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$35,000,000
4 Beds ⋅ 5 Baths ⋅ 682364 MLS
Mount Pleasant is a generational offering spanning 1,865± acres, 25 minutes from Charlottesville. Set along historic Blenheim Road, area neighbors include Monticello, Ash Lawn-Highland, Trump Winery, Dave Matthews' Blenheim Vineyards, and Jefferson Vineyards. A restored 1820 manor house overlooks 2.6± miles of the Hardware River. Around it, 1,000± acres of pasture, row crops, and open ground unfold under sweeping Blue Ridge views, framed by 800± acres of woodlands and a private 22± acre lake. Unrivaled improvements blend seamlessly with the landscape and include a tasting room, 12,000± SF private event space, 8-stall stable, farm buildings, and multiple guest and tenant houses. Infrastructure is fully modernized — fiber internet, underground power, paved internal roads, four-board pasture fencing with automatic waterers, and multiple gated entrances. Not under conservation easement, Mount Pleasant offers unparalleled flexibility for future owners, whether it's a world class private retreat, family compound, working farm, or long-term development and investment opportunity. Land of this scale, quality, privacy, and freedom rarely comes to market in central Virginia.

Scottsville

$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

$15,000,000
6 Beds ⋅ 5 Baths ⋅ 681810 MLS
Whilton is an exceptional 340-acre country estate in Greenwood, Virginia, anchored by a stately brick Georgian residence dating to 1900. Offering 6,777 square feet with six bedrooms and four-and-one-half baths, the main residence is surrounded by nearly 20 acres of impeccably maintained gardens, mature plantings and expansive lawns that create a remarkable setting within the larger estate. Additional improvements include a two-bedroom guest house, two-bedroom pool house, additional farm manager’s residence or guest house, swimming pool, clay tennis court, greenhouse with two private offices, and a handsome brick stable overlooking multiple paddocks. Together, the residences, gardens and amenities make Whilton exceptionally well suited for entertaining, equestrian pursuits and recreation, with the scale and privacy of a true Virginia country estate. Despite its sense of seclusion, Whilton is exceptionally convenient, approximately five minutes from Crozet and 20 minutes from Charlottesville and the University of Virginia. A rare opportunity to acquire one of western Albemarle County’s substantial country properties, combining 340 acres, extraordinary gardens, extensive improvements and exceptional accessibility.

Greenwood

$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

$13,000,000
680440 MLS
Prime industrial development land located adjacent to Lowes and Walmart of Ruckersville! This 139.57 acre lot is currently designated Research/Flex Technology on Greene County's future land use map located in the county's Comprehensive Plan. Research and Flex Technology potentially allows for high-tech enterprises, light manufacturing, research firms, and data-compatible infrastructure to bring new businesses, jobs, and infrastructure to Greene County! The property borders electric, water and sewer hookups! Moments from route 29, connecting Northern Virginia & Washington DC to Charlottesville & beyond. Partially cleared. Currently in land use. Come invest in the future of beautiful Greene County, Virginia! Lot lines shown are approximate.

14387 Spotswood Trl, Ruckersville

$8,750,000
8 Beds ⋅ 8 Baths ⋅ 682369 MLS
River's Edge is an outstanding 403± acre, historic Southern Albemarle estate on the Hardware River. At its center sits a fully renovated 18th century house on the edge of a 5± acre pond. Perfectly suited to the farm, the home features 8 bedrooms, 7.5 bathrooms and extensive hardscaping and outdoor spaces. Adjacent to the house is a 1-beroom guest cottage, climate controlled garage, tennis court, volleyball court, and paved go-kart track. The larger farm is an ideal blend of highly productive Piedmont land, comprised of 200± acres of pasture, 180± acres of forest, 5± vineyard, and ¾± mile of river frontage. Completing the farm is a 10,000± SF event barn. Thoroughly improved yet highly adaptable, River’s Edge is a remarkable offering that is equally suited for a best-in-class family retreat, working farm, vineyard, or long-term investment. Not under conservation easement with meaningful by-right division rights.

Scottsville

$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

$7,850,000
8 Beds ⋅ 10 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

$6,995,000
10 Beds ⋅ 12 Baths ⋅ 674640 MLS
Situated just 16 minutes from downtown Charlottesville, Rivanna Farm is an extraordinary 42-acre family compound offering a rare combination of privacy, natural beauty, versatility, and convenient access to the city. The estate features four beautifully appointed residences, along with a separate farm manager’s home, creating an exceptional setting for multi-generational living and gracious entertaining. At the heart of the property is an impressive 10,000-square-foot Georgian residence, thoughtfully updated and complemented by three beautifully finished guest houses. Together, these residences provide remarkable flexibility for extended family, children and grandchildren, visiting friends, or staff, allowing everyone to gather and enjoy the estate while maintaining the comfort and privacy of their own residence. Rolling pastures, Rivanna River frontage, and sweeping Blue Ridge Mountain views create a spectacular backdrop for the property. The estate is further enhanced by a beautifully restored barn and stables, a saltwater gunite pool and cabana, two regulation pickleball courts, and meticulously maintained grounds .Significant improvements have been made throughout the residences, grounds, and infrastructure.

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

$6,450,000
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

$6,200,000
5 Beds ⋅ 5 Baths ⋅ 681132 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 134± acres with approximately 25 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 country 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 several storage sheds.. 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.

5282 Sugar Ridge Rd, Crozet

$5,950,000
6 Beds ⋅ 7 Baths ⋅ 680886 MLS
A rare offering in one of Charlottesville’s most coveted neighborhoods, this classic c.1954 Milton Grigg residence is beautifully sited on over 2.5 manicured acres at the quiet end of Farmington Drive, fronting the 17th hole of Farmington Country Club's world class golf course. Thoughtfully expanded over the years, the original brick home blends timeless architecture with gracious, modern living. Elegant entertaining spaces flow to an open kitchen, multiple sitting and family rooms, formal dining room and informal eating areas. The main-level primary suite offers privacy and convenience. Bedroom suites thoughtfully positioned throughout the home provide exceptional accommodations for family and guests. Outdoors, a spectacular pool setting that creates a private resort-like retreat, complemented by a two-story pool house/home office with full bath. Next to the pool is a long rocky mountain stream that tumbles down a myriad of water falls, ending in a large koi pond. There are multiple terraces and decks to enjoy this private and tranquil setting. A 3-bay garage with spacious, fully equipped 1-bedroom apartment above completes this remarkable Farmington property, just minutes from UVA and Downtown Charlottesville.

320 Farmington Dr, Charlottesville

$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

$5,350,000
5 Beds ⋅ 8 Baths ⋅ 681045 MLS
Set in complete privacy & serenity on 39 acres in the Ivy Elementary School District, this contemporary farmhouse masterpiece is simply breathtaking, from the Blue Ridge views to soaring ceiling heights, to no-holds-barred system & finish selections. The outdoor living & entertaining features are incredible too. In the Summer, enjoy the saltwater pool after practice time on the putting green & invite family & friends over to grill outdoors on the Green Egg or Wolf grill. In the cooler months, enjoy gathering at the large bar that overlooks the glass-fronted wine display & storage area or gather by the outdoor fireplace on the covered deck off the great room. Interior highlights incl' stunning reclaimed blond oak floors on all 3 levels, 12" crown molding, 4 gas or woodburning fireplaces, 6 custom, walk-in closets incl' his & hers in the primary, beautiful quarzite counters, in kitchen, laundry, all baths (floors & shower surrounds too), terrace bar/kitchen and in-law suite. 6 vaulted garage bays for cars, trucks, tractors & toys. Zero road noise/visibility. Systems incl' geothermal HVAC, 30KW whole house generator, Marvin windows & custom doors. 15 mins to Charlottesville & 10 to Western Albemarle Schools, conveniences. Just WOW.

2455 Browns Gap Tpke, Charlottesville

$5,250,000
681660 MLS
Exceptional 52,000 SF flex industrial asset situated on a flat 6.26 acres, offering an ideal blend of immediate 6.92% CAP rate and sticky regional tenancy. Ideally located just 1/2 mile from the I-81 interchange with prominent Route 11 frontage and visibility, this property directly serves the heavy freight traffic of I-81 (52,000 AADT), which is currently benefiting from a $200M+ three-lane widening project and the local agriculture economy. The facility is anchored by two premier commercial vehicle service tenants essential to the Valley's logistics ecosystem: Rice Tire, a trusted anchor with 13+ years of operating history at this site, and Vanguard Truck Centers, featuring specialized investments spec’d directly to their operational needs. With a low utilization on the flat 6.26 acres providing ample fleet staging, , and major infrastructure tailwinds, this asset delivers stable going-in cash flow coupled with long-term real estate value along a major East Coast logistics corridor

3226 N Valley Pike, Harrisonburg

$5,000,000
6 Beds ⋅ 6 Baths ⋅ 681564 MLS
Privately tucked away in the coveted North Downtown enclave, Social Hall is more than a residence—it is an arrival, a statement, and a rare piece of Charlottesville’s living history. This distinguished estate masterfully unites historic character with elevated modern refinement, offering a lifestyle defined by authenticity, elegance, and quiet luxury. Set behind a sense of seclusion yet moments from the city’s vibrant heart, the home unfolds with architectural grace and thoughtful design. Over generations, Social Hall has been carefully reimagined and expanded, preserving its storied soul while introducing curated enhancements—including a resort-style pool and an exquisitely appointed pool house—creating a private oasis unlike any other. The residence is rich with character and detail. Social Hall is a rare offering - where heritage architecture, refined living and the tranquility of a hidden estate converge moments from the cultural and culinary vibrancy of Charlottesville.

109 E Jefferson St E, Charlottesville

$4,995,000
5 Beds ⋅ 7 Baths ⋅ 678910 MLS
Exceptionally rare opportunity to build your own custom home on over 21 acres of private, rolling landscape with captivating blue ridge views. Dramatic sunsets over western mountains from the elevated home site neighboring 100+ acres in conservation easement. Enjoy supreme privacy tucked away among noteworthy estates along Bloomfield Rd. Proximity of Farmington but with more privacy, space, and acreage. Moments from award winning golf, University of Virginia, and all that Charlottesville has to offer. Western Albemarle schools. Custom home and garage plans have received Architectural Review Board pre-construction approval, allowing for a streamlined path to groundbreaking. Showings by appointment only.

21 Acres Tbb Bloomfield Rd, Charlottesville

$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

$4,750,000
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