Wintergreen, VA Homes for Sale with Pool

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  /18

  $217,500

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  2224 Tanners Ridge Condos Unit 2224, Wintergreen, VA 22967

  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

  K.T. LYNN WINTERGREEN REALTY, LLC

  2224 Tanners Ridge Condos Unit 2224, Wintergreen, VA 22967
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  /23

  $244,000

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  730 Laurelwood, Wintergreen Resort, VA 22967

  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

  Yvette Stafford MOUNTAIN AREA NEST REALTY

  730 Laurelwood, Wintergreen Resort, VA 22967
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  /84

  $274,000

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  740 Laurelwood, Wintergreen Resort, VA 22967

  Turnkey, Fully finished, and just a short walk to ski slopes, Wintergreen Market, & ski lodge, beautifully updated 2-BR, 2-BA condo is ready to enjoy! Thoughtfully, renovated throughout, it features, new LVP flooring, new windows, new interior, and exterior doors, new carrier HVAC (2024), and more. The stylish kitchen offers freshly painted white cabinetry, granite countertops, new backsplash, &

  Susan Singleton Century 21 ALL-SERVICE-FOR

  740 Laurelwood, Wintergreen Resort, VA 22967
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  /51

  $599,000

  $50K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,537 Sq Ft

  952 Blue Ridge Dr, Wintergreen Resort, VA 22967

  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

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  952 Blue Ridge Dr, Wintergreen Resort, VA 22967
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  /7

  $52,500

  • Land
  • 16,117 Sq Ft
  • $141,892 per Acre

  41 Hickory Spring Rd, Wintergreen Resort, VA 22967

  A great building lot with rock outcroppings and close to all amenities at Devils Knob. This is a lot wioth an easy walk to wirther the Appalachian Trail or all the facicities or amenities of the Devils Knob Village such as restaurants, tennis and pickleball, golf, the Spa and exercize facilites, pools, etc.

  Tim Merrick WINTERGREEN REALTY, LLC

  41 Hickory Spring Rd, Wintergreen Resort, VA 22967
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  /75

  $699,500

  • 3 Beds
  • 3 Baths
  • 2,703 Sq Ft

  377 Devils Knob Loop, Roseland, VA 22967

  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

  STEVE MARIANELLA WINTERGREEN REALTY, LLC

  377 Devils Knob Loop, Roseland, VA 22967
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  /50

  $459,975

  • 2 Beds
  • 2 Baths
  • 1,237 Sq Ft

  1641 Overlook Condos, Wintergreen Resort, VA 22967

  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

  Robert Craig WINTERGREEN REALTY, LLC

  1641 Overlook Condos, Wintergreen Resort, VA 22967
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  /72

  $274,000

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  740 Laurelwood Condos, Wintergreen, VA 22958

  Turnkey, Fully finished, and just a short walk to ski slopes, Wintergreen Market, & ski lodge, beautifully updated 2-BR, 2-BA condo is ready to enjoy! Thoughtfully, renovated throughout, it features, new LVP flooring, new windows, new interior, and exterior doors, new carrier HVAC (2024), and more. The stylish kitchen offers freshly painted white cabinetry, granite countertops, new backsplash, &

  Kevin Turner CENTURY 21 ALL-SERVICE

  740 Laurelwood Condos, Wintergreen, VA 22958
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  /45

  $642,000

  Open Sat 11AM - 1PM

  • 5 Beds
  • 4 Baths
  • 2,693 Sq Ft

  48 Deerberry Ln, Wintergreen Resort, VA 22967

  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

  LISA FLOOD PEAK REALTY VIRGINIA, LLC

  48 Deerberry Ln, Wintergreen Resort, VA 22967
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  /26

  $299,000

  • 1 Bed
  • 2 Baths
  • 851 Sq Ft

  1587 Vistas Condos, Wintergreen, VA 22958

  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

  CATALINA SAN GIORGIO FOUR SEASONS REALTY 1

  1587 Vistas Condos, Wintergreen, VA 22958
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  /38

  $375,000

  • 2 Beds
  • 2 Baths
  • 923 Sq Ft

  25 Hickorynut Dr, Wintergreen Resort, VA 22967

  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.

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  25 Hickorynut Dr, Wintergreen Resort, VA 22967
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  /8

  $23,900

  $5K PRICE DROP

  • Land
  • 20,908 Sq Ft
  • $49,792 per Acre

  12 Dripping Rock Ln, Roseland, VA 22967

  Tucked away in a small cul-de-sac is this lovely wooded lot on Dripping Rock Ln at Wintergreen Resort! Such a great value at only $29,000! Convenient to Resort amenities and the thriving Nelson 151 agri-tourism corridor featuring award-winning wineries, breweries and distilleries. Located within the Firefly Fiber Internet service area.

  Yvette Stafford MOUNTAIN AREA NEST REALTY

  12 Dripping Rock Ln, Roseland, VA 22967
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  /54

  $389,000

  • 2 Beds
  • 2 Baths
  • 1,179 Sq Ft

  1808 High Ridge Ct Condos, Wintergreen Resort, VA 22967

  OPEN HOUSE, Friday, July 10, 3:00pm - 5:00pm. A rarity among mountain condos?this view condo has zero steps to the front door, and it has covered parking. This ground level condo has a large deck and an easy walkout to the grass which is wonderful to have the extra space for pets, kids, etc. The High Ridge Court decks were recently replaced. There are many upgrades over the last few years?nearly

  Kate Farley PEAK REALTY VIRGINIA, LLC

  1808 High Ridge Ct Condos, Wintergreen Resort, VA 22967
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  /3

  $48,000

  • Land
  • 9,583 Sq Ft
  • $218,182 per Acre

  lot 6 Devils Bend Unit 6, Nellysford, VA 22958

  Lot 6 is a beautifully wooded homesite located along the Devils Knob Golf Course. The lot slopes gently toward the golf course, making it well suited for a home with a walkout lower level. A wonderful opportunity for scenic mountain golf living.

  LAUREN KOCH REAL ESTATE III, INC.

  lot 6 Devils Bend Unit 6, Nellysford, VA 22958
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  /33

  $35,000

  • Land
  • 17,859 Sq Ft
  • $85,366 per Acre

  150 Shamokin Springs Trail, Roseland, VA 22967

  Wooded building lot with stunning rock formations looking across to the Shamokin Springs Nature Preserve with its trails and unique micro-environment with flora typical of upstate New York. There is a neighborhood pool within easy walking distance and hiking and walking trails in abundance. Numerous high value homes in the neighborhood and all the amenities of Wintergreen Resort to choose from.

  K.T. LYNN WINTERGREEN REALTY, LLC

  150 Shamokin Springs Trail, Roseland, VA 22967
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  /48

  $549,999

  • 3 Beds
  • 2.5 Baths
  • 1,659 Sq Ft

  1300 Blue Ridge Dr, Roseland, VA 22967

  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

  Dima Holmes PEAK REALTY VIRGINIA, LLC

  1300 Blue Ridge Dr, Roseland, VA 22967
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  /32

  $549,500

  • 4 Beds
  • 2 Baths
  • 2,367 Sq Ft

  20 Buckhorn Ln, Roseland, VA 22967

  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

  Dima Holmes PEAK REALTY VIRGINIA, LLC

  20 Buckhorn Ln, Roseland, VA 22967
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  /61

  $597,000

  • 4 Beds
  • 3 Baths
  • 1,694 Sq Ft

  93 Valley View Ln, Wintergreen Resort, VA 22967

  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

  Chastity Morgan MOUNTAIN AREA NEST REALTY

  93 Valley View Ln, Wintergreen Resort, VA 22967
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  /45

  $489,000

  • 3 Beds
  • 2.5 Baths
  • 1,323 Sq Ft

  138 Oak Ln, Wintergreen Resort, VA 22967

  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

  LISA FLOOD PEAK REALTY VIRGINIA, LLC

  138 Oak Ln, Wintergreen Resort, VA 22967
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  /41

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  93 Squirrel Tree Ln, Wintergreen Resort, VA 22967

  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

  Kate Farley PEAK REALTY VIRGINIA, LLC

  93 Squirrel Tree Ln, Wintergreen Resort, VA 22967
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  /41

  $218,000

  Open Sat 11AM - 1PM

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  905 Diamond Hill Condos Hill, Wintergreen, VA 22967

  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

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  905 Diamond Hill Condos Hill, Wintergreen, VA 22967
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  /5

  $54,000

  $16K PRICE DROP

  • Land
  • 17,859 Sq Ft
  • $131,707 per Acre

  25 Poll Axe, Wintergreen Resort, VA 22967

  Wonderful level lot with easy entry featuring mature hardwoods located on a quiet col du sac. The perfect spot to build your mountain getaway home all within walking distance to Chestnut Springs pool, several great hiking trails and the Shamokin Springs Nature Reserve. The perfect balance of nature's beauty and resort amenities never to be repeated.

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  25 Poll Axe, Wintergreen Resort, VA 22967
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  /36

  $325,000

  • 1 Bed
  • 1 Bath
  • 763 Sq Ft

  1501 Cliffs Condos, Wintergreen Resort, VA 22967

  Perched atop The Ridge with sweeping panoramic views of the Rockfish Valley and Blue Ridge beyond, this ground-floor end unit at The Cliffs offers something genuinely special: direct access to a secluded outdoor space while your upstairs neighbors are limited to their balconies ? ideal for four-season living, your pet, and morning coffee with that glorious mountain view. The 2022 renovation was

  Yvette Stafford MOUNTAIN AREA NEST REALTY

  1501 Cliffs Condos, Wintergreen Resort, VA 22967
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  /46

  $448,000

  • 2 Beds
  • 2 Baths
  • 1,136 Sq Ft

  1933 High Ridge Pl Condos, Wintergreen Resort, VA 22967

  Located in one the newest, most sought-after condo buildings on Wintergreen, this High Ridge Place condo has many smart building features?elevator access for stepless entry from parking to the condo, ski lockers at parking area, exterior access with a breezeway, and steel/concrete construction ensuring peace and privacy. Not only that, High Ridge Place has some of the most stunning views of

  Kate Farley PEAK REALTY VIRGINIA, LLC

  1933 High Ridge Pl Condos, Wintergreen Resort, VA 22967
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  /22

  $259,000

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  762 Laurelwood Condos, Roseland, VA 22967

  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

  Dima Holmes PEAK REALTY VIRGINIA, LLC

  762 Laurelwood Condos, Roseland, VA 22967
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  /23

  $265,000

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft

  2025 Stone Ridge Condos, Wintergreen, VA 22967

  This ground floor 3-bedroom condo is in the center of three major Wintergreen amenities, and an easy walk to The Spa, Devils Knob Clubhouse, and Fire & Frost! EV charging station is right outside as well! Imagine being able to easily dash down to both golf and tennis, as well as up to the aquatic's center/gym/spa/pool/hot tubs! The covered terrace at the Devils Grill is one of the best places to

  Tim Merrick WINTERGREEN REALTY, LLC

  2025 Stone Ridge Condos, Wintergreen, VA 22967
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  /24

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  280 Fawn Ridge Dr, Roseland, VA 22967

  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

  Wayne Flood PEAK REALTY VIRGINIA, LLC

  280 Fawn Ridge Dr, Roseland, VA 22967
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  /3

  $40,000

  • Land
  • 30,056 Sq Ft
  • $57,971 per Acre

  1843 Wintergreen Dr, Wintergreen Resort, VA 22967

  Excellent large .7 acre lot with seasonal views to Reeds Gap for much of the year. The slope toward the rear of the lot would be excellent for a home with a walk-out basement. There is a small creek at the rear of the property to add additional charm. With central sewer and water, underground electric, cable and fiberoptic available, you can have all the luxuries you may desire inside, a nature

  K.T. LYNN WINTERGREEN REALTY, LLC

  1843 Wintergreen Dr, Wintergreen Resort, VA 22967

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