Properties Near 34 Southshire Drive Bennington, VT

Welcome to this beautifully updated Center Hall Colonial, privately set on 2.58 wooded acres at the end of a peaceful cul-de-sac just minutes from downtown and major highways. The three bedroom, two and half bath home is truly move in ready, offering the perfect balance of comfort, style, and privacy. Step inside to an open concept main level where the kitchen flows seamlessly into the living area, creating a bright and inviting space ideal for everyday living and entertaining. The kitchen features striking concrete countertops and opens directly to a spacious dining room perfect for family meals as well as a cozy sitting room for additional relaxation. A convenient first floor laundry adds to the homes practical layout. Brand new hardwood floors run throughout the second floor, complemented by the central air and heat. For added energy efficiency and versatility, the home features both wood/oil burning furnace. A brand new architectural shingle roof will in be installed prior to closing. Enjoy beautifully stamped concrete surrounding a heated saltwater pool, hot tub, your own private retreat. A custom fire pit completes the backyard, offering a welcoming space for year round gatherings with family and friends. If you're looking for a turnkey property with an ideal mix of indoor comfort, outdoor enjoyment, and wooded privacy yet still close to town and highway access this home checks all the boxes.

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.

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.

Nestled at the end of a quiet cul-de-sac 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. --