$332,209Average Value$202Average Price per Sq Ft23Homes For Sale
A small town with a big heart in Vermont's Green Mountains
Nestled within the Green Mountains of southwestern Vermont, Bennington is a town celebrated for its rich history, outdoor trails and skiing, as well as its historic buildings along Main Street. Dating back to 1749, Bennington holds a significant place in the state’s heritage as the first town chartered in Vermont. The Old Bennington Historic District is a window to the past, where the Bennington Monument and the Old First Church Cemetery teach new residents about times of old. Today, downtown is investing in a bandstand for summer concerts, a splash pad for families and a growing arts and theater scene. “I was born and raised in Bennington. I’ve moved away a couple of times, but I’ve always moved back. Once people realize how quiet, serene and comfortable it is here, you really fall in love with the mountains,” says Brooke Thomson Drew, a Realtor with Mahar McCarthy Real Estate and lifelong local whose family has been active in the local business community for over 40 years.
The Putnam Hotel in Bennington has been restored to its original grandeur and contains retail shops and eateries.
The Bennington Monument is 306 foot obelisk dedicated to a pivotal moment in The Revolutionary War.
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Historic and modern housing options in Bennington
Old Bennington has more historic homes that can date back to the Battle of Bennington in 1777. Shaftsbury and Arlington homes are more rural, with rolling hills surrounding family farms and popular maple sugaring houses. Main Street’s historic buildings, shops and restaurants are within a short distance from downtown homes. “The nice thing about being in this area is there’s a lot of housing to cover so you can find exactly what your desired lifestyle needs.” Drew says. From new buildings to restored historic spaces, homeowners and businesses can choose from a variety of options. “There are people in all stages of life moving to Bennington,” Drew says. “I’ve helped first-time homebuyers, people who are looking for second homes near the mountains and those relocating to find a home to retire in.” The median price for a single-family home in Bennington is around $250,000, though most fully renovated options with modern features range between $300,000 and $650,000.
Rural homes sit along the hillsides of Bennington overlooking the city center.
Historical homes can be spotted throughout Bennington like this light green clapboard home.
Multifamily homes and workers' cottages are the most popular housing style near Bennington's town center.
A stone home near the Bennington Monument has a plaque on it remembering its historical significance.
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Four seasons of fun skiing, hiking and spending time outside
Bennington residents spend time outside all year, and its no wonder that famous poet Robert Frost penned stories about the beauty of nature here. “We love our four seasons,” Drew says. From the changing fall foliage, winters on mountain slopes and summers spent on hiking trails and mountain bikes, there is always something to explore. “A lot of people from all over the country move here for the natural waterfalls, rivers for fly fishing or tubing, not to mention skiers and hikers who want to live near the mountains,” Drew says. Robert Frost's home is now a museum in Bennington, tucked into the grassy hills. During winter, students spend weekday afternoons on the nearby Prospect Mountain Ski Area slopes, barely 8 miles east. The Bennington Recreation Center has an indoor pool.
A worker at Bike Hub in Bennington repairs a mountain bike.
A narrow bridge on a hiking trail crosses a tributary of the Walloomsac River in Bennington.
Lake Paran in North Bennington is a popular location for locals to ice skate in the winter and swim in the summer.
Cross country skiers participate in a race at Prospect Mountain, near Bennington.
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Main Street shops and restaurants in historic Bennington buildings
Bennington’s downtown has a classic New England charm, with historic buildings that house shops, offices and locally owned restaurants. “You’re about 25 minutes from Manchester, which has tons of restaurants and different farmers’ markets, but you’ve also got a lot of diverse restaurants here on Main Street,” Drew says. There is authentic English food, homemade ice cream, deli marts, bagel shops and cozy pubs. “Going out to eat isn’t the problem; deciding what to eat is the problem.” There are about a dozen small grocery stores and markets around town, including Bennington Community Market and Benmont Ave Produce. Aldi is located on the north side of downtown on Kocher Drive, less than a mile away from the Walmart Supercenter on Northside Drive.
The 421 Craft Bar & Kitchen in Bennington has an outdoor patio for warm weather dining.
Manchester is a town 30 minutes north of Bennington where residents can dine and shop.
Harvest Brewing in Bennington is a small bar where locals can gather for live music and great beers.
Residents of Bennington looking to shop at big box stores can buy essentials at Walmart in Monument Plaza.
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Local grade schools and higher education at Bennington College
Bennington Elementary School is graded an overall D-minus on Niche, while Mount Anthony Union Middle School is rated a C. Mount Anthony Union High School is rated a C-plus and offers students the option to take daytime career center courses at Southwest Tech. Private schools include Grace Christian School, which teaches prekindergarten through 12th grade and is rated an overall B-minus on Niche.
There are also several colleges in town, including the Community College of Vermont, Northeastern Baptist College and Castleton University Nursing School. Bennington College has a large, green campus north of downtown. It’s a private non-religious liberal arts school known for its visual and performing arts programs, as well as plenty of internship opportunities.
Bennington Elementary School serves students in grades kindergarten through 5th.
Mount Union Middle School in Bennington serves students in grades 6-8/
Mount Union High School in Bennington serves nearly 1,000 students in grades 9-12.
Bennington College, located in North Bennington is known for its unique academic plan.
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Commutes to Manchester and nearby state borders
Bennington is just 25 miles south of Manchester, which drivers can reach by traveling about 30 minutes north on US Route 7. The New York and Massachusetts borders aren’t far away, allowing residents to head southwest to Albany or southeast to Springfield. Folks don’t have to travel far to reach Southwestern Vermont Medical Center just off Dewey Street in town, and Green Mountain bus lines and micro transit services run throughout town.
Crime in Bennington
According to FBI data, incidents of both violent and property crime saw a decrease in 2023.
Written By
Shelby Sullivan
Photography Contributed By
Matt Barrett
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Brandon Flash Craigie
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On average, homes in Bennington, VT sell after 53 days on the market compared to the national average of 55 days. The median sale price for homes in Bennington, VT over the last 12 months is $287,800, up 12% from the median home sale price over the previous 12 months.
Some properties offer acreage, some offer breathtaking views, very few offer both along with a rich history worth preserving and a future waiting to be imagined. For generations, this rare south-facing farm has looked across the valley enjoying sunlight from dawn until dusk & panoramic views that are exceptional! More than productive farmland, it became a place where neighbors and families
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
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
Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience.Public water and sewer are available,
Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home.Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process.
Some properties offer acreage, some offer breathtaking views, very few offer both along with a rich history worth preserving and a future waiting to be imagined. For generations, this rare south-facing farm has looked across the valley enjoying sunlight from dawn until dusk & panoramic views that are exceptional! More than productive farmland, it became a place where neighbors and families
Secluded serenity meets unmatched convenience on this sprawling 54+/- wooded acres in beautiful and historic Bennington, VT! Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond, perfect as a future homestead centerpiece, with your home set back just beyond the pond. Good access via a paved, town-maintained road leading to level
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
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
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,
Here is the blank slate for your Vermont home, offering beautiful views of the Green Mountains and a location that is just steps from a 160-acre wildlife preserve with numerous hiking trails, wetland viewing platforms, and abundant wildlife. This cute corner lot is mostly level, cleared, and ready to build, with town water and sewer available at the street. Bring your imagination and come and
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
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 a camp
Newly Constructed Luxury Apartments in Bennington, VermontWelcome to 757 Main Street, a newly constructed apartment community offering modern living in a convenient Bennington location. Choose from a variety of thoughtfully designed studio, one-bedroom, and two-bedroom residences created for everyday comfort and easy living.The property is conveniently located near local dining,
Property Id: 810906 1 bedroom apartment is located on second floor.Month to month lease where tenants pay for their utilities such as heat electric etc..
Available June 1st. Bennington, VTAccepting applications for our lovely large downstairs apartment in a period Victorian home on a tree shaded street with much original 19 century woodwork remaining. Off street parking for one car only. Lush lawn and mature plantings. Large front porch. Hookups for washer and dryer. Every room has new paint and Scrubbed clean from stem to
Please read instructions below on how to tour or apply. The green "Request To Apply" button will cause a delay in our ability to respond.3br MANUFACTURED HOME for rent!*Open Floor Plan**Covered Porch**Fireplace*Unit: B-061Apply To: Mountain View CommunityRent: $2100/moBeds/Baths: 3 beds 2 bathsSize: 1,624 square feetPets: Cat & Dog friendly, all
Please read instructions below on how to tour or apply. The green "Request To Apply" button will cause a delay in our ability to respond.COMPLETELY RENOVATED 3br MANUFACTURED HOME for rent!*Large 2-CAR Garage!**Desirable Lot*Unit: M-009Apply To: Mountain View CommunityRent: $2125/moBeds/Baths: 3 beds 1.5 bathsSize: 980 square feetPets: Cat & Dog
4 Bedroom / 1 Bath Duplex for Rent - Charm abounds in this 3 bedroom duplex!* Downstairs: 1 bedroom/home office, living room, kitchen and dining room* Upstairs: three bedrooms with grey painted floors* Heat is oil cast iron steam radiators; oil hot water tank* Newer electric stove and energy efficient fridge* Washer/dryer hookups in the basement* Not much of a yard, but
*MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!Spacious 3 bedroom unit located in downtown Bennington. A spacious apartment with front and back entrance. Walking distance to stores, restaurants, and many more! Experience the charm of Bennington and all it has to offer from the comfort of your new home. Don't miss out on this opportunity to live
*MANAGED BY HALE APARTMENTS*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!This charming apartment offers a cozy and comfortable living space with two bedroom and one bathroom. Immerse yourself in the rich history of Bennington as you explore the vibrant downtown area, just steps away from your doorstep. The apartment boasts a convenient location, allowing you to
*MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS! Welcome to 207 Maple St. #3, located in the charming town of Bennington, VT. This cozy apartment offers 2 bedrooms and 1 bathroom, providing ample space for comfortable living. Situated in a prime location, this apartment is perfect for those seeking a convenient and hassle-free lifestyle.
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