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$175,000
2 Beds ⋅ 1 Baths ⋅ 5109415 MLS
Tired of renting? Discover the charm, convenience, and value of this adorable two-bedroom bungalow - an ideal opportunity for first-time buyers, downsizers, investors, or anyone looking for a cozy second home in town. Tucked away from the hustle and bustle, this historic home is just a short walk from downtown shopping, restaurants, transportation, and everyday conveniences. Inside, you'll find a move-in-ready space with a welcoming dining area just off the kitchen, a spacious primary bedroom, and warm natural light. Step outside and enjoy the covered wraparound porch - always a Vermont favorite. Off-street parking adds an extra layer of convenience. If you're looking to simplify, this charming little jewel is ready to welcome you home!

220 Gage St, Bennington
$385,000
3 Beds ⋅ 2 Baths ⋅ 5109164 MLS
Set on 1.84 acres in Bennington, this 3-bedroom ranch pairs a warm, character-filled interior with established gardens, a wooded backdrop, and one of the home's best surprises: an oversized screened porch made for summer living. The bright kitchen has been updated with granite counters, an apron-front sink, white cabinetry and a gas range, and opens to a cozy living/dining area with wide-plank pine floors, an exposed beam, wood stove, and a broad bank of windows overlooking the front yard. Just off the kitchen, the screened porch adds a substantial amount of usable space, complete with its own sink and a dedicated propane line for the grill. All three bedrooms and the full bath are on the main level. Downstairs, 592 square feet of finished space and a 3/4 bath create a flexible second living area well suited to guests, a media room, hobbies, or a home office. The unfinished portion of the basement offers plenty of room for storage, utilities, and workshop space. Outside, years of gardening show in the mature plantings and colorful beds surrounding the home, with open lawn around the house and woods behind. Enjoy a country setting with recreation close by at Crotched Mountain Ski & Ride and Powder Mill Pond, while downtown Peterborough is about 18 minutes away. Fiber optic internet is available. A warm and inviting home with flexible living space, established gardens, and a peaceful country setting.

224 S Bennington Rd, 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
$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
$375,000
3 Beds ⋅ 2 Baths ⋅ 5104363 MLS
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.

291 Spring Hill Rd, Bennington
$475,000
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
$162,500
2 Beds ⋅ 2 Baths ⋅ 5102057 MLS
Enjoy easy first-floor, one-level living in this two-bedroom, one-and-a-half-bath condominium in Bennington’s Nathaniel Court community. The comfortable layout features an open living and dining area, a functional brand-new stainless steel kitchen appliances, laminate flooring, and plenty of natural light throughout. Both bedrooms offer inviting spaces, while the in-unit washer and dryer add everyday convenience. Association services include landscaping, snow removal, and trash removal, providing a low-maintenance lifestyle. Sidewalks and a location close to downtown Bennington make it easy to access local shops, restaurants, cultural attractions, and other area amenities. Whether you are purchasing your first home, downsizing, or looking for a convenient Vermont getaway, this well-located condo is ready to welcome its next owner.

432 South St Unit A11, 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
$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
$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
$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
$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
$250,000
3 Beds ⋅ 2 Baths ⋅ 5088382 MLS
Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as a home office, adding flexible living space to fit today’s lifestyle. The main level includes a first-floor bedroom and ¾ bath, along with a sunroom perfect for relaxing and enjoying the surroundings. Upstairs are two additional bedrooms, including the primary suite, plus a large storage area. This home does need a little TLC, including some carpet and paint updates, but offers tremendous potential and great bones. Additional features include an attached one-car garage and a large back deck for outdoor enjoyment. Conveniently located within walking distance to downtown, the hospital, and the monument, this condo is a fantastic opportunity to make it your own.

103 Jennings Brook Dr Unit 103, Bennington

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