Esmont Charlottesville Homes For Sale

"Twenty Columns" is a rare opportunity to own a piece of Virginia history. Originally constructed for the 1907 Jamestown Exposition, the home was relocated by train to Esmont, where it is set on 18.5 acres of lush, private land. The home features a perfect blend of original architectural details and modern amenities, including a Hallman 48” gas range, oversized soapstone sink and marble countertops. Enjoy expansive views of the surrounding nature from the wrap around porch and through large picture windows. The outdoor space is ideal for relaxation and entertaining, featuring a built-in pool, fire pit and walking trails that lead to a peaceful creek. With gardens, wooded areas and open lawns, the property provides both beauty and privacy, while being less than 25 minutes to downtown Charlottesville. $699,000 Active

3132 Wynova Ln Esmont, Virginia

4 Beds 3 Baths 3,112 SqFt 18.5 Acres

Step back in time in this 1892 manor home on 22 rolling acres on the Monticello Wine Trail. Soft light pouring through tall windows welcomes you into the foyer with a wood burning fireplace. A sweeping staircase, a curved wooden handrail and carved balusters will guide your eyes upward to the soaring ceilings. This country estate currently operates as an established bed and breakfast with its own producing vineyard. It has been beautifully restored offering architectural character alongside modern comfort. Original wide plank wood flooring throughout many rooms. Main house features 6 bedrooms on three floors-one with a private bath on the first floor, 4 with private baths on the second floor, and a third-floor bedroom/rec space with a full bath.  A detached one-bedroom cottage with full living area, kitchen, bedroom, and full bath adds flexible guest or income space. This estate includes a barn, a dedicated wine-chilling building. You'll enjoy the renovated pool house with a half bath and shower. The heated in-ground pool is surrounded by lush gardens and a spacious slate deck. Covered porches offer sweeping views of the vineyard and Blue Ridge Mountains.  Minutes from Cville, UVA, Monticello, UVA Hospital and the Downtown Mall. $2,195,000 Active

6634 Porters Rd Esmont, Virginia

7 Beds 9 Baths 8,167 SqFt 21.91 Acres

Recently Sold Esmont VA Real Estate

CHESMONT is an inviting country retreat, 18 miles south of Charlottesville, in the quiet hamlet of Esmont. The property blends rural charm with surprising versatility. The main residence offers generous living space anchored by a bright open-concept kitchen/dining/living area - perfect for gathering. A first-floor primary suite provides convenience, while the sun-filled first-floor Office invites creativity. Upstairs you’ll discover bedrooms and a family room with four built-in bunkbeds, plus a hidden play nook disguised as a closet, making the home especially fun for young visitors. Front and back porches offer extra living space in shade or sun. Terrace level includes a workshop and sewing room, ideal for hands-on projects and hobbies.  Beyond the home, the Cottage with Garage creates flexible space for guests, extended family, or rental income. A substantial Barn (C: 2022) and chicken coop add to the property’s utility, while the current owners’ craftsmanship shines through in a stacked-stone water feature, fire pit, and multiple gathering spots around the grounds. With room to breathe, space to create, and thoughtful touches throughout, "Chesmont" is more than a property - it's a lifestyle. Come see what all the fuss is about! $843,670 Closed

7279 Esmont Rd Esmont, Virginia

6 Beds 6 Baths 5,757 SqFt 10 Acres

Set on 34.5 acres in Albemarle County, this custom Timberpeg hybrid home is a private retreat built for both work and play. Vaulted timber-frame ceilings, arched windows, and a travertine fireplace bring European-inspired style, while the chef’s kitchen—with arched cooking hearth, travertine sink, and island—anchors the main living space. Flexible interiors include a loft, studio above the garage, and a spacious lower level with full walkout, perfect for a gym, gaming setup, or creative workspace. Outside, trails wind through woods and past a spring-fed pond, while stone patios and landscaped gardens provide places to unplug. A separate log cabin guest house welcomes friends or serves as a private crash pad. The barn offers paddocks and pasture for horses, but with high-speed fiber internet, it also doubles as a large office, workshop, or start-up hub. Remote yet connected, this property blends total privacy with modern infrastructure—ideal for anyone seeking a self-sufficient base close to the James and Rockfish Rivers, with added value through division rights and forestry-use tax advantages. $1,425,000 Closed

4414 Mt Alto Rd Esmont, Virginia

3 Beds 3 Baths 5,908 SqFt 34.51 Acres

Have you ever dreamed of living in a truly bucolic setting without the upkeep?  Liberty Corner is your chance! In the heart of protected, rural Southern Albemarle amidst other noted properties, c. 1790 Liberty Corner on 22 acres offers a statement Virginia estate without the workload of caring for 500 acres of surrounding, pastoral vistas.  At the heart of this historic property & set in absolute tranquility, is a pristine 18th century residence in flawless condition that melds period charm w/ modern amenities.  Improved by 2 guest houses, pool, pool house, gardens and dog runs, the home enjoys stunning, panoramic views of the rolling Virginia countryside and two large lakes.  Rarely does such an incredibly well maintained, historic country property reach the marketplace.  Truly, no stone has been left unturned by the owners in their careful stewardship of Liberty Corner. Now it can be yours without the headache of caring for hundreds of acres of beautiful, open farmland and lakes that surround the manor home and its compliment of estate-worthy dependencies. 25 minutes to Charlottesville and under 10 minutes to charming Scottsville and coveniences. $2,500,000 Closed

Liberty Corner Rd Esmont, Virginia

5 Beds 4 Baths 10,816 SqFt 22 Acres