Wintergreen, VA Homes for Sale under $500,000

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

Lisa Lynch JASON MITCHELL REAL ESTATE

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

LISA FLOOD PEAK REALTY VIRGINIA, LLC

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

Discover the charm of mountain living in this inviting A-frame chalet, ideally located just a two-minute walk from the ski slopes. Enjoy quick access to several hiking trails, an easy stroll to two breathtaking overlooks, and convenient walking access to the heart of the ski village with its restaurants, shopping, and year-round amenities. Offered turn-key furnished, this inviting retreat is

Dima Holmes PEAK REALTY VIRGINIA, LLC

Welcome to your beautifully decorated two bedroom two bath home nestled around the breathtaking views of Wintergreen Mountain. You are steps away from the workout center, aquatics areas, tennis courts, golf course and ski/snowboard access. This well mainitained home is waiting for you to enjoy a turn key experience and live your best mountain life. The hiking trails and amazing wintergreen

Michael Blaylock EXIT Realty Success

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

Dima Holmes PEAK REALTY VIRGINIA, LLC

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

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

This condominium is centrally located and has been lovingly maintained. It is near the private Laurelwood pool and the Wintergreen market. The straight-in entry makes access very comfortable for all ages. It is walkable to the ski slopes, restaurants, and all of the amenities of Black Rock Village. An ideal location for family and friends to enjoy the Wintergreen lifestyle. There are cathedral

K.T. LYNN WINTERGREEN REALTY, LLC

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

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

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

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 all new appliances, renovated kitchen with new

Kate Farley PEAK REALTY VIRGINIA, LLC

Wake up to breathtaking ridgeline sunrises and experience true ski-front living from this rare top-floor end-unit Highlands condo in Wintergreen Resort. With extra windows, exceptional privacy, and panoramic mountain views, this beautifully updated 2BR/2BA retreat captures the magic of mountain living in every season. Never rented and thoughtfully maintained, the condo is offered fully furnished

LISA FLOOD PEAK REALTY VIRGINIA, LLC

Enjoy yourself at this 2 bed, 2 bath condo with gorgeous views in Wintergreen! This home presents itself with beautiful views, open floor plan and many upgrades. They say a picture is worth a thousand words, come see for yourself. Owner is a licensed agent in the Commonwealth of Virginia.

KRISTEL HARRIS EXP REALTY LLC - STAFFORD

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

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

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

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

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

Paul Hess NEST REALTY GROUP

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

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

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

Wayne Flood PEAK REALTY VIRGINIA, LLC

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

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

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

STEVE MARIANELLA WINTERGREEN REALTY, LLC

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

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

Sitting on the new deck on a perfect fall afternoon, quiet and peaceful come to mind, then location. This refurbished house is close to great hiking & trout fishing and yet a short drive to cideries, breweries and wineries of the Rockfish Valley. Wintergreen Resort is only about 8-miles away and Stoney Creek is even closer. This fully furnished house is priced well below most of the three bedroom

Tim Merrick WINTERGREEN REALTY, LLC