Wintergreen Homes for Sale

Wintergreen Homes for Sale

Welcome to Wintergreen, Virginia, a hidden gem nestled in the heart of Nelson County. This picturesque mountain community is renowned for its breathtaking views, pristine landscapes, and a vibrant four-season lifestyle. Whether you’re seeking a tranquil retreat or an adventurous playground, Wintergreen offers the perfect backdrop for your next home.

Wintergreen is celebrated for its stunning Blue Ridge Mountains, where outdoor enthusiasts can indulge in activities such as hiking, skiing, and golfing, all within a stone's throw from home. The area boasts a rich tapestry of natural beauty, with lush forests, cascading waterfalls, and panoramic vistas that will leave you in awe. Imagine waking up to the crisp mountain air and stepping outside to explore miles of scenic trails or hitting the slopes in winter.

For those looking to settle in this idyllic setting, there are a variety of homes for sale that cater to diverse tastes and budgets. From cozy cabins that exude rustic charm to modern mountain retreats with luxurious amenities, Wintergreen has something for everyone. Many of these homes offer stunning views and easy access to the community's many recreational facilities, including ski resorts, golf courses, and serene lakes.

Living in Wintergreen means embracing a lifestyle that harmonizes relaxation and adventure. With a close-knit community vibe and a wealth of outdoor activities at your doorstep, it’s no wonder that so many are choosing to call this enchanting mountain locale home. Explore the homes for sale in Wintergreen today and discover the perfect place to create lasting memories in this beautiful corner of Virginia.

Newest Wintergreen Homes for Sale

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

Listing courtesy of THOMPSON REAL ESTATE COMPANY. Contact:

4 Beds ⋅ 3 Baths ⋅ VANL2000690 MLS

Discover year-round mountain living in this spacious 4-bedroom, 4-bath, fully furnished home located on a private 0.40-acre lot overlooking the golf course at Wintergreen Resort. Perfect as a primary residence, vacation retreat, or income-producing rental. This well-appointed property offers comfort, recreation, and convenient access to all that Wintergreen has to offer such as skiing, tennis, golf course, pool access, playground, hiking trails, and water activities. The main level features a stunning open-concept great room with a fireplace, soaring ceilings, and abundant natural light. The spacious kitchen, dining, and living areas flow seamlessly together, creating an ideal setting for entertaining family and friends. High-speed internet service supports remote work and streaming, making mountain living both relaxing and practical. With four bedrooms and four full bathrooms, including a generous primary suite and multiple guest accommodations, the home comfortably hosts large families and groups. The fully finished walk-out lower level provides additional living and entertainment space, featuring a recreation room, wood stove, pool table area, bunk room, and guest bedroom. Outdoor living is a highlight, with multiple decks and gathering spaces designed to embrace the peaceful golf course setting. Enjoy morning coffee while listening to golfers tee off nearby, relax on the expansive upper deck, unwind in the screened porch, or soak in the private hot tub after a day of skiing, tennis, hiking, or golf. The home comes well-equipped and move-in ready, including a washer and dryer, multiple refrigerators for added convenience when hosting guests. Whether you're seeking a mountain escape, full-time residence, or investment opportunity, this exceptional Wintergreen home offers the perfect combination of space, comfort, and four-season resort living.

75 N Forest Dr, Wintergreen

Listing courtesy of Samson Properties. Contact: 7033768046

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

Listing courtesy of WINTERGREEN REALTY, LLC. Contact:

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

Listing courtesy of FOUR SEASONS REALTY 1. Contact:

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Ashley Dudley | Broker Owner

Ashley Dudley is a Shenandoah Valley based real estate broker known for her heart-forward approach, deep local knowledge, and steady guidance through every step of the buying and selling journey. As the Broker Owner of HomeGrown Real Estate, Ashley has built a client-centered brand that blends expertise, community connection, and the belief that real estate should feel personal… not overwhelming. Rooted in New Market and serving Shenandoah County, Rockingham County, Page County, Augusta County and the surrounding Valley, Ashley has helped countless clients navigate moves of every kind. First-time buyers searching for their foothold. Growing families moving into their next chapter. Long-time locals preparing to let go of a home filled with memories. Out-of-state buyers relocating to the mountains. Investors looking to build something lasting. Ashley guides each one with clarity, patience, and an eye for strategy. Her background as a business owner and her commitment to honest communication make her a trusted partner in a fast-moving market. She’s hands-on, detail-driven, and known for making complex processes feel manageable. Whether it's pricing a home with precision, negotiating with confidence, or helping sellers prepare their home for the market, Ashley brings both expertise and empathy to the table. At the heart of her work is a simple mission… helping people plant roots to grow their future here in the Valley. It’s a mission reflected in her community involvement, her HomeGrown events, and the relationships she builds long after closing day. When she’s not working with clients, Ashley is exploring local with her husband, Rustin, snuggling her pups, Molly and Minnie, planning community events, or dreaming up new ways to support her agents and elevate the real estate experience in the Shenandoah Valley. If you’re looking for a Realtor who knows the Valley, cares deeply about her clients, and brings both heart and strategy to every move, Ashley is ready to help you take your next step home.

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Amber Fleck | Realtor

Amber Fleck is a dedicated Realtor with HomeGrown Real Estate serving the Shenandoah Valley and surrounding communities. Amber helps buyers and sellers navigate the real estate market with confidence, clear communication, and genuine care. She believes every client deserves a smooth and enjoyable experience from the first conversation to the closing table. After graduating from James Madison University in 2019, Amber made the Shenandoah Valley her home and quickly fell in love with its mountain views, hiking trails, rivers, and local restaurants. She uses her deep local knowledge to help clients find the right home, whether they are first time home buyers, relocating to Virginia, upsizing, downsizing, or searching for land with mountain views. Amber focuses on honest guidance, strong negotiation, and marketing strategies that help sellers earn top dollar. Her philosophy is simple. You should live where you love. She is committed to helping clients plant roots and build their future in a community she adores.

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Courtney May | Realtor

Courtney May is a proud Augusta County native and Fort Defiance graduate whose resilience during the COVID-19 era shaped her dedication to helping others. Eager to serve her community, she became a licensed real estate professional and is grateful to assist neighbors with their real estate needs—whether buying or selling, and no matter the stage of life they’re in.Courtney is especially passionate about first-time homebuyers, believing homeownership is a life-changing milestone and not just a transaction. Her personalized approach and local expertise allow her to guide new buyers through the process with confidence and care.Outside of real estate, Courtney enjoys spending time with family, friends, and her dog while exploring the beauty of Augusta County. Her goal remains simple—serve her community with integrity, enthusiasm, and heart.

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Jessica Harrison | Associate Broker

Jessica is a trusted Associate Broker with HomeGrown Real Estate, proudly serving the Shenandoah Valley and surrounding communities. She works closely with buyers and sellers to provide clear communication, thoughtful guidance, and a smooth experience from the first conversation through the closing table. Jessica believes real estate is deeply personal, and every client deserves to feel informed, supported, and confident at every step. With a background in both real estate and insurance, Jessica brings a unique and well-rounded perspective to every transaction. She helps clients look beyond the surface by considering market value, long-term risk, and overall investment strategy. Her clients value her attention to detail, responsiveness, and calm, steady approach during what can often feel like a big life decision. Jessica enjoys helping clients navigate a wide range of goals, whether purchasing a primary residence, exploring investment opportunities, or planning for what comes next. With a strategic mindset and genuine care for the people she serves, she is committed to helping clients make smart, confident decisions and build a future they feel good about calling home.

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Abby Neese | Realtor

Born and raised in Shenandoah County, Abby brings a deep-rooted understanding of the local community and its unique charm to her real estate career. With over 10 years of experience in property management, she’s developed a strong foundation in client service, attention to detail, and navigating the complexities of the housing market. Now, she’s excited to transition that expertise into helping buyers and sellers achieve their real estate goals. Abby’s background has equipped her with a keen eye for property value, market trends, and the importance of clear communication—skills she uses to guide clients through every step of the buying or selling process with confidence and ease. Outside of real estate, she enjoys spending time on the golf course, cheering on her kids at their sporting events, exploring antique shops, and making lasting memories with family. Abby is passionate about building relationships and helping others find not just a house, but a place they can truly call home.

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