Properties Near 77 Winding Road West Windsor, VT

Light and thoughtful architect designed home on a lovely 12 acre hilltop. Set in a magical landscape of exposed ledge, old stone walls & established perennial gardens. Stunning views of both Mt Ascutney and Little Ascutney. Spacious and airy, large windows and south-facing skylights provide passive solar warmth throughout the 4 bedroom home. Open layout is clean and efficient with cathedral ceilings & custom touches. Drilled well. The kitchen has smart, functional design. Dining/Family room and sunken living room. Large primary bedroom with ensuite bath, laundry, and deck. A perfect spot for anyone who enjoys the outdoors. Direct access to recreational trails. Close to Ascutney Outdoors, WW Town Forest & the Brownsville Butcher & Pantry. A peaceful homestead in a truly special corner of Vermont. Listing price adjusted to reflect older roof, decks & skylights. All still serviceable.

This pristine, updated contemporary home is conveniently located on Mt Ascutney. Beautifully maintained and move in ready. The open concept main level is anchored by a fieldstone wood burning fireplace. The kitchen has plenty of counter space, quality appliances, and classic knotty pine floors running throughout. Two bedrooms, laundry/mudroom, and full bath complete the main level. Moving upstairs there is a spacious primary bedroom and a second BR with a shared 3/4 Bath, and lots of closets and storage. On the lower level the current owners have created an amazing family fun space complete with a media room, and a full on bar area complete with undercounter refrigeration, a glass washer and a very cool wall fireplace. There is also a new half bath. All new, highly efficient mechanicals Easy access to Woodstock, Hanover, I-91, and all regional recreation. All properties on Mt Ascutney are subject to a standard ROFR.

In need of the perfect ski cabin just 15 minutes from Okemo Mountain? Set on over ten private acres, this home offers the perfect mix of comfort and country charm. The main living room features cathedral ceilings, a propane stove, and access to the deck with a hot tub—ideal for relaxing after a day on the slopes. The kitchen, finished with Vermont soapstone counters and updated appliances, opens to the dining and gathering spaces so everyone can stay connected. With three separate living areas, there’s space for quiet reading, movie nights, or lively après-ski evenings around the woodstove. Upstairs, you’ll find three bedrooms, including a private primary suite. Thoughtful details—live-edge accents, built-ins, and warm wood throughout—give the home character without feeling overdone. Close to VAST trails for snowmobiling and Knapp Pond Recreation Area, great for fishing and kayaking, making this a great spot for every season. Offered furnished, so you can arrive with your gear and start enjoying life in Vermont before the snow falls. Visit the Okemo real estate community today. Taxes are based on the town assessment.

Discover this well-cared-for 2-bedroom, 1-bath contemporary home nestled in the peaceful countryside of Reading, VT. Set on a serene lot surrounded by nature, this home offers the perfect blend of comfort and privacy. The light-filled interior features an open and airy layout with thoughtful updates and a warm, inviting feel throughout. Enjoy relaxing in the cozy living spaces, preparing meals in the functional kitchen, or stepping outside to take in the quiet country views from your covered porch or yard. The time spent curating these gardens is extensive from stone work to perennial gardens including blueberries, blackberries and raspberries. Whether you’re looking for a full-time residence or a Vermont getaway, this property provides an ideal retreat in a picturesque setting while still being within easy reach of area amenities and outdoor recreation. 25 minutes to Okemo, 30 to Killington, and 40 to Pico makes hitting the slopes a breeze. There is even expansion capability, let us tell you how when you visit.