Properties Near 1059 Carlton Hill Road Woodstock, VT

"All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers unparalleled access to recreational pursuits. Its 40-acre grounds feature single-track biking, hiking, and snowshoeing trails, a firepit, patio, grills, and owned riverfront access. A 32-foot indoor pool, and hot tub under the stars make this a year-round haven. The acreage also includes a potential building lot with mountain views and an existing roadway, adding versatility. Nearby, enjoy world-class skiing, golf, and other outdoor activities, with Woodstock Village offering charming shops and restaurants. Inside, the chef’s kitchen boasts Viking appliances, granite counters, dual refrigerators, a pantry, and a custom island. Two expansive great rooms provide gathering spaces with large-screen TVs and plush seating, including a wet bar in the second-floor game room. Accommodations include four bedrooms, three full baths, and space for up to 12 guests. A highly successful Airbnb rental, “All Sessons” is an extraordinary opportunity to own a Vermont escape combining privacy, beauty, and income potential in one of the region’s most picturesque towns.

Set on over two picturesque acres along one of the most beautiful country roads in the area, this spacious and impeccably renovated contemporary farmhouse offers the perfect balance of charm and modern comfort. Just minutes from Woodstock and South Woodstock, the property enjoys both convenience and a peaceful setting. Completely remodeled in 2016 by Sargent Design Company, the home features generous living and entertaining spaces, multiple porches, and seamless indoor-outdoor flow. The main residence offers 5 bedrooms, including a large primary suite, while the converted barn includes a private guest apartment, ideal for hosting company. Highlights include a hot tub, indoor and outdoor fireplaces, and thoughtful updates throughout that make the home as efficient and easy to maintain as it is elegant. With open spaces designed for gatherings and cozy corners for retreat, this home is equally suited for year-round living or a Vermont getaway. Outdoor enthusiasts will appreciate the home’s proximity to skiing at Killington and Saskadena Six, as well as easy access to hiking, biking, and countless four-season activities. A truly exceptional property blending timeless farmhouse character with today’s modern luxuries.