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905 Diamond Hill Condos, Wintergreen
$212,000
1 Beds ⋅ 1 Baths ⋅ 677733 MLS
Charming slope-side condo featuring stunning slope and valley views with true ski-in/ski-out access. Ideally located in the heart of Center Village, just steps from restaurants, shops, and all the resort amenities. Thoughtful updates over the years include granite countertops, stainless steel appliances, washer and dryer, patio slider, and a beautiful stone fireplace hearth—plus a new HVAC system installed in 2023. A wonderful blend of location, comfort, and efficient design makes this condo perfect for mountain getaways or rental investment. Conveys fully furnished and ready to enjoy. Vacant and easy to show.

905 Diamond Hill Condos, Wintergreen
1641 Overlook Condos, Wintergreen
$430,000
2 Beds ⋅ 2 Baths ⋅ 678390 MLS
Stunning views, Stunning location and Stunning renovations. Don't miss out on this updated home located on the "Ridge." New floors, fresh paint and a new water heater make this home move-in ready now. Spacious and bright along with 2 decks that bring the outdoors in. Just steps to the superb amenities of golf, tennis and pickleball at the Devils Knob Club. Catch a workout at the Wintergarden Spa or a bite to eat at Devils Grill or Fire and Frost. Gaze over the ski resort and prepare to be mesmerized by the panoramic expanse of the mountains, valleys and Lake Monocan below. Convenient ingress/egress with only 1/2 flight of stairs up from the parking lot. Successful platinum rated rental can add a little play money to the coffers if str is your game. Spacious and well-appointed to be a primary residence or second home sanctuary. WPOA fees are $2,279 annually and Overlook Condo fees are $1,813 per quarter. Make this your dream home before someone else makes it theirs.

1641 Overlook Condos, Wintergreen
742 Laurelwood Condos, Wintergreen
$155,000
1 Beds ⋅ 1 Baths ⋅ 682166 MLS
Beautifully renovated condo that overlooks the community pool, just steps away from center village. The Laurewlwood Complex boast the convenience of location and access without the big price. Currently being used as a successful STR property, but also the perfect mountain getaway for personal enjoyment. Gross rental rev 2023-$31k, 2024-$25K, 2025-$30K. Check with agent for showing availability.

742 Laurelwood Condos, Wintergreen
2031 Stone Rdg, Wintergreen
$140,000
1 Beds ⋅ 2 Baths ⋅ 667941 MLS
This is a ground-floor one-bedroom with two baths and a nice sleep sofa in the living room for additional family. It is located on the 18th fairway of the Devils Knob Golf Course and is a short walk to the spa, pools, exercise facilities, as well as tennis, golf, and the Devils Grill restaurant. It is a great location and is being sold furnished.

2031 Stone Rdg, Wintergreen
1587 Vistas Condos, Wintergreen
$275,000
1 Beds ⋅ 2 Baths ⋅ 678691 MLS
Wake up to breathtaking panoramic mountain views and watch the sunrise paint the horizon from the comfort of your bedroom in this beautifully maintained Wintergreen condominium. Currently enrolled in the Wintergreen Rental Program, the property grossed approximately $24,000 in 2025 while still allowing the owners ample time to enjoy it as their personal mountain retreat. Both full bathrooms have been thoughtfully renovated, blending modern comfort with mountain charm. Offered fully furnished, this turnkey condo is ready for immediate enjoyment—whether as a primary residence, vacation getaway, or investment opportunity. Experience the best of mountain living with easy access to Wintergreen's year-round amenities, including skiing, golf, hiking, tennis, and dining, while also enjoying the renowned wineries, breweries, and outdoor adventures that make Nelson County such a sought-after destination.

1587 Vistas Condos, Wintergreen
1623 Overlook, Wintergreen
$524,760
2 Beds ⋅ 2 Baths ⋅ 681400 MLS
One of a kind! Step into the Big Chill on the Hill! Step out to breathtaking panoramic views from the oversized wrap-around deck that expands the outdoor space like no other. You will be mesmerized by the views to Charlottesville, the Rockfish Valley, Lake Monocan in Stoney Creek, across the Piedmont and over the mountain ridges and the Resort. Fantastic location with just steps to the pickleball courts and the Devils Knob Country Club amenities. A fully renovated home featuring a stunning farmhouse retro kitchen, spa like baths and comfortable great room define the space. Reclaimed wood accents, hickory hardwoods and slate tile are the finishing touches that makes this home a step above. Easy ingress/egress with only a half flight of stairs to the front door. Move right in to enjoy the Wintergreen Lifestyle. Make this your home before someone else makes it theirs. Condo dues are $1,813 per quarter and WPOA is $2,279 annually for 2026.

1623 Overlook, Wintergreen
2072 Stone Rdg, Wintergreen
$275,000
2 Beds ⋅ 2 Baths ⋅ 681516 MLS
Escape to the top of Wintergreen and enjoy the mountain lifestyle from this beautifully maintained, fully furnished 2BR/2BA Stone Ridge condo. Large windows fill the living space with natural light, while the striking stone gas fireplace creates a warm, inviting focal point. Step onto the private deck and take in peaceful golf-course views with glimpses of the surrounding mountains. The functional layout offers a beautiful kitchen with granite countertops, wood cabinetry and stainless steel appliances, an open dining and living area, a primary suite, second full bath and in-unit laundry. Ideally located near the top of the mountain, enjoy easy access to skiing, golf, pools, trails, dining, Devil's Knob Golf & Tennis, the Nature Foundation and WinterGarden Aquatics & Fitness Center. Fiber internet, private ski storage and strong rental history make this an equally compelling mountain retreat or investment opportunity. Sold turnkey and fully furnished.

2072 Stone Rdg, Wintergreen
42 Peavy Pt, Wintergreen
$787,500
5 Beds ⋅ 4 Baths ⋅ 676285 MLS
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 zone hvac, conditioned crawlspace and a tankless water heater. True main level living with three bedrooms and laundry on the first floor. Soaring great room windows with 2 story stone fireplace and vaulted ceiling bring the mountains and outdoors in. Three levels each with a bedroom with ensuite baths. The recently finished terrace level offers plenty of space for family and friends. Don't miss out. Make this your home before someone else makes it theirs!

42 Peavy Pt, Wintergreen
2231 Tanners Rdg, Wintergreen
$125,000
1 Beds ⋅ 1 Baths ⋅ 677206 MLS
A furnished one bedroom condo on ground level in Tanners Ridge Condo Complex, Walking distance to Wintergreen Spa, Golf, Tennis and close to advanced ski runs and also on ski shuttle to lower mountain at Mountain Inn.Upgraded LPV flooring in the main living and bedroom areas. New double Anderson sliding glass doors allow you to experience the outdoors from inside. It is one of the least expensive opportunities to have a wonderful weekend retreat or a rental property in a world class resort in the mountains of Virginia close to major cities on the east coast.

2231 Tanners Rdg, Wintergreen
2224 Tanners Rdg Unit 2224, Wintergreen
$190,000
2 Beds ⋅ 2 Baths ⋅ 672456 MLS
Don't delay in seeing this one. This is one of the rarest condominiums at Wintergreen, NO STAIRS, and easy entry. Located near the spa and golf club, Tanners Ridge is also an easy walk to Wintergreen's nature trails, the Nature Center, and the Appalachian Trail. The interior design is very efficient with an open kitchen, living area with a wood-burning fireplace, and two bedrooms and baths on a single floor. There are seasonal views into the Shenandoah Valley easily visible from the deck. A great spot to relax with family and friends. A great value.

2224 Tanners Rdg Unit 2224, Wintergreen
224 Timbers Condos, Wintergreen
$185,000
1 Beds ⋅ 2 Baths ⋅ 680608 MLS
Rare top floor, 1 bedroom 2 bath home. Perfect setup to sleep up to five people. Renovated, furnished and ready to go. Condo fees are $900 quarterly and WPOA fees are $2,279 annually for 2026. Great location in the Mountain Inn Village. Walk out of the building and jump on the slopes.

224 Timbers Condos, Wintergreen
472 Three Rdgs, Wintergreen
$151,000
1 Beds ⋅ 1 Baths ⋅ 672682 MLS
Step into this home and immediately become immersed in the Wintergreen Lifestyle. Walking distance to the Ski Slopes and the entirety of the Mountain Inn Village means your car doesn't have to leave the gated parking area. This condo is renovated and ready with recently completed kitchen and bath renovations including fresh paint. Note the LVP, ceramic tile, tankless water heater, and newer appliances including the washer/dryer. Textured walls and fireplace surround with stained beams add to the mountain home ambiance. Walk out on the patio and relax while surrounded by woods and open space or hop on the Highlands Trail to the Wintergarden Spa. Convenience and ease of maintenance make this the perfect spot to land. Act now and make this your home before someone else makes it theirs. Condo fees are only $890 per quarter and WPOA fees are $2279 annually for 2026.

472 Three Rdgs, Wintergreen
1545 Cliffs Condos, Wintergreen
$255,000
1 Beds ⋅ 2 Baths ⋅ 678654 MLS
Breathtaking views await you at this cozy, turn-key, 1 bedroom/2 full bathroom condo. This condo is on the bottom floor and enjoys a large, open deck perfect for sunrises and stargazing. Golf, tennis, pickle ball, skiing, snowboarding, restaurants and the Wintergarden Spa are all within walking distance. Miles of hiking trails both on and off property are yours to discover. This highly desirable floor plan is seldom available. What are you waiting for?

1545 Cliffs Condos, Wintergreen
415 Three Rdgs, Wintergreen
$350,000
3 Beds ⋅ 2 Baths ⋅ 679150 MLS
All the bells and whistles are here in this beautiful, two floor, top level condo in the Black Rock Village area. Restaurants, the Mountain Inn, skiing, and shops are all a very short walk away. Enjoy star gazing on the large, open deck. This property is part of the distinctive Wintergreen Rental program and is being sold fully furnished. If you are looking for a feeling of privacy, while still being close to everything, this is it.

415 Three Rdgs, Wintergreen
880 Devils Knob Loop, Wintergreen
$2,520,000
6 Beds ⋅ 8 Baths ⋅ 677667 MLS
880 Devils Knob Loop is considered by many to be the crown jewel of high-end properties at Wintergreen Mountain. The craftsmanship, architectural composition, and panoramic views are unrivaled. This 6-bedroom, 5 full and 3 half-bath home features custom wood and stonework throughout and is bathed in natural sunlight that pours through floor-to-ceiling windows across every level. The home features multiple fireplaces, with a prodigious stone hearth anchoring the vaulted great room — a grand yet welcoming space that flows seamlessly into the chef's kitchen. Luxury appointments include Ipe hardwood decking, sleek glass railings, top-tier Viking and kitchenAid appliances, and a built-in outdoor hot tub. 880 Devils Knob offers a singular experience — as though you are floating effortlessly above the mountains. This refined, elegant, and truly one-of-a-kind retreat stands in a class of its own.

880 Devils Knob Loop, Wintergreen
455 Deer Springs Ln, Wintergreen
$580,000
3 Beds ⋅ 3 Baths ⋅ 678539 MLS
Storybook cottage in a storybook setting! Come see what makes this home special and unique. Post and beam effects in the kitchen and dining room create the mountain home touch while the volume of glass in the living room combined with abundant outdoor living space leaves you lost amongst the trees. The terrace level primary suite creates the perfect hideaway, and the upper level boasts two bedrooms, bath and a large walk-in closet or playroom for the kids. Comfort is assured with a 2-zone dual fuel hvac system, tankless water heater and Andersen windows. Nestled at end of the cul de sac, just below and steps away from the Devils Knob Golf, Tennis and Pickleball facilities. Bask in the new hot tub after a hike, a day on the slopes or a workout at the Club. Create the perfect meal in the gourmet kitchen featuring gas cooking or simply grill and chill on the deck and enjoy the cool breezes of summer. Make this your home before someone else makes it theirs. Turnkey and ready to be the perfect home for your family.

455 Deer Springs Ln, Wintergreen
22 Deer Springs Ln, Wintergreen
$590,000
3 Beds ⋅ 2 Baths ⋅ 679471 MLS

22 Deer Springs Ln, Wintergreen
308 Devils Knob Loop, Wintergreen
$560,000
3 Beds ⋅ 4 Baths ⋅ 678087 MLS
Well-built home featuring a two-car garage and an inviting open-concept layout that seamlessly connects the great room and kitchen. Enjoy the warmth of the cozy fireplace and the abundance of outdoor living space with spacious decks surrounding the home. The finished basement provides additional room for family gatherings, recreation, or guests. Also included is a large Hottub. Home is located on desirable Devils Knob Loop, this property offers both comfort and convenience, making it a must-see!

308 Devils Knob Loop, Wintergreen
38 Firtree Dr, Wintergreen
$295,000
2 Beds ⋅ 2 Baths ⋅ 673865 MLS
Investors, this one's for you! After a $180,000 renovation – new roof, windows, kitchen floors, decking and siding – this chalet is ready for your final touches. Drive up the paved driveway and admire the beautiful stonework along the walkway. As you enter through the finished basement you'll see two bedrooms and a full bathroom. The deck on this level is a great drop zone for ski gear. The next level features an open concept living/dining/kitchen area and another full bathroom. The new windows throughout the home keep rooms light and airy, and the seasonal mountain views are stunning. The double deck is great for aprés ski hanging out. Large enough for a futon and games, the kids will love the upstairs loft. Avoid the condo dues and consider a single family getaway close to the slopes and Black Rock Market, and a quick drive to Nelson 151 attractions.

38 Firtree Dr, Wintergreen
476 Three Rdgs, Wintergreen
$170,000
1 Beds ⋅ 1 Baths ⋅ 672586 MLS
This beautifully updated condo is a dream retreat for outdoor lovers, perfectly situated near the ski slopes and Mountain Inn, and offers the lowest condo dues at Wintergreen. Thoughtfully renovated, it blends modern comfort with elevated mountain charm. After a day of adventure, grab a pizza from Fire and Frost and unwind while taking in the fresh mountain air.

476 Three Rdgs, Wintergreen
18 Grassy Overlook, Wintergreen
$489,000
2 Beds ⋅ 2 Baths ⋅ 668424 MLS
The house sits on a desirable corner lot with a fenced backyard—perfect for outdoor activities or pets. It is a level floor plan with a large garage. It has been used by previous owner as both a primary home and a 2nd home. It has been upgraded several times and although built in 2004, it feels newer since it has been well maintained.

18 Grassy Overlook, Wintergreen
2224 Laurel Springs Dr, Wintergreen
$705,000
4 Beds ⋅ 4 Baths ⋅ 672118 MLS
This home sits at the top of Shamokin Falls and the sounds of the waterfall are heard yearround. It has a winter view down through the Shamokin Gorge and is one of the most secluded and private sites at Wintergreen and it borders Wintergreen's protected open space and is loacted at the end of developement of the mountain at the very end of Laurel Springs. It is a biker and hiker's dream location. LIST OF IMPROVEMENTS as the current owners intended to live there ROOF, SKYLIGHTS AND GUTTERS have been replaced. The FURNACE; AIR EXCHANGE HEAT PUMP have been replace AND there is COMPLETE NEW DUCT WORK. There are 5 EXTERIOR DOORS, and 1 new WINDOW. All 3 BATHROOMS have been UPDATED. There has been a COMPLETE KITCHEN REMODEL with High-end Craftmade cabinets, new appliances with a new gas stove. The HARDWOOD FLOORS have been RESURFACED and sealed. On the lower level DOWNSTAIRS LVP FLOORING has been installed. An OAK TREAD STAIRWAY has been installed. LIGHTS AND FANS REPLACED THROUGHOUT ENTIRE HOUSE. There is a new GE WASHER AND DRYER WITH POWER EXHAUST FAN. The ENCAPSULATED CRAWL SPACE, RADON MITIGATION systemm has been created. There is a TANKLESS GAS HOT WATER and new OUTSIDE STAIRS TO REAR OF HOUSE.

2224 Laurel Springs Dr, Wintergreen
274 Laurel Springs Dr, Wintergreen
$530,000
3 Beds ⋅ 4 Baths ⋅ 676091 MLS
Overlooking one of Wintergreen’s most scenic golf settings along the 7th hole of Devil’s Knob, this thoughtfully updated mountain retreat offers a blend of privacy, natural beauty, and year-round enjoyment. Set just above the fairway, the home features peaceful mountain views and a spacious deck ideal for relaxing or entertaining. Inside, the great room includes vaulted ceilings, wood beams, a stone fireplace, and abundant natural light, while the updated kitchen with new appliances connects seamlessly to the main living and dining areas. The home offers three bedrooms, each with a private bath, including a main-level primary suite, all with deck access and golf course views—ideal for guests, full-time living, or a second home. Recent improvements, including a newer roof, updated kitchen and half bath, and washer and dryer, add peace of mind. Offered furnished. Convenient to golf, skiing, hiking, and more, this property offers an ideal mountain retreat with both lifestyle and investment appeal.

274 Laurel Springs Dr, Wintergreen
646 White Oak Condos, Wintergreen
$262,825
2 Beds ⋅ 2 Baths ⋅ 675201 MLS
Just Wow! Prime location, renovated and an end unit! Walk to the Mt Inn Village and the Ski Slopes. Enjoy low maintenance condo living in a townhome design. Only one adjoining neighbor means nobody else lives above or below. This is where peace and tranquility co-exist along with the active Wintergreen Lifestyle. Catch the cool summer breezes and seasonal views from the deck or patio. Three levels for family and friends to spread out. Terrace level walk out is perfect for kids and pets to enjoy the rear yard area. Condo lives like a three bedroom and sleeps six comfortably with the additional bonus space in the loft. There are very limited opportunities to call White Oak home. Act now and make this your home before someone else makes it theirs. Condo fees are $1155 quarterly and WPOA is $2279 annually for 2026.

646 White Oak Condos, Wintergreen
131 Crawfords Edge, Wintergreen
$782,500
4 Beds ⋅ 4 Baths ⋅ 674294 MLS
Unicorns do exist. Rarely does a home at Wintergreen deliver truly breathtaking views without the oversized footprint that usually accompanies. Perfectly sized at 2,268 sqft, this beautifully updated 4BR/3.5BA retreat offers million-dollar views. Cathedral ceilings and walls of windows fill the great room with light and frame the landscape beyond, anchored by a dramatic two-story stone wood-burning fireplace. The open floor plan flows effortlessly to multiple decks where sweeping mountain views stretch for miles and the peaceful sound of the stream meandering through creates an unforgettable setting. Evenings are best spent soaking in your private hot tub under star-filled skies. Two primary suites—including one on the main level—offer ideal flexibility for owners and guests. Lower level provides additional living space with three bedrooms. Backing to hundreds of acres of open space, the combined .76-acre homesite ensures exceptional privacy with only one WPOA fee. SIGNIFICANT UPDATES THROUGHOUT. A new driveway with drainage, Tesla/EV charger, and lighted stairs complete this rare mountain retreat. Views. Water. Privacy. Perfection. Opportunities like this at Wintergreen are incredibly rare. Don't miss this one!

131 Crawfords Edge, Wintergreen
91 Shamokin Springs Trl, Wintergreen
$75,000
673580 MLS
Winter Views, great location with a nice slope. Perfect for a home with a walk out basement or a multi- level home, an easy building lot. Seller says bring all offers!!

91 Shamokin Springs Trl, Wintergreen
18 Trillium Close, Wintergreen
$249,000
2 Beds ⋅ 3 Baths ⋅ 671893 MLS
Nestled in the woods in the Devils Knob Village. The perfect "Place" as it is close to everything! Walk to the Wintergarden Spa, Nature Foundation, Fire and Frost Restaurant or the Devils Knob Country Club. Easy access to the Highlands ski slopes or take the Highlands Leisure Trail to the Mt. Inn Village. Comfortable and spacious Townhome living with no worries of noise from above or below. Two bedrooms and two and a half baths offer plenty of room for the family and friends to spread out. Deck provides privacy and a wooded buffer to enjoy a little nature. Ski or Ride now but remember Spring is around the corner so plan your golf, tennis, pickle ball or a hike right out of the back door. Act now as Trillium Place has very limited opportunities. Turnkey furnished and ready for the next family. Make this your home before someone else makes it theirs. Location, Location, and Location....is what you, your family, and friends need. Trillium quarterly assessments are $1250 and WPOA is $2279 annually for 2026.

18 Trillium Close, Wintergreen
1448 Highlands Condos, Wintergreen
$399,675
2 Beds ⋅ 2 Baths ⋅ 672984 MLS
Imagine a top floor end two-bedroom condo with two baths on two levels which looks like it was hung off the clouds. This lovely condo is heavily rented through Wintergreen Resort and gross income figures can be provided upon request. It is at the top of the advanced ski runs at The Highlands Slopes and is very close to the ski runs and could be termed ski in & ski out, especially with a good blanket of snow, otherwise it is a very short walk to the slopes (measured in yards). It is on one of the ski shuttle stop to the lower mountain and The Mountain Inn. Due to its premium location, it is across the street from the Spa and the Fire and Frost Restaurant. Just down the road are the tennis courts (indoor and outdoor) and pickleball courtsand the Devil Knob Golf Course and the famous Devils Grill restaurant at the mountain clubhouse. Finally, there are the views. Click on the pictures to see probably the best the year round views at Wintergreen. Sq. footage is approximate; agents and buyers should rely upon their own resources for an exact sq. footage. Condo dues are $1700 per quarter.

1448 Highlands Condos, Wintergreen
1635 Overlook Condos Unit 1635, Wintergreen
$430,000
2 Beds ⋅ 2 Baths ⋅ 671148 MLS
Fabulous 2 bedroom hard to find end unit in Overlook. Being sold mostly furnished.

1635 Overlook Condos Unit 1635, Wintergreen
30 Stony Cove Ln, Wintergreen
$455,000
3 Beds ⋅ 3 Baths ⋅ 662906 MLS
Three words come to mind when describing this lovely chalet: Peace, then Quiet, & finally Quality. It is a place where one would go to unwind and recapture the tranquility of being in the forest in one of the most special places on Earth. This mountain chalet is at the end of a very quiet cul de sac not too far from the major facilities of Devils Knob It borders open space, the head waters of Stoney Creek, and the old A.T. It sits on a private lot with large trees and in the sounds of the headwaters of Stoney Creek are just off the rear deck.

30 Stony Cove Ln, Wintergreen

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