$324,244Average Value$196Average Price per Sq Ft28Homes 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.
1/2
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.
1/4
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.
1/4
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.
1/4
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.
1/4
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
Peter West,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Bennington, VT sell after 50 days on the market compared to the national average of 56 days. The median sale price for homes in Bennington, VT over the last 12 months is $285,250, up 6% from the median home sale price over the previous 12 months.
Welcome home to this 3-bedroom, 2-bath raised ranch nestled on 1.72 beautifully landscaped acres in a peaceful neighborhood. The picturesque property is adorned with a variety of mature fruit trees and offers stunning mountain views. A spacious back deck overlooks the above-ground pool, making it the perfect setting for relaxing, entertaining, or taking in the scenery. Inside, you'll find an
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.
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
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 SquiersKW 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
This beautifully renovated 2-unit home by JDN Properties offers exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family residence with a luxurious upstairs primary suite and kitchenette, use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize
Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering living room, large kitchen, formal dining room and office/study. Covered porch and patio. Privacy bushes and yard. Property is being sold "as-is".
Max SquiersKW Vermont - Brenda Jones Real Estate Group
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
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 porch,
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..
First floor two bedroom- walk to town- living room, dining room, kitchen, full bathroom with shower stall, comes with newer electric stove and fridge, washer/dryer hookups- heat is forced hot air (fuel oil)- rent DOES NOT INCLUDE utilities- I pay for lawncare, plowing and garbage- I take first month's rent, last month's rent and one month's rent as a security deposit (3x
About a mile from the four corners. Well kept unit. W/D hookups in the unit. Heat pump system does heating and cooling. Sorry, no pets allowed. First/last/security due at lease signing. Credit and background checks required. Water/sewer, and lawn care included.
Second floor two bedroom in quiet neighborhood.- two good sized bedrooms, each with closet- living room- eat in kitchen with new floor- bathroom with shower stall- new windows- newer carpet / newly painted- great quiet neighborhood but still close to downtown- propane heat (tenant pays)- off peak electric hot water (tenant pays)- property owner pays for
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
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
