Wintergreen, VA Homes for Sale under $400,000

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

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

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

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

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

This is a ground-floor one-bedroom with two baths and a nice sleep sofa in the living room for additional family. It is located on the 18th fairway of the Devils Knob Golf Course and is a short walk to the spa, pools, exercise facilities, as well as tennis, golf, and the Devils Grill restaurant. It is a great location and is being sold furnished.

Tim Merrick WINTERGREEN REALTY, LLC

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

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

CHASTITY MORGAN MOUNTAIN AREA NEST REALTY

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

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

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

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.

Paul Hess NEST REALTY GROUP

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

In the heart of Wintergreen, steps away from skiing, dining, shopping, hiking trails, and with its own community pool. This light-filled 1-bedroom condo is centrally located and has been lovingly maintained. Ready to be your perfect mountain getaway. Tastefully furnished, updated, and move-in ready, enjoy all that Wintergreen has to offer! With the cool temps in summer, play a round of golf, a

Devon Dempsey KW Realty Lakeside

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

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