37

Wintergreen, VA Homes for Sale under $300,000

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  • /14

    $39,000

    $11K PRICE DROP
    • Land
    • 16,988 Sq Ft
    • $100,000 per Acre

    462 Deer Springs Ln, Roseland, VA 22967

    Own a parcel that is like no other especially if you love nature, rock wall/outcropping and expansive views of the woods! Rare opportunity to feel like you own so much more land because this property borders open space. Much of it is in the back allowing a home to be sited to have long range views of woods/forest and NOT neighbors. In addition, right border of the parcel is a huge rock wall/ledge

    Agent Photo

    MARLO ALLEN

    MOUNTAIN AREA NEST REALTY

    462 Deer Springs Ln, Roseland, VA 22967
  • /66

    $254,900

    $14K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,090 Sq Ft

    12 Ivy Glen Ln, Roseland, VA 22967

    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 conversation area centered around a wood-burning fireplace, while the

    Agent Photo

    Myra R. Beams

    REAL BROKER LLC

    12 Ivy Glen Ln, Roseland, VA 22967
  • /21

    $249,500

    • 2 Beds
    • 2 Baths
    • 907 Sq Ft

    473 Three Ridges Condos, Wintergreen Resort, VA 22967

    Welcome to your mountain retreat in one of Virginia's most cherished resort communities. This two-bedroom, two-bathroom condo offers comfortable living space surrounded by the stunning Blue Ridge Mountains. The thoughtfully designed layout balances cozy charm with practical functionality. A bright, airy kitchen makes cooking a pleasure, and both bedrooms provide restful retreats, while two full

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    Ben Holmes

    PEAK REALTY VIRGINIA, LLC

    473 Three Ridges Condos, Wintergreen Resort, VA 22967
  • /12

    $40,000

    • Land
    • 18,295 Sq Ft
    • $95,238 per Acre

    270 Timber Camp Dr, Roseland, VA 22967

    Just a short walk to the pool!! What a great spot to build your vacation home or primary residence. Less than 15 minutes to the "Nelson 151" Breweries , cideries and wineries. A great location and great Value!!

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    FRANCESCA SAN GIORGIO

    FOUR SEASONS REALTY 1

    270 Timber Camp Dr, Roseland, VA 22967
  • /24

    $125,000

    • 1 Bed
    • 1 Bath
    • 374 Sq Ft

    2076 Stone Ridge Condos, Wintergreen Resort, VA 22967

    Looking for a pristine Wintergreen condo without breaking the bank? This beautifully renovated unit is move-in ready and offers the perfect opportunity to enjoy all that Wintergreen Resort has to offer. Recent upgrades include a new HVAC system and water heater, adding comfort and peace of mind. Just bring your suitcase and start enjoying the mountains, skiing, hiking, and resort lifestyle!

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    FRANCESCA SAN GIORGIO

    FOUR SEASONS REALTY 1

    2076 Stone Ridge Condos, Wintergreen Resort, VA 22967
  • /26

    $89,987

    • Land
    • 16,988 Sq Ft
    • $230,736 per Acre

    0 Blackrock Cir Unit LotWP001, Wintergreen Resort, VA 22967

    Welcome to your slice of paradise nestled in the breathtaking Blue Ridge Mountains! Own one of the last remaining building lots on Wintergreen Resorts prestigious Blackrock Circle and create your dream home where every morning begins with a stunning sunrise. Imagine sipping your coffee on the back porch, soaking in the panoramic views of the mountains as the sun crests over the horizon, shining

    KYLE WATERS Whitetail Properties Real Estate

    0 Blackrock Cir Unit LotWP001, Wintergreen Resort, VA 22967
  • /37

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,126 Sq Ft

    2072 Stone Ridge Condos, Wintergreen, VA 22958

    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

    HARRY RINDLER LONG & FOSTER - CHARLOTTESVILLE

    2072 Stone Ridge Condos, Wintergreen, VA 22958
  • /10

    $41,000

    • Land
    • 19,602 Sq Ft
    • $91,111 per Acre

    433 Laurel Springs Dr, Roseland, VA 22967

    Very nice building site in a great location. Pause on the elevated knoll and experience the partial seasonal pocket views of the Ridge lines, Shenandoah Valley and the Golf Course. Common area and elevation provide privacy and the WPOA buffer leads to the Park Service Land and the Appalachian Trail. Common area buffer across the street can provide access to Shamokin Springs and to the 7th fairway

    Robert Craig WINTERGREEN REALTY, LLC

    433 Laurel Springs Dr, Roseland, VA 22967
  • /11

    $37,500

    $12K PRICE DROP
    • Land
    • 29,185 Sq Ft
    • $55,970 per Acre

    37 Coopers Vantage, Roseland, VA 22967

    Current owner has a home at Wintergreen and had intended to build on this site. He has identified a wonderfully built cabin that could be built on this site which is on a small cul de sac between two very attractive homes. Plans and building estimates are in the docs section of the listing description. The best house location has already been flagged. Please note: the lot is being sold as vacant

    Tim Merrick WINTERGREEN REALTY, LLC

    37 Coopers Vantage, Roseland, VA 22967
  • /41

    $249,975

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,220 Sq Ft

    2084 Stone Ridge Condos, Wintergreen, VA 22967

    Just Wow! Coveted top floor end, 2 bedroom, 2 bath. This home has convenient ingress/egress with no steps from the parking area to the building and only 1/2 flight of stairs to the front door! Location rules as you are just steps away from the Devils Knob Country Club, Wintergarden Spa and Fire and Frost restaurant. Resort Amenities, Food and Drink and cool spring/summer breezes await. Relax on

    Robert Craig WINTERGREEN REALTY, LLC

    2084 Stone Ridge Condos, Wintergreen, VA 22967
  • /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
  • /5

    $45,000

    $25K PRICE DROP
    • Land
    • 17,859 Sq Ft
    • $109,756 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
  • /22

    $89,987

    • Land
    • 16,988 Sq Ft
    • $230,736 per Acre

    00 Blackrock Cir, Wintergreen Resort, VA 22967

    Welcome to your slice of paradise nestled in the breathtaking Blue Ridge Mountains! Own one of the last remaining building lots on Wintergreen Resorts prestigious Blackrock Circle and create your dream home where every morning begins with a stunning sunrise. Imagine sipping your coffee on the back porch, soaking in the panoramic views of the mountains as the sun crests over the horizon shining

    KYLE WATERS WHITETAIL PROPERTIES REAL ESTATE

    00 Blackrock Cir, Wintergreen Resort, VA 22967
  • /5

    $59,000

    $6K PRICE DROP
    • Land
    • 16,117 Sq Ft
    • $159,459 per Acre

    355 Devils Knob Loop, Roseland, VA 22967

    Golf front site, nearly level and wooded in hardwoods. On the 13th hole of the Devils Knob Golf Course and convenient to walking trails and all resort amenities.

    K.T. LYNN WINTERGREEN REALTY, LLC

    355 Devils Knob Loop, Roseland, VA 22967
  • /32

    $240,000

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,220 Sq Ft

    2074 Stone Ridge, Roseland, VA 22967

    Enjoy four-season mountain living in this 2-bedroom, 2-bath Stone Ridge condominium at Wintergreen Resort. Whether you're seeking a weekend retreat, investment property, or full-time mountain home, this inviting condo offers comfort, convenience, and easy access to everything the resort has to offer. Step inside to find a bright, open living area perfect for relaxing after a day on the slopes,

    Wayne Flood PEAK REALTY VIRGINIA, LLC

    2074 Stone Ridge, Roseland, VA 22967
  • /23

    $265,000

    $34K PRICE DROP
    • 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
  • /21

    $80,000

    • Land
    • 21,780 Sq Ft
    • $160,000 per Acre

    805 Devils Knob Loop, Roseland, VA 22967

    Situated at the highest point of Wintergreen, this Devils Knob Mountain lot is a mountaineer's dream—this is the ultimate destination at the top. Currently, there are absolutely incredible seasonal views to the south. Because the trees are not tall at the peak of the mountain, there could be opportunity for year-round views depending on the positioning and the design of the house. Homes on the

    Kate Farley PEAK REALTY VIRGINIA, LLC

    805 Devils Knob Loop, Roseland, VA 22967
  • /22

    $45,000

    • Land
    • 12,632 Sq Ft
    • $155,172 per Acre

    112 Fairway Oaks Ln, Wintergreen, VA 22958

    This property is to the right of the 3rd tee of the Devils Knob Golf Course and at the end of a quiet, almost completely developed street. The property will have a golf view and has the potential for a spectacular view into the Shenandoah Valley. Year round golf views, private and close to Devils Knob facilities.

    Tim Merrick WINTERGREEN REALTY, LLC

    112 Fairway Oaks Ln, Wintergreen, VA 22958
  • /27

    $265,000

    • 2 Beds
    • 2 Baths
    • 978 Sq Ft

    2114 Fairway Woods, Wintergreen Resort, VA 22967

    Beautifully updated golf front mid level condo with few stairs to enter. Enjoy the central location close to the Wintergarden Spa, and a short walk to the golf clubhouse. Great views of the action on the 18th hole of the golf course. Updated flooring, kitchen and baths, most furnishings convey. Condo dues are $1750/ quarter. WPOA dues are $2279/year, listed as road maintenance, and include some

    BETTY GREEN WINTERGREEN REALTY, LLC

    2114 Fairway Woods, Wintergreen Resort, VA 22967
  • /72

    $274,000

    • 2 Beds
    • 2 Baths
    • 936 Sq Ft

    740 Laurelwood Condos, 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, &

    Kevin Turner CENTURY 21 ALL-SERVICE

    740 Laurelwood Condos, Wintergreen Resort, VA 22967
  • /10

    $21,900

    $1K PRICE DROP
    • Land
    • 15,246 Sq Ft
    • $62,571 per Acre

    383 Timber Camp Dr, Wintergreen Resort, VA 22967

    Enjoy the perfect blend of privacy, natural beauty, and convenience with this attractive homesite in Wintergreen, VA. The property offers an almost level building site, making it ideal for a variety of mountain home designs. One side of the lot is bordered by a stunning natural rock formation that creates a beautiful backdrop while providing a natural buffer from the neighboring property. The

    Dima Holmes PEAK REALTY VIRGINIA, LLC

    383 Timber Camp Dr, Wintergreen Resort, VA 22967
  • /16

    $215,000

    • Land
    • 1.65 Acres
    • $130,303 per Acre

    2242 Laurel Springs Dr, Wintergreen Resort, VA 22967

    These combined lots (C & D) offer one of the most unique opportunities for privacy, views, seclusion and location at Wintergreen. The two home sites have underground water & sewer, high speed internet, electricity and telephone. The lots are at the end of Laurel Springs drive and are located at the top of Shamokin Falls with great view potential down thru the Gorge. There can never be a house

    Tim Merrick WINTERGREEN REALTY, LLC

    2242 Laurel Springs Dr, Wintergreen Resort, VA 22967
  • /67

    $218,000

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft

    905 Diamond Hill, Wintergreen Resort, VA 22967

    Come see this ground level slope side condo located on the Diamond Hill Ski Slope (Wintergreen Resort). This unit features a sliding door to patio that is literally on the mountain overlooking the Blue Ridge. This unit also features an open floor plan that has a bed, spacious living room, fireplace, kitchen, pantry, bathroom, and comes fully furnished! Included with this home comes 2 additional

    James Bauslaugh ROCKWISE REALTY LLC

    905 Diamond Hill, Wintergreen Resort, VA 22967
  • /28

    $219,000

    • 2 Beds
    • 2 Baths
    • 812 Sq Ft

    2244 Tanners Ridge, Wintergreen Resort, VA 22967

    Experience mountain living in this beautifully cozy 2 bedroom condo, perfectly situated in Wintergreen Resort. Whether you are searching for a personal retreat, a full time residence, or a proven income-producing investment, this property checks all the boxes. Recent updates include vinyl plank flooring, new microwave, fresh paint, bathroom lighting and decor creating a fresh relaxed space to

    Kim Rente Coldwell Banker Premier

    2244 Tanners Ridge, Wintergreen Resort, VA 22967
  • /23

    $49,900

    • Land
    • 17,424 Sq Ft
    • $124,750 per Acre

    TBD Shamokin Springs Trail, Wintergreen Resort, VA 22967

    Fantastic wooded homesite with some winter views in Chestnut Springs near the Chestnut Springs Pool & Park, Laurel Springs overlook, and tennis & pickleball facilities. Just a quick jaunt to Fire & Frost, Devils Knob Grill, and Wintergarden pool & spa. Gentle slope allows for easy driveway access and walkout basement. Listen for babbling creek and peace & quiet!

    Michael Gaffney COMPASS-CHARLOTTESVILLE

    TBD Shamokin Springs Trail, Wintergreen Resort, VA 22967
  • /26

    $150,000

    • Land
    • 23,958 Sq Ft
    • $272,727 per Acre

    340 Chestnut Place, Roseland, VA 22967

    This homesite is directly below High Ridge Condominiums and, with judicious placement and pruning, should offer at least seasonal views similar to those offered from the condominiums. Park at High Ridge, walk around the building and look at the view and this site on the cul-de-sac directly below. It is easy to identify from above since there is an existing home on one side and a home under

    K.T. LYNN WINTERGREEN REALTY, LLC

    340 Chestnut Place, Roseland, VA 22967
  • /22

    $255,000

    $4K PRICE DROP
    • 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
  • /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
  • /23

    $239,000

    $5K PRICE DROP
    • 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
  • /33

    $35,000

    $6K PRICE INCREASE
    • 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
  • /2

    $35,000

    $25K PRICE DROP
    • Land
    • 20,037 Sq Ft
    • $76,087 per Acre

    32 Chestnut Ln, Wintergreen Resort, VA 22967

    Beautiful lot, spectacular views

    GREG BALDWIN CORE REAL ESTATE PARTNERS LLC

    32 Chestnut Ln, Wintergreen Resort, VA 22967
  • /17

    $137,000

    $12K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 384 Sq Ft

    2052 Stone Ridge Condos, Wintergreen, VA 22958

    Welcome to your dream mountain retreat! This renovated condo, nestled within the Wintergreen Resort, offers the perfect blend of elegance and comfort. Located directly on the prestigious golf course and within a block away from the spa and Devil's Knob Grill, this property provides a lifestyle for those seeking relaxation and recreation.

    CATALINA SAN GIORGIO FOUR SEASONS REALTY 1

    2052 Stone Ridge Condos, Wintergreen, VA 22958
  • /41

    $218,000

    • 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
  • /3

    $36,900

    $11K PRICE DROP
    • Land
    • 9,583 Sq Ft
    • $167,727 per Acre

    lot 6 Devils Bend, 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, Nellysford, VA 22958
  • /26

    $289,000

    $10K PRICE DROP
    • 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
  • /8

    $40,500

    • Land
    • 21,780 Sq Ft
    • $81,000 per Acre

    11 Fairway Oaks Ln, Wintergreen Resort, VA 22967

    An incredible opportunity to build your mountain retreat at an unbeatable price! This generously sized corner home site offers a gentle slope for easy access and flexible home siting, giving you plenty of options when it comes to designing the perfect getaway or full-time residence. Conveniently located near Chestnut Springs Pool and just minutes from golf, tennis, pickleball, dining, and other

    Lisa Flood PEAK REALTY VIRGINIA, LLC

    11 Fairway Oaks Ln, Wintergreen Resort, VA 22967
  • /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

Home Price Trends

Median Sale Price
$250,000
Median Single Family Sale Price
$1,500,000
Median 2 Bedroom Sale Price
$259,000
Median 1 Bedroom Sale Price
$151,000
Average Price Per Sq Ft
$284
Number of Homes for Sale
9
Last 12 months Home Sales
23
Months of Supply
4.70
Median List Price
$262,487
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-14%
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