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$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: (703) 714-9030
$1,350,000
5 Beds ⋅ 4 Baths
Want privacy? You've got it! Surrounded by nature? You've got it! Top of the line finishes? 5 Bedroom 3.5 baths? It's all here at "Black Bear Meadow" in this Custom-Built Cape Cod with deep wrap around porches on almost 19 acres, R-1, with 5440 Sq Ft finished! Work from home in the private office with redundant options for WIFI. Large main level owner’s suite has steam shower, a sunroom/sitting room with access to the outdoor patio and unique attached nursery/second bedroom area. REAL solid oak hardwood 6” flooring. This Seller spared no expense in finishing this home, note the impressive Adam’s trim on all three floors. The Gourmet Kitchen features a walk-in butler’s pantry and opens to the living room plus the floor to ceiling, stone, wood-burning fireplace and built-in library shelving. There is a matching outdoor patio fireplace for quiet evenings watching fireflies float up into the treetops. There's a mudroom & laundry on the main level with more built-in cubbies. The lower level, just finished in June, has full size 5th bedroom, full exercise room with TV, padded flooring, and has a level walk out to second patio. Off the main game room there is a media room with double thick walls and additional sound insulation...Sound studio waiting on your musical inspirations. Lower-level Family Room includes an antique bar that awaits final connection to water in wall. There are hiking & riding trails throughout the property. And a clear garden area. Come, sit on the porch for a while, listen to the serenade of birds. Recenter every day. You will fall in love!

3411 Fenny Hill Rd, Delaplane

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$835,000
4 Beds ⋅ 5 Baths
Space, flexibility, privacy, and meaningful updates in the heart of Delaplane. Set on 1.76 acres with peaceful views and a highly adaptable layout, 3608 N Red Oak Ln offers the kind of room and versatility that is hard to find at this price point. Inside, the home features 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 creates excellent flexibility for guests, extended stays, work-from-home needs, recreation space, multigenerational living, or simply spreading out with more privacy. Recent improvements add real value and peace of mind. The bathrooms have been renovated, and major system updates include a new HVAC system, 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. The outdoor setup is another standout feature. The property includes multiple fenced sections, creating separate outdoor areas for entertaining, pets, gardening, play, or quiet relaxation. With nearly two acres, pasture and wooded views, and room to enjoy the outdoors, the home offers a true country-living feel without giving up access to Northern Virginia, wineries, Sky Meadows State Park, Marshall, Middleburg, and major commuter routes. 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. If you have been looking for an updated Delaplane home with privacy, space, two kitchens, flexible living areas, and room to live, work, host, and unwind, 3608 N Red Oak Ln deserves a closer look.

3608 N Red Oak Ln, Delaplane

Listing courtesy of Signature Move Real Estate. Contact: 2028581101
$825,000
3 Beds ⋅ 2 Baths
Major price reduction! 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, parcel size and price to new construction- this Home is a steal! Nestled on a lush, 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. Schedule your private showing today!

3545 Cobbler Mountain Rd, Delaplane

Listing courtesy of TTR Sotheby's International Realty. Contact: (703) 714-9030
$4,995,000
2 Beds ⋅ 1 Baths
Set on 120 pristine acres in the heart of Virginia’s hunt country, this exquisitely restored 1860s Victorian farmhouse offers a rare opportunity to own a private estate with sweeping 360° Blue Ridge Mountain views. Overlooking Goose Creek and framed by spectacular sunsets, the property blends timeless elegance with modern comforts, featuring thoughtfully designed interiors, a spa-inspired bath, and inviting indoor-outdoor living with expansive porches and firepit entertaining areas. Perfectly positioned just minutes from route 66, Upperville, Middleburg, and some of the region’s most prestigious wineries and equestrian events, this estate is ideally suited for the discerning buyer seeking both tranquility and proximity to the country’s premier horse community. With ample acreage for riding, recreation, or future equestrian pursuits, this is a truly exceptional offering in one of Virginia’s most coveted settings in Orange County Hunt territory. Also available as 50 acres including the house, pending boundary line adjustment. Contact seller agent for more details. Agent related to seller. Professional interior shots coming soon

9078 Maidstone Rd, Delaplane

Listing courtesy of Thomas and Talbot Estate Properties, Inc.. Contact: 5406876500
$1,450,000
4 Beds ⋅ 4 Baths
2nd Chance Opportunity! Welcome to an extraordinary private estate set on over 25 acres of scenic countryside, where refined living meets the beauty of open farmland. A picturesque, tree-lined drive and gravel approach create a grand sense of arrival, offering both privacy and timeless elegance. Inside, a stunning foyer welcomes you with rich wood flooring, setting the stage for the sophisticated interiors that follow. Designed with both luxury and comfort in mind, the home offers expansive living spaces ideal for entertaining and everyday living alike. The kitchen features stainless steel appliances, granite countertops and wood cabinetry, with windows that highlight the plush landscape, perfect for gathering and hosting with ease. Thoughtfully designed spaces flow seamlessly throughout the home, including a dedicated media room—perfect for cinematic experiences in the comfort of your own residence. Each bedroom serves as a private sanctuary, enhanced by distinctive features such as cozy fireplaces, serene balconies, and spacious walk-in closets, delivering a true retreat-like experience. The owner's suite has a custom California Closet System in the oversized closet. The fully finished basement introduces a private, self-contained living area complete with its own kitchen and laundry room, along with custom flagstone flooring sourced from the property itself. and a steam shower. This versatile space is ideal for extended family, guests, or potential income-producing opportunities, all while maintaining a high level of comfort and privacy. Step outside to discover resort-style living at its finest. An expansive deck overlooks the beautifully maintained grounds, while the recently serviced pool and charming gazebo provide the perfect backdrop for elegant outdoor entertaining or quiet relaxation. Additional amenities include a detached two-car garage and a state-of-the-art 25KW in-ground solar system, valued at approximately $100,000 and fully conveying with the property—offering both sustainability and impressively low electric costs. With over 25 acres of versatile farmland, this estate presents a rare opportunity to embrace a lifestyle of luxury, privacy, and possibility—whether for equestrian pursuits, agriculture, or simply enjoying the tranquility of your own expansive retreat. This is more than a home—it is a legacy property.

9393 Briar Ln, Delaplane

Listing courtesy of Redfin Corp. Contact: 3016586186
$875,000
3 Beds ⋅ 2 Baths
Price Reduction! Full restoration. Step back in time—without sacrificing modern comfort—in this beautifully restored circa 1875 farmhouse, a rare offering that has remained in the same family for generations until this year. Crafted in stucco-over-frame construction, the home is undergoing a thoughtful, top-to-bottom restoration that preserves its rich history while elevating its livability for today. Inside, you’ll find 3 charming bedrooms, 2 full baths, and a welcoming fireplace, all blending period character with refreshed style and comfort. (See attachments for the full list of improvements.) Set on 9.50 acres of gently rolling, mostly open land, the property enjoys bold, unobstructed mountain views and is surrounded by large conservation-easement farms, ensuring enduring privacy and rural beauty. A natural spring on the land offers potential for a future pond. Additional historic features include an old frame-and-stone barn and a family cemetery, adding to the unique story of the property. One family member was even a soldier in Mosby’s Rangers during the Civil War, deepening the home’s historical connection. A truly special opportunity to own a piece of Virginia’s past—revived for the next century.

11066 Moreland Rd, Delaplane

Listing courtesy of Sheridan-MacMahon Ltd.. Contact:

$1,999,900
4 Beds ⋅ 3 Baths
Discover Pohick’s Corner — a stunning 96-acre country retreat in the heart of Virginia’s horse and wine country, just one hour from Washington, D.C. Set amid rolling hills and preserved landscapes, this exceptional property offers both serenity and opportunity. Protected by a Fauquier County conservation easement, Pohick’s Corner and its neighboring property will forever maintain their breathtaking views and rural charm. The easement allows for the construction of an additional 6,000 sq. ft. home and multiple outbuildings — imagine your dream estate with space for a garage, barn, sheds, or pool house — all while enjoying the existing cozy cottage pool house and low taxes. Built in 2023, the four-bedroom home combines comfort, accessibility, and craftsmanship. Designed for one-level living, it features ramps, wide doorways, and open spaces ideal for easy movement. Inside, you’ll find vaulted and 9ft ceilings, hardwood floors throughout, and marble floors in the kitchen, half bath, and laundry room. A constant-pressure, variable-speed pump delivers water from the 100-gallon-per-minute well, and the five-bedroom septic system allows for future expansion. Step outside to the two-lane lap pool with a zero-entry ramp, perfect for relaxing or daily exercise. The land itself is a rare find — 96 acres of rich, diverse soils, ideal for pasture, grazing, or crops, bordered by two creeks and containing a natural spring. Whether you’re looking to create a private compound, a luxury farm retreat, or simply enjoy country living with modern comfort, Pohick’s Corner offers it all — unmatched privacy, natural beauty, and endless potential.

4050 Carrington, Delaplane

Listing courtesy of Homecoin.com. Contact: 8884002513
$3,999,000
4 Beds ⋅ 7 Baths
VISIT OUR OPEN HOU Introducing Ashleigh, a storied 98-acre estate with sweeping views of the Delaplane countryside. Originally part of Chief Justice John Marshall’s Oak Hill holdings, this Greek Revival manor was built for his granddaughter and remains one of Virginia’s most admired historic properties. Ashleigh is listed on both the National Register of Historic Places and the Virginia Landmarks Register, and is further protected by a conservation easement with The Land Trust of Virginia. The main residence showcases grand proportions, 12’ ceilings, heart pine floors, triple-sash windows, and elegant entertaining spaces including a double drawing room, formal dining room, paneled study, and a sun-filled gallery entry. The east wing features an extraordinary octagonal library added in 2001, while the west wing hosts a private and refined owner’s suite. The grounds are truly exceptional—renowned gardens with three outdoor garden rooms, curated plantings, wisteria-draped pergola, massive boxwoods, sculptures, a 100’ fountain, heated pool, and a pool/guest house with full kitchen and two bedrooms. Additional structures include three stables (17 stalls combined), run-in sheds, machine shed, farm manager apartments, and a charming 2-bedroom guest cottage near the main house. Perfectly positioned at the intersection of Route 17 and Route 55, with quick access to I-66, Ashleigh offers unmatched beauty, privacy, and historic pedigree—an extraordinary Delaplane opportunity rarely available.

3252 Winchester Rd, Delaplane

Listing courtesy of Samson Properties. Contact: 7033788810
$4,999,000
4 Beds ⋅ 5 Baths
Seaton Place Farm — A legacy estate of scale, privacy, and distinction in the heart of Hunt Country. Back on market through no fault of the property or sellers. Originally under contract as a secondary country retreat, the buyers' circumstances and timing changed. Inspections were completed successfully, and the reports are available upon request. Set between Upperville and Delaplane, on the edge of coveted Mellon land and within Piedmont Hunt territory, this 55± acre estate represents a category of ownership rarely available—and increasingly impossible to recreate. Defined by land, location, and architectural presence, it offers a level of privacy and permanence that distinguishes it from typical offerings. The circa-1840 brick residence—spanning approximately 5,800 square feet—has been carefully evolved to meet modern expectations while preserving its historic integrity. Positioned to command the landscape, the home is surrounded by curated outdoor environments including formal stone courtyards, a koi pond, a marble and wrought-iron rotunda, and a pool designed for both entertaining and retreat. Interiors are grounded in authenticity yet executed with refinement. Original materials—exposed brick, antique flooring, hand-blown glass, and period mantels—are complemented by elevated updates and a cohesive design approach. The primary suite offers privacy, natural light, and elevated views across the property, reinforcing a sense of quiet separation from the everyday. A newly reimagined kitchen and great room anchor the residence with a distinctly modern luxury sensibility. Featuring an imported Lacanche range, bespoke cabinetry, premium appliances, and a cathedral ceiling framed by a substantial stone fireplace, the space delivers both visual impact and functional excellence. Published and thoughtfully designed, it is the true center of the home. A separate carriage house introduces flexibility without compromise. Fully independent, with three bedrooms, two baths, and a complete kitchen, it functions equally well as a guest residence, staff quarters, or income-producing asset. Its established record as a highly rated luxury rental underscores both its quality and appeal. The estate’s amenities extend beyond expectation. A private Par 3 golf course—with three professionally designed greens and eleven tee boxes—offers a rare, low-maintenance recreational asset. A substantial pond with dock, an established barn complex, and extensive supporting infrastructure position the property for equestrian use or broader lifestyle pursuits. The barn includes six stalls with individual run outs, a wash stall, dual tack rooms, loft storage, and flexible auxiliary space suitable for modern adaptations—fitness, storage, or collection use. Additional features include fenced pastures, run-in sheds, a creek-fed field, greenhouse, garden, and supporting agricultural structures—creating a fully realized estate environment. This is a property that operates at a different level. Private, complete, and inherently limited by geography and legacy land constraints, Seaton Place Farm offers a compelling opportunity for the buyer seeking scale, discretion, and long-term value in one of Virginia’s most established and tightly held regions. A refined Hunt Country estate—offered for those who understand the difference.

1787 Light Horse Ln, Delaplane

Listing courtesy of Compass. Contact: (703) 310-6111