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$2,475,000
4 Beds ⋅ 4 Baths ⋅ 673250 MLS
This remarkable 4 bedroom, 3.5 bathroom fieldstone residence was designed by Jack Arnold and constructed by revered local builder Ralph Dammann (now retired). The private setting of the 3.5 acre lot will not change as all parcels around it have been built upon. Noteworthy features include soaring ceilings (10 ft minimum and main areas, 14ft), arched doorways, 2 oversized stone fireplaces (gas or woodburning) and an expansive rear, bluestone courtyard with access from the living room, primary and kitchen/family room. Timeless finishes include honed granite in the kitchen and large laundry room, heavy/high quality hardware throughout, cherry cabinetry and bookshelves in the home office and bar, and extensive built-ins in the family room. Recent improvements incl' all new, high efficiency HVAC, tankless, instant hot water. 1 Gig+ fiber internet. Public water & sewer. The residence is within easy walking distance of all club and hotel amenities incl private and fine dining, golf, tennis, 2 pools, and incredible spa. Extensive trail system! Under 12 minutes to Downtown yet a world away.

880 Club Dr, Keswick

$2,450,000
4 Beds ⋅ 3 Baths ⋅ 678959 MLS
A rare opportunity to own one of the area's most exceptional wedding venues-- a well-established, income-producing property with room to grow. Whistle Hollow Farm is currently owner-operated with on-site living, there is strong potential to increase revenue by offering the two residences as short-term rentals for wedding parties, families, or guests. Set on just over 30 picturesque acres in Rockbridge County, this farm enjoys a stunning backdrop of the Blue Ridge & the Allegheny Mountains in the heart of the Shenandoah Valley. The property is fully equipped as a wedding and special event venue, featuring two homes, an approximately 4,500 sq ft event space, plus additional barns and outbuildings for storage and operations.A full list of business assets that convey is available in the documents section. 65 Whistle Hollow has been thoughtfully renovated, opening the kitchen, dining and living areas into a bright, open-concept layout. Improvements include new LVP flooring and custom white oak cabinetry by Walkers Creek Cabinet Work. The partially finished lower level provides flexible space, ideal for additional guest accommodations or expanded rental use.

65 & 190 Whistle Hollow Ln, Fairfield

$2,395,000
3 Beds ⋅ 3 Baths ⋅ 681653 MLS
Like New Virginia Tidewater-style cottage in the heart of Keswick, less than 10 miles from Historic Downtown Charlottesville and minutes to Keswick Resort and Golf Course, and Chef Jean-Georges acclaimed restaurant Marigold. Comprehensively renovated in 2023 by a highly respected interior designer, the home is truly Architectural Digest-worthy, with a thoughtful blend of modern luxury and timeless character. Generously scaled rooms feature floor to ceiling windows, soaring ceilings, handsome built-ins, exquisite trim work, and rich architectural details. The stunning new kitchen features handmade custom cabinetry, thick marble countertops, heated floors and Wolf and Sub-Zero appliances. The great room centers around a woodburning fireplace and cozy spaces throughout the home offer warmth and intimacy. A first-floor primary suite with sitting room features a primary bath with walk in shower, soaking tub and Ann Sacks tile. A front porch welcomes guests, while the covered rear porch features a floor to ceiling stone fireplace and opens to a spacious outdoor terrace. Located on a quiet street surrounded by farmland the property combines sophisticated design, exceptional craftsmanship and the enduring charm of a Virginia cottage.

5432 Stony Point Pass, Keswick

$2,395,000
4 Beds ⋅ 5 Baths ⋅ 675887 MLS
Architectural masterpiece set on nearly 5 private acres in Inglecress, ideally positioned at the end of a peaceful cul-de-sac. This 4,432 SF custom home, fully reimagined by Alexander-Nicholson, offers 4 bedrooms, 3 full and 2 half baths, and striking modern design with exceptional craftsmanship throughout. A dramatic mahogany pivot door opens to sun-filled interiors with soaring ceilings, sleek steel-and-oak staircases, and walls of glass framing sweeping pastoral and wooded views. The chef’s kitchen features Thermador appliances, marble waterfall counters, and custom cabinetry, flowing seamlessly into expansive living and dining spaces with multiple fireplaces and a NanaWall system opening to an elevated deck. The luxurious primary suite is a private retreat with French doors overlooking Ivy Creek and a spa-inspired bath. A vaulted guest suite crowns the top floor, while the walkout level offers a family room, wet bar, and 2-car garage. Elevator and whole-house generator. Enjoy park-like grounds with fire pit, trail access, and 825 ft of waterfront.

1500 London Rd, Charlottesville

$2,395,000
3 Beds ⋅ 3 Baths ⋅ 588695 MLS
Elevated Living, Tailored to You: Penthouse 801 Experience the pinnacle of Charlottesville living in this extraordinary 3,629-square-foot penthouse. Currently under professional build-out, Suite 801 offers the rare advantage of a brand-new, high-end construction paired with a significant custom finish allowance. From the floor-to-ceiling windows overlooking the Blue Ridge Mountains and the Historic Downtown Mall to the expansive 1,310-square-foot private terrace, every inch of this residence is designed for impact. As the new owner, you will partner with the build team to select your own custom cabinetry, premium countertops, flooring, and designer fixtures. Skip the complexities of a raw shell and move straight to the artistry of selecting the finishes that define your style. This is your downtown oasis, realized.

218 Water St W Unit 801, Charlottesville

$2,375,000
7 Beds ⋅ 9 Baths ⋅ 681108 MLS
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.

6634 Porters Rd, Esmont

$2,350,000
4 Beds ⋅ 4 Baths ⋅ 681962 MLS
Historic elegance meets modern living with 4 bedrooms, 3.5 baths. A complete gut renovation inside this circa 1875 home with almost 6000 sqft located in one of Staunton Virginia’s prime historical districts. Soaring 10–11ft ceilings, quartersawn oak floors, and incredible millwork are just a few of the many stunning features. Beyond the 8’ mahogany entry door, a curved staircase and Italian brass chandelier create a dramatic first impression. 3 fireplaces enrich the living room, dining room and expansive kitchen. The kitchen has direct access to a private terrace, cherry cabinetry and is a cook's dream. There are also 2 kitchenettes, one on the lower level and the other on the bedroom level, making it convenient for morning coffee or a midnight snack. The stunning library with wet bar and wine storage includes built-in bookcases, a built-in desk and cabinetry, all with architectural detail in cherry wood. The lower level is well suited for guests, work or a rental. Virginia Blue Stone surrounds a large part of the property and the landscaping is “grass free”. The front porch and terraces are an entertainer’s paradise. Two car garage and parking pad for 3 cars. This property is a must see!

104 Church St, Staunton

$2,350,000
5 Beds ⋅ 3 Baths ⋅ 677568 MLS
Purchase or Rent. With its incredible location adjacent to Farmington & Boar's Head, this property has the potential to be a stunning, boutique wealth advisory firm, family office or event space. Constructed in 1922 of brick & slate, the noted White Gables manor home offers stately architecture & timeless finishes in an incredible location just west of town, with multi-use potential. The residence's occupant for many years was a wealth advisory group however conversions back to a single family, 5 bed, 3.5 bath home would be quite simple. Walk to Farmington, Birdwood & Boar's Head. Host pre-game gatherings in the central location. Alternatively, this property provides an ideal location for a family office or wealth management company. 2 full bathrooms upstairs & a 3rd could easily be restored, creating a lovely primary suite + 4 more bedrooms and 3 full baths. Or leave as-is and there are a total of 8 offices plus conference room and break-out room. 4 dedicated parking spaces & 2 addit'l spaces avail. Parcel allows for the creation of 3-4 more dedicated spaces. Renovations in 2005 included refinished oak floors, new HVAC, all exterior surfaces and systems, mechanical and electrical systems. Exterior just repainted.

410 White Gables Ln, Charlottesville

$2,250,000
5 Beds ⋅ 5 Baths ⋅ 681152 MLS
Privately situated on approximately 2.43 acres in desirable Inglecress, this distinctive 5-bedroom, 4.5-bath residence offers approximately 4,800 finished square feet just minutes from Farmington Country Club, Boar's Head Resort, UVA & Barracks Road. A grand two-story foyer and striking eucalyptus floors introduce gracious interiors with wonderful architectural character and an exceptional flow for entertaining. The main level features a sunken living room with fireplace, formal dining room, study/den and spacious primary suite. The well appointed kitchen offers granite countertops, handsome wood cabinetry, center island with gas cooktop and recently upgraded appliances. Living, dining & kitchen spaces open direclty to the private rear deck overlooking a small stream and peaceful wooded natural area. Three bedrooms and two full baths are upstairs. The finished lower level offers a fifth bedroom, full bath, recreation room and exercise room. Pella windows and doors and a two-car garage complete this exceptional Inglecress home.

1235 Inglecress Dr, Charlottesville

$2,200,000
4 Beds ⋅ 7 Baths ⋅ 682205 MLS
Defined by exceptional quality and thoughtful design, this modern country estate extends well beyond the home and it's professional landscaping, with expansive acreage for biking, sledding down the hills or swinging in the shade of an old tree. The current owners lovingly christened the property “The Grands,” bringing to life their vision of a special place to gather and create lasting memories for generations. Dream sweetly in either the exquisite upper private owner's retreat with spa-style bath or the lovely main level primary suite. A whimsical secret passageway adds an element of fun! The spacious main deck steps down to an amazing copper-roofed summerhouse. On cooler days, cozy up to the warmth of the stone fireplace. Since 2019, the owners carried out a sustained, whole-property renovation—expanding the homesite, rebuilding core systems, and adding significant new living space. The carriage house is accessed from a shaded porch through sliding track barn doors and offers a generous multi-use space with hardwood floors, high vaulted ceilings, and a half bath. The bank barn is planned for 5 stalls, wash station and 2 potential tack rooms. Come relax, breathe, and feel the peace, all while being minutes from nearby amenities.

2852 Milton Rd, Charlottesville

$2,190,000
674103 MLS
Well-maintained 10,950 SF two-story brick medical office for sale or lease. Constructed in 1998, this attractive property offers a highly functional layout featuring 20 exam rooms, 18 offices, a conference room, 9 restrooms, multiple storage rooms, a kitchen/meeting room, 3 separate entrances, ample parking on a 1.02-acre site. The property is ideally located in a strong medical and retail corridor, surrounded by numerous national retailers and professional offices. It is situated just 0.5 miles from James Madison University and less than 2 miles from Sentara RMH Medical Center, making it a strategic location for continued medical or professional office use. Excellent opportunity for investors or future owner-users. The current tenant will move out by the end of September 2026.

1947 Medical Ave, Harrisonburg

$2,100,000
2 Beds ⋅ 3 Baths ⋅ 676162 MLS
A rare sixth-floor, professionally decorated, fully furnished residence offering ample space, privacy, and stunning long-range views over downtown to Carters Mountain. This is urban living at its finest, set in the heart of downtown Charlottesville, yet elevated enough to feel serene and secluded. Recent upgrades and curated furnishings make this a truly turn-key offering: walk in and start living. The chef’s kitchen features top-of-the-line appliances, custom cabinetry, and a large island, seamlessly opens into an expansive living area with large windows that take in the stunning view. The layout includes a large, private primary suite and bath, second bedroom with ensuite bath, and a sun-filled den and outdoor porch and deck. Ideal for buyers looking to downsize or as an easy second home. Just one block from the historic Downtown Mall, with its restaurants, theaters, and music venues. Grand proportions. High-end finishes. Privacy, views, and an unbeatable location. Most furnishings rugs etc. convey as part of the sale.

218 Water St W Unit 601, Charlottesville

$2,100,000
4 Beds ⋅ 4 Baths ⋅ 676038 MLS
Welcome to Morley Ridge Park. Nestled in the heart of Virginia's Shenandoah Mountains, this remarkable 111-acre farm offers breathtaking Blue Ridge Mountain views, unparalleled privacy, and exceptional equestrian amenities. The custom-built home features 4 bedrooms, 3.5 baths, and a versatile lower-level suite ideal for guests, extended family, or multi-generational living. Enjoy the award-winning kitchen, generous gathering spaces, and expansive windows and skylights that fill the home with natural light while framing spectacular mountain views throughout. Outside, enjoy expansive decks perfect for stargazing, spectacular sunrises, colorful mountain sunsets, a charming detached studio, miles of private trails, mature hardwood forests, rolling fields, abundant wildlife, and endless opportunities to explore the surrounding landscape. For more than 30 years, this farm has been thoughtfully cared for and improved by the current owners, creating a place where horses thrive, family and friends gather, and the beauty and peace of the Shenandoah Valley can be enjoyed every day. A rare opportunity to become the next steward of an extraordinary Virginia farm.

665 Newport Rd, Spotswood

$2,000,000
6 Beds ⋅ 7 Baths ⋅ 681428 MLS
Custom brick estate home on a quiet corner lot in Glenmore. This thoughtfully and fully updated home offers gracious proportions and flexible living across three finished levels, including a main-level primary suite and remodeled walk-out terrace level. Inside, hardwood floors, coffered and vaulted ceilings, custom millwork and tilework, and designer wall coverings shine. Gourmet kitchen -- fully renovated in 2026 -- features quartz counters and high-end appliances, including a 48-inch range, and opens to a vaulted great room with stunning fireplace, custom wet bar, and built-in shelving. Main-level primary suite includes a sitting room, huge walk-in closet and updated owners bath w/soaking tub. Impressive custom-designed office with coffered ceiling and fireplace. Upstairs includes 4 bedrooms, two with en-suite baths (one recently remodeled). Terrace level includes a second kitchen, movie room, exercise room, and guest suite ideal for multigenerational living. Enjoy resort-style outdoor living: an expansive deck, custom brick patio, outdoor kitchen with built-in Viking grill and smoker, and a waterfall koi pond. Walkable to Glenmore club- amenities include a staffed gatehouse, golf, tennis, pickleball, and swimming.

3210 Prestwick Pl, Keswick

$2,000,000
3 Beds ⋅ 3 Baths ⋅ 679886 MLS
Experience the perfect blend of luxury, craftsmanship, and country living in this exceptional timber-frame home near Ferncliff in Louisa County. Built in late 2024, this custom lodge-style home showcases Douglas Fir timber framing by Blue Ridge Timberwrights, white oak columns, pine vaulted ceilings, Hardie Board & Batten siding, Andersen SmartSun windows, energy-efficient Mitsubishi mini-split systems and 40 yr. shingles. The thoughtfully designed interior features: solid oak hardwood floors, rustic solid beech cabinetry, quartzite countertops, custom steel railings leading to the finished walk-out basement, and countless high-end upgrades throughout, including a Viking 6 burner gas range, & GE Café refrigerator. Step outside to enjoy a covered rear deck, attached 2 car garage with a 14'x20' studio, and a newly constructed 50' x 32' metal barn with concrete floors, electric, covered equipment & hay storage, livestock facilities, professionally maintained pastures with new 8 strand high tensile wire, a scenic 1/2 acre pond and a weathered antique barn awaiting restoration. Offering exceptional quality, modern comfort, and turnkey farm amenities, this one-of-a-kind property is ideally located between Charlottesville and Richmond!

2353 Holland Creek Rd, Louisa

$1,997,000
5 Beds ⋅ 5 Baths ⋅ 679078 MLS
Custom-built at the base of Massanutten Mountain, this 5 bedroom, 4.5 bath estate offers 5,400+ finished sq ft on 4.2 private acres, just five minutes from resort amenities with no HOA dues. Built with ICF construction, geothermal heat pumps, India stone details, West Virginia post-and-beam craftsmanship, Andersen windows, and recently updated major systems, the home offers real substance behind the finishes. The open main level features a vaulted great room with stone gas fireplace, a chef's kitchen with large island, top-tier granite, Wolf and Sub-Zero appliances, wet bar and custom mill cabinetry throughout. The main-level primary suite includes a large walk-in closet and spa-like bath with oversized tile shower with body jets and separate sauna. The floor plan also includes an office, bonus room, abundant storage, two-car garage and a finished lower level with rec room, pool/ping pong area, theater space, extra living area, and private bedroom suites. Outside, a large wraparound composite deck and outdoor pavilion with pizza oven and attached workshop create exceptional entertaining space. A rare Shenandoah Valley property with privacy, craftsmanship, efficiency and excellent STR potential - being offered turnkey!

1380 Bloomer Springs Rd, Mcgaheysville

$1,995,000
3 Beds ⋅ 7 Baths ⋅ 677299 MLS
Beauty abounds at this lovely French provincial style property, conveniently located on Route 33, near Massanutten. Enter through handsomely crafted stone pillars, with lights and an electric wrought-iron gate, and follow the driveway around the immaculately maintained grounds filled with lush landscaping. Grounds also feature a replica of the historic Mabry Mill, a pond, multiple courtyards, stone paths, walkways, and more. The exterior features expertly crafted quoin brickwork, arches, and stone masonry, with expansive covered brick patios. Enter the property through a grand front entrance into a large foyer and gallery/great room. The main level features a great room, kitchen, sunroom, multiple offices, workspace, and a production wing (currently used for business purposes). The second level features the residence with three primary bedroom and ensuite bathrooms, a luxurious dining room, a spacious kitchen with an island and plenty of countertop and cabinetry space. The property currently operates with a special use permit for a photography studio. Other business opportunities are allowed in A2 zoning, check with your real estate agent or the county for more details.

12517 Spotswood Trl, Elkton

$1,995,000
5 Beds ⋅ 6 Baths ⋅ 676101 MLS
A stately residence in a coveted Ivy location features an exceptional floor plan that includes a first-floor primary suite and allows for seamless connectivity throughout thoughtfully designed rooms. The well-appointed kitchen is tailored for both everyday living and entertaining, featuring high-end appliances, a gas range, two dishwashers, a wet bar, a breakfast bar, and a sunlit breakfast room. Formal living and dining rooms offer timeless entertaining spaces, while a handsome study creates an ideal work-from-home setting. The inviting family room, anchored by a fireplace, opens to a delightful screened porch, perfect for relaxing or gathering. Upstairs, three generously sized bedrooms each feature ensuite bathrooms, while a fifth bedroom offers flexibility as a nursery or second office. A spacious recreation room above the three-car garage adds versatility. A massive unfinished basement with roughed-in bedroom, bathroom, and fireplace allows room for expansion. This home has it all, from a welcoming marble foyer with curved staircase to two laundry rooms and a mudroom. Enjoy Blue Ridge views from the front yard in this supremely convenient, pedestrian-friendly, picturesque neighborhood.

515 Rocks Farm Dr, Charlottesville