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$399,900
4 Beds ⋅ 2 Baths ⋅ 5088223 MLS
This c. 1936 4BR/2BA home has been beautifully updated to blend timeless architectural character with modern comfort and convenience. Meticulously maintained throughout, it features gleaming hardwood floors, vintage details and thoughtful updates designed for today’s lifestyle. The stunning granite kitchen offers rich cherry cabinetry and stainless steel appliances, all new in 2024, creating a warm and functional space for cooking and gathering. The expansive primary suite is a true retreat, complete with an oversized walk-in shower, double vanity with granite countertop, and abundant space to unwind. Three additional guest bedrooms and a full guest bath provide flexibility for family, guests, or home office needs. The finished attic is perfect for a playroom or creative space and the home offers abundant storage throughout. Step outside to enjoy the brand-new expansive deck overlooking the yard, along with a shed and additional outbuilding for hobbies, gardening, or extra storage. Located in the Clarks Woods neighborhood, this charming home is convenient to the country club, hospital, and other local amenities while offering the comfort of a lovely residential setting. 0.33 acre.

23 Pageant St, Bennington
$219,000
3 Beds ⋅ 1 Baths ⋅ 5088016 MLS
This cute 3-bedroom, 1-bath cape offers comfortable in-town living with a fully fenced yard and recently renovated kitchen and bath. The laundry hookups are on the first floor which adds everyday convenience. Enjoy morning coffee or evening relaxation in the enclosed 3-season porch with outdoor fenced space perfect for pets, play, or gardening. The upstairs bedroom features unique built-ins that add both charm and storage. Conveniently located close to shopping, dining, recreation, and just minutes to the Bennington Recreation Center, this home combines comfort, character, and accessibility in a desirable neighborhood.

99 Coolidge Ave, Bennington
$279,000
3 Beds ⋅ 2 Baths ⋅ 5087836 MLS
Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout. Enjoy the convenience of first floor laundry, a beautiful front porch perfect for morning coffee or evening cocktails, and a private backyard ideal for entertaining, gardening, or simply relaxing while still enjoying the benefits of in town living. Owned and cherished by the same family for many years, this property has been exceptionally cared for and offers too many updates to count. From the inviting turquoise staircase to the unique character and charm found throughout the home, every corner tells a story. Take a stroll to local coffee shops, dinner spots, and community events, or enjoy hearing music drifting from the nearby Park-McCullough concert series on summer evenings. This home offers the perfect balance of neighborhood living, privacy, and small town charm. A true North Bennington gem full of warmth, character, and uniqueness this is a must see property. Call today for your private showing. This one will not last long!

8 West St, Bennington
$475,000
6 Beds ⋅ 6 Baths ⋅ 5087015 MLS
15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R & D, climate controlled storage, or if you are a service provider company (electrical, plumbing and heating, etc.) in need of more space for at grade storage of inventory, vehicles and offices with easy access it is ideal space to run a service business from. Significant renovations have been completed to the interior 2nd floor of the building. This space is roughly 6,000 sq ft and is a blank slate at present but has been prepped for a residential buildout including plumbing for bathrooms, fire alarm and full sprinkler system, electrical service and other new systems in place. Informal plans have configured 2 to 7 possible apartments in this space depending on size and cost vs. income analysis OR possibly a large in-town owners' residence with skiing, hiking and other year-round outdoor recreational opportunities in the Green Mountain National Forest and Lakes and Rivers within it just a short drive away. Final state and local permits required for finalized development plan. This space combined with the flex space and retail storefronts along main street would be an ideal mixed-use income property. If creating value and optimizing income with creative development of a fantastic building is intriguing, this is an unbelievable and very unique opportunity. At this price point it would be challenging to find another commercial/residential building of this size and condition with this much potential to be solid income property with tremendous equity gain in a very quick timeframe.

425 Main St, Bennington
$275,000
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
$209,900
2 Beds ⋅ 1 Baths ⋅ 5086144 MLS
Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a large garage with an attached storage shed and ample paved parking.

1083 Main St, Bennington
$309,900
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
$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
$269,000
3 Beds ⋅ 1 Baths ⋅ 5083898 MLS
This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back deck. Featuring replacement windows for energy efficiency, a paved driveway, and ample yard space, this property is ideal for anyone seeking extra room to play and entertain. Sidewalks and streetlights make evening strolls safe and pleasant, and the proximity to downtown ensures you're close to shopping, dining, and public transportation. For outdoor enthusiasts, the location is unbeatable: just 10 minutes from Prospect Ski Area, 30 minutes to Mt. Snow, 45 minutes to Albany Airport, 3 hours to New York City or Boston, and 2 hours to Hartford. This home is ready for your finishing touches to make it truly your own.

951 Gage St, Bennington
$209,000
4 Beds ⋅ 1 Baths ⋅ 5083528 MLS
Charming home in the heart of the Village of North Bennington, set on a beautiful village lot and offering solid bones with great potential. This well-maintained property features 4 bedrooms and a 3/4 bath, along with a first-floor bonus room. Wood floors lie beneath the carpet, ready to be revealed. Laundry hookups are in place for added convenience. Some updates are needed, providing an excellent opportunity to add your own finishing touches and build equity in a highly desirable location. Enjoy true village living with walkable access to cafés, restaurants, and trails, plus close proximity to Lake Paran and the Park-McCullough House. School choice at the elementary level adds flexibility. Just minutes to downtown Bennington for additional shopping, dining, and amenities, with easy access to multiple ski destinations. Conveniently located approximately one hour to Albany International Airport and about three hours to NYC and Boston. A rare opportunity to own in one of North Bennington’s most sought-after settings.

20 Sage St, Bennington
$429,000
3 Beds ⋅ 2 Baths ⋅ 5080205 MLS
Stunning split-level home in a close-to-town location offers the perfect blend of comfort and convenience. With 3 bedrooms, 2 bathrooms, and 1219 sq ft of living space, this open concept gem is ideal for families & those seeking a spacious retreat. Step inside and be greeted by a beautifully designed kitchen/dining/living area. The seamless flow allows for easy entertaining and quality family time. The kitchen boasts ample storage space, granite countertops & a center island. The primary bedroom comes complete with an en-suite bathroom for privacy and convenience. 2 additional well-appointed bedrooms provide space for guests, children, or a home office. Enjoy the low maintenance vinyl plank flooring throughout the home, providing both durability & a sleek aesthetic. With easy-to-clean surfaces, you can spend less time worrying about maintenance & more time enjoying your new home. Parking is a breeze with the two-car garage located underneath the home, providing shelter for your vehicles and additional storage options. Step outside onto the rear deck and unwind in the fresh air. It's the perfect spot for barbecues, coffee, or reading your favorite book. Conveniently situated close to town, golf course and Crotched Mtn ski area, this home offers the best of both worlds - a quiet residential area w/easy access to everything you need. Located less than 40 minutes from Concord and I-93, ensuring a convenient journey for work or leisure.

Lot 10-48-2 Old Stagecoach, Bennington
$810,000
2 Beds ⋅ 3 Baths ⋅ 5078962 MLS
*Price improvement*Business owners, investors, and creative owners take notice!! This stylishly built small home with attached 60 x 75 4 bay garage complete with commercial office space offers a realm of possibilities!! Live here/work here, live here and rent the commercial space, or rent both spaces. With under an hour to Concord, Manchester, and Keene, whether you are commuting or reaching your customer base this country location offers a rare opportunity to to enjoy the privacy of a country setting while generating income. Buyer to verify all measurements and preform all due diligence.

237 N Bennington Rd, Bennington
$1,495,000
7 Beds ⋅ 6 Baths ⋅ 5075253 MLS
Elegant and stately, this distinguished 1910 home is beautifully set in the heart of Old Bennington, Vermont. Thoughtful renovations began in 2000, carefully preserving the home’s historic character while enhancing comfort and functionality throughout. Offering over 6,000 square feet of gracious living space, the residence features seven bedrooms, six baths, and six fireplaces, with timeless architectural details at every turn. Enter into a large, welcoming foyer highlighted by a grand staircase that sets the tone for the home’s classic elegance. Generous living and gathering spaces flow seamlessly, while the chef’s kitchen enjoys dramatic eastern views, filling the home with morning light. The primary suite is a true retreat, complete with its own fireplace and a large sunroom perfect for quiet mornings or evening relaxation. A convenient second-floor laundry area enhances everyday living. Outside, the 4.5-acre setting is framed by stacked stone walls, a serene spring-fed pond, and lovely birch trees. A two-story carriage barn with garage space complements the property, completing this rare offering where historic beauty, thoughtful updates, and pastoral Vermont charm come together effortlessly.

16 West Rd, Bennington
$90,000
3 Beds ⋅ 1 Baths ⋅ 5074746 MLS
House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front porch, an ample front lawn and backyard, and a spacious attached 2-car garage with workshop space too! Bennington is a great location, with many amenities, and close proximity to Manchester outlets and Albany transportation. Opportunities like this are often quickly seized and quickly profited from; be the one to win this chance today!

109 Evergreen Dr, Bennington
$230,000
3 Beds ⋅ 1 Baths ⋅ 5068744 MLS
Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry. Step inside to find gleaming newly upgraded flooring, a warm and inviting layout, and stylish updates throughout, including new kitchen and bathroom cabinetry. The bright kitchen flows seamlessly into the dining and living areas, creating an ideal space for everyday living and entertaining. Relax on the covered front porch and enjoy your morning coffee while taking in the neighborhood atmosphere. Outside, the large detached garage offers excellent space for vehicles, hobbies, or additional storage, while solar panels help keep energy costs low. Combining the charm of downtown living with thoughtful modern improvements, this move-in ready home is one you won’t want to miss. Schedule your private showing today!

113 Main St, Bennington
$529,000
3 Beds ⋅ 3 Baths ⋅ 5067086 MLS
Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can be surmised that this property was for the intent of upper management housing for the farm. With sprawling views to the north, south and west, this location does not disappoint! A typical farmhouse style home that esthetically blends rustic and modern elements for easy living. A generously sized kitchen is perfection for entertaining and for spending time with family and friends. The living room invites a space for conversation, a cozy fire during the chilly Vermont evenings, or simply relaxing taking in the divine views at sunset. More casually, the family room offers exposed beams, vaulted ceilings and abundance of natural light. A formal dining room is strategic to the kitchen for holidays and family gatherings. The second floor boasts three bedrooms and two bathrooms, while the third bath is on the first level for convenience. And have I mentioned the renovated space above the garage? Wow! Breathe in the fresh air, take a walk up a country road and hunker down for the most genuine, spectacular sunsets. This is the type of special property that you will not want to miss.

58 Mount Anthony Rd, Bennington
$357,500
4 Beds ⋅ 2 Baths ⋅ 5048567 MLS
Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience, just steps from scenic hiking trails and close to Bennington College. Step inside to discover a freshly renovated kitchen and bathroom, complemented by new flooring throughout the home. Brand new first floor half bath and mudroom entrance recently added. The dining room features a sliding glass door that opens to a spacious back deck, perfect for outdoor dining and relaxing. A covered front porch adds classic New England charm and a welcoming touch. With a large attached garage offering plenty of storage and workspace, this home is as practical as it is inviting. Whether you're enjoying the peaceful surroundings or entertaining guests, this home provides comfort, style, and a true sense of place in a friendly, walkable neighborhood. Don’t miss this North Bennington gem, schedule your showing today!

19 Royal St, Bennington

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