Bennington Real Estate

Welcome to Bennington, Vermont, a charming town nestled in the picturesque Green Mountains. Known for its rich history and vibrant arts scene, Bennington is a place where small-town charm meets stunning natural beauty. With a population of just over 15,000, this tight-knit community offers a welcoming atmosphere that makes newcomers feel right at home.

Bennington is steeped in history, with roots dating back to the late 18th century. The town is home to several historical landmarks, including the Bennington Battle Monument, which commemorates a pivotal battle in the American Revolutionary War. Strolling through the quaint downtown area, you’ll discover unique shops, delightful cafes, and art galleries that showcase the talents of local artisans.

Nature enthusiasts will find plenty to love about Bennington. The surrounding mountains provide ample opportunities for outdoor activities, from hiking and biking to skiing and snowboarding in the winter months. The nearby Green Mountain National Forest offers breathtaking views and trails for all skill levels, ensuring that adventure is always just around the corner.

Bennington also boasts a vibrant cultural scene, with events and festivals happening year-round. The Bennington Museum showcases the region's art and history, while the local theater company offers performances that entertain and inspire.

Whether you’re looking to settle down in a cozy home, explore the great outdoors, or immerse yourself in a rich cultural tapestry, Bennington is the perfect place to call home. Discover the magic of this enchanting town and see why so many are drawn to its beauty and charm.

Newest Listings in Bennington

$385,000

3 Beds ⋅ 2 Baths ⋅ 5109164 MLS

Set on 1.84 acres in Bennington, this 3-bedroom ranch pairs a warm, character-filled interior with established gardens, a wooded backdrop, and one of the home's best surprises: an oversized screened porch made for summer living. The bright kitchen has been updated with granite counters, an apron-front sink, white cabinetry and a gas range, and opens to a cozy living/dining area with wide-plank pine floors, an exposed beam, wood stove, and a broad bank of windows overlooking the front yard. Just off the kitchen, the screened porch adds a substantial amount of usable space, complete with its own sink and a dedicated propane line for the grill. All three bedrooms and the full bath are on the main level. Downstairs, 592 square feet of finished space and a 3/4 bath create a flexible second living area well suited to guests, a media room, hobbies, or a home office. The unfinished portion of the basement offers plenty of room for storage, utilities, and workshop space. Outside, years of gardening show in the mature plantings and colorful beds surrounding the home, with open lawn around the house and woods behind. Enjoy a country setting with recreation close by at Crotched Mountain Ski & Ride and Powder Mill Pond, while downtown Peterborough is about 18 minutes away. Fiber optic internet is available. A warm and inviting home with flexible living space, established gardens, and a peaceful country setting.

224 S Bennington Rd, Bennington

$240,000

3 Beds ⋅ 2 Baths ⋅ 5109090 MLS

Well maintained and updated 2011 double wide with 3 bedrooms and 2 full bathrooms situated on 1.33 acres in Bennington. Offering new flooring through most of the house and new appliances. Large living room, kitchen and laundry room. Primary bedroom has a private full bath. Nice property and great location.

2200 Chapel Rd, Bennington

$589,900

3 Beds ⋅ 4 Baths ⋅ 5108314 MLS

Magnificent Views & 7.05 Acres in North Bennington Experience the beauty and tranquility of the Vermont countryside from this inviting three-bedroom, three-and-a-half-bath home, privately situated on 7.05 scenic acres in North Bennington. A circular driveway welcomes you to a picturesque setting of expansive lawns, mature trees, and magnificent long-range mountain views, offering an exceptional combination of privacy, open space, and classic Vermont scenery. Inside, generous, versatile living spaces include a family room, recreation room, dining room, and kitchen, providing plenty of room for everyday living and entertaining. Two fireplaces add warmth and character, while a four-season sunroom directly off the living room offers an inviting place to relax year-round. The magnificent mountain views can be enjoyed from inside the home as well, including a picture-perfect view directly from the kitchen. One of the property's most impressive features is the massive deck overlooking the countryside and distant mountains—perfect for morning coffee, outdoor dining, entertaining, or simply relaxing and enjoying Vermont's spectacular changing seasons. A fenced area provides additional space for outdoor living and activities. A solar array significantly reduces electric costs, adding energy efficiency and substantial savings. The two-car garage features an oversized storage area behind it, providing exceptional space for equipment, recreational gear, lawn and garden supplies, or additional storage. With 7.05 acres, breathtaking views, spacious living areas and a peaceful country setting, this special North Bennington property captures the beauty of Vermont living.

436 Matteson Rd, Bennington

$325,000

3 Beds ⋅ 2 Baths ⋅ 5106631 MLS

Welcome to this inviting Cape-style home offering 3 bedrooms, 2 baths and a comfortable layout designed for both everyday living and entertaining. The main level features an open-concept kitchen and dining area that flows directly onto a huge back deck—an ideal spot for summer dinners, gatherings or simply relaxing while overlooking the secluded, wooded backyard. With both a living room and separate family room, there is plenty of space to spread out, while first-floor laundry adds everyday convenience. The partially finished basement offers additional flexible space for a home office, recreation room, gym or hobbies. Outside, enjoy a peaceful Vermont setting with mountain views, nearby trails and a creek just a short walk away that’s a favorite local spot for cooling off on warm summer days. Tucked away in a private setting yet conveniently close to downtown Bennington, this home offers the best of both worlds: room to relax, space to entertain and easy access to everything the area has to offer.

171 Garbrooke Dr, Bennington

$349,900

5106581 MLS

Side-by-side duplex in a sought-after area in the heart of Bennington, offering the charm of yesteryear with modern conveniences. This well-maintained property presents an excellent investment opportunity, whether you're looking for a rental property generating substantial income or the option to owner-occupy one unit while renting the other to help offset your mortgage. Boasting many tasteful renovations and updates in recent years, both units feature gorgeous refinished hardwood floors and a spacious, functional layout. Each unit offers a living room, dining room, kitchen, and half bath on the first floor. Upstairs, you'll find three bedrooms, an office space, and a full bath. Each unit has its own large, inviting front porch with peeks of mountain views, perfect for relaxing or enjoying time with family and friends. Private back decks overlook the spacious backyard, while a three-car garage provides additional parking and storage. A full basement is divided between the two units, providing separate storage and laundry areas, while a walk-up attic offers even more storage space. Each unit has its own electrical and heating systems, with utilities paid by the tenants. Additional features include forced hot air heating systems with new ductwork, town water and sewer, and a classic slate roof. Ideally located near Southwestern Vermont Medical Center, public transportation, scenic hiking trails, and Bennington's vibrant Main Street, with its shops, restaurants, and year-round community events. A wonderful opportunity to own an income-producing property in a convenient Bennington location while enjoying the character and charm of a classic Vermont home.

219-221 Washington Ave, Bennington

$395,000

4 Beds ⋅ 2 Baths ⋅ 5106470 MLS

Charming 4-bedroom, 1.5 bathroom house on private lane in desirable North Bennington, steps from Bennington College and a short walk to the Village center's restaurants, library, and shops. The home's first floor features an updated eat-in kitchen with granite countertops, dining room, living room with fireplace, half bath, and study with built-in bookcases, as well as a sun room which leads to the covered back porch. Upstairs, there are 4 bedrooms and a full bath. An airy sunroom off the primary bedroom could function as an office or a yoga/exercise room. With beautiful hardwood floors and kitchen and bathroom tile installed in 2018, the house features wildlife and tree-filled views from nearly every window. There is a 1-car attached garage with automatic opener, off-street parking, and a large, picturesque front yard with fruit trees and beds for gardening if desired. Park McCullough's bucolic trails are just a half-mile away. A half-hour drive to Williamstown and Manchester, North Bennington is a quiet, historic area. North Bennington Village School and close to downhill and cross-country skiing, hiking, and snowmobile trails. A quintessential New England village.

2 Bromley Ln, Bennington

$199,900

3 Beds ⋅ 1 Baths ⋅ 5106353 MLS

Discover the potential of this charming 3-bedroom, 1-bath cabin situated on 2.17 private acres. Offering a peaceful and secluded setting while still conveniently located close to town, this property provides the best of both worlds. The property also includes a barn, providing additional space for storage, hobbies, or other possibilities. The home is served by an existing well and septic system, and all contents currently in the house and garage will remain with the property. Whether you're looking for a year-round home, a quiet getaway, or a property to make your own, this cabin offers plenty of potential in a private setting.

12 Hurley Ln, Bennington

$179,900

2 Beds ⋅ 1 Baths ⋅ 5106352 MLS

Cute, cozy, and move-in ready! This freshly renovated 2-bedroom, 1-bath home has been updated from the ground up and offers comfortable, low-maintenance living in a convenient Bennington location. Recent improvements include a brand-new kitchen and bathroom, new flooring, fresh paint, new baseboards, new roof, front porch and expanded driveway. The home features electric baseboard heat along with a pellet stove for added warmth and comfort, plus washer and dryer hookups. Public water and sewer add to the convenience. Small and easy to maintain, this charming home is ideal for a first-time buyer, someone looking to downsize, or anyone searching for a turnkey property. Conveniently located close to shopping, dining, recreation, and all the amenities Bennington has to offer. Move right in and enjoy!

301 Beech St, Bennington

$330,000

2 Beds ⋅ 2 Baths ⋅ 5106263 MLS

Completely renovated, turnkey single-level home offering mountain views, modern finishes, and a beautiful country setting. All major systems and cosmetic updates were completed within the last year, including a brand-new roof and new windows. The light-filled interior layout features 2 bedrooms, 2 full bathrooms, brand-new wood flooring across all main living areas, plush new bedroom carpeting, and a cozy wood-burning fireplace. Enjoy the modern kitchen and designer bathrooms with high-end contemporary finishes, plus the convenience of an in-unit laundry room built directly into the primary suite's walk-in closet. The home also includes an attached 1-car garage and a huge, clean unfinished basement providing exceptional storage, workshop space, or potential future expansion. Outside, the property is fully set up for relaxation and privacy with a fully fenced backyard, multiple front and rear patios, a detached storage shed, a mature apple tree, and a private, fenced-in hot tub accessible directly via a private door off the primary bath. Conveniently located with quick access to Route 9, local amenities, and outdoor recreation.

1141 Burgess Rd, Bennington

$449,000

3 Beds ⋅ 3 Baths ⋅ 5106158 MLS

TO BE BUILT: This charming 3-bedroom Cape offers a comfortable and functional layout with a desirable first-floor primary ensuite bedroom, convenient first-floor laundry, and two additional bedrooms on the second level. The home features stylish vinyl plank flooring and granite countertops, blending modern finishes with everyday practicality. Situated in a quiet residential neighborhood close to town, this property provides easy access to local amenities, golf course, and the popular Crotched Mountain ski area. Conveniently located less than 40 minutes from I-89, I-93, and Concord, this home offers both small-town charm and commuter accessibility.

Lot 10-48-1 Old Stagecoach, Bennington

$4,750,000

11 Beds ⋅ 7 Baths ⋅ 5106118 MLS

Located in the heart of the Monadnock Region, reknown for its cultural offerings, close knit communities, protected landscapes and recreational amenities including Crotched Mountain Ski area in town and nearby Crotched Mountain Golf Club. An impressive farm since the early 1800's, Pierce Hill Farm was transformed to a gentleman's estate in 1909. . Its over 306 acres feature extensive hayfields managed by a local farmer, cut stone walls built by Irish masons, gravel carriage roads, walking paths, a private pond, and mountain views. The three story main house has been conscientiously maintained and enjoys lovely grounds with gardens, broad lawn, in-ground pool with patio, tennis court and beautiful views. The first floor boasts large, gracious rooms for entertaining or family gathering. The second floor had a primary suite, two guest bedrooms and four small bedrooms in the kitchen wing. On the third floor are four large bedrooms and two more baths. Also dating from 1909 are the two bedroom, two bath guest house, the five bedroom, two bath farm manager's residence, and the former milk house, now a two bedroom one bath residence. An additional two bedroom 1 bath residence was built in 1961. All the houses enjoy a screened porch with a lovely, private outlook. Farm buildings incude the old dairy barn with slate roof, full hayloft, 2 bay vehicle storage, 4 animal pens and water hydrant. Its attached ell has a tractor bay, box stalls,hayloft, and more animal pens below. The horse barn was built as a showplace with a vaulted two story entry. Clerestory windows light the hayloft below the slate roof. The main aisle is floored with wood bricks and the stall walls have been removed, creating a light open space. The main floor also has a heated workshop, old plumbing, and storage rooms. A full, walkout lower level is used for storage. Additional outbuidings include a garden house, sap house, equipment barn, and old ice house now used for storage.

92,94,96,98,100 Pierce Hill, Bennington

$325,000

3 Beds ⋅ 1 Baths ⋅ 5105313 MLS

There is something special about a home with character, and this charming 3BR property has it in abundance! Set in an established neighborhood within sight of the Mt. Anthony Country Club, this inviting home offers the warmth and craftsmanship of an earlier era combined with the comforts buyers are looking for. From the moment you arrive, the covered front porch welcomes you home. With generous space for rocking chairs or outdoor seating, it's the perfect place to enjoy your morning coffee, unwind after a long day, or simply take in the peaceful surroundings. Step inside and you'll immediately notice the beautiful hardwood floors and natural wood trim that carry throughout the main living spaces. The spacious living room flows seamlessly into the dining room, creating a comfortable layout for both everyday living and entertaining. The kitchen is bright, cheerful, and functional, with white cabinetry, granite countertops, stainless steel appliances, glass-front cabinetry, and excellent natural light. A distinctive painted wood floor adds personality and charm while providing a fun contrast to the traditional finishes throughout the rest of the home. Upstairs, you'll find three bedrooms, each with hardwood flooring and generous windows. In addition to the covered front porch, the property features an enclosed back porch which leads to a beautiful stamped concrete patio, creating a wonderful space for outdoor dining, entertaining, or simply enjoying a summer afternoon. The property also offers a 1 car garage, providing convenient parking and additional storage. The setting is particularly appealing, with the golf course just across the way, while the established neighborhood offers a sense of community and timeless New England charm. If you're looking for a home with genuine character, a wonderful setting, and spaces that feel both gracious and livable, you'll want to see this one soon!

51 Pageant St, Bennington

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