277 houses for sale in Old Bennington village

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This well-maintained New Englander offers the perfect balance of classic character and comfortable living. Featuring four bedrooms and two updated bathrooms. The home provides spacious, comfortable living throughout. The recently renovated kitchen is both stylish and functional, while the updated bathrooms add contemporary appeal. Large rooms and a thoughtful layout create a welcoming atmosphere for everyday living and entertaining. Outside, you'll find a deep, fully fenced backyard with plenty of room for recreation, gardening, or pets. A beautiful deck provides the perfect setting for outdoor dining, relaxing, and entertaining. Enjoy the convenience of an in-town location within walking distance of downtown restaurants, shops, and local attractions. The property is also just minutes from services and all the amenities Bennington has to offer. Albany airport is 45 minutes driving, ski areas to the north and east, also approximately 45 minutes, NYC and Boston are both a 3 hour drive

Build Your Dream Home-Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own. This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision. Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully designed floor plan offers the flexibility and convenience of one-level living-with a bedroom, full bath, laundry, kitchen, dining area, and living room all located on the main level. Love the idea of extra space' The walkout basement provides incredible future potential and may be finished for an additional price-perfect for expanding living space, creating a family room, home office, gym, or guest suite. Enjoy all the benefits of energy-efficient new construction in a location close to walking trails, shopping, healthcare, and everything Bennington has to offer. ' New Construction ' 4 Bedrooms 2 Ful

Welcome to this lovely Colonial home, formerly a charming carriage house, nestled in one of Bennington's most desirable walkable neighborhoods. Offering over 1,500 square feet of inviting living space, this well maintained home features 3 bedrooms, 2 bathrooms, and a versatile bonus room perfect for a home office or potential fourth bedroom. Inside, you'll find beautiful wood floors and trim, rustic beams, and newly installed plush carpeting. The sunny interior is filled with natural light thanks to large windows that flood the home with brightness. The kitchen offers stainless steel appliances direct access to the back deck. Updated bathrooms and ample closet space blend modern convenience with the timeless charm of the home. Step outside to enjoy the beautifully landscaped yard, complete with a newly painted deck ideal for entertaining and gatherings, as well as stunning mountain views. The level, usable yard offers plenty of space for outdoor enjoyment, room for a garden, and a larg

Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you'll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026. What truly sets this property apart is its incredible versatility. The bonus space presents endless possibilities for a home based business, professional office, hobby space, expanded living area, or potential in-law accommodations. Whether you're looking for room to grow, work from home, or create a space tailored to your lifestyle, this home offers the flexibility to make it happen. The generous lot and rear garage access provide additional opportunities for future improvements. Buyers may appreciate the potential to enhance accessibility and functionality with a redesigned driveway configuration, such as a circular drive, while maximizing the

Enjoy easy first-floor, one-level living in this two-bedroom, one-and-a-half-bath condominium in Bennington's Nathaniel Court community. The comfortable layout features an open living and dining area, a functional brand-new stainless steel kitchen appliances, laminate flooring, and plenty of natural light throughout. Both bedrooms offer inviting spaces, while the in-unit washer and dryer add everyday convenience. Association services include landscaping, snow removal, and trash removal, providing a low-maintenance lifestyle. Sidewalks and a location close to downtown Bennington make it easy to access local shops, restaurants, cultural attractions, and other area amenities. Whether you are purchasing your first home, downsizing, or looking for a convenient Vermont getaway, this well-located condo is ready to welcome its next owner

Welcome home to this meticulously maintained 3 bedroom, 1.5 bath ranch, perfectly nestled in a highly desirable neighborhood. Offering over 1,400 square feet of single level living space, this home combines classic charm, everyday comfort, and an unbeatable location. Rich hardwood floors flow throughout most of the home creating a warm and inviting atmosphere from the moment you step inside. The spacious layout offers comfortable living areas filled with natural light, generous-sized bedrooms, and a floor plan designed for effortless everyday living and easy entertaining. A charming breezeway connects the home to the attached one-car garage, providing a practical transition space that's perfect in every season while adding timeless New England character. Outside, the yard offers room to garden, play, or simply relax and enjoy the peaceful surroundings. Location is everything, and this home delivers. Tucked into an established neighborhood known for its welcoming feel, you'll be just mi

Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout. Enjoy the convenience of first floor laundry, a beautiful front porch perfect for morning coffee or evening cocktails, and a private backyard ideal for entertaining, gardening, or simply relaxing while still enjoying the benefits of in town living. Owned and cherished by the same family for many years, this property has been exceptionally cared for and offers too many updates to count. From the inviting turquoise staircase to the unique character and charm found throughout the home, every corner tells a story. Take a stroll to local coffee shops, dinner spots, and community events, or enjoy hearing music drifting from the nearby P

Charming home in the heart of the Village of North Bennington, set on a beautiful village lot and offering solid bones with great potential. This well-maintained property features 4 bedrooms and a 3/4 bath, along with a first-floor bonus room. Wood floors lie beneath the carpet, ready to be revealed. Laundry hookups are in place for added convenience. Some updates are needed, providing an excellent opportunity to add your own finishing touches and build equity in a highly desirable location. Enjoy true village living with walkable access to cafes, restaurants, and trails, plus close proximity to Lake Paran and the Park-McCullough House. School choice at the elementary level adds flexibility. Just minutes to downtown Bennington for additional shopping, dining, and amenities, with easy access to multiple ski destinations. Conveniently located approximately one hour to Albany International Airport and about three hours to NYC and Boston. A rare opportunity to own in one of North Benningto

Build Your Dream Home-Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own. This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision. Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully designed floor plan offers the flexibility and convenience of one-level living-with a bedroom, full bath, laundry, kitchen, dining area, and living room all located on the main level. Love the idea of extra space' The walkout basement provides incredible future potential and may be finished for an additional price-perfect for expanding living space, creating a family room, home office, gym, or guest suite. Enjoy all the benefits of energy-efficient new construction in a location close to walking trails, shopping, healthcare, and everything Bennington has to offer. ' New Construction ' 4 Bedrooms 2 Ful

Set along tree-lined Monument Avenue in prestigious and historic Old Bennington, the Spargo House offers a rare opportunity to own a distinctive piece of Vermont history. Dating to circa 1800, this remarkable home was once the longtime residence of noted author, historian and collector John Spargo, founder and longtime director of the Bennington Museum. Just below the Bennington Battle Monument, the home blends historic character with thoughtful updates throughout its 2,692 square feet of living space. The bright kitchen features abundant cabinetry, generous counter space, stainless appliances and a center island, while exposed brick, arched openings and period details preserve the character of the home. Four bedrooms include an expansive primary suite with an exposed beam, sitting area, recently renovated bath and convenient in-suite laundry, while mini-split cooling adds modern comfort throughout the home. Outside, the deep one-acre lot stretches from Monument Avenue to Catamount Lan

Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208+/- sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property's historic character, while modern updates support comfortable living and reliable income potential. Situated on a 0.63-acre lot with ample parking and room for future expansion or additional development. A rare opportunity to own a piece of Bennington's history with strong rental appeal and endless versatility. Ideally located within walking distance of Bennington's vibrant downtown shops, restaurants and community services-offering exceptional convenience for residents and strong visibility for commercial tenants

Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again. Inside, you'll find generous living space ready for your vision and updates. A fully enclosed front porch provides additional usable space, while the rear mudroom offers a practical everyday entry. Whether you're looking to restore the home's character, add value through renovations, or explore income-producing possibilities, this property presents a wealth of opportunity. Conveniently located close to downtown, shopping, dining, walking trails, and the hospital, the location adds to the property's appeal. Bring your ideas and imagination, this is a rare chance to transform a property with outstanding potential into something truly special

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 a home office, adding flexible living space to fit today's lifestyle. The main level includes a first-floor bedroom and 3/4 bath, along with a sunroom perfect for relaxing and enjoying the surroundings. Upstairs are two additional bedrooms, including the primary suite, plus a large storage area. This home does need a little TLC, including some carpet and paint updates, but offers tremendous potential and great bones. Additional features include an attached one-car garage and a large back deck for outdoor enjoyment. Conveniently located within walking distance to downtown, the hospital, and the

Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out. The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even a pantry! The kitchen flows seamlessly into the dining room and the the living room, creating an open and inviting atmosphere where family and guests can easily gather. Laminate flooring throughout the first floor provides durability and a clean, cohesive look. Convenience is key with a practical mudroom entry and first-floor laundry. The full bathroom on the main level features a relaxing soaking tub with jets, perfect for unwinding after a long day. Upstairs, you'll find three comfortable bedrooms with attractive wood flooring, along with a half bath. The primary bedroom includes a walk-in clos

Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with rental income from the other, or continue using the property as an investment. Appears well suited for FHA, VA, USDA, and conventional financing. Conveniently located near shopping, dining, schools, medical facilities, and other everyday amenities in downtown Bennington. Bennington continues to benefit from ongoing investment and redevelopment throughout the downtown area, adding to the appeal of this location

Welcome to this lovely Colonial home, formerly a charming carriage house, nestled in one of Bennington's most desirable walkable neighborhoods. Offering over 1,500 square feet of inviting living space, this well maintained home features 3 bedrooms, 2 bathrooms, and a versatile bonus room perfect for a home office or potential fourth bedroom. Inside, you'll find beautiful wood floors and trim, rustic beams, and newly installed plush carpeting. The sunny interior is filled with natural light thanks to large windows that flood the home with brightness. The kitchen offers stainless steel appliances direct access to the back deck. Updated bathrooms and ample closet space blend modern convenience with the timeless charm of the home. Step outside to enjoy the beautifully landscaped yard, complete with a newly painted deck ideal for entertaining and gatherings, as well as stunning mountain views. The level, usable yard offers plenty of space for outdoor enjoyment, room for a garden, and a larg

This well-maintained village home located on a dead end rd is move-in ready and filled with inviting features. Set on a desirable corner lot, the property offers an updated bath, spacious covered front and rear porches, and a cozy pellet stove. The kitchen was just updated as well as painted in side and out. The large front entry provides additional usable space, while the one-car insulated and heated garage with electricity adds convenience and functionality. Enjoy a quiet neighborhood with mountain views, close to hiking trails, the YMCA, and all that downtown Bennington has to offer. Open Hose August 2nd from 11am to 2pm No showing prior to the open house

Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a must see location

Lovingly custom built in 1989 and offered for the first time, this beautifully maintained expanded Cape is a rare opportunity to own a home that has been cherished by its original family from the very beginning. Thoughtfully designed with generous room sizes and a timeless floor plan, the home offers warmth, comfort, and quality throughout. Inside, generous room sizes, timeless design, and quality craftsmanship create a warm and inviting atmosphere. Rich hardwood floors, a wood-burning fireplace, and tasteful decor blend traditional charm with everyday comfort. The spacious kitchen features a desirable walk-in pantry, while the home's exceptional condition makes it completely move-in ready. A new roof installed in 2021 adds peace of mind. The grounds are equally impressive, showcasing mature landscaping, retractable awnings, and a charming garden shed. Beautifully maintained inside and out, this turnkey home reflects decades of pride of ownership and offers a rare opportunity to become

Offered for the first time since it was built in 1973, this longtime homestead presents a rare opportunity to create something special in a beautiful setting with an outstanding mountain view. Conveniently located for an easy commute to both Williamstown, MA, and Bennington, VT, the property combines generous living space, practical features, and tremendous potential for a buyer ready to update and make it their own. The main level offers three bedrooms and a full bath, along with an unusually spacious and flexible collection of gathering areas. The living room opens to the kitchen and breakfast nook, while a substantial addition provides a large dining area and family room with closets and direct access to the rear deck and patio. The kitchen also opens outdoors, creating an easy connection to the above-ground pool, hot tub, lawn and surrounding landscape. Downstairs, the finished recreation room has unmistakable vintage character, with a rustic bar, brick accents, and antique barn-bo

Former Church Offers So Many Opportunities. What might be your dream or requirements' This 1889 Church located in the quiet country village of North Pownal, Vermont, could fill them, however big or small. A single family home for all seasons and celebrations' A wedding venue' A place to live and work, rolled into one with plenty of space no matter what you do, from sculpting to computer imaging' This amazing building has so many possibilities. With the exterior restoration just completed and some very attractive new interior spaces for living including the fully equipped kitchen, delightful bedroom, walk-in closet, and three quarter bath, and second floor bedroom suite, one can move right in while you imagine how you might like to change the other very large spaces on both floors