Bennington Homes with Outbuildings Exterior Features

Welcome to Bennington, Vermont—a charming town nestled in the picturesque Green Mountains, where history, natural beauty, and a vibrant community come together to create an idyllic living experience. Known for its rich heritage, Bennington boasts a delightful blend of quaint shops, local eateries, and cultural attractions, including the renowned Bennington Museum and the iconic Bennington Battle Monument. With its stunning landscapes, outdoor recreational opportunities, and a strong sense of community, it’s no wonder that Bennington is a sought-after destination for homebuyers looking for a peaceful yet engaging lifestyle.

One of the most appealing aspects of living in Bennington is the availability of homes with outbuildings. These properties not only offer additional space for storage or hobbies but also provide endless opportunities for creativity and functionality. Imagine having a rustic barn for your gardening tools, a workshop for your DIY projects, or even a cozy studio for your artistic endeavors—all just steps away from your main residence.

The exterior features of these homes often showcase beautiful landscaping, expansive yards, and charming architectural styles that reflect the area’s rich history. Many properties are set against the backdrop of stunning mountain views, allowing you to enjoy the changing seasons in all their glory. Whether you’re looking for a serene retreat or a vibrant family home, Bennington offers a variety of options that cater to your lifestyle needs. Embrace the charm of this captivating town and discover the perfect home with outbuildings that will inspire your next chapter in life.

Newest Bennington Homes with Outbuildings Exterior Features

$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

$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

$132,900

2 Beds ⋅ 1 Baths ⋅ 5101539 MLS

Very well kept single-wide mobile home on it's own land. Cozy 2 bedroom, 1 bathroom home with single level living. Living room, kitchen with dining area, main level laundry and more. Has 2 enclosed porches. The smaller one is used as a pantry and the larger one is heated. Outside 2 sheds and the sounds of the nearby babbling brook. Also has RV electric hook up.

60 Tori Ln, Bennington

$250,000

4 Beds ⋅ 2 Baths ⋅ 5101031 MLS

Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to downtown restaurants, theater, and parks, the location is exceptionally convenient while still feeling like a true residential neighborhood. Inside, generous rooms, abundant natural light, hardwood floors, wide moldings, and original architectural details give the home warmth and personality. The spacious living room offers flexibility for gathering, relaxing, or creating multiple seating areas, while the adjoining dining room provides an inviting setting for everyday meals and entertaining. The bright kitchen features abundant wood cabinetry, generous counter space, a farmhouse-style sink, gas range, and direct access to the rear deck. Upstairs are four bedrooms and a full bath, offering ample flexibility for household needs, guests, a home office, or creative space. The primary bedroom includes two closets, and each bedroom has a ceiling fan and overhead light. The full basement houses the laundry and utilities, provides useful storage, and includes an additional toilet. There's a hot air furnace, Rinnai water heater, 100-amp panel, and town water/sewer. Outside, the rear deck overlooks the lawn, established garden beds, and a partially fenced area. A detached one-car garage adds convenient parking, storage, or workshop potential. The home is comfortable and offers a strong foundation. Exterior painting and porch restoration will be up to the next owner, creating an opportunity to refresh the property, make it their own, and build equity over time. With its gracious proportions, original charm, outdoor space, and exceptional location, 301 Elm St is ready for its next chapter.

301 Elm 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

$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

$460,000

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! Owner relocating. Offer encouraged.

498 Town Line Rd, Bennington

$695,000

4 Beds ⋅ 2 Baths ⋅ 5089246 MLS

Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the serenity and natural beauty for years to come. The thoughtfully designed open-concept main level features a bright and inviting living area, ideal for entertaining or relaxing while taking in the surrounding landscape. The primary bedroom and an additional guest bedroom are conveniently located on the main floor, along with a three quarter bath. A versatile loft area provides the perfect space for a home office, study area, or cozy kids’ hangout. The finished lower level expands the living space with two additional guest bedrooms, full bath, mechanical room with laundry hookups and ample storage. A one-car garage adds convenience and functionality. Step outside to the expansive deck designed for exceptional three-season living, where you can unwind, entertain, and enjoy amazing views in complete privacy. Fully renovated and move-in ready, including a new roof installed in 2024 as well as new furnace, new skylights, new flooring on the lower level and more, this special property combines modern comfort with the peace and beauty of a protected natural setting.

515 Quarry Rd, 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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