Wintergreen, VA Houses for Sale

Discover year-round mountain living in this spacious 4-bedroom, 4-bath, fully furnished home located on a private 0.40-acre lot overlooking the golf course at Wintergreen Resort. Perfect as a primary residence, vacation retreat, or income-producing rental. This well-appointed property offers comfort, recreation, and convenient access to all that Wintergreen has to offer such as skiing, tennis,

Melinda Johnson Samson Properties

Quench your thirst for the Wintergreen Lifestyle at the "Thirsty Bear". Five bedrooms and 4 baths with stunning views over Laurel Springs Ridge towards the Shenandoah Valley. Privacy abounds at the end of the cul de sac and spend the lazy days of summer at the Chestnut Springs pool which is just steps away. Or on those chilly mornings take a soak in the hot tub. Find efficiency features such as 2

Robert Craig WINTERGREEN REALTY, LLC

Renovated mountain retreat with seasonal mountain views located minutes from the slopes & walkable to scenic trails. Perfect for families and groups, this open concept, light-filled home features a cozy fireplace in the living room, bonus family room and screened porch for relaxing after adventure-filled days. Zero stairs to the front door with a primary bedroom/bath on the entry level – a rare

CHASTITY MORGAN MOUNTAIN AREA NEST REALTY

Available October 1, 2026 $2,500/Month Minimum Lease Term - One Year Welcome to 1449 Laurel Springs Drive in beautiful Wintergreen Resort, Virginia. This newly constructed mountain home offers approximately 1,660 square feet of thoughtfully designed living space, featuring 3 bedrooms, 2.5 bathrooms, and an attached one-car garage. The floor plan is highlighted by a stunning two-sided fireplace

DAVID LAMBERT LONG & FOSTER - CHARLOTTESVILLE

Custom-built and truly one of a kind, this exceptional golf-front mountain home is ideally situated on a beautifully landscaped, private lot along prestigious Devil's Knob Loop. Lovingly maintained by its original owners & never rented, this distinctive residence showcases stunning custom stonework throughout and offers the perfect combination of craftsmanship, comfort, & mountain charm. Designed

STEVE MARIANELLA WINTERGREEN REALTY, LLC

Discover the charm of mountain living in this inviting A-frame chalet, ideally located just a two-minute walk from the ski slopes. Enjoy quick access to several hiking trails, an easy stroll to two breathtaking overlooks, and convenient walking access to the heart of the ski village with its restaurants, shopping, and year-round amenities. Offered turn-key furnished, this inviting retreat is

Dima Holmes PEAK REALTY VIRGINIA, LLC

Charming mountain retreat ideally situated on the 5th fairway of Devils Knob Golf Course, offering a private setting at the end of a short cul-de-sac and within easy walking distance of Chestnut Springs Pool Park and nearby hiking trails. This turnkey home features a welcoming open-concept floor plan with cathedral ceilings, a striking stone wood-burning fireplace, and a seamless flow between the

Dima Holmes PEAK REALTY VIRGINIA, LLC

Welcome to your mountain escape in the heart of Wintergreen Resort! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of comfort, privacy, and four-season adventure. Offered turnkey with a solid rental history. Whether you're looking for a full-time residence, weekend getaway, or investment property, this home delivers mountain living at its best. Highlights include

Wayne Flood PEAK REALTY VIRGINIA, LLC

Beautifully updated 4BR, 3BA mountain Craftsman offering spectacular year-round southern mountain views that become even more expansive from late fall through early spring. Tucked away in one of Wintergreen's most private settings, this home backs to the George Washington National Forest and sits directly across from the Shamokin Springs Falls Trail. The open floor plan features a dramatic great

Dima Holmes PEAK REALTY VIRGINIA, LLC

This charming mountain house is back on market due to buyers remorse. It has been a successful rental and family vacation spot for the current owners, averaging $30K gross annually. This home features only two steps to enter, Brazilian soap stone counter tops in the kitchen and Travertine stone floors throughout, vaulted ceilings, wood burning FP, and natural wood accents. Spacious layout w/ 5

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

The ultimate little Wintergreen cottage located in Black Rock Village, just a short walk to the main lodge. Efficient layout with 2 bd & 2 bath, open floor plan w/ wood burning FP in LR. Several updates including new heat pump, new flooring, kitchen counters, hot tub & shed. Level driveway with only two step entry. Not currently a rental but in the past did average $21k annual gross revenue.

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

Nestled in the heart of Wintergreen Resort, this beautifully maintained two-story home offers the perfect blend of mountain living, comfort, and convenience. Situated on a rare, level lot, the property backs directly to the renowned Devil's Knob Golf Course, providing peaceful fairway views and a picturesque setting year-round. Inside, you'll find spacious living areas designed for relaxing after

Jimmy Snyder Real Broker, LLC

Welcome home to this spacious 5 bedroom home with gracious front porch, sparkling hardwood floors, high ceiling providing great natural light, elevated back deck for grilling and enjoying the peace and quiet of this mountain setting. Kitchen with granite counters, custom hickory cabinets, and stainless appliances. Close to the Devil's Grill, Devil's Knob Golf and Tennis and Wintergarden Spa. Main

BETTY GREEN WINTERGREEN REALTY, LLC

Welcome to your dream mountain getaway or easy-living primary residence on the highly desirable Catoctin Drive. Crafted by RM Gantt, one of the mountain’s most reputable builders, this home perfectly balances rustic charm, modern luxury, and low-maintenance living. With a level, paved driveway and only three steps to enter, accessibility is a breeze. Inside, you’ll find a vibrant, fun home

Jill Vlasic RE/MAX Gateway

Beautifully positioned along the 6th hole of Devils Knob Golf Course, this spacious 5-bedroom, 4-bath home offers the perfect blend of privacy, comfort, and year-round enjoyment. Located on a quiet cul-de-sac with easy access to golf, hiking, skiing, tennis, dining, and all that Wintergreen has to offer, it's equally well suited as a primary residence, vacation home, or investment property. The

LISA FLOOD PEAK REALTY VIRGINIA, LLC

Located on the 13th hole of Devils Knob Golf Course, 44 E Catoctin Drive is a standout among Wintergreen's detached property listings. Centrally situated within the resort, this single-owner home has been carefully maintained and updated since its construction in 1982. Enjoy dramatic sunrises and partial mountain views from the front of the property and serene pastoral views from the rear. One of

Paul Hess NEST REALTY GROUP

A wonderfully maintained home with nice mountain views and lots of space to expand. They have incorporated the home sites on either side and with WPOA's permission can be sold off. There is an invisible fence around the center of the property. All the baths and the kitchen have been upgraded within the last couple of tears.

RANDY THOMPSON THOMPSON REAL ESTATE COMPANY

There is truly nothing else like this at Wintergreen—an authentic circa 1801 log cabin, originally built in Madison County and reconstructed in 2000 by renowned builder Lewis Ramsey and his son, Luke. Featured in Historic Preservation Magazine for his craftsmanship, Ramsey used hand-hewn chestnut, poplar, and oak logs that reflect early Virginia building traditions. The kitchen, a historic

Dima Holmes PEAK REALTY VIRGINIA, LLC

Nestled on a peaceful and private wooded homesite, this custom Craftsman-style mountain retreat blends beautifully with its natural surroundings, including several dramatic rock formations that create a truly special setting. Built in 2007 and lovingly maintained, the home offers a thoughtful floor plan designed for comfortable mountain living. The open-concept main level features cathedral

Dima Holmes PEAK REALTY VIRGINIA, LLC

Perched at the end of a quiet cul-de-sac in Wintergreen Resort, this beautifully updated mountain cottage offers the ideal balance of privacy, comfort, and walkable access. Seasonal mountain views and a peaceful wooded setting create the feeling of a true retreat, while skiing, hiking, dining, and year-round resort amenities remain just minutes away. Sold fully turn-key, the home is ready for

LISA FLOOD PEAK REALTY VIRGINIA, LLC