Courtesy: MOUNTAIN AREA NEST REALTY
434-361-2440
Tucked into the trees at Wintergreen, this 2BR/2BA ground-floor, walk-out end unit offers easy living with minimal steps from parking. Walking distance to the slopes, the Mountain Inn, and Black Rock Market, it's in a great location. The great room centers on a wood-burning fireplace beneath a warm wood-beamed ceiling, with a wall of windows and a sliding door opening to a private patio surrounded by wooded, seasonal mountain views. The kitchen features granite counters and a breakfast bar open to the living space, ideal for entertaining or quiet mornings with coffee. The primary suite includes a private bath and ample closet space, while the second bedroom offers flexibility for guests, family, or a home office. In-unit stacked laundry and generous foyer storage add everyday convenience. Laurelwood is the only condo association at Wintergreen with its own private pool, and the association even provides firewood for the fireplace. HOA includes area maintenance, road maintenance, snow removal, security, and more. A true low-maintenance mountain retreat.
Courtesy: REAL BROKER LLC
855-450-0442
Spacious end-unit townhome in the heart of Wintergreen Resort, situated on the largest lot in Westwood and offering two dedicated parking spaces. Enjoy exceptional outdoor living with extensive stone patios with a perfect spot for a hot tub, a spacious deck, and a covered front porch. Inside, the inviting living room features a sunken conversation area centered around a wood-burning fireplace, while the open layout flows easily into the dining area. A convenient half bath completes the main level. Upstairs, the primary suite features a walk-in closet, cedar-lined closet, and ensuite bath with double vanities and a whirlpool tub. An additional guest bedroom and full bath provide comfortable accommodations for family and friends. The fully finished walk-out lower level offers flexible additional living space. Located near the ski shuttle stop and just a scenic walk to hiking trails, the Nature Foundation, and Wintergarden Spa & Aquatics Center. Ideal as a full-time residence, mountain getaway, or rental opportunity! HOA covers roof replacement, exterior painting, landscaping, and snow removal. See it today!
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.,Granite Counter,Maple Cabinets,Fireplace in Dining Room,Fireplace in Family Room,Fireplace in Living Room,Fireplace in Master Bedroom
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.,Formica Counter,Painted Cabinets,Fireplace in Great Room
Courtesy: PEAK REALTY VIRGINIA, LLC
434-325-3335
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.
Courtesy: NEST REALTY GROUP
434-566-0121
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.
Courtesy: PEAK REALTY VIRGINIA, LLC
434-325-3335
This tree loft actually feels like a treehouse, as the design was intended. If you're looking for a special and memorable mountain getaway, you'll find that here perched among the trees with wonderful seasonal views and a 40 second walk to the ski slopes access. In 2020, the house underwent a huge renovation, including new roof, siding, deck, hot tub, completely renovated kitchen and bathrooms with custom maple cabinetry and granite, and additional square footage was added to create the foyer—keep the cold air out and have a landing zone for ski gear, bench, storage closet, towel cubby for the hot tub, and a designated place for laundry. Also uncommon at the tree lofts is HVAC with ductwork; there's a central air (dual fuel), gas fireplace w/ slate surround, and a tankless water heater—all propane-powered. Impressively cared for and improved in nearly every way, this mountain home set high in the forest is the magical getaway you're looking for to both escape the heat and enjoy winter sports in the mountains.
This beautifully updated 2-bedroom, 2-bath condo offers comfort, style, and convenience in one of the resort's most desirable associations. Step inside to find a bright, open floor plan enhanced by luxury vinyl plank flooring, providing both modern elegance and easy maintenance throughout. HVAC is from 2020 and water heater from 2024. The spacious living room is perfect for relaxing or entertaining, with plenty of natural light. The well-appointed kitchen features ample cabinetry, great counter space. Enjoy all the benefits of condo life, including low-maintenance living, resort amenities, and a fantastic location close to Devils Knob Golf & Tennis and the WinterGarden Aquatics & Fitness Center.,Granite Counter,Wood Cabinets,Fireplace in Living Room
Beautifully designed 4BR, 3.5BA split-level mountain retreat offering 3,140 finished sqft at Wintergreen Resort. This 2.5-level home features a highly functional floor plan ideal for comfortable living and entertaining, with a large private primary suite occupying the entire top floor and a second primary suite on the first level. The dramatic main level showcases a soaring cathedral-ceiling great room with a stunning floor-to-ceiling stone gas-log fireplace, seamlessly flowing into the dining area and spacious kitchen. Just beyond is the wonderful four-season sunroom leading to a large screened porch with a peaked roof, perfect for enjoying cool mountain summers, alfresco dining, and peaceful evenings surrounded by nature. A large deck, level paved driveway, and turnkey furnished interior add to the appeal. Bordering the George Washington National Forest, the property enjoys seasonal mountain, Shenandoah Valley, and sunset views from early November through early May, while the top-floor primary suite offers a window of mountain views year-round. Ravens Roost Overlook and access to the Old Appalachian Trail are just a short walk away. Exceptionally private and serene, this home feels like a true mountain retreat.,Formica Counter,Painted Cabinets,Wood Cabinets,Fireplace in Great Room
Courtesy: PEAK REALTY VIRGINIA, LLC
434-325-3335
With a two minute walk from the house to the ski slopes access point, this ski chalet is an easy stroll to hop on Tyro to go skiing and snowboarding at your leisure. While most tree lofts have one deck/outdoor area, this property also has a very private patio space with a fire pit and new hot tub. Walk inside, and the whole property is charmingly decorated. Perfectly appointed, with many upgrades to the kitchen, bathrooms, and new windows/glass, these stylish spaces will have you loving your time inside in between skiing, hiking, golfing, and tennis. All details are thoughtfully chosen. A small spring provides a seasonal water feature and lush backyard. This peaceful mountain getaway is sold turn-key and will have you enjoying every season here.
Courtesy: PEAK REALTY VIRGINIA, LLC
434-325-3335
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.
Courtesy: Mountain Area Nest Realty
434-361-2440
Tucked into the trees at Wintergreen, this 1BR/1BA ground-level condo offers a wooded, private feel from the moment you arrive via the footbridge entry. The walkout patio is shaded by mature hardwoods and pines — perfect for morning coffee or unwinding after a day on the mountain. Inside, a wood-burning fireplace with tile surround sets a cozy mountain tone, opening to a living and dining area with durable LVP flooring. The kitchen has been nicely updated with granite countertops, stainless appliances, and open shelving. The spacious primary bedroom features vaulted ceilings, a generous closet, and access to an updated full bath with granite vanity. In-unit washer/dryer adds everyday convenience. Close to the ski shuttle stop, this is an efficient, low-maintenance retreat — and a perfect place to relax after a day exploring the wineries and breweries along Nelson 151. Enjoy all Wintergreen has to offer: skiing, golf, hiking, and four-season mountain recreation, just minutes from your door.
Courtesy: Peak Realty Virginia, Llc
434-325-3335
Set high on Wintergreen's coveted ridgeline, this tastefully renovated two-bedroom, two-bathroom condo combines refined comfort with a setting nature lovers adore. Housed in arguably the nicest building on the ridge, it arrives fully furnished with quality pieces, plus a new heating and cooling system, a walk-in shower, and convenient elevator access—so settling in takes little more than unpacking a suitcase. Both bedrooms offer restful retreats, while the bright living areas welcome leisurely mountain mornings and unhurried evenings. The surroundings steal the show. The Nature Foundation at Wintergreen sits just minutes away, ideal for trails, wildlife watching, and seasonal programs throughout the year. Adventure seekers will appreciate easy access to Skyline Drive, the Virginia 151 corridor, and the legendary Blue Ridge Parkway—three of the most scenic routes in the country—along with the welcoming Devils Backbone Basecamp nearby. Come see all that Wintergreen, VA and the Blue Ridge Mountains have to offer.
Courtesy: Jason Mitchell Real Estate
917-626-3747
Welcome to the heart of Wintergreen Resort! Turnkey, high-performing, proven short-term rental opportunity. This sought-after Laurelwood condominium comfortably sleeps six guests and is ideally positioned for year-round enjoyment and strong rental demand. Laurelwood is the only condominium complex within Wintergreen Resort to offer a private pool and access to two additional resort pools. Enjoy the convenience of being just a short walk to ski slopes, restaurants, shopping, and resort amenities. Whether you're seeking a vacation retreat, income-producing investment, or both, this property offers an exceptional combination of location, amenities, and proven rental appeal. Walk right out your back deck to trails, skiing, or sunbathing enjoying all that mountain living can offer.
4 Trillium Lane sits at one of the highest vantage points in the Trillium development, offering direct views of the golf course. The property is within easy walking distance of the Wingarden Spa and Fire & Frost restaurant, making it a convenient base for enjoying Wintergreen's core amenities. For buyers prioritizing space, it offers some of the best square footage per dollar in the development.
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.,Soapstone Counter,Fireplace in Living Room
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 the few detached homes at Wintergreen to feature an attached garage, this property is equally suited as a mountain getaway or permanent residence. Property Highlights: 4 bedrooms ? 4 bathrooms ? Attached garage (rare at Wintergreen) ? On the 13th hole, Devils Knob Golf Course ? Mountain views front, pastoral views rear ? Central to all Wintergreen amenities ? Single owner, maintained and updated throughout.
Courtesy: Peak Realty Virginia, Llc
434-325-3335
21 Trillium Close is one of the nicest townhouses at Wintergreen with a great central location. It is completely and tastefully updated with new flooring, a fully renovated kitchen, high quality bathrooms, a gas fireplace and newer furniture throughout. The location can't be beat for accessibility to the Wintergreen Nature Foundation, Highlands ski lift and other resort amenities. Explore the Blue Ridge Parkway, hiking, the Nelson 151 Trail, resort amenities and all that the mountains have to offer.
Courtesy: Peak Realty Virginia, Llc
434-325-3335
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.
Courtesy: Mountain Area Nest Realty
434-361-2440
This one is an absolute stunner! Escape to this beautifully maintained and renovated 3br/3ba Ledges condo with minimal steps as you enter the building. The living room has vaulted ceilings, the space softly showered with an abundance of natural light. Perch yourself on the deck and take in breathtaking mountain views. This unit has a primary bedroom on each floor! Upstairs, you will find a primary bedroom suite that has a primary bath, laundry and a large closet space. The main level's open concept floor plan is great for entertaining, or just cozying up to the fireplace on cool nights. Subtle under cabinet lighting in the kitchen illuminates your counter space. Close by is the second primary bedroom with its own bathroom. A third bedroom – currently used as a bunk room – would also make a great home office. The third bathroom is just down the hall, before you get to the living room. Though its been most recently used as a private getaway, this condo would be a great short term rental. Stream and telework with fast broadband internet. Convenient to slopes, golf and pickleball, not to mention miles of hiking trails, retreat to this lovely home after a day exploring all of Nelson 151's attractions.
Bright and welcoming 3-bedroom, 3-bath end-unit condo offers the perfect blend of comfort, convenience, and mountain charm. Enjoy easy, one-level living with no stairs and elevator access right from the parking area. The entire interior has just been painted and is immaculate?never used as a rental and is truly move-in ready. Newer windows throughout. An open floor plan features a cozy wood-burning fireplace and a wall of windows that frame gorgeous sunrises and mountain views, while filling the space with natural light. Two primary suites each have their own private bath, while the third bedroom sits beside a full hallway bath?ideal for guests or a third suite. Step outside onto the new composite deck to relax and take in the views. This condo is right on the ski shuttle route, making it super convenient to skiers who also want to enjoy ridge line views while at Wintergreen! Offered turn-key furnished. Pack your bags and move right in! A rare find with zero stairs, easy access, and stunning views?mountain living made simple! Don't miss this one!,White Cabinets,Wood Cabinets,Fireplace in Living Room
Courtesy: Peak Realty Virginia, Llc
434-325-3335
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.
Experience the ultimate mountain lifestyle in this premier ski-front studio at Wintergreent! Boasting one of the best locations on the mountain, this condo offers true slopeside access & breathtaking mountain views right from your private deck. In the warmer months, you're steps away from the courtyard, the heart of the resort's vibrant festivals, concerts, and craft fairs. Enjoy the ultimate convenience with a short stroll to restaurants, shopping, coffee shops, the market, and kids' programs.This is a fantastic, affordable opportunity to step into the Wintergreen experience. The studio is offered fully furnished and turnkey?simply bring your gear and start making memories. Perfect as a personal escape or a savvy rental investment!,Formica Counter,Wood Cabinets
Beautifully renovated and tastefully decorated 2BR, 2BA condo in the desirable Laurelwood neighborhood at Wintergreen Resort. This one-level villa offers a bright and inviting open floor plan with the kitchen flowing seamlessly into the dining and living areas, centered around a stunning stone wood-burning fireplace. The spacious primary suite features an attached private bath, while the second bedroom and full bath provide comfortable accommodations for family and guests. Step outside onto the deck and enjoy the peaceful wooded setting and refreshing mountain air. Laurelwood is conveniently located in the heart of Wintergreen Resort village, next to The Market and within a short walk of skiing, hiking trails, restaurants, shopping, and resort amenities. Laurelwood is also the only condo neighborhood at Wintergreen with its own private outdoor swimming pool. Offered turn-key furnished, this move-in-ready mountain retreat is ideal as a weekend getaway.,Granite Counter,Wood Cabinets,Fireplace in Living Room
Beautiful 4-bedroom, 3.5-bath mountain retreat located in the highly desirable Westwood section of Wintergreen Resort. This spacious townhome offers approximately 1,840 square feet of comfortable living space with exceptional privacy and no units above or below. Recent updates include renovated kitchen countertops, new luxury vinyl plank flooring throughout the main level and bathrooms, new second-floor carpeting, updated lighting fixtures, and newer appliances including dishwasher, stove, refrigerator, washer, and dryer. The inviting family room features a wood-burning fireplace with custom built-in shelving, creating the perfect mountain getaway atmosphere. Additional features include a separate dining area, central air conditioning, two-car garage, and ample storage.Offered fully furnished and turnkey, the home includes furniture, appliances, kitchenware, electronics, and big-screen TV ? ideal for immediate personal enjoyment or continued short-term rental use. Strong Airbnb rental history offers excellent investment potential. Conveniently located near the golf course, Wintergarden Spa, hiking trails, skiing, tennis, and the Nature Foundation, this property provides year-round access to the best of resort living.,Quartz Counter,Fireplace in Family Room
Information is provided by Charlottesville Area Association of Realtors®. Information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interestedin purchasing. Copyright © 2026 Charlottesville Area Association of Realtors®. All rights reserved.
Wintergreen Resort is located in Virginia. Wintergreen Resort, Virginia has a population of 858.
The median household income in Wintergreen Resort, Virginia is $71,502. The median household income for the surrounding county is $67,707 compared to the national median of $69,021. The median age of people living in Wintergreen Resort is 40.3 years.
The average high temperature in July is 87.3 degrees, with an average low temperature in January of 24.5 degrees. The average rainfall is approximately 43 inches per year, with 14 inches of snow per year.
