$305,091Average Value$188Average Price per Sq Ft25Homes 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
Video By
Brandon Flash Craigie
Interested in learning more about homes in this area?
Reach out to
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an experienced agent in this area.
On average, homes in Bennington, VT sell after 57 days on the market compared to the national average of 53 days. The median sale price for homes in Bennington, VT over the last 12 months is $251,300, down 2% from the median home sale price over the previous 12 months.
Cute as a button! This charming one-owner home is the perfect opportunity for a first-time homebuyer or for those looking to downsize! The main level features a welcoming layout with bright living spaces and plenty of natural light. The eat-in kitchen flows seamlessly into the living area. There are two spacious bedrooms, lots of closet space and a full bathroom. The basement level features a
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.
Welcome to 203–205 Northside Drive, a truly unique property that combines residential living with commercial potential all in one. Are you looking for the flexibility to live in an apartment while generating income from multiple rental units, or would you prefer to restore the property back into a spacious single-family residence? This property gives you both options. Currently configured with
This beautifully detailed 1880 Victorian in Bennington's residential commercial district offers flexibility and income potential all in one. Currently operating as a successful, fully furnished Airbnb, this 5-bedroom, 2-bath property is ready for its next owner. Whether you're an investor looking for cash flow or a buyer seeking a spacious and charming single family home. The main level
Well-maintained provider office space available for lease, offering approx. 1,120 sq ft. Layout includes a waiting room with half bath, reception area, 2 operatories (or rooms), private office, and an additional half bath. Shared kitchen with the adjacent unit. Staff enjoy a separate entrance and designated parking, distinct from the public entry and lot. Rent includes electric, heat/AC,
This freshly painted, recently renovated 2 bedroom unit is now available! 1300/month rent. Washer and Dryer hookups in the unit. Heat pump system with multiple heads handles the heat and cooling. Water/Sewer included in the rent. Owner willing to consider pets with a pet deposit and additional monthly fee. No smoking. First/last/security due at lease signing. Credit and background checks required.
Fantastic whole house rental available! This 2 bed, one bath house is a rare rental find. Starting outside it features a large back deck, and a 1 car garage. Moving inside it is all updated! stainless steel appliance, life-proof flooring throughout, ceiling fan in the primary bedroom, and even a finished basement for tons of extra space! There is even a security system if you choose to do a
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