Chestnut Springs Trail

1639 Overlook is a recently renovated four-bedroom, four-bath Wintergreen condo with panoramic mountain views, golf course proximity, and small-dog-friendly policy. 1639 Overlook was recently renovated to showcase four bedrooms, four baths, pet-friendly policies for small dogs, and sweeping Wintergreen vistas beside the golf course.

779 Blue Ridge Drive is a four-bedroom, 4.5-bath mountain home with hot tub, gas fireplace, and king beds in every suite, located four minutes from skiing. Four king suites, a bubbling hot tub, and a great room anchored by a stone fireplace make 779 Blue Ridge Drive a go-to for families who want to be on the slopes in under five minutes.

Adventure Awaits is a pet-friendly Wintergreen home two minutes from the slopes with hot tub, fire pit, multiple living areas, and five smart TVs. Adventure Awaits lives up to its name with a hot tub, multiple lounges, pet-friendly policies, and a location two minutes from Wintergreen's slopes and hiking shuttles.

Afton Mountain Inn is an 1848 farmhouse turned boutique hotel with six suites and a premium villa offering premium bedding, Wi-Fi, robes, snack bar, two hot tubs, pool, decks, fire pits, badminton, and private trail across ten acres. Built in 1848, more than a decade before the start of the American Civil War, our historic farmhouse features original heart pine flooring, ornate woodwork, and a stained glass entryway.

Nestled among pines and dogwoods in Nelson County, this modern A-frame was created to balance luxury and warmth, where every detail invites you to slow down, reconnect, and stay a little longer..

Allen Creek Nature Preserve is a 0.7-mile, family-friendly Wintergreen loop through a rare high-elevation wetland, complete with interpretive guides describing the braided streams and northern plant species that thrive there.