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$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

$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

$140,000
5 Beds 2 Baths 5096965 MLS
Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again. Inside, you'll find generous living space ready for your vision and updates. A fully enclosed front porch provides additional usable space, while the rear mudroom offers a practical everyday entry. Whether you're looking to restore the home's character, add value through renovations, or explore income-producing possibilities, this property presents a wealth of opportunity. Conveniently located close to downtown, shopping, dining, walking trails, and the hospital, the location adds to the property's appeal. Bring your ideas and imagination, this is a rare chance to transform a property with outstanding potential into something truly special.

127 Dewey St, Bennington

$180,000
3 Beds 2 Baths 5096423 MLS
Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful atmosphere rarely found in properties with such versatile potential. A large barn provides abundant storage, workshop space, or the opportunity for a variety of future uses. Inside, the home is ready for renovation and updates, making it an ideal project for investors, entrepreneurs, or buyers looking to bring their own vision to life. The main level features a well designed layout, highlighted by a spacious eat-in kitchen, a full bathroom, and a cozy living room with a pellet stove. The front door leads to a covered porch overlooking the scenic golf course at Mount Anthony Country Club. A separate dining room and a versatile room that can serve as a bedroom, den, or home office complete the first floor. Upstairs, a generous landing provides additional living space as a family room, along with two bedrooms and a shared three-quarter bathroom. With commercial zoning already in place, the property offers flexibility for a wide range of permitted uses beyond residential living (subject to local approvals). Whether you're seeking a live/work opportunity, business location, investment property, or a charming riverside renovation project, this property combines a peaceful natural setting with outstanding potential. Bring your ideas and unlock the possibilities of this rare offering. Conveniently located near the local country club and golf course, with easy access to nearby walking trails, the property offers an appealing blend of recreation, nature, and opportunity.

105 Hicks Ave, Bennington

$595,000
5 Beds 3 Baths 5093651 MLS
Step into this beautifully built post-and-beam house by well-known local builders Blue Heron Construction. Built in 1989 in classic Blue Heron style with an earthy exterior and a warm, glowing, golden interior, the house retains its original features, just waiting to be embraced by its next occupant. The location of the home couldn’t be better, nestled on 9+ secluded acres in North Bennington. Create your own walking trails or explore the lovely rural roads in the neighborhood. Practical and cultural amenities are just minutes away by foot, car, bike or snowshoes. Entering the home through the brick-floored mudroom, you arrive in a large, open living/kitchen area with high ceilings, exposed beams and a cozy wood stove. Surrounding this inviting space, you will find a master bedroom with bathroom annex, a dining room, an office/library, and a second ground floor bedroom. Up the bespoke wooden staircase are 3 more rooms with bathroom and separate entrance, perfect for extended family or multi-generational living. Back downstairs, you will be stunned by the size of the huge, heated workshop, with plenty of room for a woodworker, potter, jeweler, painter or sculptor to work their magic. Above this workspace is a large second-floor studio apartment with private entrance and a spacious screened porch. A substantial barn/garage with a loft area provides even more space for vehicles, equipment, storage, or future expansion. If you’re looking for multi-generational living, short or long term rental opportunities, or room for home-based business, this house could be perfect for you. The property is accessible from College Road but also has approximately 100 feet of road frontage on Matteson Road which could present future building opportunities, subject to local approvals. This house is a spacious North Bennington jewel. Move in right away, or take your time with a retrofit, as this house offers the versatility and flexibility to be whatever you want it to be.

81 Honeysuckle Ln, Bennington

$550,000
5 Beds 2 Baths 5088350 MLS
Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home. Situated on over 17 acres, this property offers not one but two barns, established fenced pastures, and the kind of setting that feels like a Vermont dream. Listen to the breeze move through the grass, watch the leaves change color in the fall, and enjoy the privacy and beauty that surround you. Inside, you’ll find five bedrooms and two full bathrooms, with space that invites family dinners, holiday gatherings, and everyday moments that make a house feel special. The usable basement offers excellent storage, workshop potential, tool space, or room for tack and farm equipment. Whether you have horses, farm animals, or simply want the charm and comfort of country living, this property offers the Vermont lifestyle so many people dream about. This is more than a house it’s the feeling of finally coming home.

971 S Stream Rd, Bennington

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