Bennington, VT Homes for Sale with Acreage

Soak up the mountain view from a brand new custom built home. Desirable neighborhood with paved town maintained roads. Just outside of Old Bennington and close to SVMC hospital, downtown restaurants and theaters. An easy commute to Bennington College, 22 minute drive to Williamstown, MA or an hour to Albany Int'l Airport. Nestled at the base of Mount Anthony, hikers will appreciate direct access

Jenifer Prouty Hoffman Hoffman Real Estate

Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

Monique Geannelis Mahar McCarthy Real Estate

The House that Love Built-Multigenerational Comfort &Thoughtful Design Tucked away in a peaceful neighborhood, set back from a well maintained town road. This beautifully maintained home is perfect for wildlife watching and enjoying serene solitude.Designed with multigenerational or accessible living in mind, the home features a private in-law suite with it's own ramp entry, wide doorways,

Beatrice O'Connell Maple Leaf Realty

Built in 1866, this French Provençal–inspired stone estate is a rare and distinguished offering, blending historic grandeur with pastoral beauty on 94.56 acres just outside historic Bennington, Vermont. Commanding sweeping mountain views, the property delivers exceptional privacy while remaining conveniently close to town amenities. The main residence offers 9 bedrooms and 7 bathrooms,

Kelley Mccarthy Mahar McCarthy Real Estate

Welcome to this charming Cape-style home, nestled in a peaceful country setting just moments from Bennington College and scenic walking and hiking trails. This inviting property offers the perfect blend of rural tranquility and convenient access to town. Located just 10 minutes from downtown Bennington, you’ll have quick access to local shops, restaurants, cultural attractions, and everyday

Thomas Martins Maple Leaf Realty

Welcome to your peaceful country retreat just over the Bennington town line in Shaftsbury! This 3BR/2BA ranch offers effortless one-level living on a generous 3.5-acre lot surrounded by nature and abundant wildlife. The heart of the home features a modern eat-in kitchen with granite countertops, custom Kraftmaid cabinets installed in 2022 and durable vinyl plank flooring throughout, creating a

Vicki Wilson Maple Leaf Realty

Convenient one-level living meets modern style and design in this beautifully crafted ranch home, situated on a spacious 1.4-acre lot within a newer, private four-home subdivision. Relax on the impressive 52-foot farmer’s porch—perfect for enjoying cool summer breezes, stunning sunsets, entertaining guests, or simply taking in the expansive yard and thoughtfully designed plantings. Inside the

Matt Waddington Hoffman Real Estate