Wintergreen, VA Homes for Sale under $600,000

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

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

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

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

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

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

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

Welcome home to this spacious 5 bedroom home with gracious front porch, sparkling hardwood floors, high ceiling providing great natural light, elevated back deck for grilling and enjoying the peace and quiet of this mountain setting. Kitchen with granite counters, custom hickory cabinets, and stainless appliances. Close to the Devil's Grill, Devil's Knob Golf and Tennis and Wintergarden Spa. Main

BETTY GREEN WINTERGREEN REALTY, LLC

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

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

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

Michael Gaffney COMPASS-CHARLOTTESVILLE

Welcome to your dream mountain getaway or easy-living primary residence on the highly desirable Catoctin Drive. Crafted by RM Gantt, one of the mountain’s most reputable builders, this home perfectly balances rustic charm, modern luxury, and low-maintenance living. With a level, paved driveway and only three steps to enter, accessibility is a breeze. Inside, you’ll find a vibrant, fun home

Jill Vlasic RE/MAX Gateway

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

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

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

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

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

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

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