Windsor, VT homes for sale & real estate

Windsor, VT Homes for Sale

Step into timeless New England charm with this historic circa 1760's expanded Cape, offering a great blend of early craftsmanship and character. The home showcases classic timber-frame construction with hand-hewn beams, beautiful plank floors, and period details that create warmth and authenticity throughout. With three bedrooms and two full bathrooms the layout includes a highly desirable first floor primary bedroom and bath, allowing for convenient single-level living while still offering flexible space for family and guests. Set on an expansive 15.55-acre parcel, the property provides mountain views, 47 blueberry bushes, and endless possibilities for agricultural, equestrian, or recreati

Windsor, VT Homes for Sale

This one is a definite handyman's project. The property was allowed to entirely freeze-up before the owner was able to secure possession of the property. It needs new everything; except maybe the furnace and ductwork. The owner had previously utilized this as an investment property and has disclosed that the septic system needs some work. Property being sold as-is; at the price offered the owner is not planning any property cleanout or repairs. This property is not financeable. Under favorable purchase terms, the owner may be inclined to offer to hold a note on the property. Showings of the property are delayed until Monday, 22 December 2025.

Windsor, VT Homes for Sale

Step into a great opportunity to embrace peaceful, single-level living on over seven captivating acres in the heart of rural Vermont. This property offers the coveted serenity of the countryside while maintaining a short, convenient distance to all modern amenities. Inside, you'll discover a home thoughtfully prepared for its next owner with fresh updates, including a brand-new metal roof ensuring durability and peace of mind, fresh interior paint throughout providing a bright, clean canvas, new, appealing flooring in key areas, and upgraded bathroom features such as a new toilet and vanity in one bath. Offering a practical layout, this home features three comfortable bedrooms and two full

Windsor, VT Homes for Sale

Stunning contemporary home on 6+ acres. Great proximity to the Upper Valley/RT 91 and only 12 miles to skiing at Okemo! Sit in the panoramic south facing dining room and take in the Black River and local mountain views. Your own Vermont paradise! Quiet dead end road. This 1973 residence has a 2008 addition and has been transformed over the years. Many upgrades and updates, some just completed! Recent work includes new faux stone facade, upgrades to the lower level gym space, some new lighting fixtures and exterior trim paint. Since the 2008 addition, upgrades include a renovated kitchen, two Italian marble baths, a Bosch boiler, wood ceilings with added insulation, some new Anderson windows

Windsor, VT Homes for Sale

Iconic 1854 Gothic Revival home, known as the Lilac Cottage is located in the heart of South Woodstock Village, just a short stroll to The Ransom Tavern at Kedron Valley Inn, The South Woodstock Store, and Kedron Pond. Many new state of the art updates and improvements throughout this versatile, turn-key home, all honoring and highlighting the period detail. The rooms are spacious, bright and flow beautifully for entertaining and every day living. Recent expansion/restoration of the attached carriage barn offers additional opportunity as an in-law, a guest suite, an income producing rental unit, or as a spectacular Great Room addition to the main home with a private deck. The grounds are lo

Windsor, VT Homes for Sale

Well-maintained Nordic Haus 1BR/BA condo with loft and separate study, ready for new owners. This corner unit has a covered porch, an updated kitchen, and upgraded flooring. Enjoy comfortable, low-maintenance living just steps from Ascutney Outdoors for hiking, biking, skiing, and winter tubing. Minutes from the acclaimed Brownsville Butcher Pantry, with easy access to I-91. This property is ideal for first-time buyers, investors, or those seeking a weekend getaway. Right of First Refusal (ROFR)