$316,603Average Value$197Average Price per Sq Ft19Homes 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
Wendy Larson,
an experienced agent in this area.
GreatSchools:
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On average, homes in Bennington, VT sell after 52 days on the market compared to the national average of 57 days. The median sale price for homes in Bennington, VT over the last 12 months is $265,000, up 2% from the median home sale price over the previous 12 months.
Charming Ranch in a Desirable Neighborhood!Are you looking for a 3 bedroom, 2 bath ranch with room to grow in a great neighborhood? This beautifully maintained home offers the perfect blend of comfort, style, and flexibility.Enjoy a fully renovated kitchen featuring soft close drawers and a dedicated coffee bar perfect for starting your day. Stay comfortable year round with central air,
Whether you’re seeking a full-time downtown lifestyle, a lock-and-leave home base for travel, or you’re ready to make the leap from renting to owning, this is the kind of property that checks every box—location, character, and simplicity. Offered publicly for the first time, Unit 302 is filled with natural light from tall windows that frame the energy of downtown Bennington. Soaring ceilings,
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.
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
Charming Ranch in a Desirable Neighborhood!Are you looking for a 3 bedroom, 2 bath ranch with room to grow in a great neighborhood? This beautifully maintained home offers the perfect blend of comfort, style, and flexibility.Enjoy a fully renovated kitchen featuring soft close drawers and a dedicated coffee bar perfect for starting your day. Stay comfortable year round with central air,
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
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
Welcome to 41 Audrey Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) 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
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,
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
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,
Move right in to this immaculate 2-bedroom condo in the highly desirable Apple Ridge community! Meticulously maintained and thoughtfully cared for, this home offers effortless one-level living with nothing left to do but unpack. Step inside to discover a freshly painted interior complemented by new flooring and carpeting throughout. The bright and inviting kitchen features beautiful cabinetry and
Charming downtown family home with modern upgrades.This beautifully updated 3-bedroom home is perfectly situated on a desirable corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, with a recent addition of a first-floor primary bedroom and new mudroom back entrance.Step inside to find gleaming hardwood floors and a warm, inviting layout. The dining
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
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.BRAND NEW 3br MANUFACTURED HOME for rent!*Be the FIRST Tenant!*Unit: A-196Apply To: Mountain View CommunityRent: $1595/moBeds/Baths: 3 beds 1.5 bathsSize: 980 square feetPets: Cat & Dog friendly, all animals must be
Welcome to Putnam Block, Winslow Studio #307– Fully renovated studio apartment available for rent in downtown Bennington– Large windows, wood floors, high ceilings– Utilities Included (electric, heat, water and AC)– Off street parking– Free, on-site laundryThis is an income qualifying affordable unit. Annual household income for single occupancy may not exceed
$2,041 per month
Putnam Hotel – $2,041 – 1 Bedroom/1 Bathroom, 755 SQ.FT. – UTILITIES INCLUDED
Welcome to Putnam Block, Hotel #307– Beautifully renovated 1 bedroom/1 bathroom apartment available for rent in downtown Bennington– Large windows, wood floors, high ceilings– Granite countertops– Stainless steel appliances– Washer and dryer in unit– Utilities INCLUDED (electric, heat, water and AC)– Elevator– Off street parkingThis is an income
$2,041 per month
Putnam Hotel – $2,041 – 1 Bedroom/1 Bathroom, 690 SQ.FT. – UTILITIES INCLUDED, Available Immediately
Welcome to Putnam Block, Hotel #305– Beautifully renovated 1 bedroom/1 bathroom apartment available for rent in downtown Bennington– Large windows, wood floors, high ceilings– Granite countertops– Stainless steel appliances– Washer and dryer in unit– Utilities INCLUDED (electric, heat, water and AC)– Elevator– Off street parkingThis is an income
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