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$549,000
3 Beds 3 Baths 681786 MLS
Nestled among the peaceful woods of Wintergreen Mountain Resort, this impeccably maintained and tastefully updated 3-bedroom, 2.5-bath home offers an inviting mountain retreat designed for year-round enjoyment. Thoughtful improvements include a remodeled kitchen, replacement of the Qest plumbing throughout the home, a newer propane furnace and heat pump, updated deck surface and railings, pellet stove and chimney liner, and a brand new roof. The home features central heating and air conditioning, a highly desirable paved circular driveway, and a fenced backyard. Conveniently located near scenic hiking trails and waterfalls, resort amenities, and great dining options, this beautifully cared-for home makes it easy to enjoy the mountain and everything Wintergreen has to offer in every season.

72 Forest Dr N, Wintergreen Resort

Listing courtesy of LORING WOODRIFF REAL ESTATE ASSOCIATES. Contact:

$585,000
3 Beds 3 Baths 681076 MLS
This energy-efficient, SIPs style home is deftly designed and constructed to make maintaining and owning a mountain getaway effortless. The layout features a large open great room with vaulted ceiling and plenty of windows to take in the outdoors. With three bedrooms and a bonus space at the loft, there's room for an office, reading nook, exercise area, or fourth sleeping space. Located just a short 1/3 mile walk to the Tyro ski slope, you'll be on snow and skiing in 5 minutes! Recent upgrades include hot tub with deck expansion, fire pit, gravel driveway, landscaping, new tankless water heater, new LVP flooring in the bedrooms, new light fixtures, and interior paint. As a short term rental, the property brought in nearly $70K in rental income in 2025.

27 Pedlars End, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$529,900
3 Beds 3 Baths 680506 MLS
Rare opportunity to own a beautifully updated mountain home in an exceptional location along Shamokin Spring! The entire rear boundary follows the bold, picturesque stream, with wonderful views and the soothing sound of rushing water enjoyed from the home and expansive rear deck. The inviting open floor plan features a great room with cathedral ceilings and a dramatic floor-to-ceiling wood-burning stone fireplace, renovated kitchen, and a light-filled dining room surrounded by glass on three sides. The main-level primary suite offers deck access and a newly renovated tile shower. Upstairs are two generously sized bedrooms, including one with a private balcony. The spacious rear deck spans the home and features a newer hot tub overlooking the water, with seasonal golf fairway views beyond. Recent improvements include mostly new furnishings, lighting, fresh paint in all three bedrooms, and newly stained deck and front porch. Close to hiking trails and currently a successful short-term rental, this is a truly special mountain retreat in a rare Shamokin Spring setting.

426 Laurel Springs Dr, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$645,000
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:

$514,500
4 Beds 2 Baths 678617 MLS
If you have been searching for a mountain home with soul, this is it. Tucked among towering hardwoods and dramatic natural rock formations, this one-of-a-kind 4 BR mountain retreat offers exceptional character, privacy and a setting that feels worlds away. At 2,367 sq ft, there is plenty of room for family and guests, with multiple gathering spaces and four fireplaces adding warmth and atmosphere throughout. The home's remarkable story begins with an authentic circa-1801 Virginia log structure, carefully reconstructed here in 2000 by Lewis and Luke Ramsey. Hand-hewn chestnut, poplar and oak logs, reclaimed heart-pine floors, beautiful stonework by Jimmy Arrington and a standing-seam copper roof showcase craftsmanship rarely found today. An updated kitchen with granite counters adds modern convenience while preserving the home's historic character. Whether envisioned as a personal mountain getaway or a distinctive vacation rental, this is the kind of property guests will remember. The beautiful wooded setting and impressive boulders surrounding the home make it even more special. An adjoining homesite is also available separately, offering the opportunity for additional privacy or future possibilities.

20 Buckhorn Ln, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

$474,500
4 Beds 3 Baths 678333 MLS
Charming mountain retreat overlooking the 5th fairway of Devils Knob Golf Course, tucked away at the end of a quiet cul-de-sac and within walking distance of Chestnut Springs Pool Park and nearby hiking trails. Offered fully furnished and turnkey, this home features a thoughtfully designed floor plan ideal for larger families, shared ownership, or rental use, with two bedrooms and a full bath on both the main and upper levels, plus a convenient half bath on the main level for guests. The open-concept living area is highlighted by soaring cathedral ceilings, a striking stone wood-burning fireplace, and seamless flow between the great room, dining area, and kitchen. Each bedroom offers two closets, allowing owners to reserve one for personal belongings if using the home as a rental. A loft overlooking the living area provides flexible space for a home office, reading nook, or game area. Relax on the screened porch or spacious rear deck overlooking the golf course. Freshly painted front porch and deck complete this inviting mountain getaway, ready to enjoy from day one.

20 Blue Ridge Ct, 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:

$569,000
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:

$599,000
5 Beds 4 Baths 676279 MLS
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 bd, 4 bth, a LR & Den on separate levels and two large porches to enjoy the Blue Ridge. Recent updates include all new interior paint, new water heater, hot tub, and chimney & flu cleaning. Super well maintained and tastefully furnished and professionally decorated. Located a short distance to Chestnut Springs pool, Shamokin Springs Nature Preserve and hiking trails. Conveys fully furnished and ready to enjoy.

952 Blue Ridge Dr, Wintergreen Resort

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

$749,000
5 Beds 6 Baths 672639 MLS
This lovely home is located on the 14th green of the Devils Knob Golf Course. Featuring a spacious and open floorplan which is perfect for entertaining with a stone fireplace that anchors the living space. The main house features four bedrooms with two primary suites and a bunkroom. A large living room and den allow for separate activities for guests. Relax in the hot tub after a long day of skiing. The carriage house offers two garage bays and a full apartment above. Buyers interested in rentals can rent it as a package or independently. Wintergreen is well located to maximize your Blue Ridge adventures. Minutes from the Blue Ridge Parkway, Appalachian Trail, Skyline Drive and the Nelson 151 Trail. Combined with resort amenities you'll have years of good times in your future.

278 Catoctin Dr E, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact: