Bennington, VT Homes for Sale with Acreage

Come Explore this 7 +/- acre wooded lot located among a rural residential neighborhood in Bennington VT. This is the lot Behind the Homes and is accessed by a deeded and surveyed 50’ ROW off the paved and town-maintained Gore Road. Power and services are at the road frontage. The property contains a mature hardwood forest primarily of Oak and Maple. Ever so slightly sloping, with a

Curtis Trousdale

Prime redevelopment opportunity in Bennington. 720 North Branch Street offers 6 acres of level land with frontage and easy access—ideal for residential or mixed-use development. Included in the sale is 702 North Branch Street, a two-unit duplex with a 3-bedroom apartment on the first floor and a 2-bedroom unit upstairs. Recent improvements include a new boiler, oil tank, and hot water heater.

Paul Carroccio TPW Real Estate

Nestled in one of Bennington’s most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm—all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System (BATS).The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious

Ann Greenwood Alton + Westall Real Estate Agency, LLC

Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about everything:All

Harvey Roettinger RE/MAX North Professionals

Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

Chris DeFelice Four Seasons Sotheby's Int'l Realty

Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all enhanced by

Kelley Mccarthy Mahar McCarthy Real Estate

Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision.Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

David White OwnerEntry.com

Experience the quintessential Vermont lifestyle at the historic Nickerson-Jewett farm. Only 5 minutes to Bennington attractions and amenities and 15 minutes to Williamstown, MA. This appealing country home is located on a town maintained dead-end road. Privately nestled on 134.46 acres of scenic beauty, the charming 4 bedroom, 2.5 bath mid nineteenth century farmstead includes a well-preserved

Jason Saphire www.HomeZu.com

A beautiful opportunity awaits on Mount Anthony Road in Bennington, Vermont—11.2 acres of wooded land nestled along a quiet, scenic dirt road. This property offers the perfect blend of seclusion and convenience, giving you the best of both worlds.Currently wooded, the land can be selectively cleared to reveal potential stunning views of the surrounding Vermont landscape. Imagine building a camp

Kelley Mccarthy Mahar McCarthy Real Estate

Historic structure on the Walloomsac River and close to the Northside Drive/Kocher Driver commercial core.

Paul Carroccio TPW Real Estate

Take a look at an incredible development opportunity located in the heart of Bennington. These two adjacent parcels of land, one situated off Fillmore Street encompassing 31.19 acres and the other off Gore Road spanning 48.46 acres, together offer over 75 acres of prime, buildable terrain.Notably, the property is bordered by two existing housing developments to the east (East St, West St and

Lilli West Maple Leaf Realty