Wintergreen Real Estate

Wintergreen Real Estate

Welcome to Wintergreen, Virginia—a hidden gem nestled in the breathtaking Blue Ridge Mountains. This picturesque mountain community is not only a haven for outdoor enthusiasts but also a serene retreat for those seeking tranquility and natural beauty. With its scenic vistas, year-round recreational opportunities, and charming atmosphere, Wintergreen offers a lifestyle that many only dream of.

Wintergreen is renowned for its stunning landscapes, featuring rolling hills, lush forests, and panoramic views that stretch for miles. Whether you’re an avid hiker, skier, or simply someone who enjoys the beauty of nature, this area has something for everyone. In the winter months, the slopes come alive with skiers and snowboarders, while summer invites you to explore miles of hiking and biking trails that weave through the stunning terrain.

The community is also home to a variety of amenities, including cozy mountain lodges, delightful restaurants, and unique shops that reflect the local charm. The nearby Wintergreen Resort offers a plethora of activities, from golf and tennis to spa treatments and family-friendly events, ensuring there’s never a dull moment.

In addition to its recreational offerings, Wintergreen boasts a close-knit community atmosphere where neighbors become friends. The town’s commitment to preserving its natural beauty and fostering a welcoming environment makes it an ideal place to call home.

If you’re looking for a peaceful retreat with a vibrant community spirit, Wintergreen, VA, is the perfect destination. Embrace the mountain lifestyle and discover the beauty that awaits you in this enchanting corner of Virginia!

Newest Listings in Wintergreen

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.

112 Fairway Oaks Ln, Wintergreen

2 Beds ⋅ 2 Baths ⋅ 679076 MLS

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, & brand-new appliances, including refrigerator, oven, microwave, microwave & dryer. Updated, lighting, mirrors, & faucets add a fresh, modern touch throughout. Designed for convenience, this smart home includes remote control of HVAC, hot water heater, water supply, and primary bath heater, and keyless entry for easy access. After a day on the slopes or trails unwind by the cozy wood-burning fireplace or relax on your private deck overlooking Laurelwood's exclusive outdoor pool - the only private condo pool at Wintergreen. Most furnishings brand new, this exceptional condo is truly move-in ready.

740 Laurelwood Condos, Wintergreen

4 Beds ⋅ 3 Baths ⋅ 678844 MLS

A wonderfully maintained home with nice mountain views and lots of space to expand. They have incorporated the home sites on either side and with WPOA's permission can be sold off. There is an invisible fence around the center of the property. All the baths and the kitchen have been upgraded within the last couple of tears.

24 Pedlars Pt, Wintergreen

1 Beds ⋅ 2 Baths ⋅ 678691 MLS

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 been thoughtfully renovated, blending modern comfort with mountain charm. Offered fully furnished, this turnkey condo is ready for immediate enjoyment—whether as a primary residence, vacation getaway, or investment opportunity. Experience the best of mountain living with easy access to Wintergreen's year-round amenities, including skiing, golf, hiking, tennis, and dining, while also enjoying the renowned wineries, breweries, and outdoor adventures that make Nelson County such a sought-after destination.

1587 Vistas Condos, Wintergreen

2 Beds ⋅ 2 Baths ⋅ 678390 MLS

Open House Saturday 8/8 2:00 pm- 4:00 pm. 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 or a bite to eat at Devils Grill or Fire and Frost. Gaze over the ski resort and prepare to be mesmerized by the panoramic expanse of the mountains, valleys and Lake Monocan below. Convenient ingress/egress with only 1/2 flight of stairs up from the parking lot. Successful platinum rated rental can add a little play money to the coffers if str is your game. Spacious and well-appointed to be a primary residence or second home sanctuary. WPOA fees are $2,279 annually and Overlook Condo fees are $1,813 per quarter. Make this your dream home before someone else makes it theirs.

1641 Overlook Condos, Wintergreen

5 Beds ⋅ 4 Baths ⋅ 676285 MLS

Quench your thirst for the Wintergreen Lifestyle at the "Thirsty Bear". Five bedrooms and 4 baths with stunning views over Laurel Springs Ridge towards the Shenandoah Valley. Privacy abounds at the end of the cul de sac and spend the lazy days of summer at the Chestnut Springs pool which is just steps away. Or on those chilly mornings take a soak in the hot tub. Find efficiency features such as 2 zone hvac, conditioned crawlspace and a tankless water heater. True main level living with three bedrooms and laundry on the first floor. Soaring great room windows with 2 story stone fireplace and vaulted ceiling bring the mountains and outdoors in. Three levels each with a bedroom with ensuite baths. The recently finished terrace level offers plenty of space for family and friends. Don't miss out. Make this your home before someone else makes it theirs!

42 Peavy Pt, Wintergreen

1 Beds ⋅ 1 Baths ⋅ 674840 MLS

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.

2052 Stone Rdg, Wintergreen

2 Beds ⋅ 2 Baths ⋅ 674199 MLS

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 the Deck overlooking the Golf, Tennis and Pickleball Club with a sneak peek across the Shenandoah Valley to the Virginia Highlands. New flooring and paint throughout complement one of the newer condo buildings. Furnish to your tastes and prepare to experience the lifestyle that Wintergreen and Nelson County have to offer. Act now! Make this your home before someone else makes it theirs. Stone Ridge condo dues are $1,575 per quarter and WPOA is $2,279 annually for 2026.

2084 Stone Rdg, Wintergreen

4 Beds ⋅ 3 Baths ⋅ 672554 MLS

Own a home at beautiful Wintergreen Resort with many amenities of hiking, sking, golf, reasturants and benefits of Nelson county. This home has 4 bedrooms and 3 baths with a nice deck for dining and entertaining, 2 car garage and a new roof(2025), with a little updating you would have a great investment and charming home.

20 Red Cedar Ct, Wintergreen

1 Beds ⋅ 2 Baths ⋅ 667941 MLS

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.

2031 Stone Rdg, Wintergreen

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.

355 Devils Knob Loop, Wintergreen

Beautiful lot, spectacular views

32 Chestnut Ln, Wintergreen

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Matthew Pettway

With over 5 years of real estate experience and deep roots in the Shenandoah Valley, Matthew Pettway brings a thoughtful, hands-on approach to every client relationship. A local native, he offers extensive knowledge of the area and is known for clear communication, strong negotiation skills, and a steady, can-do mindset that helps clients feel confident at every stage—whether buying their first home, selling an investment property, or building something new. Matthew lives in Augusta County with his wife and three children and is deeply connected to the community he serves. His personable demeanor, attention to detail, and commitment to his clients are reflected in the many reviews that highlight his dedication to helping people navigate one of life’s biggest decisions.

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