Properties Near 245 Southshire Drive Bennington, VT

Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, Vermont Set 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 gleaming wood floors. A large formal living room and dining room provide excellent flow for entertaining. Practicality meets charm with a mudroom, dedicated laundry area, and a substantial walk-in pantry. The primary suite includes a private bath and a serene sunroom retreat-perfect for morning coffee or quiet reflection. Two additional bedrooms and a recently updated bathroom with a new walk-in shower complete the main level. The walk-out lower level is a true bonus-featuring new laminate wood flooring throughout, it offers incredible potential as an in-law suite, home office, or recreation space, with plenty of room to add a kitchenette. Enjoy the peaceful surroundings from your large private deck, ideal for outdoor dining, relaxing, or entertaining guests. A rare find in a prime location-don’t miss your opportunity to own this versatile and spacious home in beautiful Bennington.

Welcome to 203–205 Northside Drive, a truly unique property that combines residential living with commercial potential all in one. Are you looking for the flexibility to live in an apartment while generating income from multiple rental units, or would you prefer to restore the property back into a spacious single-family residence? This property gives you both options. Currently configured with three additional income-producing units, it offers immediate revenue potential for investors or owner-occupants alike. Set in one of the most unique and convenient locations in our community, this property enjoys steady foot traffic by day yet remains quiet and peaceful at night. Whether you envision keeping it as a multi-unit income generator, creating a live/work space, or converting it back into a single-family home, the possibilities are endless. Don’t miss the chance to own this one-of-a-kind property with built-in income opportunities right at your fingertips. Call today before it’s gone!

House hunting in Vermont and can't find what you want? Or it sold before you had time to tour or think it through? This brand new custom built home could be the answer. Desirable neighborhood with paved town roads, close to SVMC hospital, Bennington College, downtown restaurants and events, and one hour from Albany Int'l Airport. Nestled at the base of Mount Anthony, there's direct access to the Bennington Area Trail System and phenomenal views of the mountains and Monument. Construction will meet or exceed Vermont's energy efficiency standards. Proposed house is a Ranch with one floor living: 3 bedrooms, 2 bathrooms, open concept kitchen/dining/living room, laundry room, mudroom, and covered front and rear porches. Realtor & Builder design team will walk you through all the choices you get to make, from exterior siding to interior paint colors, flooring and light fixtures, cabinets to countertops, and more. Base price includes luxury vinyl plank throughout the main rooms, carpeted bedrooms, tiled bathrooms, quartz or granite countertops, and Stainless Steel kitchen appliances. If you love the location but want to consider a different layout or house style, we can redesign, renegotiate and build it to your satisfaction. Sold as a package with land and construction by Jonathan G. Hoffman Builder, a local general contractor with 40 years of experience. Seller is a Vermont licensed real estate broker.

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 living room featuring a wood-burning fireplace and French doors that open to a private deck overlooking the park-like backyard. A separate study offers space for work or reading, while a dedicated laundry room, half bath, and entry to the attached two-car garage add convenience. Upstairs, you’ll find four generously sized bedrooms, including a serene primary suite with a walk-in closet, an additional shoe closet, and a private en suite bath. A full hall bath serves the remaining bedrooms. The fully insulated basement provides excellent storage and features a new electric hot water tank with temperature controls. Outside, mature trees, lilacs, hydrangeas, berry bushes, herbs, and chestnut trees create a lush, beautifully landscaped setting. Move-in ready and meticulously maintained, this turn-key home offers classic comfort in a truly idyllic location. --

Step into timeless elegance with this beautifully restored Victorian home, showcasing stunning woodwork and thoughtful updates throughout. This spacious residence offers five bedrooms, one being on the first floor, and two updated bathrooms blending classic character with modern comfort. A whimsical hidden quarter bath under the stairs adds both charm and function. The home’s gracious layout highlights detailed millwork, soaring ceilings, and large updated and energy efficient windows that flood each room with natural light. A welcoming front porch and stately exterior details reflect the home’s historic charm. It has been meticulously restored and maintained from top to bottom in recent years. The carriage house, with its new, custom doors, provides endless possibilities—perfect for storage, a workshop, or conversion into a creative studio space. With its blend of period craftsmanship and modern updates, this property offers a rare opportunity to own a piece of history while enjoying all the conveniences of today. Just steps from downtown and the hospital and less than an hour to the Albany airport, this is the one you've been waiting for.

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, and a custom roll in shower. Just outside the suite, enjoy a private deck offering easy access and a peaceful place to relax. The main level includes custom woodwork, hardwood floors, passive solar windows, and fresh paint throughout. The cozy kitchen has a window over the porcelain sink, a pantry and newer appliances. Upstairs features new vinyl flooring, a sunlit primary bedroom, a second spacious bedroom, and a full bath. Bonus features include a 3-year old roof with leaf guard gutters, A Webb Pro Boiler (recently serviced) and a 15kw backup generator. The laundry offers front-load washer/dryer, a sink and access to a 448 sq ft attic roughed in for future living space (with plumbing, heating and structural framing in place). Peaceful setting, thoughtful design-this truly is The House That Love Built.