$249,000 $177 per sq.ft. Village of North Bennington in Town of Bennington VT Home »


Price Change! Reduced by $50,000 down 20% on September 10th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1408  |  Acres: 0.25
Listed on Friday May 8, 2026
Description: 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 floor laundry, a beautiful front porch perfect for morning coffee or evening cocktails, and a private backyard ideal for entertaining, gardening, or simply relaxing while still enjoying the benefits of in town living. Owned and cherished by the same family for many years, this property has been exceptionally cared for and offers too many updates to count. From the inviting turquoise staircase to the unique character and charm found throughout the home, every corner tells a story. Take a stroll to local coffee shops, dinner spots, and community events, or enjoy hearing music drifting from the nearby Park-McCullough concert series on summer evenings. This home offers the perfect balance of neighborhood living, privacy, and small town charm. A true North Bennington gem full of warmth, character, and uniqueness this is a must see property. Call today for your private showing. This one will not last long! See Listing Details & 33 images. Includes a Virtual Tour

$255,000 $190 per sq.ft. Village of Bennington in Town of Bennington VT Home »


Price Change! Reduced by $40,000 down 16% on September 10th 2026
3 Beds | 1 Baths |   Total Sq. Ft. 1344  |  Acres: 0.25
Listed on Thursday Apr 16, 2026
Description: This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back deck. Featuring replacement windows for energy efficiency, a paved driveway, and ample yard space, this property is ideal for anyone seeking extra room to play and entertain. Sidewalks and streetlights make evening strolls safe and pleasant, and the proximity to downtown ensures you're close to shopping, dining, and public transportation. For outdoor enthusiasts, the location is unbeatable: just 10 minutes from Prospect Ski Area, 30 minutes to Mt. Snow, 45 minutes to Albany Airport, 3 hours to New York City or Boston, and 2 hours to Hartford. This home is ready for your finishing touches to make it truly your own. See Listing Details & 45 images.

Under Contract Bennington VT Home for sale $265,000 $157 per sq.ft.

$265,000 $157 per sq.ft. Bennington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1688  |  Acres: 0.26
Listed on Saturday Jul 11, 2026
Description: Welcome to this 3 bedroom, 1.5 bath Cape style home located in a planned commercial zone. Offering 1,688 square feet of well-designed living space on a manageable 0.26-acre lot, this inviting residence is perfect for comfortable family living. Offers beautiful hardwood floors gracing the upstairs bedrooms, as well as the spacious living and dining rooms--ideal for gathering with loved ones. The sunroom provides a bright and tranquil spot to relax or enjoy morning coffee, while the two-car garage ensures plenty of space for vehicles and storage. See Listing Details & 28 images.

$299,000 $212 per sq.ft. Bennington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1411  |  Acres: 0.18
Listed on Wednesday Jun 17, 2026
Description: Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out. The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even a pantry! The kitchen flows seamlessly into the dining room and the the living room, creating an open and inviting atmosphere where family and guests can easily gather. Laminate flooring throughout the first floor provides durability and a clean, cohesive look. Convenience is key with a practical mudroom entry and first-floor laundry. The full bathroom on the main level features a relaxing soaking tub with jets, perfect for unwinding after a long day. Upstairs, you'll find three comfortable bedrooms with attractive wood flooring, along with a half bath. The primary bedroom includes a walk-in closet, offering excellent storage and organization. Additional living space awaits in the partially finished basement, which is already prepared for radiant heat, providing exciting possibilities for future expansion. Recent energy-efficient improvements include heat pumps for year-round heating and cooling, as well as added attic insulation to enhance comfort and reduce utility costs. Appliances have all been updated rescently - Microwave, dishwasher, heat pump system, stove, washer, dryer, and refrigerator, and a basement refrigerator and chest freezer. The boiler was also replaced in 2022. Outside, the property offers even more versatility with two outbuildings for storage, along with a charming gazebo that creates the perfect setting for outdoor relaxation, or entertaining. Combining functional updates, flexible living space, and attractive outdoor amenities, this property is ready to welcome its next owners home. See Listing Details & 52 images.

Under Contract Bennington VT Home for sale $299,000 $163 per sq.ft.

$299,000 $163 per sq.ft. Bennington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1829  |  Acres: 0.93
Listed on Wednesday Jun 17, 2026
Description: 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 incredible versatility. The bonus space presents endless possibilities for a home based business, professional office, hobby space, expanded living area, or potential in-law accommodations. Whether you're looking for room to grow, work from home, or create a space tailored to your lifestyle, this home offers the flexibility to make it happen. The generous lot and rear garage access provide additional opportunities for future improvements. Buyers may appreciate the potential to enhance accessibility and functionality with a redesigned driveway configuration, such as a circular drive, while maximizing the usefulness of the garage space and expansive yard. Enjoy the convenience of being just minutes from downtown Bennington's shops, restaurants, coffee houses, and local attractions, while still enjoying the privacy of a large lot. With easy access to area hiking trails, ski resorts, and major routes to Boston and New York, this property combines location, character, and opportunity in one exceptional package. See Listing Details & 38 images.

Under Contract Bennington VT Home for sale $309,900 $163 per sq.ft.

$309,900 $163 per sq.ft. Bennington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1900  |  Acres: 0.31
Listed on Tuesday Apr 21, 2026
Description: Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a must see location. See Listing Details & 38 images.

$319,900 $213 per sq.ft. Village of North Bennington in Town of Bennington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1500  |  Acres: 0.53
Listed on Monday Apr 20, 2026
Description: Much larger than it looks and completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom with private bathroom and an additional bedroom. Outside you'll find a large front yard that has been partially fenced, a large covered, wrapping deck for entertaining and outdoor dining and a dog fenced area. Great location across the road from a calm river. This home is larger than it appears from the road. A must see home in move in ready condition that could possibly sold furnished. See Listing Details & 43 images.

$325,000 $260 per sq.ft. Bennington VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1248  |  Acres: 0.34
Listed on Sunday Aug 16, 2026
Description: 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! See Listing Details & 38 images.

$325,000 $193 per sq.ft. Bennington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1688  |  Acres: 0.29
Listed on Tuesday Aug 25, 2026
Description: 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. See Listing Details & 25 images.

Under Contract Bennington VT Home for sale $349,000 $183 per sq.ft.

$349,000 $183 per sq.ft. Bennington VT Home »


Price Change! Reduced by $26,000 down 7% on August 29th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1911  |  Acres: 1.16
Listed on Tuesday Aug 11, 2026
Description: Tucked into a beautifully maintained neighborhood, 21 Russett Drive is the kind of home that feels welcoming the moment you arrive. Beautiful landscaping, a charming Dutch door, and a thoughtfully cared for yard give this property an almost secret garden feel private, inviting, and full of character. Inside, the versatility of this home truly shines. The main level offers a comfortable living room with striking open wood ceilings that naturally become the focal point of the space, creating a warm setting for relaxing and gathering with family and friends. The kitchen flows easily into the dining area, making everyday meals and entertaining feel effortless. A convenient first floor laundry room adds to the home's functionality. With three bedrooms and two bathrooms, there is plenty of space for everyone, while the additional den/family room offers endless possibilities. Use it as a family room, playroom, home office, guest space, or even a first floor bedroom the choice is yours. Upstairs, one of the bedrooms could easily be transformed into a dedicated office, reading room, or creative space. Step outside onto the new deck and enjoy a backyard that has been lovingly landscaped and maintained, offering a wonderful extension of the home's living space. Served by town water and septic, this property has been meticulously cared for and is truly move in ready. Its thoughtful layout, flexible spaces, inviting outdoor areas, and ability to adapt as your needs change make 21 Russett Drive a home you can settle into today and continue to make your own for years to come. A home with character, versatility, and room to grow this is one you'll want to see. See Listing Details & 33 images.

$375,000 $186 per sq.ft. Bennington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2016  |  Acres: 1.6
Listed on Tuesday Aug 11, 2026
Description: Tucked into Bennington's established Spring Hill neighborhood, this inviting 3 bedroom, 2 bath home offers nearly 2,000 square feet of comfortable living space with a setting that makes it easy to enjoy the outdoors. From the backyard, follow the grass walking trail to the community owned pond, a wonderful extension of your outdoor space and a beautiful spot to enjoy the changing Vermont Seasons. Inside, the living room opens naturally to the kitchen and dining area, creating a connected space for everyday living and entertaining. A separate family room provides plenty of room to spread out and features a woodstove hookup, ready to add warmth and ambiance on chilly evenings. The four season sunroom is a standout, offering a cozy year round spot for morning coffee, reading, relaxing or simply enjoying the backyard views. The home is ready for some cosmetic updating, offering the perfect opportunity to bring your own style and vision while building on an already comfortable and functional layout. Three bedrooms, a deck overlooking the backyard, attached garage and paved driveway, there's plenty here to work with. Add your personal touches and make this Spring Hill home your own. See Listing Details & 37 images.

Under Contract Bennington VT Home for sale $389,900 $279 per sq.ft.

$389,900 $279 per sq.ft. Bennington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2098  |  Acres: 1.72
Listed on Monday Aug 3, 2026
Description: 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 oversized, updated kitchen featuring soft-close cabinetry and plenty of space for gathering. The breakfast nook overlooks the inviting living room, where a cozy pellet stove creates a warm and welcoming atmosphere. A formal dining room provides additional space for hosting family and friends. The mostly finished basement offers endless possibilities, whether you're looking for a recreation room, home office, workout space, or the ultimate man cave, while still providing ample storage. The heated two-car garage is equipped with an electric vehicle charger, adding modern convenience to this thoughtfully cared-for home. Combining comfortable living spaces, beautiful outdoor amenities, and a sought-after location, this home is ready for its next chapter! See Listing Details & 33 images.

$589,900 $246 per sq.ft. Bennington VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 2800  |  Acres: 7.05
Listed on Friday Sep 4, 2026
Description: 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. See Listing Details & 50 images.

Under Contract Bennington VT Home for sale $595,000 $250 per sq.ft.

$595,000 $250 per sq.ft. Bennington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2379  |  Acres: 16.96
Listed on Saturday Jul 11, 2026
Description: Nestled on 16.96 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and welcoming space for relaxing or entertaining. The flexible floor plan provides three bedrooms plus an additional room that can easily serve as a fourth bedroom, home office, or hobby space. The walkout unfinished basement offers endless possibilities for future expansion, storage, or a workshop. Outside, you'll find an attached two-car garage along with a separate bonus garage, providing ample space for vehicles, recreational equipment, or additional storage. Set well back from the road, the property's 16.96 acres offer room to explore, garden, or simply enjoy the peace and beauty of Vermont. The home is serviced by a private well and efficient oil heat source, making it a wonderful opportunity for those seeking country living without sacrificing comfort. See Listing Details & 30 images.

$1,695,000 $411 per sq.ft. Bennington VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 4120  |  Acres: 5.63
Listed on Saturday Aug 15, 2026
Description: 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. See Listing Details & 53 images. Includes a Virtual Tour

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