Bennington Vermont Real Estate

Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience. Public water and sewer are available, making the lot ready for development and easy to build on. Ideally located just minutes from downtown North Bennington, you’ll enjoy close proximity to local shops, dining, and everyday amenities, along with quick access to major routes for commuting to Albany, New York City, Boston, and beyond. Situated within a desirable school choice embrace the Vermont lifestyle with nearby walking trails, scenic outdoor spaces, and a peaceful country setting, all while being conveniently close to local amenities and the area hospital. This property offers the perfect balance of quiet surroundings and accessibilities, set in a welcoming neighborhood that captures the charm and character Vermont is known for. A prime, build ready parcel bring your vision and get started.

Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home. Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process. Located on a publicly maintained road, this property combines convenience with a peaceful, well kept neighborhood setting. Enjoy close proximity to local amenities including shopping, dining, and the hospital, while also benefiting from easy access to major routes connecting you to Albany, Boston, and New York City. Outdoor enthusiasts will appreciate nearby walking and biking trails, along with year round Vermont recreation including hiking, skiing, and exploring the natural beauty of the area. Set within the North Bennington area and served by the local elementary school, this lot offers the ideal blend of location, lifestyle, and readiness. A prime opportunity to bring your vision to life in a scenic Vermont setting.

Level building lot with town sewer and water at the edge of town. Possible owner financing.

Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life.

This 5.6-acre lot is ideally situated at the edge of town, offering a peaceful retreat surrounded by nature. Furnace Brook winds through the backside of the property, providing a soothing sound that lulls you to sleep each night. Observe the abundant wildlife as they visit the stream with the Mountain view as the backdrop, this location is perfect for building your Vermont dream home.

Your chance to own over 9 acres of raw land in beautiful Vermont! Access from the town maintained Evergreen Drive makes the possibility of building your dream home or business even easier. Enjoy seclusion and mountain views while being close to shopping, schools, restaurants, public transportation, and all that Bennington has to offer.

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 endless. From a gate on the north side, the property proceeds back and behind two residences at 996 and 1058 Silk Road, opening up to a wide field protected by treelines to the east and west. The property was successfully perc tested years ago, and has access to town water. Electricity is available at the road. Please note a small portion of the land is inaccessible on the opposite side of the Bennington Bypass and this opportunity is priced accordingly.

Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for financing and insurance. The property’s value is anchored by a substantial, two-story detached storage garage located on the back corner of the lot. This structure is in excellent condition, offering immediate utility for secure equipment storage, a workshop, or contractor inventory while a primary building is being constructed. With 114 feet of direct frontage on Northside Drive and high daily traffic counts, the visibility for signage and branding is exceptional. Located within the Northside Design Review District, this site ensures long-term investment protection, making it a sophisticated gateway location for your next business venture. Ground Lease option available

Discover the potential at 720 & 702 North Branch Street—a rare 7-acre offering in a prime Bennington location. With level land, generous frontage, and easy access, this property is perfectly positioned for residential or mixed-use development, with municipal water and sewer available at the street. The sale includes a well-maintained duplex at 702 North Branch, featuring a 3-bedroom unit on the first floor and a 2-bedroom unit upstairs. Recent updates—new boiler, oil tank, and hot water heater—make this an excellent source of immediate rental income. Tenants pay all utilities. A conceptual development plan is available for review, highlighting the potential for up to 100 residential units. Whether you're looking to invest, develop, or do both, this is a unique opportunity to shape a piece of Bennington’s future.

Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand drivers. Ideal for investors seeking a site with traffic, frontage, and future upside in an established commercial corridor.