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526 Jennings Brook Dr, Bennington
$350,000
2 Beds ⋅ 2 Baths ⋅ 5084448 MLS
Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy feel. Enjoy year-round comfort with radiant heat throughout and efficient mini-split heat pumps. Step outside to a private back deck: perfect for relaxing or entertaining. A one-car attached garage adds convenience and additional storage. Located in a well-maintained and welcoming HOA, this property offers excellent walkability to nearby amenities, making it ideal for a variety of lifestyles. Listing agent is owner.

526 Jennings Brook Dr, Bennington
93 Russett Dr, Bennington
$350,000
4 Beds ⋅ 3 Baths ⋅ 5080194 MLS
Welcome to this charming mid-century home set on 1.27 acres, offering 4 bedrooms and 3 bathrooms. This property blends character, functionality, and unique design throughout. At the heart of the home, a beautiful open concept kitchen and living area creates the perfect space for gathering and entertaining. A stunning fireplace anchors the room, offering warmth and ambiance whether you’re hosting guests, enjoying family dinners, or settling in for a cozy evening. Natural light pours through the home, highlighting the striking cathedral ceilings and gorgeous parquet hardwood floors. The inviting entryway features classic slate flooring, setting the tone for the thoughtful details found throughout. The lower level offers a truly unique bonus space with a spacious family/game room featuring a show stopping two sided fireplace, along with a convenient half bath and laundry area ideal for flexible living and entertaining. Step outside and enjoy the peaceful setting, where birdsong and nature surround you perfect for those who appreciate wildlife and the simple joy of feeding birds right from your own yard. This home offers the best of both worlds privacy and convenience. Set in a quiet location, yet just minutes to shopping, schools, and local hospitals, it’s perfectly positioned for today’s lifestyle. Whether you’re looking to be close to town or tucked into a private neighborhood, this is the home you’ve been waiting for. Additional features include town water, private septic, and a spacious two-car garage with extra workspace. With its unique mid-century charm, desirable amenities, and prime location, this home is priced to sell. Don’t miss your opportunity schedule your showing today before it’s gone!

93 Russett Dr, Bennington
149 Jewett Dr, Bennington
$350,000
4 Beds ⋅ 2 Baths ⋅ 5077814 MLS
Tucked just outside of town with sweeping views in every direction, this 4-bedroom, 2-bath raised ranch offers the space and setting you're looking for. Hardwood floors run throughout the main level, where the sun-filled living room features a cozy wood-burning fireplace—perfect for gathering on chilly evenings. The finished lower level provides flexible space to grow, including the third and fourth bedrooms , a rec room for movie nights or play space, and a bonus room set up as a home gym. Laundry is conveniently located downstairs, keeping daily routines organized and efficient. Step outside to a large, level yard designed for making memories—complete with an above-ground pool for summer fun, a spacious deck for cookouts, and a firepit for evenings under the stars. The two-car garage offers plenty of room for vehicles, bikes, and all the extras that come with an active Vermont lifestyle! Peaceful country feel just minutes from town amenities—this home offers room to spread out, inside and out.

149 Jewett Dr, Bennington
103 Norton St, Bennington
$329,000
4 Beds ⋅ 2 Baths ⋅ 5062804 MLS
Beautifully Renovated 4-Bedroom Home with Modern Upgrades! Welcome to this stunning, move-in ready home that has been fully renovated with care and style. Offering 4 spacious bedrooms, 2 brand-new bathrooms, and 1,728 square feet of thoughtfully designed living space, this home is the perfect blend of comfort and modern living. Step inside to find gleaming hardwood floors that flow throughout the home. The completely updated kitchen is a true showstopper-featuring sleek cabinetry, new appliances, and contemporary finishes that make it ideal for both everyday living and entertaining. Both bathrooms have been fully remodeled with high-end fixtures and stylish finishes, creating serene, spa-like spaces. Additional upgrades include: New high-efficiency heating system, Heat pump water heater, New insulation, New exterior vinyl siding and all-new electrical wiring and panel. Situated on a manageable 0.13-acre lot, the property also includes a detached one-car garage for added convenience and storage.

103 Norton St, Bennington
523 Jennings Brook Dr, Bennington
$327,000
2 Beds ⋅ 2 Baths ⋅ 5080506 MLS
Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy feel. Enjoy year-round comfort with radiant heat throughout and efficient mini-split heat pumps. Step outside to a private back deck—perfect for relaxing or entertaining. A one-car attached garage adds convenience and additional storage. Located in a well-maintained and welcoming HOA, this property offers excellent walkability to nearby amenities, making it ideal for a variety of lifestyles. Listing agent is owner.

523 Jennings Brook Dr, Bennington
21 Pageant St, Bennington
$325,000
4 Beds ⋅ 2 Baths ⋅ 5092315 MLS
This well-maintained ranch-style home offers the convenience of one-level living with 3 bedrooms plus a spacious primary suite. Set on a large lot, the property features two decks, providing plenty of outdoor space for entertaining, relaxing, or enjoying the backyard. An easy walk to the local golf course adds to the appeal of this desirable location. The updated kitchen boasts beautiful granite countertops and a convenient pass-through to the oversized dining room, creating an open and inviting atmosphere for gatherings. A bright and welcoming living room is filled with natural light and showcases hardwood floors throughout most of the home. Both bathrooms have been tastefully updated, complementing the home's move-in-ready condition. Recent upgrades include central air conditioning, a newer forced-air furnace, and an energy-efficient hybrid hot water heater, offering year-round comfort and efficiency. The home is also equipped with 200-amp electrical service and is wired for a generator, providing added convenience and peace of mind. With its functional floor plan, modern mechanical updates, and desirable single-level layout, this property is ready for its next owner to move in and enjoy. The large yard, two decks, updated interior, and proximity to the golf course make it an ideal place to relax, entertain, and embrace an active lifestyle. This is easy living at its best.

21 Pageant St, Bennington
1803 Harwood Hill Rd, Bennington
$325,000
3 Beds ⋅ 2 Baths ⋅ 5087666 MLS
Set on a spacious lot and move-in ready raised ranch offers major updates, flexible living space, and excellent value. Recent improvements include a brand-new septic system, new roof, beautifully renovated kitchen, and new deck — giving buyers peace of mind and modern comfort from day one. The versatile lower level provides additional finished space ideal for a home office, family room, guest area, gym, or hobby space, offering flexibility to fit today’s lifestyles. The raised ranch layout provides separation between living and recreation spaces while maintaining an open, functional flow upstairs. Solar panels help offset energy costs and are currently leased; the new owner may choose to continue the lease or have the system removed. Conveniently located with easy access to Manchester, this home offers a great balance of country living and accessibility to shopping, dining, recreation, and everyday amenities. Enjoy outdoor living, updated systems, and a location close to downtown Bennington and Southern Vermont attractions.

1803 Harwood Hill Rd, Bennington
343 Safford St, Bennington
$325,000
5086322 MLS
An investment gem or owner-occupied standout in the heart of Bennington, this renovated property features three distinct units, each offering the privacy and feel of a single-family home. Unlike traditional stacked apartments, all three units boast a two-story layout with 2 bedrooms and 1 full bath, ensuring no neighbors above or below. Each features modern finishes, bright living spaces, and a thoughtful flow between the main floor living area and the second-floor bedrooms. The "crown jewel" of the property is the beautifully converted two-story barn; this detached third unit offers total independence and opens up to its own beautiful, private backyard—a rare luxury for a multi-family setup.

343 Safford St, Bennington
2 Pine Rd, Bennington
$303,000
3 Beds ⋅ 2 Baths ⋅ 5084585 MLS
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.

2 Pine Rd, Bennington
56 Hildur Hl, Bennington
$302,000
3 Beds ⋅ 2 Baths ⋅ 5086658 MLS
Charming Ranch in a Desirable Neighborhood! Are you looking for a 3 bedroom, 2 bath ranch with room to grow in a great neighborhood? This beautifully maintained home offers the perfect blend of comfort, style, and flexibility. Enjoy a fully renovated kitchen featuring soft close drawers and a dedicated coffee bar perfect for starting your day. Stay comfortable year round with central air, and unwind after a long day in the jetted bathtub. The lower level offers excellent versatility, including a second bathroom with laundry and additional living space. A downstairs bedroom provides the perfect option for a home office, guest space, or potential in law setup. Step outside to a spacious, fully fenced backyard ideal for pets, play, or relaxing in your own private outdoor space. Whether you’re looking for easy single family living or a home with room to expand, this property adapts to your needs. Conveniently located close to shopping, dining, and the hospital, this home offers both comfort and accessibility. However you envision it, this is a place you can truly make your own. Don’t miss your opportunity this one won’t last long! Call today to schedule your private showing.

56 Hildur Hl, Bennington
105 Albe Dr, Bennington
$300,007
3 Beds ⋅ 2 Baths ⋅ 5089522 MLS
Tucked into an established and desirable neighborhood, this well-maintained 3-bedroom, 2-bath home offers the kind of easy, low-maintenance living that’s increasingly hard to find. Built in 1999 and thoughtfully designed with comfort and practicality in mind. The layout provides flexibility for a variety of lifestyles with approximately 1,700 square feet of finished living space, generous room sizes, and abundant storage throughout. The main level features a spacious eat-in kitchen with center island, pantry, and ample counter space, along with a bright living room with custom built-ins. The first-floor primary bedroom includes an oversized walk-in closet and access to a full bathroom, offering the convenience of one-level living if desired. Upstairs are two exceptionally large bedrooms, another walk-in closet, and a second full bath with dual sinks and a hallway linen closet. The full concrete basement provides excellent utility, storage, or workout space with potential for future finishing. Boiler is only 4 years old and there's a heat pump water heater. Sale includes all appliances, including the washer and dryer, along with the Generac standby generator. The one-car garage connects to the home by a covered walkway for added convenience during rain and snow. Outside, the manageable lot is designed for easy upkeep and includes a private patio area bordered by mature trees. With vinyl siding and windows, modern construction, public utilities, and move-in-ready condition, this property offers a comfortable and efficient option close to downtown Bennington, shopping, restaurants, SVMC, and local amenities.

105 Albe Dr, Bennington
207 Silver St, Bennington
$299,000
4 Beds ⋅ 2 Baths ⋅ 5070659 MLS
Tastefully renovated antique home that retained it character 4 bed 2 bath home with gleaming hardwood floor in through out with Vinyl plank in the bathrooms and Laundry room. The downstairs Ensuite is currently being used as an in home office with private entrance. This would make a great room for a in-law space with private bath and the 3 season sunroom could easily be converted into a Livingroom or studio space with plenty of natural light. The detached garage rounds out the move in ready Village Home. A short walk to all downtown amenities, coffee shops, restaurants and shopping The Boiler is 5 years old and the kitchen appliances were also recently replaced. 1 hour to Albany International Airport And Albany Medical, 2 Hours to Dartmouth Medical center 3 hours to Boston, 3.5 hours to Manhattan, 30 minutes to Mt Snow Come see what Bennington has to offer.

207 Silver St, Bennington
302 Prospect St, Bennington
$296,000
3 Beds ⋅ 2 Baths ⋅ 5086287 MLS
Welcome to this lovely Colonial home, formerly a charming carriage house, nestled in one of Bennington’s most desirable walkable neighborhoods. Offering over 1,500 square feet of inviting living space, this well maintained home features 3 bedrooms, 2 bathrooms, and a versatile bonus room perfect for a home office or potential fourth bedroom. Inside, you’ll find beautiful wood floors and trim, rustic beams, and newly installed plush carpeting. The sunny interior is filled with natural light thanks to large windows that flood the home with brightness. The kitchen offers stainless steel appliances direct access to the back deck. Updated bathrooms and ample closet space blend modern convenience with the timeless charm of the home. Step outside to enjoy the beautifully landscaped yard, complete with a newly painted deck ideal for entertaining and gatherings, as well as stunning mountain views. The level, usable yard offers plenty of space for outdoor enjoyment, room for a garden, and a large paved driveway accommodates up to six vehicles. A generously sized shed offers perfect storage for your outdoor items. Additional highlights include low-maintenance vinyl siding, replacement tilt-out windows for easy cleaning, and an updated metal roof. In the basement you will find a finished rec room, laundry area and extra storage with peg wall for your tools and a sump pump. Connected to town water and sewer, this home offers added ease of maintenance. Enjoy the peace and comfort of this quiet neighborhood while being just minutes from the hospital, shopping, and vibrant downtown Bennington. An hour from Albany International Airport, close to all Southern Vermont and the tri-state area has to offer. A true gem in the heart of town, you won’t want to miss this one!

302 Prospect St, Bennington
166 Cardinal Ln, Bennington
$295,000
3 Beds ⋅ 2 Baths ⋅ 5089120 MLS
Discover the charm and potential of this one-of-a-kind mid-century home, offered for sale for the first time. Set on 3.20 private acres with mature, lush landscaping, this spacious property offers a peaceful and serene setting while remaining conveniently close to shopping, schools, restaurants, and the hospital. Originally built in 1964, the home has grown through multiple additions over the years, creating a distinctive layout filled with character and generous living space. Offering 3 bedrooms, 2 full bathrooms, multiple porches, and two sunrooms, this home provides endless possibilities for comfortable living, entertaining, or creating your own private retreat. Additional features include a Buderus furnace and a generator with its own dedicated propane tank, offering comfort and peace of mind year-round. Ready for its next chapter, the property will benefit from some TLC to restore its warmth and beauty. Whether you're looking for a full-time residence or a weekend escape, this special home presents a wonderful opportunity to make it your own. Ideally located just 3 hours from NYC and Boston, and only 45 minutes from Albany International Airport, this rare offering combines privacy, convenience, and timeless appeal. Come explore the possibilities and bring new life to a home ready to be loved again.

166 Cardinal Ln, Bennington
113 S St Unit 302, Bennington
$295,000
1 Beds ⋅ 2 Baths ⋅ 5086029 MLS
Whether you’re seeking a full-time downtown lifestyle, a lock-and-leave home base for travel, or you’re ready to make the leap from renting to owning, this is the kind of property that checks every box: location, character, and simplicity. Offered publicly for the first time, Unit 302 is filled with natural light from tall windows that frame the energy of downtown Bennington. Soaring ceilings, original hardwood floors, and preserved trim details speak to the building’s mid-1800s origins, while a thoughtful 2009 renovation brings everything forward with comfort and ease. The kitchen is both handsome and functional, with granite countertops, quality cabinetry, and stainless appliances opening to a bright, connected living and dining space... perfect for slow mornings, easy evenings, and gathering with friends. The bedroom suite feels like a retreat, complete with a private bath, walk-in closet, and separate laundry closet with stacked washer and dryer for everyday convenience. There is a second walk-in closet off the foyer providing exceptional storage (an uncommon find in condo living). Whether you take the elevator or the stairs, access is simple, with nearby public parking in a well-lit lot. Outside your door, downtown unfolds; coffee shops, restaurants, live music, theater, parks, and year-round events are all just steps away. Positioned as a corner unit, this home captures beautiful natural light and mountain sunrises, along with a front-row view of downtown’s daily rhythm. Condos with this level of light, character, and storage rarely come to market in downtown Bennington. Enjoy easy access to the region and beyond with just about an hour's drive to Albany International Airport and Saratoga Springs, and roughly three hours to both New York City and Boston.

113 S St Unit 302, Bennington
136 North St, Bennington
$294,000
5079239 MLS
Downtown mixed-use investment opportunity located on North Street near the Four Corners intersection of Routes 7 and 9 in the heart of Bennington. The property features six total units, including four residential apartments (three two-bedroom units and one one-bedroom unit) and two street-level commercial storefronts with direct North Street frontage providing strong visibility for retail, office, or service uses. The building extends deep into the lot with rear access from the back of the property and is conveniently located near public parking. Located within Bennington’s Downtown (D) zoning district supporting mixed residential and commercial uses and maintaining active street-level commercial space along North Street. Current rents present potential upside for investors through future lease adjustments, operational improvements, or updates over time. Income and expense information available to qualified buyers.

136 North St, Bennington
48 Mountain Rd, Bennington
$290,000
3 Beds ⋅ 1 Baths ⋅ 5093296 MLS
Nestled in a peaceful country setting just moments from Whittemore Lake, Crotched Mountain Ski Area and Crotched Mountain Country Club, this charming 3 bedroom, 1 bathroom home offers the perfect opportunity to enjoy the beauty and tranquility of Bennington, New Hampshire. Situated on 1.3 acres surrounded by mature trees, 48 Mountain Road provides privacy, space, and a connection to nature while remaining conveniently located near town amenities. Inside, you'll find 1,112 square feet of living space featuring a practical layout with spacious bedrooms, a first-floor laundry area, and a welcoming enclosed porch that's perfect for enjoying your morning coffee or relaxing after a day outdoors. The home offers plenty of potential for personalization and updates to make it truly your own. Outside, the detached two car garage provides ample room for vehicles, storage, hobbies, or workshop space. The expansive yard offers opportunities for gardening, recreation, and enjoying the peaceful surroundings. Whether you're looking for a year round residence, a weekend retreat, or an investment opportunity, this property combines country living with easy access to nearby lakes, hiking, snowmobiling, skiing, golf and all that the Monadnock Region has to offer. Schedule a private showing

48 Mountain Rd, Bennington
935 Gage St, Bennington
$287,800
3 Beds ⋅ 2 Baths ⋅ 5088129 MLS
Nestled in the Village of Bennington, this charming three-bedroom, two-bath Cape-style home offers comfort, character, and beautiful outdoor living. Step inside to find all fresh flooring, just painted throughout, and inviting spaces filled with natural light. Fireplace in the living room and new glass slider to the deck. Second floor is one large room with spacious closet and full bath-an ideal primary suite. Outside, perennial gardens add color and charm while the brand-new back deck creates the perfect place to relax or entertain. Spend your summer evenings gathered around the fire pit, listening to the peaceful sounds of the nearby creek in your shaded backyard retreat. Conveniently located close to downtown shops, dining, schools, and local amenities, this move-in-ready home combines village convenience with the tranquility of Vermont living.

935 Gage St, Bennington
124 Albe Dr, Bennington
$286,000
2 Beds ⋅ 1 Baths ⋅ 5085209 MLS
Charming Ranch with Easy First Floor Living! This desirable 2 bedroom, 1 bath ranch offers convenient one level living in a sought after neighborhood. The home features a recently renovated kitchen and bathroom, a spacious family room, and a dining area perfect for everyday living. Enjoy the ease of first floor laundry and a single car garage. The semi finished basement provides additional space with most of the work already completed just finish the ceiling and add heat to maximize its potential. Step outside to the beautifully upgraded Trex deck, offering low maintenance, durable outdoor space that's back for ideal for relaxing or entertaining. Conveniently located with easy access to ski areas, as well as commuting distance to Albany, Boston, and New York City. Move in ready and waiting for its next owner this home won’t last long!

124 Albe Dr, Bennington
341 Chester Knoll Dr, Bennington
$285,500
3 Beds ⋅ 2 Baths ⋅ 5086769 MLS
Enjoy low-maintenance living in this 3-bedroom, 1.5-bath home, ideally located in Bennington. This home offers a comfortable interior along with a private back deck perfect for relaxing or entertaining. The HOA covers trash removal, snowplowing, and landscaping, making ownership simple and stress-free. Conveniently situated near downtown Bennington, local shops, dining, and area amenities, this property is a great option for easy Vermont living.

341 Chester Knoll Dr, Bennington
31 Bible Hill Rd, Bennington
$280,000
3 Beds ⋅ 2 Baths ⋅ 5081439 MLS
Located in Bennington, this 3-bedroom, 2-bath home offers a great opportunity for buyers ready to bring their vision and restore its potential. Built in 1958 and totaling approximately 2,124 sq ft, the home features a fully finished basement with additional rooms that provide flexible space for offices, hobbies, or storage. The property sits on a 1.08-acre lot with a fenced backyard and large garage, offering plenty of outdoor space and room for projects, vehicles, or equipment. Although some sweat equity will be needed to bring this back to life, the home has solid bones and strong potential. This property is being sold as-is and presents a chance to renovate and build equity in a desirable Hillsborough County setting. Whether you're an investor looking for a new project or a homeowner looking to create your dream home while gaining immediate equity, this is the opportunity for you! The sale of this property being listed is contingent upon the proposed Seller (or "Owner") completing his /her/its purchase of this property. "Seller" currently has this property under contract for purchase.

31 Bible Hill Rd, Bennington
32 Albe Dr, Bennington
$277,700
2 Beds ⋅ 1 Baths ⋅ 5090246 MLS
MOVE RIGHT IN AND MAKE YOURSELF AT HOME This beautifully maintained residence is perfect for those looking for the convenience of first floor living. Featuring tastefully painted rooms, bamboo flooring and modern appliances. The kitchen includes a dedicated eating area for family dining while the living room offers a warm and cozy gathering space. Both bedrooms are generously sized with large closets and a full bath, plus a dedicated laundry area, all conveniently located on one level. The large, finished basement provides additional space, ideal for a home office, guest area or hobbies. The attached garage ensures easy access and the back deck offers a peaceful spot to relax while enjoying the soothing sounds of the Roaring Branch river. Situated in a quiet, friendly neighborhood. This house is a wonderful place to settle in and enjoy life.

32 Albe Dr, Bennington
212 Dewey St, Bennington
$277,000
2 Beds ⋅ 3 Baths ⋅ 5090068 MLS
Move right in or continue operating as a short-term rental—this fully furnished 2-bedroom, 2.5-bath ranch offers comfort, convenience, and flexibility all in one package. Currently used as an Airbnb, all contents are included, making this a true turnkey opportunity. Inside, you’ll find recently refinished hardwood floors, and skylights that fill the home with natural light. A pellet stove for ambiance (main heat is hot water baseboard) adds warmth and character, while the central cooling system keeps the home comfortable year-round. The large heated basement offers excellent ceiling height and endless possibilities for storage, workshop space, or future finishing. Efficient Buderus boiler with multiple heating zones adds to the home’s quality and functionality. Additional features include an attached 2-car garage, small rear deck for relaxing outdoors, and a peaceful stream running through the property for a tranquil setting. This property checks all the boxes.

212 Dewey St, Bennington
26 Knoll Crest Ln, Bennington
$275,000
3 Beds ⋅ 1 Baths ⋅ 5089377 MLS
Beautifully updated Cape-style home nestled in a quiet, sought-after neighborhood with picturesque views of Mount Anthony. Full of charm and character, this move-in-ready home perfectly blends comfort, style, and convenience. Tucked away on a dead-end street, it’s ideally located near SVMC hospital, public transportation, scenic hiking trails, and Bennington’s vibrant Main Street, which offers shops, restaurants, and year-round community events. The main level features a spacious great room with beautifully refinished hardwood floors (2024), an updated kitchen with new cabinetry, butcher block countertops, and new appliances (refrigerator and dishwasher, 2024), along with a convenient first-floor bedroom and a full bath with a beautifully tiled shower surround. Upstairs, you’ll find two additional bedrooms with ample storage, including charming custom hallway built-ins that add both timeless character and functionality. The full basement provides excellent potential for additional living space, with one side open and ready to be finished, while the other is currently configured as a workshop/hobby area along with the laundry and mechanical systems. Step outside onto the expansive 20ft x 15ft back deck and take in the scenic mountain views—the perfect setting for relaxing or entertaining guests while overlooking the backyard. The yard offers ample space to enjoy without being overwhelming to maintain, providing the perfect balance of open outdoor living and easy upkeep. It’s a blank canvas ready for new owners to add their own gardens, landscaping, and personal touches to truly make it their own. Additional recent upgrades include a 200-amp electrical panel (2024), a heat pump hot water heater (2024), foam insulation throughout with new sheetrock upstairs following insulation (2023), seamless edge gutters (2024), and a complete interior repaint in 2024.  Truly move in condition and ready for its new owners to start making their own memories.

26 Knoll Crest Ln, Bennington
1808 East Rd, Bennington
$275,000
3 Beds ⋅ 1 Baths ⋅ 5082307 MLS
Well-maintained 3-bedroom, 1-bath ranch set on a beautifully landscaped half-acre in Bennington. This inviting home offers easy single-level living with a bright picture window framing peaceful views, an attached heated two-car garage, and a convenient shed for additional storage. Pride of ownership is evident throughout, with solid systems and thoughtful care over the years, while offering an opportunity for cosmetic updates, if desired, to make it your own! A full, unfinished basement provides exceptional space for storage, hobbies, or future finishing potential. Enjoy a low-maintenance lifestyle in a quiet, pleasant setting just minutes to downtown shops, dining, and local amenities. Ideally located approximately one hour to Albany International Airport and 3 hours to NYC and Boston. Come see and call it home!

1808 East Rd, Bennington
2092 N Bennington Rd, Bennington
$269,900
3 Beds ⋅ 2 Baths ⋅ 5074418 MLS
Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedrooms upstairs and a pocket half bathroom. downstairs has a master bedroom with a newly remodeled ensuite, kitchen with breakfast table area, 4 seasons living space in the back and a front living room with new flooring. The previous owner used the 4 seasons room as a formal dining room since it has panoramic view of the Hoosic River. The front living room has a fireplace option (has a chimney and fireplace structure but just needs updating) and it has enough space to use as a living room and dining room combo. There is plenty of storage in the full-size, walkout basement where the washer and dryer are located. This house also has 2 sheds, 2 car ports and 2 driveways. This house is cozy indoors and offers dreamlike outdoor living with walkout access to the river where you can raft, go inner tubing, boating and fishing. Two spacious decks for outdoor dining, grilling, entertaining, hosting a wedding, bird watching or just relaxing and enjoying the view. In the very large backyard, you can pitch a tent, for camping, or gardening. The possibilities for this house are endless. Great for those who love the outdoors. This house is close to ski resorts, hiking trails, schools, shops, places for dining, parks, gas station (is just down the road), Movie theater and a short drive to the Highway. You’re 10 minutes away from downtown Bennington. Close to Lake Paran, a short 15 minutes ride to Ny and 30minutes ride to Massachusetts. There are not a lot of houses like this one. And in such a prime location. Don’t miss out on this once in a lifetime opportunity!

2092 N Bennington Rd, Bennington
111-113 Booth Ter, Bennington
$265,000
5081825 MLS
Exceptional opportunity to own a beautifully maintained duplex in the heart of Bennington. Each spacious unit offers 3BR and 1.5BA, featuring warm wood floors, generous living space, and thoughtful layouts that appeal to both tenants and owner-occupants alike. Renovated and updated through the years, the property has been meticulously cared for and has an organized, efficient setup throughout. Both units benefit from separate utilities, dedicated basement and attic storage, and four off-street parking spaces—rare and valuable amenities that enhance everyday livability and long-term investment performance. Ideally located just minutes from downtown Bennington, enjoy convenient access to local shops, dining, and community amenities. Commuters will appreciate being approximately one hour to Albany Airport and 3 hours to NYC and Boston. A turnkey, low-maintenance asset with strong fundamentals, flexibility, and future upside—this is a standout opportunity in today’s market.

111-113 Booth Ter, Bennington
13 Hall St, Bennington
$265,000
4 Beds ⋅ 2 Baths ⋅ 5080292 MLS
Full of potential, this 4-bedroom, 2-bath North Bennington home is a true hidden gem with space to grow and a location to love. Cozy up in the living room with its fireplace and hardwood floors, host dinners in the formal dining room, and enjoy the open flow from the kitchen into a large family room. The main floor primary suite offers comfort and privacy with its own bath and walk-in closet, while upstairs features three additional bedrooms and a full bath. Step outside to a rear deck, plus a detached garage with plenty of storage. All set in a walkable neighborhood close to the elementary school and the charm of North Bennington’s village center.

13 Hall St, Bennington
2867 Chapel Rd, Bennington
$261,000
3 Beds ⋅ 2 Baths ⋅ 5100537 MLS
Tucked into a private wooded setting on the outskirts of town, this distinctive 3-bedroom, 1.5-bath Adirondack-inspired chalet blends rustic character, flexible living space, and an exceptional connection to the outdoors. Its steep roofline, front balcony, exposed beams, and metal roof give the home memorable architectural presence, while the peaceful surroundings create a true retreat from the everyday. Inside, hardwood floors and dark ceiling beams add warmth and character to the main living and dining area, where a propane stove set against a brick hearth creates a cozy focal point. Brand-new windows throughout bring in abundant natural light, complemented by new French doors that open directly to the deck. The efficient kitchen offers generous cabinetry and slate-finish appliances, all included. An adjacent unfinished mudroom provides an opportunity to create a convenient entry and additional storage. A main-level bedroom and full bath offer the flexibility of one-floor living, comfortable guest accommodations, or work-from-home space. Upstairs, two bedrooms feature dramatic cathedral ceilings and exposed beams. One opens to a private covered balcony overlooking the yard and woods... an inviting place to enjoy morning coffee, read, or simply take in the quiet surroundings. A half bath completes the upper level. The basement adds valuable versatility with a laundry room, finished bonus room, workshop, and utility room. The detached 1-car garage provides even more space for a vehicle, tools, equipment, or recreational gear. Outside, there is plenty of room to enjoy every season, including a spacious deck, fire pit, private backyard, multiple woodland trails, and a charming screened outbuilding for bug-free relaxation, dining, or summer gatherings. Full of personality and surrounded by nature, this wonderfully distinctive Vermont home offers space to live, work, gather, and unwind.

2867 Chapel Rd, Bennington
69 Birch Glen Dr Unit #7, Bennington
$260,000
2 Beds ⋅ 3 Baths ⋅ 5090137 MLS
Minutes from Crotched Mountain, this turnkey Birch Glen condo offers the low-maintenance mountain retreat buyers are searching for. Spend winter weekends skiing, summer evenings on the deck, and enjoy a renovated interior with room for guests and gear. This spacious townhouse-style home features 2 bedrooms, 2.5 baths, and an open-concept layout designed for easy living. The fireplaced living room provides a cozy setting ideal for relaxing after a day on the slopes or nearby hiking trails. The kitchen and dining area offer generous cabinet and counter space and sliding doors leading to a private back deck. Upstairs there are two ensuites including a spacious primary suite with oversized closets and a private balcony with seasonal mountain views. There's additional flexible space in the unfinished walkout basement offering endless possibilities for a recreation room, home office, fitness area, or additional guest accommodations. Many updates have been completed to include a new roof last year, as well as an updated kitchen, bath, and flooring. Whether you're searching for a year-round residence or a weekend escape, this low-maintenance condo delivers the best of New Hampshire living all within easy reach of Manchester, the Seacoast, and Boston. Come see this gem for yourself.

69 Birch Glen Dr Unit #7, Bennington

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