Bennington Real Estate

Nestled in the scenic Green Mountains of southwestern Vermont, Bennington is a charming town that beautifully blends rich history with vibrant community life. Known for its picturesque landscapes and welcoming atmosphere, Bennington offers a unique quality of life that attracts both residents and visitors alike.

With a population of just over 15,000, this quaint town is steeped in history, dating back to the Revolutionary War. Bennington is home to several historical landmarks, including the Bennington Battle Monument, which commemorates a pivotal battle in American history. Strolling through the charming downtown area, you'll find an array of boutique shops, delightful cafes, and art galleries that showcase the creativity of local artisans.

Nature enthusiasts will find Bennington to be a paradise, with countless opportunities for outdoor activities. The nearby Green Mountain National Forest offers hiking trails, fishing spots, and breathtaking views that change with the seasons. The fall foliage here is nothing short of spectacular, drawing visitors from all around to witness the vibrant colors.

Bennington also boasts a strong sense of community, with numerous events throughout the year, such as the Bennington Potters' Festival and summer farmers' markets. Local schools are well-regarded, making it an ideal place for families looking to settle down.

Whether you're drawn by its historical charm, natural beauty, or the warmth of its community, Bennington is a delightful place to call home. Experience the best of Vermont living in this enchanting town, where every corner tells a story and every day brings new adventures.

Newest Listings in 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

$189,900

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

$345,000

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

$439,000

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 40 acres +/- of 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

$1,695,000

3 Beds ⋅ 3 Baths ⋅ 5105174 MLS

Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom guest cottage. The stunning chef's kitchen is truly the centerpiece of the home, featuring high-end appliances, a dramatic quartz waterfall countertop, and a generous 10-foot island designed for both everyday living and entertaining. Just off the kitchen is a gorgeous screened-in porch, creating a wonderful extension of the living space and the perfect place to enjoy the tranquil setting. Throughout the main level, beautiful white oak floors add warmth and elegance. The home retains the charm and character expected of a historic property while offering the comfort and efficiency of today's modern systems. The thoughtful renovation continues throughout the home, with details such as automated shades in the primary bedroom and library and a convenient second-floor laundry closet. A fireplace adds warmth and character, while expansive views bring the beauty of the surrounding landscape indoors. The separate one-bedroom guest cottage provides even more versatility for guests, extended family, a private office, or potential rental use. Outside, the property is equally impressive, with gorgeous front and side patios designed for outdoor dining and entertaining, a screened-in porch, beautiful grounds, and a storage shed. A rare combination of historic architecture, exceptional renovation, modern technology, expansive acreage, and flexible living spaces, this property offers a level of quality and versatility rarely found in the Bennington market.

1944 Monument Ave, Bennington

$58,000

5104588 MLS

This lot in beautiful North Bennington is ready to go! Building plans have been drawn up and available to come with the property for an approx. 2200 sq ft 3 bed, 2 bath home with decks facing the mountains. This lot has the electric, water, and sewer available at the street. Beyond having school choice for the elementary it also boasts being the second highest elevation lot in the development, mountain views, and abuts fields owned by Bennington College. The parcel is one property away from paved walking paths that join into the Bennington Ninja Trail.

33 Asas Way, Bennington

$595,000

5104539 MLS

Some properties offer acreage, some offer breathtaking views, very few offer both along with a rich history worth preserving and a future waiting to be imagined. For generations, this rare south-facing farm has looked across the valley enjoying sunlight from dawn until dusk & panoramic views that are exceptional! More than productive farmland, it became a place where neighbors and families gathered. In 1970, the roadside farm stand sold fresh corn, tomatoes warm from the sun, potatoes, pumpkins and seasonal produce. Visitors wandered the fields to pick strawberries, while others stopped to find the day's harvest.The farm was home to beef cattle, horses and the flock of nearly sixty geese. The farm supplied local restaurants and markets with potatoes. Today, the old farm stand still watches over the fields, quietly waiting for its next chapter. Whether restored as a seasonal market, transformed into a cider tasting room with a boutique orchard, an artist's studio, or simply enjoyed as part of a beautiful country estate, the possibilities are as expansive as the landscape itself. Beyond the farm stand, the land rises gently through open meadows to what could be an exceptional homesite with panoramic south facing views. Once part of the pasture and hayfields where cattle and horses grazed, this peaceful hillside offers an extraordinary setting for a country home, where mornings begin with birdsong and evenings end with spectacular sunsets. Although it feels wonderfully private, the property is remarkably convenient. A genuine rural lifestyle with easy access to culture, travel and the city. Bennington is minutes away for shopping/restaurants, healthcare and Bennington College. Williamstown 20 min, Albany Int'l Airport & train station 45 min, Boston 3 hrs/Montreal 4 hrs.Some places are purchased, the rare ones are entrusted to their next caretaker. Come see this spectacular property for yourself, walk the land and absorb how special and unique this Vermont property is!

3213 West Rd, Bennington

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