest house, a welcoming heated pool, and an outdoor lounge designed for relaxation and entertainment. At the lower end of the property, an additional detached garage has been creatively transformed into a nostalgic retro diner, providing a unique gathering space for family and friends. Property is surrounded by the scenic Virginia countryside and enrolled in land use, seller not responsible for roll-back taxes.

2525 Gibson Ct, Delaplane

Listing courtesy of TTR Sotheby's International Realty. Contact:

3545 Cobbler Mountain Rd, Delaplane
$749,000
3 Beds ⋅ 2 Baths
Owned by the same family since the 1950s, this Home has been thoughtfully renovated over the years and from top-to-bottom between 2023–2026. Beautifully maintained and remodeled, this 3-bedroom, 2-bath brick ranch sits on a highly sought-after 3.7-acre lot in Delaplane. Offering convenient main-level living with modern updates and timeless charm this Home has an excellent price per square foot for the quality of upgrades conveyed. Recent upgrades include new windows, roof, gutters, soffits, HVAC, kitchen and coffee nook, bathrooms, laundry room, full basement, generator, water filtration system, vinyl siding, porch addition, gas log fireplace, garage doors, interior doors, lighting, switches, and more! Compare location, generous parcel size and price to new construction- this Home is a steal! Nestled on a lush, 3.7 acre landscaped lot surrounded by mature trees, the property combines privacy, convenience, and exceptional curb appeal. Inside, the bright and open floor plan showcases beautiful (renewed) oak hardwood floors, spacious living areas, abundant natural light, and large new windows throughout. Designed for both everyday living and entertaining, the home offers comfortable gathering spaces on both the main and lower levels and exterior. Relax on the inviting covered front porch or host guests on the private screened-in backyard patio. With its classic brick exterior, beautifully maintained grounds, and prime location near Delaplane, Marshall, and Front Royal — with easy access to I-66 — this charming property truly has it all. 40 mins to Dulles Airport and Fairfax. 45 to Reston and Tysons. 1 hour to DC. Schedule your private showing today!

3545 Cobbler Mountain Rd, Delaplane

Listing courtesy of TTR Sotheby's International Realty. Contact:

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