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$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
$499,900
3 Beds ⋅ 3 Baths ⋅ 5102749 MLS
Welcome to this beautifully maintained Cape-style home in the desirable Pine Meadows neighborhood of Bennington. At only 6 years young and meticulously maintained, this move-in ready home offers the perfect combination of modern construction, energy efficiency, and comfortable living space. The thoughtfully designed floor plan features a sought-after first-floor primary suite with a walk-in closet and private full bath, providing the convenience of single-level living. The bright, open-concept kitchen, dining, and living areas create an inviting space for everyday living and entertaining. Just off the kitchen, a stunning 10' x 20' sunroom extends your living space and serves as the perfect spot to enjoy morning coffee, unwind with a book, or host guests. With direct access to the backyard, it creates a seamless connection between indoor and outdoor living. Upstairs, you'll find two additional bedrooms both with walk-in closets and a full bath between them, while the finished lower-level bonus room offers excellent flexibility as a family room, home office, fitness area, or hobby space. Year-round comfort is provided by an efficient Buderus boiler and a five-head mini-split system offering heating and cooling throughout the home. Additional highlights include a two-car attached garage, generator-ready electrical setup, paved driveway, first floor laundry, and a beautifully maintained one-acre lot offering space to relax, garden, and enjoy the outdoors. Conveniently located just minutes from downtown Bennington, Antrim, Peterborough, hiking trails, golf, and the many amenities of the Monadnock Region, this exceptional home offers the ideal balance of peaceful neighborhood living and modern convenience. With quality construction, thoughtful upgrades, and meticulous care throughout, this is a home you'll be proud to own.

82 Pine Meadows Cir, Bennington
$739,900
3 Beds ⋅ 3 Baths ⋅ 5102468 MLS
Owner-built and thoughtfully maintained, this spacious home offers room for everyone with three bedrooms, three bathrooms, a three-car direct-entry garage with a walk-up attic, and equestrian amenities including a three-stall stable, fenced pasture, and nearby area trails. Follow the slate walkway to the 16' x 25' storage barn, or enter from the covered porch and enjoy the quiet surroundings. Inside, a bright and welcoming foyer opens to a staircase and balcony hall, a private living room with a rock-faced wood-burning fireplace, and a formal dining room with wainscoting. The kitchen features stainless steel appliances, granite countertops, a pantry closet, desk area, breakfast bar, and a sunny breakfast nook that flows into the family room and out to the 11' 15" x 31' 2" rear deck overlooking an owner’s garden area. Hardwood and tile flooring run throughout the home, and all floors are heated with oil-fired radiant heat. The newly renovated primary bath includes a walk-in shower, double sinks, cabinetry with linen storage, tile flooring, and fresh paint throughout. The basement-level recreation room features new flooring, a built-in entertainment center, and a newly constructed bar area with a sink. The walk-out basement also provides an ideal shop or workspace. A place for everyone, this property is only moments from the center of Bennington, skiing at Crotched Mountain, Crotchet Mountain Golf Club and just 4 miles from NH Route 202.

97 Onset Rd, Bennington
$259,000
4 Beds ⋅ 2 Baths ⋅ 5098985 MLS
Well maintained and thoughtfully updated, this 4-bedroom, 2-bath home offers the ease of single-level living on a beautiful level one-acre lot in Bennington's desirable west end. Enjoy stunning mountain views from the spacious back deck or sip your morning coffee on the covered front porch. Inside, you'll find an updated kitchen, refreshed bathrooms, a cozy fireplace, central air conditioning, a 2023 roof, an updated heating system, and a spacious primary suite featuring a jetted step-in tub and separate shower. Offering the perfect blend of comfort, convenience, and low-maintenance living, there's also room to add your own personal touches over time. Enjoy a peaceful setting just minutes from downtown Bennington for dining, shopping, cultural attractions, and everyday conveniences, with easy access to multiple ski destinations. Conveniently located approximately one hour from Albany International Airport and about three hours from both New York City and Boston.

549 Houran Rd, Bennington
$230,000
3 Beds ⋅ 2 Baths ⋅ 5097604 MLS
Blending vintage charm with modern updates, this beautifully refreshed 3-bedroom, 2-bath home offers comfortable in-town living close to local amenities. Recent improvements include a newer roof installed just three years ago and new flooring throughout, creating a fresh and inviting atmosphere. Other additions include new kitchen appliances, furnace, and heat pump hybrid water heater, making the home incredibly efficient. The bright, open, kitchen is filled with natural light and features a sliding door leading directly to the private brick patio, perfect for outdoor dining, entertaining, or relaxing. A covered front entrance adds welcoming curb appeal, while the enclosed porch provides excellent potential as a practical mudroom entry. Upstairs, you'll find generous attic space offering abundant storage possibilities. Outside, the backyard is enhanced by a charming newly added shed complete with a screened-in section, creating an ideal retreat for hobbies, gardening, or enjoying warm summer evenings. This move-in-ready home combines character, functionality, and modern convenience.

104 Short St, Bennington
$189,000
4 Beds ⋅ 2 Baths ⋅ 5096338 MLS
This well-maintained New Englander offers the perfect balance of classic character and comfortable living. Featuring four bedrooms and two updated bathrooms. The home provides spacious, comfortable living throughout. The recently renovated kitchen is both stylish and functional, while the updated bathrooms add contemporary appeal. Large rooms and a thoughtful layout create a welcoming atmosphere for everyday living and entertaining. Outside, you'll find a deep, fully fenced backyard with plenty of room for recreation, gardening, or pets. A beautiful deck provides the perfect setting for outdoor dining, relaxing, and entertaining. Enjoy the convenience of an in-town location within walking distance of downtown restaurants, shops, and local attractions. The property is also just minutes from services and all the amenities Bennington has to offer. Albany airport is 45 minutes driving, ski areas to the north and east, also approximately 45 minutes, NYC and Boston are both a 3 hour drive.

209 Depot St, Bennington
$480,000
4 Beds ⋅ 3 Baths ⋅ 5095717 MLS
If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the owners in the '80s. The 3300+ square feet of living area on the upper level and another 3300+ on the lower level ready to be finished. As you can see, the lower level has plenty of windows and will be very flexible space to use. The two-car garage is attached to the house. From there, into the mudroom. The kitchen is very generous...There's room for your breakfast table, a couple of easy chairs and a love seat, and the woodstove will make this a cozy country kitchen to be. This is a 'cooks dream'. The commercial range will make your friends jealous, as will the pantry and stained glass on the upper cabinets. Off the kitchen is a large sunroom which leads out to the deck. Large dining room perfect for entertaining and a very comfortable formal living room. There are two guest rooms that share a tile bath. The primary suite has its own tile bath and a room that could be a nursery or an office. The lower level is ready to finish into living space if you need it. A few spots will need a bit of TLC, but the end result will be fantastic. Several updates have been done. For the handyman or animal lover, there is a 23x46 foot barn with room for several vehicles or machinery. There are two garage doors, and it even has a pit for working under your vehicles. The open land is gorgeous. Stonewalls and woodland await. If you enjoy sunny locations, this is a perfect spot. There is enough land to enroll the property into Vermont's Current Use program. This may be the spot you have been waiting for! Available due to owner relocation.

498 Town Line Rd, Bennington
$179,000
3 Beds ⋅ 3 Baths ⋅ 5089968 MLS
Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to own a large condo unit with the space and versatility of a single-family home, paired with the ease of low-maintenance living. The main living level boasts an open-concept kitchen, dining, and living area ideal for entertaining, along with a half bath with laundry, a spacious bedroom with en-suite bath, and an additional bedroom. The third floor serves as a stunning private retreat featuring a second primary en-suite, skylights, and flexible bonus space perfect for a home office, library, exercise area, or cozy reading nook. Just minutes from downtown Bennington’s shops, restaurants, recreation, and cultural attractions, this move-in ready condo offers low-maintenance living without sacrificing space or style. A truly unique offering in a highly convenient location!

432 South St Unit D2, Bennington
$319,900
3 Beds ⋅ 2 Baths ⋅ 5084514 MLS
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.

683 Water St, Bennington

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