Bennington, VT Homes for Sale with Garage

Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

Max Squiers KW Vermont - Brenda Jones Real Estate Group

Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as

Kelley Mccarthy Mahar McCarthy Real Estate

2-Unit Multi-Family with Professional-Grade Workshop!Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast,

Lori Hurley Four Corner Properties LLC

Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom

Kelley Mccarthy Mahar McCarthy Real Estate

Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

Lindsey Martin Maple Leaf Real Estate

Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create

Lindsey Martin Maple Leaf Real Estate

Completely renovated, turnkey single-level home offering mountain views, modern finishes, and a beautiful country setting. All major systems and cosmetic updates were completed within the last year, including a brand-new roof and new windows.The light-filled interior layout features 2 bedrooms, 2 full bathrooms, brand-new wood flooring across all main living areas, plush new bedroom

Kate Barry EXP Realty

Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

Julie Glover Mahar McCarthy Real Estate

Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups - perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street.

Julie Glover Mahar McCarthy Real Estate

Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful atmosphere rarely found in properties with such versatile potential. A large barn

Angela Bevin Maple Leaf Real Estate

200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities. Showings start 8/18/2026

Dan Mason Perrott Realty

If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

Betty McEnaney Diamond Realty

Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the

Vicki Wilson Maple Leaf Real Estate

Tucked into Bennington's established Spring Hill neighborhood, this inviting 3 bedroom, 2 bath home offers nearly 2,000 square feet of comfortable living space with a setting that makes it easy to enjoy the outdoors. From the backyard, follow the grass walking trail to the community owned pond, a wonderful extension of your outdoor space and a beautiful spot to enjoy the changing Vermont Seasons.

Faith Rhodes Maple Leaf Real Estate

Side-by-side duplex in a sought-after area in the heart of Bennington, offering the charm of yesteryear with modern conveniences. This well-maintained property presents an excellent investment opportunity, whether you're looking for a rental property generating substantial income or the option to owner-occupy one unit while renting the other to help offset your mortgage. Boasting many tasteful

Matt Waddington Hoffman Real Estate

15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R

Chris Long BHG Masiello Brattleboro

Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes

Jenifer Prouty Hoffman Hoffman Real Estate

Nestled on 16.96 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and

Kelley Mccarthy Mahar McCarthy Real Estate

Thoughtfully crafted with a distinctive European-inspired character and beautifully updated throughout, this custom-built 4-bedroom, 3-bath home offers the perfect blend of quality craftsmanship, privacy, and convenience on a picturesque, landscaped lot just minutes from downtown Bennington. The bright and inviting interior features a beautifully renovated kitchen, spacious living areas with

Jeffrey Dorman

Welcome to this inviting Cape-style home offering 3 bedrooms, 2 baths and a comfortable layout designed for both everyday living and entertaining. The main level features an open-concept kitchen and dining area that flows directly onto a huge back deck—an ideal spot for summer dinners, gatherings or simply relaxing while overlooking the secluded, wooded backyard. With both a living room and

Lilli West Maple Leaf Real Estate

Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. Custom Kitchen with granite countertops, custom tile shower unit. The open-concept layout is highlighted by a spacious kitchen and a

Lilli West Maple Leaf Real Estate

Nearly Lakefront Living in the Heart of North Bennington!Come for the space, stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

Nicholas Charest Maple Leaf Real Estate