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138 Oak Ln, Wintergreen Resort
$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:

490 Three Ridges Condos, Wintergreen Resort
$165,000
1 Beds ⋅ 1 Baths ⋅ 677531 MLS
Nestled in the picturesque Wintergreen Ski Resort, this charming one-bedroom condo offers a perfect blend of modern comfort and rustic charm. Recently renovated, the condo features beautiful new flooring throughout, New furnishing, and new kitchen:equipped with modern appliances and ample counter space.The living room boasts of a cozy fireplace, ideal for warming up after a day on the slopes or enjoying a relaxing evening in. The bedroom is a tranquil retreat, featuring a comfortable bed, tasteful decor. The back porch is great if you have a dog, open to a back yard or a quiet place to have your AM coffee. One of the condo's standout features is its prime location. Just a short walk to the slopes!

490 Three Ridges Condos, Wintergreen Resort

Listing courtesy of FOUR SEASONS REALTY 1 LLC/HOWARD HANNA REAL ESTATE SERVICES. Contact:

1817 High Ridge Ct, Wintergreen Resort
$449,000
3 Beds ⋅ 3 Baths ⋅ 677526 MLS
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!

1817 High Ridge Ct, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

1707 High Rdg, Wintergreen Resort
$399,700
2 Beds ⋅ 2 Baths ⋅ 677518 MLS
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.

1707 High Rdg, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

280 Fawn Ridge Dr, Wintergreen Resort
$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:

17 Ivy Glen Ln, Wintergreen Resort
$440,000
4 Beds ⋅ 4 Baths ⋅ 677064 MLS
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 w 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 & turnkey, the home includes furniture, appliances, kitchenware, electronics, & 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, & the Nature Foundation, this property provides year-round access to the best of resort living. Freshly painted! 7-26

17 Ivy Glen Ln, Wintergreen Resort

Listing courtesy of WINTERGREEN REALTY, LLC. Contact:

762 Laurelwood Condos, Wintergreen Resort
$255,000
2 Beds ⋅ 2 Baths ⋅ 677216 MLS
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.

762 Laurelwood Condos, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

67 Forest Dr S, Wintergreen Resort
$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:

24 Trillium Close, Wintergreen Resort
$329,000
4 Beds ⋅ 4 Baths ⋅ 675784 MLS
This beautifully updated and spacious 4BR, tri–level, Townhome is just steps from the Wintergarden Spa & Fitness Center and close to golf, tennis, skiing, and the Nature Foundation. An ideal retreat for rental potential or for hosting two families with ease. Enjoy the privacy and spacious feel of a detached home—without the upkeep. As part of a well managed association, this townhome offers low maintenance living while still giving you room to spread out and relax. The main area features a bright and open living space with high ceilings and a wood burning fireplace (Firewood provided by the association), updated kitchen with stainless steel appliances and granite counters. Upstairs is the large master suite with an additional 3 bedrooms and updated bathrooms. New carpet and LVP flooring throughout. Seller credit of $10K towards new windows. Move in ready and perfectly located for year-round resort living!

24 Trillium Close, Wintergreen Resort

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

278 E Catoctin Dr, Wintergreen Resort
$724,999
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 E Catoctin Dr, Wintergreen Resort

Listing courtesy of PEAK REALTY VIRGINIA, LLC. Contact:

23 Trillium Close, Wintergreen Resort
$580,000
4 Beds ⋅ 4 Baths ⋅ 664635 MLS
Welcome to this incredibly renovated and upgraded 4 level townhouse in Trillium Close. No stone has been left unturned - high end finishes abound! Enter the main floor where this entire level has heated floors. Cozy living room with wood burning fireplace and gorgeous surround - with firewood included by the HOA! - that flows nicely to wooded back deck facing a golf hole. High end kitchen with fantastic cabinet space and full height quartz backsplash. The second level has a huge primary bedroom with walk-in closet and upgraded bathroom plus secondary bedroom, hall bath, and two linen closets. The top floor continues with two more nice size bedrooms with a bath between. The lower level comprises of an entertainment room with its own mini split plus a mud room to store the golf clubs and skis. Large two car garage with professionally epoxied floors has great storage and opens to a parking pad for two more cars. Fantastic mountain location in close proximity to the Devils Knob Complex with spa, aquatics, fitness, and restaurants. Easy drive out of Wintergreen to the 151 brewery and winery trail!

23 Trillium Close, Wintergreen Resort

Listing courtesy of COMPASS-CHARLOTTESVILLE. Contact: