Vintage homes for sale & real estate in Windsor County, VT

Vintage Home for sale in Windsor County, VT:

Now offered at $795,000 – A Vermont farmhouse with a historic orchard, mountain views, and income potential. Set amid rolling hills and breathtaking mountain vistas, this classic Vermont farmhouse sits on one of the first Macintosh apple orchards in the country. Rich with history and surrounded by natural beauty, the property offers a rare blend of character, comfort, and opportunity. A three-story barn provides exceptional versatility, featuring an in-law suite with a hot tub that currently generates $15,000–$20,000 annually in short-term rental income. Ideal for guests or turnkey rental use, the space enhances both lifestyle and value. Enjoy peaceful days by the private pond,

Vintage Home for sale in Windsor County, VT:

Two buildings on one parcel in desirable Hartland, Vermont! This flexible and well-maintained property includes a single-family home and a duplex, offering outstanding potential for owner occupancy, multi-generational living, or investment income. Ideally situated just 25 minutes from Hanover, NH, and 10 minutes from Woodstock, VT, this location provides the perfect balance of convenience and rural charm. The single-family home features one bedroom upstairs and two additional rooms downstairs. The duplex offers 2 two-bedroom apartments—perfect for reliable rental income or to offset your living expenses. Both buildings include laundry facilities, and the property benefits from ample p

Vintage Home for sale in Windsor County, VT:

US Route 4 in Vermont - the east/west corridor from I-89 and the Killington Ski Area. Highway frontage between Quechee and Woodstock, VT. Minutes from Dartmouth College in Hanover, NH; near the intersection of I-89 and 91 at the Connecticut River; also close to Northern New England’s major DH Medical complex and Cancer Center in Lebanon, NH, as well as the VA Hospital in White River Junction. 1.5 story Cape (3 bedroom/2 bath - 2,334 sq ft) from 1850, with numerous outbuildings. The site of a very successful farmers market for many years, then Fool on the Hill, a gift/crafts/novelties business. In addition to the barn, 3 large sheds (1,440 sf - 810 sf - 500 sf) suitable for outdoor eve

Vintage Home for sale in Windsor County, VT:

Excellent Upper Valley investment opportunity! This well-maintained six-unit multifamily property features a desirable mix of 3 one-bedroom apartments and 3 two-bedroom apartments, ideally situated in the heart of Wilder. The property sits directly across from the bus stop and offers convenient access to major employers and amenities — just 9 minutes (4.2 miles) from Dartmouth College and 17 minutes (7.1 miles) from Dartmouth Hitchcock Medical Center. Residents enjoy walking access to two nearby parks and a coin-operated laundry on-site. The property includes a rare in-town developable lot, currently partially used for parking, which presents a unique opportunity for future expansion