Wintergreen, VA Homes for Sale under $500,000

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

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

Charming mountain retreat overlooking the 5th fairway of Devils Knob Golf Course, tucked away at the end of a quiet cul-de-sac and within walking distance of Chestnut Springs Pool Park and nearby hiking trails. Offered fully furnished and turnkey, this home features a thoughtfully designed floor plan ideal for larger families, shared ownership, or rental use, with two bedrooms and a full bath on

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

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

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

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

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

Perched high on the mountain, this spacious 5 BR, 4.5 BA villa offers 1,992 sq ft and beautiful year-round mountain, Shenandoah Valley and sunset views that become even more expansive and dramatic from early November through early May. The versatile multi-level floor plan features two primary suites plus a private top-floor guest suite with its own bath—ideal for hosting family and friends. The

Dima Holmes PEAK REALTY VIRGINIA, 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

Breathtaking Sunrise Mountain Views | High Ridge Court. Wake up to endless ridge views in this turn-key, end-unit condo tucked away in desirable High Ridge Court. Offering total main-level accessibility with no steps required to enter, this retreat delivers the perfect blend of cozy mountain charm and modern luxury.Interior Highlights: Open-Concept Living: The bright living space features a

Jill Vlasic RE/MAX Gateway

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. Fully Furnished. Ready for short term renters from day of closing. Owner is a licensed agent in the Commonwealth of Virginia.

KRISTEL HARRIS EXP REALTY LLC - STAFFORD

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

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

Experience elevated mountain living in this beautifully maintained, furnished 4-bedroom, 3.5-bath townhome situated on the 12th fairway of Devils Knob Golf Course. Designed for both comfort and entertaining, the spacious multi-level floor plan features a generous living room, separate dining room, and two private primary suites—one on the second level and another on the third. Step onto the

Julie Slayton OLD DOMINION REALTY INC - AUGUSTA

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

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