Bennington, VT Homes for Sale

Opportunity awaits with this well-built and meticulously maintained 3-bedroom, 2-bath home nestled on a rare and highly desirable 1.84-acre flat lot in the peaceful countryside—just a short drive to town amenities, shops, and schools, this property features town water, a new roof, nearly new boiler and an attached two-car garage. Set back from the road, this property offers space, privacy, and

Cassie Barbeau Mahar McCarthy Real Estate

This spacious 5-bedroom, 4-bath Colonial in Bennington's sought-after Maplewood neighborhood offers over 3,600 sq ft of flexible living space, including a finished walk-out in-law suite with full kitchen and private entry. Thoughtfully updated with granite counters, stainless steel appliances, and a smart home system including ADT security, glass break sensors, and a smart thermostat. The vaulted

Nick Sicard EXP Realty

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

Ann Greenwood Alton + Westall Real Estate Agency, LLC

Across from the 5th Fairway of the Mount Anthony Country Club you’ll find this charming, meticulously maintained 3 bedroom 2 bath home. The spacious open layout, custom kitchen, and expansive deck are warm and inviting. Relax on your front porch and enjoy the scenic mountain vistas of Mount Anthony and the Bennington Monument. Fabulous, convenient location! The home began as a bungalow, the

Margretta Fischer Wohler Realty Group

Step into this beautiful 1930s classic home, filled with character and endless possibilities. This home offers three bedrooms, one bathroom, and a layout that seamlessly combines classic details with comfortable living spaces. The heart of the home is the large dining area, perfect for hosting gatherings or enjoying quiet family meals. Adjacent, you will find a spacious living room with a

Margretta Fischer Wohler Realty Group

Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about everything:All

Harvey Roettinger RE/MAX North Professionals

Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet 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

Kelley Mccarthy Mahar McCarthy Real Estate

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

Chris Long BHG Masiello Brattleboro

Imagine owning the oldest home in downtown Bennington full of history and amazing detail. Built by Joseph Safford after opening Bennington's first Grist Mill, then fully renovated during the Italianate Victorian area for much of it's current design. This historic Inn along the Walloomsac River is now being used as an Air BnB rental as well as a separate leased 2 bedroom apartment. The Fully

Lilli West Maple Leaf Realty

House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front

Zachary Zupan EXP Realty

Motivated seller.!!! Move in asd add your finishing touches to this Antique House located in Downtown on a generous corner. This 2 story, 4 bedroom, 1 bath Bennington home has great character featuring a Dutch front door, enclosed front porch, and beautiful bay window. Property has an eat-in kitchen, dinning room, laundry room with washer and dryer, living room, basement, and den! Enjoy being

Dan Mason Perrott Realty

A completely renovated gem in a fantastic location awaits its new owner. This beautifully restored cape-style home in Bennington's desirable Chester Knoll community offers a stunning and worry-free living experience. Adhering to the newest Vermont energy codes, this energy-efficient home boasts an Energy Star propane heating system for optimal comfort and savings.Chester Knoll provides an

Lori Hurley Four Corner Properties LLC

Welcome to this beautifully maintained 3-bedroom, 1.25-bath home nestled on a corner lot in Bennington. This inviting property blends classic charm with thoughtful updates, offering comfort and style both inside and out.Step into the spacious kitchen featuring stunning wood cabinetry, granite countertops, and a functional island with a bar sink-perfect for entertaining or everyday living. The

Kelley Mccarthy Mahar McCarthy Real Estate

Great Investment Opportunity! This well-maintained 3-unit property is a fantastic opportunity for savvy investors. Two of the units are currently rented, providing immediate income potential. Situated just a short stroll from downtown, you'll find charming shops, popular restaurants, and close proximity to the Bennington trail system—perfect for outdoor enthusiasts. Just 1 hour from Albany and

Thomas Martins Maple Leaf Realty

Welcome to Unit #1 at Norton Potters, a quaint and quiet townhouse community nestled in a lovely neighborhood setting. This end-unit two-bedroom home is full of character and natural light, offering a peaceful retreat with a deck that overlooks a serene stream.The main level features a spacious living room, dining area, kitchen with a generous pantry, a convenient half bath, and laundry area.

Faith Rhodes Maple Leaf Realty

Own a piece of Bennington history! Alex Drysdale House, c. 1850. The grocery store (formerly 138 River Street) operated under the name "A. Drysdale & Son" and was built in 1876. Today this historic property is set up as a four-unit with great income potential. It currently houses three apartments: a freshly renovated four bedroom (used as an Airbnb), three bedroom, and efficiency, along with the

Justine Curry Maple Leaf Realty

Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

Chris DeFelice Four Seasons Sotheby's Int'l Realty

Located in a charming Bennington neighborhood, this home offers both convenience and comfort, with shopping, schools, the post office, and the hospital just a short distance away. The welcoming three-season front porch is perfect for enjoying your morning coffee or winding down after a long day. Inside, the spacious, eat-in kitchen has brand-new flooring and newer appliances, adding a fresh and

Kelley Mccarthy Mahar McCarthy Real Estate

Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision.Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

David White OwnerEntry.com

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.

Dan Mason Perrott Realty

Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

Kelley Mccarthy Mahar McCarthy Real Estate

Charming Downtown Victorian - Income Opportunity Meets Timeless StyleTucked behind the classic facade of this downtown Bennington gem lies an incredible opportunity-for homeowners and investors alike. Located in the heart of downtown on a street known for both professional and residential appeal, this Victorian-style duplex offers versatility, character, and reliable income potential. Each

Kelley Mccarthy Mahar McCarthy Real Estate

Experience the quintessential Vermont lifestyle at the historic Nickerson-Jewett farm. Only 5 minutes to Bennington attractions and amenities and 15 minutes to Williamstown, MA. This appealing country home is located on a town maintained dead-end road. Privately nestled on 134.46 acres of scenic beauty, the charming 4 bedroom, 2.5 bath mid nineteenth century farmstead includes a well-preserved

Jason Saphire www.HomeZu.com

Mixed use development site in the heart of Downtown Bennington. .88 acre site with Zoning, Preservation and Stormwater approvals for a 60,000 sq ft mixed use building with planned commercial occupancy on the first floor and three stories of residential occupancy above - 60 units total with 12 units of workforce housing.

Paul Carroccio TPW Real Estate

Level building lot with town sewer and water at the edge of town.Possible owner financing.

Dan Mason Perrott Realty

A beautiful opportunity awaits on Mount Anthony Road in Bennington, Vermont—11.2 acres of wooded land nestled along a quiet, scenic dirt road. This property offers the perfect blend of seclusion and convenience, giving you the best of both worlds.Currently wooded, the land can be selectively cleared to reveal potential stunning views of the surrounding Vermont landscape. Imagine building

Kelley Mccarthy Mahar McCarthy Real Estate

Historic structure on the Walloomsac River and close to the Northside Drive/Kocher Driver commercial core.

Paul Carroccio TPW Real Estate

Take a look at an incredible development opportunity located in the heart of Bennington. These two adjacent parcels of land, one situated off Fillmore Street encompassing 31.19 acres and the other off Gore Road spanning 48.46 acres, together offer over 75 acres of prime, buildable terrain.Notably, the property is bordered by two existing housing developments to the east (East St, West St and

Lilli West Maple Leaf Realty

Welcome to 72 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Lewis model manufactured home offers 2 bedrooms, 2 bathroom, and 825 sq. ft. (16 x 56 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

Kate Barry EXP Realty

Welcome to 78 86 Ethans Way, Lot 86E Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polo model manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. of thoughtfully designed living space.Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

Kate Barry EXP Realty

Charming Home with River Views & Tons of PotentialThere’s so much potential waiting to be unlocked in this spacious 4-bedroom, 1.5-bath home! With a classic layout that includes a dining room, fireplaced living room, and a cozy den, there’s room for everyone to spread out and make it their own.A large covered front porch invites you to relax and take in the neighborhood charm, while the back

Linda Benoit Highland Realty