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$22,000,000
655181 MLS
Prime parcel w/ long frontage on Seminole Trail and Berkmar Drive.

Seminole Trl, Charlottesville
$17,000,000
5 Beds ⋅ 6 Baths ⋅ 679439 MLS
Few US properties possess the historical gravity and architectural purity of Tuckahoe. Boyhood home of Thomas Jefferson, this extraordinary 557 acre estate overlooking the James River represents a rare opportunity to acquire one of the most complete and authentic early 18th century plantation layouts in North America. At the heart of the estate stands the irreplaceable H frame manor house, masterfully constructed by William Randolph between 1733 and 1740. As the only surviving Randolph home still on its original site, the residence retains a breathtaking degree of original material, from period windows and detailed entrances to the legendary, fully paneled black walnut salon. The timeless, cedar lined approach leads to manicured formal grounds and the remarkably preserved Plantation Street. Here, the original quarters, kitchen, smokehouse, storehouse, barn, and overseer’s office still stand. Most notable is the original one room schoolhouse where a young Thomas Jefferson received his earliest formal education beneath a unique domed ceiling. Protected in perpetuity by historic conservation easements, this National Historic Landmark stands as an undisturbed sanctuary of early American architecture and a legacy estate without peer.

12601 River Rd, Richmond
$14,000,000
6 Beds ⋅ 4 Baths ⋅ 670948 MLS
The most significant offering of Albemarle County acreage to reach the market in recent years—529.65 acres with sweeping Blue Ridge Mountain views, over 12 acres of open water across multiple ponds and a lake, and a setting of scale and possibility rarely found this close to Charlottesville. The property includes two residences and is served by multiple entrances along Earlysville Road, providing flexibility for future use. Open pastures, wooded acreage, and expansive water features combine to create a landscape equally suited for farming, recreation, or a private estate of exceptional presence. Its location is unmatched—minutes to Route 29 North, NGIC, and the Charlottesville-Albemarle Airport, with quick access to UVA and downtown Charlottesville. A property that offers both privacy and proximity, ready to support the next generation of vision in northern Albemarle.

3260 Earlysville Rd, Earlysville
$8,800,000
5 Beds ⋅ 5 Baths ⋅ 665249 MLS
Situated at the foothills of the Blue Ridge Mountains, White Hall Estate offers a rare blend of natural beauty, viticultural pedigree, and architectural distinction - just 14± miles from the City of Charlottesville. Spanning 212± acres with approximately 48 acres of established estate vineyards within the acclaimed Monticello AVA - recently named the top wine region in the U.S. - this turnkey winery and farm offers both lifestyle enjoyment & production success. The stone manor home, custom built in 1992, with 5 bedrooms and 4.5 baths, is on a gentle rise, framing absolutely breathtaking panoramic views of the Blue Ridge Mountains & Shenandoah National Park. The over 12,600 sq.ft. winery building is the perfect flex space for a variety of pursuits and is equipped for not only production but also for events. The property also includes a tenant home and numerous outbuildings. A haven for wine enthusiasts, investors, and those seeking an elegant rural retreat, the property combines elevated terroir, proven varietals, and timeless design in a setting of serene grandeur. Whether as a private estate, boutique label, or hospitality venture, White Hall Estate is a legacy opportunity in the heart of Virginia wine country.

5190 Sugar Ridge Rd, Crozet
$8,750,000
675728 MLS
Here is a singularly exceptional sanctuary of rare scale and convenience mins E of Charlottesville and UVa. The immediate neighbors are Thomas Jefferson’s Monticello, President James Monroe’s Highland (Ash Lawn), and historic Morven, ca. 1821, owned by the UVa Foundation. Rooks Ford Farm has recently witnessed a stunning restoration under well-informed, exemplary land stewardship creating pastures and improving nearly 20 miles of roads/trails suitable for horses, carriages, walking or biking. Here, too, is the Crows Nest, living quarters of two bedrooms, full kitchen, living area, laundry and bath with attached equipment bays. Multiple streams cross from west to east feeding Buck Island Creek. The pine & hardwood forest is a haven for native quail in which several coveys reside. Bald Eagles float above trophy deer, bear and turkeys. There are many private settings for construction of a home and dependencies, each with views westerly across Morven to Carters’s Mountain and Monticello and/or easterly across “Jefferson’s sea”. Jefferson’s 1765 observation of a stream crossing “Rooks Ford” over then “Buckeye Land Creek" gives the farm its name. Visit https://www.rooksford.com for photos of restoration.

Tbd Rolling Rd, Charlottesville
$8,500,000
4 Beds ⋅ 6 Baths ⋅ 661914 MLS
12 Ridges is a breathtaking 268-acre mountaintop retreat along the Blue Ridge Parkway, offering unmatched seclusion with sweeping 360-degree mountain views. Positioned at 3,300 feet elevation, this exceptional property combines natural beauty with the potential of a thriving vineyard, where expert vintners harness the land’s unique qualities to craft expressive wines. With its vineyards at high elevations, Virginia is rapidly emerging as a premier wine region, surpassing more traditionally renowned areas. The property also features a serene pond, a private tennis court, and beautifully remodeled spaces, including the main home and tasting room. Located near Charlottesville, Staunton, and Lexington, 12 Ridges is an extraordinary opportunity for those seeking a private mountain estate with a touch of vineyard charm.

24981 Blue Ridge Pkwy, Vesuvius
$8,000,000
655183 MLS
Prime parcel front Seminole Trail and Berkmar Drive

TBD Seminole Trl, Charlottesville
$7,865,000
677397 MLS
Jefferson Lake Farm - Incredible opportunity to own 1,156+ contiguous acres within 15-20 minutes of Charlottesville, UVA, Monticello and James Monroe Highland. Parcel features a private, well-stocked 12 acre lake plus a smaller 3-4 acre pond. Wildlife galore with deer and turkey. Approximately 250+ acres of open pasture with remaining balance in mixed wood, with miles of streams and trails to enjoy this special parcel. Improvements include 3 rental cottages, equipment shed/workshop and a barn. This unique parcel is in a conservation easement with the Virginia Outdoor Foundation offering only 2 division rights.

317 Lake View Ln, Palmyra
$7,850,000
8 Beds ⋅ 9 Baths ⋅ 658424 MLS
Nestled on 77 acres in the Virginia countryside, Mount Sharon offers an extraordinary blend of Georgian architecture, rich history, and exquisite gardens. Designed by renowned architect Louis Bancel LaFarge, the 10,000+ square-foot main house is complemented by 10 acres of meticulously crafted Italian, French, and English-style gardens, with breathtaking views of the Blue Ridge Mountains. The main house is designed for gracious living and entertaining, offering expansive spaces ideal for hosting guests, gatherings, and large celebrations. The property also features multiple outbuildings, including a farm manager’s house and a guest house with an office on the main level—perfect for accommodating staff, guests, or business needs. For equestrian enthusiasts, the estate includes a seven-stall stable with a tack room, along with 147 acres of adjoining land available for purchase at $1.25 million. The additional land features a classic 1930s Sears Belmont-style barn with 20 stalls, rolling pastures, a pond, 4 run-in sheds, and multiple paddocks. Together, these create a 224+ acre world-class equestrian estate.

19184 Mt Sharon Rd, Orange
$7,560,000
660899 MLS
Prime Development Parcel by Whole Foods Just Off Route 29. Surrounded by Major Retailers with Long Road Frontage on Hillsdale Drive. This 2.54 Acre Parcel is Available By Right for Almost Any Use. No Proffers. No BAR Required. Much Utility Work Already Mitigated. Sidewalks Completed. Potential for Multi Family (Up to 10 Stories By Right), Retail, Restaurant, Professional Office, and More. Rare Opportunity to Develop a Prime Commercial Parcel Quickly in Charlottesville, Virginia.

India Rd, Charlottesville
$7,500,000
2 Beds ⋅ 2 Baths ⋅ 677801 MLS
A true 350± acre mountaintop compound in southwest Virginia. Private, remote, secure, and self-contained, with sweeping 360-degree views. Three cabins, multiple outbuildings, a beautiful 3/4 acre pond, an 800-foot STOL airstrip, helipad, and hangar. The South Cabin has full off-grid capabilities. Borders thousands of acres of Jefferson National Forest, and the property and surrounding area offer some of the best outdoor recreational opportunities in all of Virginia. Offered turnkey. Under 2.5 hours to Roanoke, Charlotte, Winston-Salem, and Greensboro.

1064 Frazier Ln, Elk Creek
$7,495,000
10 Beds ⋅ 12 Baths ⋅ 674640 MLS
RIVANNA ESTATE: Set upon 42 acres of Rivanna River sanctuary, this remarkable estate offers sweeping views of the Blue Ridge Mountains, a landscape of rolling pastures and serene water frontage. This exceptional property encompasses five distinct residences with the most impressive being the Georgian Manor, a masterpiece of architectural grace and craftsmanship, featuring soaring ceilings, handcrafted millwork and wide plank hickory floors and an elevator. This home was taken down to the studs and thoughtfully reimagined for elegant entertaining and daily living. On either side of the manor stand two exquisite mirror image companion residences with spacious interiors and cozy hearths. An adorable stone cottage, blends charm, comfort and privacy. The groundskeepers home provides practical on site living for estate management. Additional improvements include a renovated bank barn. stables with lunging ring, saltwater gunite pool and cabana, two regulation pickleball courts, and a 50K backup generator. The main residence and immediate dependencies have all been extensively renovated with new HVAC. plumbing, electrical and septic systems. A once in a generation offering

1859 Rivanna Farm, Charlottesville
$6,995,000
5 Beds ⋅ 4 Baths ⋅ 650903 MLS
One of the State’s finest examples of Classical Revival/Neoclassical architecture, sited on 716-acres of rolling, highly productive crop land and pasture land with nearly 1.5 miles of frontage on the Rapidan River. The home is instantly recognizable with its 4 massive Doric columns and “M” shaped copper roof. Built in 1854, the well-proportioned residence with 11+ foot ceilings was meticulously restored by high-end contractor, Alexander Nicholson, to its present condition. The restoration kept the original doors, mantels, woodwork, and most of the heart pine floors intact. Listed on the National Register and VA Landmarks Register. The Rapidan River and its lowlands offer endless recreation including canoeing/kayaking, fishing and some of the area’s best duck hunting (enhanced by duck impoundment pond). Additional improvements include a restored, period summer kitchen/office, guest cottage, conservatory, pool and pool house, stables, managers cottage and farm infrastructure.

23501 Greenville Rd, Culpeper
$6,499,000
6 Beds ⋅ 8 Baths ⋅ 668818 MLS
This extraordinary Georgian estate is set on 179 acres with two ponds, seven natural springs, and two barns, offering timeless elegance in a truly remarkable setting with additional subdivision and vineyard potential. Designed for both entertaining and everyday living, the home blends historic charm with modern comfort, all while capturing breathtaking mountain views from nearly every room. The main level offers a graceful mix of formal and casual spaces, including a first-floor primary suite, antique heart pine floors, and a handsome study. Upstairs, a second primary suite with a renovated bath enjoys panoramic vistas, complemented by three additional bedrooms with en-suite baths. The lower level is designed for recreation with a large screen viewing area, wet bar, billiards room and provides a welcoming guest bedroom, full bath and office. Seven fireplaces add warmth and character. Outdoor living boasts a free-form pool, wide porches, and sweeping vistas. A four-car garage with portico has a second floor roughed-in. Every detail reflects quality and sophistication, making this estate a rare opportunity where land, luxury, and lifestyle come together, and every feature is designed to elevate gracious country living.

3365 Stony Point Rd, Charlottesville
$6,450,000
4 Beds ⋅ 5 Baths ⋅ 665653 MLS
Greenfields Farm spans 753 acres just outside historic Scottsville, VA. A rare blend of rolling pasture, mature timber, and rich history, the property features a 1904 Colonial Revival main house with original architectural detail, a grand spiral staircase, arched transoms, and sweeping views from the widow’s walk. The residence offers copious amounts of living space, with three separate apartments and a caretaker’s home providing options for guests, staff, or extended family. Formerly a working horse farm, Greenfields includes fenced paddocks, a spring-fed creek, a stocked pond, a lake, and five wells. Equestrian facilities include a stable with 48 stalls, an indoor arena, a tack room, foaling stalls, grooming bays, hay storage, offices, and wash bays. Additional improvements include two equipment barns, grain silo, dog kennels, riding trails, and four gated entrances. With ties to Governor Wilson Cary Nicholas and Lady Astor, Greenfields is a legacy estate of rare scale and beauty.

9313 Greenfield Farm, Scottsville
$6,250,000
658190 MLS
Staunton Crossing, 50 acres of prime B-2 divisible land ideal for retail development, is in a great location in rapidly growing Staunton, VA. This property is an ideal setting for retail and land investment opportunities and offers excellent transportation characteristics that make it accessible to businesses and customers alike. One of the key transportation features of Staunton Crossing is its almost 1-mile frontage on Interstate 81 at Exit 222 and its location at the intersection of I-81 and I-64. This central location provides easy access to major highways, making it an accessible location for businesses to transport goods and services in the heart of the Shenandoah Valley.

1300 Richmond Ave, Staunton
$5,999,000
3 Beds ⋅ 3 Baths ⋅ 649399 MLS
Beautiful 2788 sq ft Antebellum style Mansion. Needs work, new windows, updated baths, huge Rooms, new mini split A/C and heat plus oil baseboard heat.. Could be Community Association Building for Residential Property development. IT IS WORTH KEEPING. Property suitable for development in HIGHLY SOUGHT OUT AREA OF ROCKINGHAM COUNTY.

370 Friedens Church Rd, Mount Crawford
$5,950,000
5 Beds ⋅ 7 Baths ⋅ 673369 MLS
An Architecturally Distinguished Albemarle Estate. Nestled among rolling history hills, vineries, and protected countryside, this exceptional French Provençal–style estate spans 133.8 private acres and is introduced by a gated entrance that sets the tone for quiet grandeur. Comprising eight adjoining parcels, the property presents an extraordinary opportunity for a conservation easement, enhanced by thoughtfully crafted trails that wind through the landscape, ideal for recreation, and preservation. The stunning residence is both elegant and welcoming, offering a floor plan suited for formal entertaining and relaxed daily living. Highlights include five en-suite bedrooms, an expansive first-floor primary suite, and four wood-burning fireplaces that add warmth and character throughout, the beautifully appointed kitchen flows seamlessly into the dining room, living spaces, library, and outdoor areas—creating a natural harmony between interior and exterior living. A three-car detached garage complements the estate. Ideally located just minutes from Jefferson’s Monticello, Monroe’s Highlands, Morven, and other esteemed Albemarle estates, this rare offering is also only 20 min to the vibrant downtown of Charlottesville

2621 Coopers Ln, Charlottesville
$5,575,000
5 Beds ⋅ 5 Baths ⋅ 670256 MLS
Discover Edgewood, a historic farm offering 453± acres of Blue Ridge Mountain views and extensive Rapidan river frontage. Full of character, the farm is thoroughly improved and features multiple dwellings, well preserved historic outbuildings, and an event barn. It borders the Rapidan River for 2.4± miles, has two stocked ponds, and 270± acres of fenced pasture. Superbly positioned just 10 minutes outside of Orange, while Charlottesville is 45 minutes away. Both Richmond and Washington, D.C. can be reached in approximately 90 minutes. Property is not under conservation easement.

575 Arcadian Way, Orange
$5,250,000
628681 MLS
Prime industrial parcel next to Walmart Distribution Center with frontage on I-81, Harrisonburg Sub-Market. 26.3 Acres +/- all zoned industrial. Across from future Buc-ee's. Easy access to interstate ramp. Thriving east coast industrial corridor.

Tbd Walton Way, Mount Crawford
$5,000,000
672987 MLS
Established and well maintained retail strip center for sale. Many long term tenants achor this property located in the rapidly expanding retail area of Waynesboro near exit 94 on Interstate 64. Tenant rates are strong with inclusive NNN charges.

109 Lucy Ln, Waynesboro
$4,950,000
8 Beds ⋅ 9 Baths ⋅ 678608 MLS
Nestled in a private valley where the Jackson River descends into Richardson Gorge, Folly Farm is a rare, generational estate opportunity in the heart of Bath County. Originally built in the early 1800s, this historic property has been painstakingly restored, seamlessly blending its rich heritage with the finest luxuries of modern living. Spanning 40 pristine acres, including over a third of a mile of private river frontage on both banks, the property offers a main residence and a charming guest cottage affectionately known as the “Doghouse,” totaling 8 bedrooms. Folly Farm is designed for seamless indoor-outdoor entertaining. Unwind in the screened-in “Riverhouse” perched directly on the water’s edge, or spend sunny afternoons by the heated pool and pool house. From a custom mini-golf hole to world-class fly fishing right in your backyard, the outdoor pursuits are endless. While offering total seclusion, this private sanctuary is just a ten-minute drive from the historic Omni Homestead Resort, offering effortless access to world-class golf, dining, and spa amenities.

7449 Richardson Gorge Rd, Hot Springs
$4,950,000
4 Beds ⋅ 6 Baths ⋅ 667777 MLS
Keswick Springs | Set on five acres blending manicured gardens with natural beauty in Keswick Estate just outside Charlottesville, this 4,900+ sq ft home offers 4 bedrooms and 4 full-plus-2 half baths, combining traditional Southern architecture with modern livability. Light-filled interiors include a refined dining room, library, chef’s kitchen with scullery and wet bar, and multiple spaces for entertaining. The primary suite is a private retreat, while additional bedrooms and a snug studio offer flexibility for guests or work. Custom wallpaper, artisan-crafted millwork, and expansive windows frame garden and water views. Outdoor living features deep porches, a screened porch, and terraces overlooking native plantings, kitchen gardens, fruit trees, and a tranquil lake. Within Keswick Estate, owners have the option to join the Keswick Club, offering Pete Dye’s Full Cry championship golf course, an adults-only infinity-edge pool, tennis courts, fitness center, spa, and dining at Marigold by Jean-Georges. Enjoy a rare blend of timeless design, resort-style amenities, and a serene natural setting in one of Virginia’s most prestigious communities.

2863 Palmer Dr, Keswick
$4,950,000
4 Beds ⋅ 4 Baths ⋅ 664419 MLS
Set on 102 acres just minutes from Charlottesville, Shack Mountain is a remarkably private estate where architecture and landscape exist in quiet balance. Designed by Fiske Kimball and inspired by Thomas Jefferson’s Farmington, the residence reflects timeless proportion and intention. A long drive reveals sweeping views and complete seclusion. The home is elevated yet restrained, offering light-filled interiors and a seamless connection to the surrounding land. The acreage provides both scale and serenity—rolling terrain, mature trees, and a rare sense of calm just minutes from town. A property of architectural significance that remains deeply livable, Shack Mountain offers a unique opportunity to own a private, legacy estate in one of Virginia’s most storied landscapes.

1790 Lambs Rd, Charlottesville
$4,775,000
660573 MLS
Incredible Multi-Purpose Property on 22+/- Acres with Over 110,000 SF of Building Structures. Some Structures have 24 Foot Plus Ceiling Clearance. Long Road Frontage along Mule Academy Rd and Access to Shoffner Lane. Minutes off I-64 and across from Augusta Health Hospital. Land is Mostly Flat. Potential Uses Include: Multi-Family Residential, Warehouse/Distribution, Self Storage, Professional and Medical Office, and Many More. Please Do Not Visit the Property without Broker.

272 Mule Academy Rd, Fishersville
$4,750,000
4 Beds ⋅ 5 Baths ⋅ 677782 MLS
A Somerset landmark along the Rapidan River, historic Glenwood offers gracious living on a 290 acre working farm of cropland and a beef cattle operation. The c. 1850 manor is newly renovated and revitalized with sumptuous features, four bedrooms, four full and one half bathrooms over a finished English basement. The original summer kitchen is steps from the house and offers an ideal space for work and creative pursuits. The three bedroom farm manager's house is also newly renovated. Outdoor living spaces offer long views of open, rolling countryside and the Southwest Mountains. The Rapidan River, popular for fly fishing and canoeing, forms a nearly mile-long boundary. Farm features include 225 acres of fenced pasture, 55 acres of highly productive riverbottom cropland, cattle feedlot for 350 head, silos, and barns. Minutes from James Madison's Montpelier, Glenwood was part of an 18th century patent by the Barbour family, whose members figure prominently in early American history. Fiber optic internet installation is underway and will be available by fall.

481 Race Ground Rd, Rochelle
$4,500,000
5 Beds ⋅ 4 Baths ⋅ 670379 MLS
One of the State's finest examples of Classical Revival/Neoclassical architecture, sited on 312-acres of rolling highly productive crop and pasture land with approximately half a mile of frontage on the Rapidan River. The home is instantly recognizable with its 4 massive Doric columns, and "M" shaped copper roof. Built in 1854, the well-proportioned residence with 11+ foot ceilings was meticulously restored by high-end contractor Alexander Nicholson, to its present condition. The restoration kept the original doors, mantels, and most of the heart pine floors intact. Listed on the National Register, and VA Landmarks Register, and protected by a conservation easement. The Rapidan River and its lowlands offer endless recreation including canoeing/kayaking, fishing, and some of the area's best duck hunting. Additional improvements include a restored, period summer kitchen/office, guest cottage, conservatory, pool and pool house, stables, managers cottage and farm infrastructure. An additional 403 acres can also be purchased.

23501 A Greenville Rd, Culpeper
$4,500,000
597151 MLS
Prime commercial pad sites offering exception visibility. Up to 11 acres available. May also be leased and possible build to suit. Located between the Waynesboro Town Center and Interstate 64, this site provides line of site visibility from I-64 and the shopping center and offers easy access from Exit 94. Target and Kohl's anchor this active center and commercial neighborhood which includes Pet Smart, Michael’s, McDonald’s, Chic-Fil-a, Aldi’s, and many more. Site acreage can be adjusted or combined with contiguous acres and is also available for land lease. Total available currently 11 acres. Call agent for pricing on smaller parcels.

200 Shenandoah Village Dr, Waynesboro
$4,495,000
5 Beds ⋅ 7 Baths ⋅ 673615 MLS
Just 10 minutes from Charlottesville, Milton Farm spans 54 acres of rolling countryside with a well-designed estate and exceptional amenities. The nearly 8,000 sq. ft. main residence includes five bedrooms, six baths, and generous indoor and outdoor living spaces. The pool, hot tub, and pool house offer a perfect space for entertaining, complemented by expansive patios and landscaped grounds. Three cottages provide ample guest accommodations or rental opportunities. A detached three-car garage includes an upper-level suite, perfect for an office, gym, or private guest retreat. Equestrian facilities include a three-stall barn, a run-in shed, a large paddock, and an outdoor riding ring. An equipment and tractor shed offers convenient storage. The property has two ponds—one located in the paddock and the other stocked, featuring a dock and bubbler for private use. Recreational amenities feature a lighted sport court for pickleball and basketball, a sunken firepit, and wooded trails for walking, running, or riding. Open fields and wooded areas create a balance of usable land and natural beauty. Milton Farm offers a rare mix of comfort, space, and prime location—with easy access to UVA, Downtown, I64 & Keswick Hall.

2687 Milton Farm, Charlottesville
$4,450,000
5 Beds ⋅ 6 Baths ⋅ 677366 MLS
Set amidst 17 beautifully landscaped acres, Monte Ventoso is an extraordinary Italian-inspired villa offering the ambiance of a private Mediterranean retreat in the foothills of the Blue Ridge Mountains. Ideally positioned between Washington, D.C. and Charlottesville, VA, the estate combines exceptional privacy with convenient accessibility. A handcrafted fountain imported from Italy creates a striking first impression and sets the tone for the home’s timeless character and tranquil setting. The property features refined architectural details with modern comforts, designed for both daily living and elegant entertaining. The main residence and primary guest cottage offer radiant heated floors, whole-house generators, gourmet kitchens, and quality touches around every corner. Outdoor living spaces include an ozone pool, hot tub, and cold plunge, an outdoor kitchen, dual-sided fireplace, and multiple terraces and gardens overlooking the surrounding natural beauty. Monte Ventoso presents a rare opportunity to experience a private oasis where European-inspired design, resort-style amenities, and the serenity of Virginia’s countryside come together in an unforgettable setting.

4578 Ruth Rd, Madison