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60 Tori Ln, 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
903 Gage St, Bennington
$232,500
3 Beds ⋅ 2 Baths ⋅ 5101468 MLS
You can make this home your own! With a little TLC, this charming 3 bedroom, 2 bath, Cape has the potential to become the perfect home. Featuring a large, level yard, a two-car, detached garage, with attached outdoor room, mudroom to the kitchen, wood floors, fireplace (condition unknown) and with this central location, it offers endless possibilities. Whether you are looking to renovate, personalize, or invest, this is a fantastic opportunity to create your vision. Close to downtown, schools, skiing, shopping and a short ride to Albany NY and Williamstown, MA. Next to most everything you will need.

903 Gage St, Bennington
128 Northside Dr, Bennington
$265,000
3 Beds ⋅ 2 Baths ⋅ 5099392 MLS
Welcome to this 3 bedroom, 1.5 bath Cape style home located in a planned commercial zone. Offering 1,688 square feet of well-designed living space on a manageable 0.26-acre lot, this inviting residence is perfect for comfortable family living. Offers beautiful hardwood floors gracing the upstairs bedrooms, as well as the spacious living and dining rooms—ideal for gathering with loved ones. The sunroom provides a bright and tranquil spot to relax or enjoy morning coffee, while the two-car garage ensures plenty of space for vehicles and storage.

128 Northside Dr, Bennington
549 Houran Rd, Bennington
$259,000
4 Beds ⋅ 2 Baths ⋅ 5098985 MLS
Well maintained and thoughtfully updated, this 4-bedroom, 2-bath home offers the ease of single-level living on a beautiful level one-acre lot in Bennington's desirable west end. Enjoy stunning mountain views from the spacious back deck or sip your morning coffee on the covered front porch. Inside, you'll find an updated kitchen, refreshed bathrooms, a cozy fireplace, central air conditioning, a 2023 roof, an updated heating system, and a spacious primary suite featuring a jetted step-in tub and separate shower. Offering the perfect blend of comfort, convenience, and low-maintenance living, there's also room to add your own personal touches over time. Enjoy a peaceful setting just minutes from downtown Bennington for dining, shopping, cultural attractions, and everyday conveniences, with easy access to multiple ski destinations. Conveniently located approximately one hour from Albany International Airport and about three hours from both New York City and Boston.

549 Houran Rd, Bennington
118 Foster Dr, Bennington
$190,000
5 Beds ⋅ 2 Baths ⋅ 5098066 MLS
Invest in the potential with this unique split-level ranch and guest house. This property presents an exceptional opportunity for anyone looking to roll up their sleeves and bring a property back to life. Set on expansive acreage surrounded by peaceful woodlands, the property offers a tranquil rural setting while remaining just a short drive from town amenities. The main residence features three bedrooms and one bathroom, with a practical layout flowing from the kitchen into the dining area and living room. A rear deck overlooks the wooded landscape, providing a peaceful spot to enjoy the surrounding natural setting. The detached guest house offers two bedrooms, one bathroom, and a kitchen area, creating potential for a separate living space, guest quarters, multi-generational living, or rental income. The property offers flexibility and plenty of possibilities for those willing to put in the work. With its acreage, privacy, two separate living structures, and versatile layout, this property offers tremendous potential for the right buyer. Bring your vision, tools, and imagination and transform this property into something truly special.

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

127 Dewey St, Bennington
109 County St, Bennington
$264,900
4 Beds ⋅ 2 Baths ⋅ 5096457 MLS
The renovations are done, just move in! Nearly everything is NEW at 109 County Street, including the price! In addition, the seller is offering a $5K credit towards the buyer’s closing costs. This extensively renovated 4BR/2BA home with a fully fenced yard gives you the opportunity to enjoy the benefits of a much newer home without the time, expense, and stress of renovating one yourself. Featuring 3 generous bedrooms and a bathroom w/tiled shower on the second level, and a first floor bedroom, bathroom, and laundry on the main level. New roof. New windows. New siding. New insulation. New Deck. New electrical. New plumbing. New walls. New flooring. New Appliances. New lighting. New doors and trim. Fresh paint. And that's just the beginning. The beautifully renovated kitchen features brand-new cabinetry, countertops, and stainless-steel appliances, while the updated bathrooms offer modern fixtures and finishes. This renovation goes far beyond a fresh coat of paint- the seller has invested in the major systems and countless details that make home ownership truly low maintenance. This is the kind of house where you can unpack your boxes, and start living. No renovation projects. No wondering what needs to be replaced next. No spending your weekends working on the house. And now there's even more value: the seller is offering $5K toward the buyer's closing costs with an acceptable offer. That's money you can keep in your pocket for moving expenses, furnishings, or simply enjoy the benefit of a lower cash requirement at closing. Whether you're a first-time buyer, downsizing, looking for an investment, or simply want a beautiful home without a renovation project, this property deserves a look. Located just minutes from downtown Bennington, shopping, restaurants, schools, and everyday conveniences, 109 County Street combines extensive updates with practical location and exceptional value. Why buy a home that needs work when you can buy one where the work is already DONE?

109 County St, Bennington
105 Hicks Ave, Bennington
$170,000
3 Beds ⋅ 2 Baths ⋅ 5096423 MLS
Back on the market- This one is for the buyer that sees potential, not perfection! 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
107 Lyons St, Bennington
$80,000
4 Beds ⋅ 2 Baths ⋅ 5096159 MLS
Situated on a peaceful dead-end street, this home offers tremendous potential for investors, contractors, or buyers looking to create their dream home. The property features 3 bedrooms, with the possibility of a fourth, along with 2 bathrooms, providing a highly desirable layout and ample living space. With some vision, care, and updates, this home can be transformed into a beautiful residence in a convenient location. Just minutes from the high school and only a short distance from downtown Bennington's shops, restaurants, and local amenities. The price is firm, and the sale will require an all-cash transaction.

107 Lyons St, Bennington
498 Town Line Rd, 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
406-408 Gage St, Bennington
$249,900
5095558 MLS
Bring this historic gem back to life and unlock its incredible potential! Rich with the timeless character and charm of a late-1800s home, this unique property features spacious rooms and many original architectural details waiting to shine again. The building includes three two-bedroom units, including a generously sized two-story unit with a kitchenette and full bathroom on the upper level. Enjoy a large covered front porch, private off-street parking in the rear, and a storage shed for added convenience. Ideally located near downtown shopping, restaurants, recreation facilities, and public transportation, this property offers both charm and accessibility. Whether you're an investor, renovator, or someone with a vision, this is a rare opportunity to build equity and restore a piece of history. With strong income potential and endless possibilities, this property is ready for its next chapter. Don't miss out!

406-408 Gage St, Bennington
89 Merson St, Bennington
$299,000
3 Beds ⋅ 2 Baths ⋅ 5095251 MLS
Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026. What truly sets this property apart is its incredible versatility. The bonus space presents endless possibilities for a home based business, professional office, hobby space, expanded living area, or potential in-law accommodations. Whether you’re looking for room to grow, work from home, or create a space tailored to your lifestyle, this home offers the flexibility to make it happen. The generous lot and rear garage access provide additional opportunities for future improvements. Buyers may appreciate the potential to enhance accessibility and functionality with a redesigned driveway configuration, such as a circular drive, while maximizing the usefulness of the garage space and expansive yard. Enjoy the convenience of being just minutes from downtown Bennington’s shops, restaurants, coffee houses, and local attractions, while still enjoying the privacy of a large lot. With easy access to area hiking trails, ski resorts, and major routes to Boston and New York, this property combines location, character, and opportunity in one exceptional package.

89 Merson St, Bennington
262 Union St, Bennington
$299,000
3 Beds ⋅ 2 Baths ⋅ 5095149 MLS
Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out. The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even a pantry! The kitchen flows seamlessly into the dining room and the the living room, creating an open and inviting atmosphere where family and guests can easily gather. Laminate flooring throughout the first floor provides durability and a clean, cohesive look. Convenience is key with a practical mudroom entry and first-floor laundry. The full bathroom on the main level features a relaxing soaking tub with jets, perfect for unwinding after a long day. Upstairs, you'll find three comfortable bedrooms with attractive wood flooring, along with a half bath. The primary bedroom includes a walk-in closet, offering excellent storage and organization. Additional living space awaits in the partially finished basement, which is already prepared for radiant heat, providing exciting possibilities for future expansion. Recent energy-efficient improvements include heat pumps for year-round heating and cooling, as well as added attic insulation to enhance comfort and reduce utility costs. Appliances have all been updated rescently – Microwave, dishwasher, heat pump system, stove, washer, dryer, and refrigerator, and a basement refrigerator and chest freezer. The boiler was also replaced in 2022. Outside, the property offers even more versatility with two outbuildings for storage, along with a charming gazebo that creates the perfect setting for outdoor relaxation, or entertaining. Combining functional updates, flexible living space, and attractive outdoor amenities, this property is ready to welcome its next owners home.

262 Union St, Bennington
193 Finley Dr, Bennington
$450,000
2 Beds ⋅ 3 Baths ⋅ 5094280 MLS
Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes laundry, creating true one-floor convenience. Main living spaces are warm, bright, and inviting, with hardwood floors, bay windows, abundant natural light, and a distinctive two-sided brick fireplace with gas insert anchoring both the living and dining rooms. Built-in shelving adds character and function, while the easy flow between rooms makes the home comfortable for everyday living and welcoming for guests. The galley kitchen sits at the center of the home, with space for a breakfast table and direct access to the large deck. Big picture windows frame the surrounding greenery and mountain view, bringing the setting beautifully indoors. The finished lower level adds substantial flexibility, featuring a spacious rec room with wet bar, pool table, and gas stove. It's an ideal space to enjoy game nights, hobbies, movie watching, or relaxed entertaining. This level also includes a half bath, updated utilities, and a large storage room. With both an attached 2-car garage and a detached 2-car garage, there is outstanding room for vehicles, storage, equipment, workshop space, or recreational gear. Outside, the property feels private and established, with open lawn, mature landscaping, garden space, and room to enjoy the quiet surroundings. Built in 1987 and offered by its original owner, this property presents a special opportunity for buyers seeking space, privacy, mountain views, main-level living, and exceptional utility in one complete package.

193 Finley Dr, Bennington
524 Jennings Brook Dr, Bennington
$350,000
2 Beds ⋅ 2 Baths ⋅ 5090266 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.

524 Jennings Brook Dr, Bennington
432 South St Unit D2, 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
103 Jennings Brook Dr Unit 103, 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
8 West St, Bennington
$249,000
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
69 Birch Glen Dr Unit 12, Bennington
$265,000
2 Beds ⋅ 3 Baths ⋅ 5087755 MLS
BACK ON MARKET! Enjoy low-maintenance living at The Birches of Bennington, ideally located just minutes from Crotched Mountain for skiing, snowboarding, hiking, and year-round outdoor recreation. This spacious 2-bedroom, 2.5-bath condo features a bright and inviting living room with a cozy wood-burning fireplace, perfect for relaxing after a day on the slopes. The open-concept kitchen and dining area offers abundant cabinet and counter space, appliances, a breakfast bar, and sliding doors leading to the back deck for easy indoor-outdoor living. Upstairs, you’ll find two generously sized bedrooms, each with its own ensuite bath. The primary suite includes two oversized double closets and a private balcony with views of the mountain slopes. The unfinished lower level provides excellent potential for a recreation room, home office, gym, or additional living space. Conveniently located just 90 minutes from Boston and about an hour from Manchester and the Seacoast region, this is the perfect opportunity to enjoy four-season living in a sought-after mountain community. Don’t miss your chance to live where you play! SELLER FINANCING AVAILABLE

69 Birch Glen Dr Unit 12, Bennington
425 Main 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
1083 Main 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
340 Pleasant St, Bennington
$179,000
5085882 MLS
Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with rental income from the other, or continue using the property as an investment. Appears well suited for FHA, VA, USDA, and conventional financing. Conveniently located near shopping, dining, schools, medical facilities, and other everyday amenities in downtown Bennington. Bennington continues to benefit from ongoing investment and redevelopment throughout the downtown area, adding to the appeal of this location.

340 Pleasant St, Bennington
2 Hamlin Ave, Bennington
$199,900
5085771 MLS
2-Unit Multi-Family with Professional-Grade Workshop! Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast, or premium climate-controlled storage rental, this workspace provides an incredible environment for any business or hobby. Located directly above the shop are two freshly painted 1BR/1BA apartments with a remarkable decade-long track record of consistent tenancy. The property currently generates a steady $1,850 in monthly income. The property provides plenty of off-street parking suitable for automobiles or equipment, plus a 12' x 20' shed for additional storage. Unmatched versatility and a turnkey footprint.

2 Hamlin Ave, Bennington
683 Water St, 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
951 Gage St, Bennington
$255,000
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
20 Sage St, Bennington
$199,900
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
318 North St, Bennington
$265,000
5081898 MLS
Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a wide range of commercial uses including retail, food and beverage, office, studio, and personal services. The second-floor apartment, renovated by a prior owner approximately 10 years ago, provides comfortable living space ideal for an owner-occupant or steady rental income. The first floor and basement, formerly home to a long-standing florist shop, now offer a bright, open layout with the removal of the walk-in cooler, making the space feel larger and more adaptable than ever. Recent updates include fresh paint, new flooring, LED lighting, and a convenient half bath. For investors or those seeking a full residential conversion, the layout and separate entrances offer a clear opportunity to reconfigure the first floor into a second living unit, establishing a true duplex. The basement adds valuable storage with built-in shelving, while the walk-up attic offers additional storage or future expansion potential. Additional features include separate electric meters, shared boiler and oil tank (both replaced in 2020), vinyl siding and windows, architectural shingle roof, town water and sewer, and high-speed internet. Off-street parking for both units enhances functionality. Situated along one of North Street’s most traveled corridors, the property benefits from excellent visibility, signage potential, and proximity to established neighbors like Blue Benn Diner, Wassick’s Tire Service, and the Vermont Veterans Home. Whether you’re looking for an investment property, live/work setup, or a redevelopment opportunity, this flexible property is ready to meet your vision.

318 North St, Bennington
124 S Branch St, Bennington
$275,000
5081521 MLS
Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups - perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street. With a level lot just over half-acre, off-street parking, and 1 car garage/barn with additional storage, plus a prime location near downtown shops and restaurants, this is an ideal opportunity for both investors and owner-occupants!

124 S Branch St, Bennington
116-118 S Branch St, Bennington
$269,000
5081518 MLS
Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car garage. Ideally located just minutes from downtown shops, restaurants, and nightlife. A fantastic opportunity for owner-occupants or investors alike!

116-118 S Branch St, Bennington
527 Jennings Brook Dr, Bennington
$375,000
2 Beds ⋅ 2 Baths ⋅ 5080868 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. Custom Kitchen with granite countertops, custom tile shower unit. 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.

527 Jennings Brook Dr, Bennington

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