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 359 Hickory Hill! Tucked away at the end of a peaceful cul-de-sac on 2.58 acres, this beautifully updated Center Hall Colonial offers privacy, space, and convivence just minutes from downtown Bennington and major highways to New York City, Boston, and beyond. This three bedroom, two and a half bath home is truly turnkey and move in ready. Inside, you'll find gleaming hardwood and tile floors throughout, a spacious open concept living area, first floor laundry, and even potential for a first floor primary suite. A brand new architectural shingle roof adds curb appeal and long term peace of mind it has the elegant look of slate without the maintenance. This home has already been pre inspected and fully updated, so all the work is done for you. Whether you're looking for a primary residence or a second home getaway, 359 Hickory Hill checks all the boxes. Enjoy energy efficient heating and cooling, with both wood-burning and oil furnace to suit your preferences. Step outside to your private backyard oasis, featuring a saltwater heated in-ground pool, hot tub, custom stamped concrete with a beautiful fit pit perfect for entertaining, relaxing, or weekend staycations. Just unpack, settle in, and start enjoying the lifestyle this special property offers.

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. --

Historic building in heart of downtown Bennington with solid income from existing commercial tenancy and a fantastic second floor begging to be utilized as residential space. This loft type space is approx. 8,000 sq. ft. and would be an amazing living space (or several) with varying exposure, views of mountains in the distance and of the downtown area. The building offers an abundance of indoor direct entry parking for the resident(s) with ingress and egress stairs from Main Street in the front or from Union Street and the indoor parking in the rear. The space has been prepped with plumbing and electrical for kitchens and baths and also for HVAC to be installed. There are new framed walls with sheetrock and base coat of paint. This is not a blank slate! The hard work has been done and awaits your vision. The space even has south facing roof top decks possible and a sliding glass door already installed to this outdoor area. An awesome opportunity for those who want to be in the heart of a vibrant Vermont town with endless year-round recreation a short drive away in all directions. The area offers some of the best skiing, snowmobiling, hiking, biking, fishing, boating and much more and the Green Mountain National Forest is a short distance away. A fantastic alternative to an expensive single family due to income from two core commercial tenants on the main level. Very unique situation at an affordable price point. Residential use is permitted but may require permits.