$314,859Average Value$195Average Price per Sq Ft17Homes 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
Margretta Fischer,
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 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 $258,000, down 1% from the median home sale price over the previous 12 months.
Welcome to this charming mid-century home set on 1.27 acres, offering 4 bedrooms and 3 bathrooms. This property blends character, functionality, and unique design throughout.At the heart of the home, a beautiful open concept kitchen and living area creates the perfect space for gathering and entertaining. A stunning fireplace anchors the room, offering warmth and ambiance whether you’re
Escape to your own private sanctuary on this sprawling 54+/- acre wooded retreat in beautiful Bennington, VT. Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond situated entirely within its southeastern boundary, perfect as a future homestead centerpiece. Enjoy easy access via a paved, town-maintained road leading to level
Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a
Exceptional opportunity to own a beautifully maintained duplex in the heart of Bennington. Each spacious unit offers 3BR and 1.5BA, featuring warm wood floors, generous living space, and thoughtful layouts that appeal to both tenants and owner-occupants alike. Renovated and updated through the years, the property has been meticulously cared for and has an organized, efficient setup throughout.
Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for
A must see, well-kept 2-unit property offering flexibility for owner-occupants or investors. The main-level unit features 3 bedrooms, a full bath, a spacious eat-in kitchen with new cabinets, and a laundry room with washer and dryer. The upstairs unit offers 1 bedroom, a full bath, eat-in kitchen, and a cozy living room with hardwood floors. Exterior features include a nice, level backyard, 2
Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups—perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street. With
Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car
Freshly updated 2-story townhouse in a convenient downtown Bennington location! This 2BR home features brand new stainless steel appliances, new vinyl plank flooring, and a fresh interior paint palette throughout. The open-concept main level offers a bright kitchen, dining, and living area—perfect for everyday living and entertaining—along with a pantry, half bath, and dedicated laundry room for
Updated and ready to go. This 2 bedroom upstairs condo is perfect for those who don't want to rent, would like to build equity and would like low maintenance. A corner unit with great light and being upstairs means no neighbors overhead. 2 bedrooms, 2 bathrooms (one 3/4 and one half bath). With rents in the area rising this is a great option for most!
Max SquiersKW Vermont - Brenda Jones Real Estate Group
This 5.6-acre lot is ideally situated at the edge of town, offering a peaceful retreat surrounded by nature. Furnace Brook winds through the backside of the property, providing a soothing sound that lulls you to sleep each night. Observe the abundant wildlife as they visit the stream with the Mountain view as the backdrop, this location is perfect for building your Vermont dream home.
Welcome to your new home in North Pownal, VT! This charming property offers spectacular views in a serene setting while being just 20mins to Bennington and Williamstown. Ideal for those seeking a peaceful lifestyle while being within reach of local amenities.The spacious floor area provides ample room for relaxation and entertainment, making it a delightful place to call
This property is available now, and is fully furnished. Water/sewer, plowing, and lawn care included. The whole interior of the home has just been repainted in the last couple of years. Wood floors sanded. New stove. New Washer and Dryer, new flooring in the kitchen. Two bedrooms, 2.5 baths. The basement holds huge potential for storage. Small back deck to enjoy the creek. Two car garage. Just
203 Union St, Downstairs Back ApartmentIncluded with rent: Heat, Lawncare, Hot Water, Water/SewerFreshly painted first floor unit available at 203 Union St for $1,400 per month.This unit offers a clean, freshly painted living space in a convenient location. The apartment is ready for immediate occupancy. There is a large porch area for extra storage.Rent: $1,400
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
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
Second Floor Renovated Two Bedroom Apartment- second floor 2 bedroom, each bedroom has a closet- renovated, new windows and entry door- washer/dryer hookups in kitchen- new stove, new fridge- egress windows and carbon monoxide detectors- includes heat, garbage, plowing and lawncare- tenant pays hot water (electric) and electric - all new!- walk to all amenities,
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.
