Wintergreen Resort Homes for Sale

Wintergreen Resort Homes for Sale

Welcome to Wintergreen Resort, a hidden gem nestled in the heart of Virginia’s Blue Ridge Mountains. This enchanting destination is not just a haven for outdoor enthusiasts; it’s a vibrant community where the beauty of nature meets the comforts of home. With its breathtaking vistas, lush landscapes, and an array of four-season recreational activities, Wintergreen Resort is the perfect place to find your dream home.

Imagine waking up to the crisp mountain air and stunning views of the rolling hills – a daily reminder of the beauty that surrounds you. Whether you’re an avid skier, a hiking enthusiast, or simply someone who enjoys the tranquility of nature, Wintergreen offers an abundance of activities year-round. In winter, the resort transforms into a winter wonderland with skiing, snowboarding, and tubing, while summer invites you to explore miles of hiking trails, golf courses, and refreshing mountain streams.

The real estate market in Wintergreen Resort is as diverse as its natural beauty. From charming cabins that exude rustic charm to modern homes with panoramic views, there’s something for everyone. Whether you’re looking for a cozy retreat for weekend getaways or a permanent residence to enjoy the mountain lifestyle, Wintergreen has it all.

Explore the homes for sale in this picturesque community and discover the perfect place to create lasting memories. With a strong sense of community and a lifestyle that embraces the great outdoors, Wintergreen Resort is not just a location; it’s a way of life waiting to be embraced. Don’t miss your chance to be part of this extraordinary mountain haven!

Newest Wintergreen Resort Homes for Sale

$469,000
4 Beds ⋅ 2 Baths ⋅ 679952 MLS
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 ready to enjoy from day one. The interior has been freshly painted, creating a bright and welcoming atmosphere. The open-concept great room, dining area, and kitchen make the home live much larger than its footprint, while the thoughtfully designed entry mudroom is perfect for mountain living—an ideal place to leave wet ski boots, hiking gear, and outdoor equipment. Relax on the spacious deck surrounded by a private wooded setting in the summer, with seasonal mountain and sunset views in the winter. Central heat and air conditioning provide year-round comfort, making this an excellent choice for personal enjoyment, a vacation getaway, or a rental investment.

23 Blackrock Cir, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$642,000
5 Beds ⋅ 4 Baths ⋅ 679161 MLS
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 thoughtfully designed floor plan features two generous living areas, two wood-burning fireplaces, and two spacious primary suites, including a private upper-level suite with its own deck. Vaulted ceilings, granite countertops, stainless appliances, and custom cabinetry create warm, inviting spaces throughout. Expansive rear decking overlooks the golf course and provides plenty of space for entertaining or simply enjoying the peaceful setting. Crawlspace encapsulated with dehumidifier. Recently pressure-washed decks, and professionally cleaned windows. Offered tastefully furnished for immediate enjoyment. The adjoining homesite is also owned by the sellers and is available for purchase separately, offering the opportunity for additional privacy or future expansion.

48 Deerberry Ln, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$597,000
4 Beds ⋅ 3 Baths ⋅ 679146 MLS
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 find on the mountain! The main level also offers vaulted ceilings and access to the spacious rear deck. The upper level features two additional bedrooms and a full bath. Lower level with family room, 2nd primary bedroom/bath and a second large deck. This home offers plenty of space to spread out or come together. All of this plus fiber internet and EV Charger!! The home is ideal for those looking to enjoy the dining, shopping, hiking, skiing and swimming options on the mountain, as well as amenities along Nelson 151, and Ravens Roost park is only steps away.

93 Valley View Ln, Wintergreen Resort

Listing courtesy of NEST REALTY GROUP. Contact:

$699,500
3 Beds ⋅ 3 Baths ⋅ 678962 MLS
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 for both relaxation & entertaining, multiple exterior decks create inviting outdoor living spaces surrounded by mature landscaping, walking trails, & beautiful stone accents. Unwind in the private sauna, rinse off in the exterior shower after a day on the trails or slopes, or take advantage of the existing plumbing for a future hot tub. Inside, you'll find spacious, thoughtfully designed living areas w/ abundant storage throughout, central heating & AC and a versatile bonus room above the primary suite—ideal as a home office, reading nook, or additional sleeping space for children. A dedicated workshop off the rear deck provides valuable space for hobbies, outdoor gear, or projects. The kitchen has been refreshed with new appliances in 2024, while a new roof was installed in 2025. A $10K flooring allowance & home warranty included!

377 Devils Knob Loop, Wintergreen Resort

Listing courtesy of WINTERGREEN REALTY, LLC. Contact:

$549,999
3 Beds ⋅ 3 Baths ⋅ 678821 MLS
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 ceilings in the great room, a beautiful stone fireplace with gas logs, and seamless flow into the kitchen and dining areas. The well-appointed kitchen offers granite countertops, maple cabinetry, and a gas range, making it ideal for both everyday living and entertaining. The main-level primary suite provides convenience and privacy, complete with a walk-in closet and a luxurious bathroom featuring a stunning tiled shower. Upstairs, you'll find two generously sized guest bedrooms and a beautifully finished full bath. Additional features include durable HardiePlank siding, central heat and air conditioning, and quality craftsmanship throughout. Offered fully furnished and move-in ready, this charming mountain home is located just a short distance from hiking trails and outdoor recreation. A wonderful mountain gem ready to be enjoyed from day one.

1300 Blue Ridge Dr, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$549,500
4 Beds ⋅ 2 Baths ⋅ 678617 MLS
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 structure of similar age moved from Nelson County, blends beautifully with the cabin. Master stonemason Jimmy Arrington created the striking dry-stack fireplaces, while the standing-seam copper roof by Harold Conley & Sons and reclaimed heart-pine floors on the main and upper levels add exceptional warmth and character. Highlights include four fireplaces (two gas, two wood-burning), cathedral ceilings in the kitchen and dining area, new LVT flooring on the lower level, new granite kitchen counters, level driveway, and multiple outdoor living spaces. Privately set among dramatic rock formations near the ski shuttle and hiking trails, this is a true historic treasure and a remarkable rental opportunity.

20 Buckhorn Ln, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$365,000
2 Beds ⋅ 2 Baths ⋅ 678251 MLS
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. Vacant and easy to show.

25 Hickorynut Rd, Wintergreen Resort

Listing courtesy of RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE. Contact:

$499,500
4 Beds ⋅ 3 Baths ⋅ 678333 MLS
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 great room, dining area, and kitchen—perfect for gathering with family and friends. The thoughtfully designed layout is ideal for two-family ownership, with two comfortable bedrooms and a full bath on the main level, mirrored by two additional bedrooms and a full bath upstairs. Each of the four bedrooms offers exceptional storage with two closets, allowing owners to reserve one for personal belongings if using the home as a rental. A cozy loft overlooking the living area provides flexible space for a home office, game area, or relaxing reading nook. Enjoy the outdoors from the screened porch or the generous rear deck overlooking the golf course. The deck and front porch have been freshly painted, enhancing the home's appeal and readiness for immediate enjoyment. Offered fully furnished and turnkey.

20 Blue Ridge Ct, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$3,100,000
7 Beds ⋅ 10 Baths ⋅ 678190 MLS
Welcome to one of the most impressive homes at Wintergreen, with expansive views of the mountain village, ski slopes and the beautiful Blue Ridge mountains. Perfect for entertaining with a soaring great room, open floorplan and a well designed kitchen featuring double refrigerators and double dishwashers. There are seven substantial bedrooms and all have attached full bathrooms. The oversized den includes a modern wet bar. Enjoy the expansive decking and soak in the stars while relaxing in the hot tub. The current owners installed new flooring throughout, updated the kitchen, all 8 full baths and both half baths, painted and generally modernized this class chalet. This is truly one of the premier properties at Wintergreen.

20 Knob Hill Pl, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$489,000
3 Beds ⋅ 3 Baths ⋅ 677731 MLS
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 immediate enjoyment as a personal getaway or continued success as a short-term rental. Inside, warm and inviting spaces are designed for relaxing after a day outdoors, while the gas fireplace and newer hot tub make cozy mountain evenings unforgettable. The fenced area, spacious deck, and ample off-street parking add to the home’s easy livability. Extensive updates since 2020 include a renovated kitchen and bathrooms, new roof, tankless water heater, complete chimney rebuild, paved driveway, interior and exterior paint, upstairs carpet, encapsulated crawlspace with dehumidifier, rebuilt exterior stairs, stained deck, and more. A rare move-in ready Wintergreen cottage that combines charm, updates, privacy, and convenience in one exceptional package.

138 Oak Ln, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$599,000
4 Beds ⋅ 3 Baths ⋅ 677472 MLS
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 spacious open-concept living area with vaulted ceilings, stone fireplace perfect for cozy winter evenings, kitchen with granite countertops & stainless steel appliances. Hardwood floors and abundant natural light throughout. Lower level family room is being used partially as a 4th bedroom.

280 Fawn Ridge Dr, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$579,000
4 Beds ⋅ 4 Baths ⋅ 676949 MLS
Nestled high near the top of Wintergreen Resort, this unique Wintergreen property that offers a perfect blend of luxury and comfort, ideal for year-round living, short term rentals or a weekend getaway. Unlike others this property has a detached garage with a driveway and pull off area. Surrounded by breathtaking mountain views and lush, natural beauty, this home features an open-concept living space filled with natural light, creating an inviting atmosphere for family gatherings or entertaining guests. The spacious living room, with its cozy fireplace and large windows, seamlessly connects to a well-appointed kitchen complete with modern appliances and ample counter space. Enjoy meals in the adjacent dining area or step outside to the expansive deck, perfect for al fresco dining or simply soaking in the serene surroundings. With four generously-sized bedrooms, including a master suite with an en-suite bathroom, this home provides plenty of space for family and friends. Located just minutes from skiing, hiking, brewery's, wineries, Route 151 festivities and all the recreational activities that Wintergreen Resort has to offer, this property is a true paradise

67 Forest Dr S, Wintergreen Resort

Listing courtesy of RE/MAX NEW HORIZONS. Contact:

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