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$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
$219,000
5086669 MLS
This well maintained 2-unit home exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family. use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize rental income with separate 2-bedroom and 3-bedroom units, this property is designed to adapt to your lifestyle. Each unit is equipped with independent Utilities, ensuring privacy and convenience. Located village neighborhood, a short distance from The Bennington Bike path, the Bennington are trail system and downtown Bennington’s vibrant shops and restaurants, and Southwestern Vermont Medical Center. 15 minutes to Prosepct Ski area 30 minutes to Mt Snow 1 hour to Albany Airport, Boston. Manhatten and Hartford are all within 3 hours.

205 County 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
$55,000
5086024 MLS
Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home. Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process. Located on a publicly maintained road, this property combines convenience with a peaceful, well kept neighborhood setting. Enjoy close proximity to local amenities including shopping, dining, and the hospital, while also benefiting from easy access to major routes connecting you to Albany, Boston, and New York City. Outdoor enthusiasts will appreciate nearby walking and biking trails, along with year round Vermont recreation including hiking, skiing, and exploring the natural beauty of the area. Set within the North Bennington area and served by the local elementary school, this lot offers the ideal blend of location, lifestyle, and readiness. A prime opportunity to bring your vision to life in a scenic Vermont setting.

29 Asas Way, Bennington
$55,000
5086022 MLS
Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience. Public water and sewer are available, making the lot ready for development and easy to build on. Ideally located just minutes from downtown North Bennington, you’ll enjoy close proximity to local shops, dining, and everyday amenities, along with quick access to major routes for commuting to Albany, New York City, Boston, and beyond. Situated within a desirable school choice embrace the Vermont lifestyle with nearby walking trails, scenic outdoor spaces, and a peaceful country setting, all while being conveniently close to local amenities and the area hospital. This property offers the perfect balance of quiet surroundings and accessibilities, set in a welcoming neighborhood that captures the charm and character Vermont is known for. A prime, build ready parcel bring your vision and get started.

24 Asas Way, Bennington
$215,000
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
$150,000
5085591 MLS
Endless Possibilities Await - Approved Plans in Place! This exceptional piece of property offers exciting development potential with blueprints for storage units approved by the town - saving you time and hassle. The cleared site is ready for your vision and offers flexibility for various uses. Whether you're looking to build a single-family residence, multi-unit development (with town approval), or bring the approved storage unit project to life, this land is a rare find. Located in a desirable area with easy access, the property is being transferred in "Current Use" tax status, offering additional savings. Don't miss your chance to unlock the potential of this diamond in the rough - opportunities like this don't come around often!

M16-L02 Us Highway 202, 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
$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
$997,000
5081713 MLS
Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for financing and insurance. The property’s value is anchored by a substantial, two-story detached storage garage located on the back corner of the lot. This structure is in excellent condition, offering immediate utility for secure equipment storage, a workshop, or contractor inventory while a primary building is being constructed. With 114 feet of direct frontage on Northside Drive and high daily traffic counts, the visibility for signage and branding is exceptional. Located within the Northside Design Review District, this site ensures long-term investment protection, making it a sophisticated gateway location for your next business venture. Ground Lease option available

153 Northside Dr, 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
$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
$198,000
5081020 MLS
Secluded serenity meets unmatched convenience on this sprawling 54+/- wooded acres in beautiful and historic Bennington, VT! Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond, perfect as a future homestead centerpiece, with your home set back just beyond the pond. Good access via a paved, town-maintained road leading to level Class IV gravel frontage (gravel portion is not plowed or maintained by the town – 400+/- ft). A gate is currently in place, but the town will remove or relocate upon request. Essential utilities are highly accessible: town water runs along the frontage with confirmed adequate pressure for development, while power and high-speed cable internet sit just 250 feet west. State mapping indicates favorable conditions for a wastewater system and a previous purchaser performed soils test indicating a 6-bedroom residential mound system but opted not to purchase; they wanted a home much closer to the road, where the State maps indicate a small wetland. This should be easily avoidable. Experience the best of both worlds - a secluded, off-the-beaten-path atmosphere with immediate access to the Route 7 corridor. You are just minutes from historic downtown Bennington’s shops, dining, and the iconic Bennington Battle Monument. For outdoor lovers, enjoy proximity to the Green Mountain National Forest and premier skiing at Mount Snow and Stratton. Whether dreaming of an expansive recreational haven or a brilliant investment opportunity, this versatile acreage is ready for your vision.

399 Bard Rd, Bennington
$379,000
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
$65,000
5080317 MLS
This 5.6-acre lot is ideally situated at the edge of town, offering a peaceful retreat surrounded by nature. Furnace Brook winds through the backside of the property, providing a soothing sound that lulls you to sleep each night. Observe the abundant wildlife as they visit the stream with the Mountain view as the backdrop, this location is perfect for building your Vermont dream home.

80 Crossover Rd, Bennington
$65,000
5080306 MLS
Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life. Perk test were positive for a inground leaching system, results available.

2041 East Rd, Bennington
$2,190,000
5072776 MLS
Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand drivers. Ideal for investors seeking a site with traffic, frontage, and future upside in an established commercial corridor.

301 Northside Dr, Bennington
$950,000
5072098 MLS
A rare opportunity to acquire one of Southern Vermont's most adaptable residential investment properties. Currently known as the South Shire Inn, this landmark Victorian estate offers investors immediate income potential along with exceptional opportunities for future residential or mixed-use redevelopment. The property includes nine guest accommodations, owner's quarters, expansive common areas, a detached carriage house with additional guest accommodations, a commercial kitchen, and an established Thai restaurant providing existing rental income. Its flexible floor plan and MU1 zoning support a variety of permitted residential and mixed-use possibilities, including multifamily conversion, long-term or short-term rentals, workforce housing, owner occupancy, senior living, residential care, and other redevelopment opportunities, subject to local approvals. Originally built in 1887 by renowned architect William C. Bull, the property has been thoughtfully restored while preserving its architectural character. Located within walking distance of downtown Bennington's shops, restaurants, and cultural attractions, it offers investors a distinctive asset with exceptional long-term flexibility and redevelopment potential. Seller financing and lease-to-own opportunities may be available for qualified buyers.

124 Elm St, 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
$399,000
5064754 MLS
Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential. Situated on a 0.63-acre lot with ample parking and room for future expansion or additional development. A rare opportunity to own a piece of Bennington’s history with strong rental appeal and endless versatility. Ideally located within walking distance of Bennington’s vibrant downtown shops, restaurants and community services—offering exceptional convenience for residents and strong visibility for commercial tenants.

126 Washington Ave, Bennington
$96,406
2 Beds ⋅ 2 Baths ⋅ 5050696 MLS
Welcome to 32 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is 100% complete. Home is available for showing. This property participates in the Mobile Home Infill Program (MHIP) and is open to anyone who works or lives in Vermont.

32 Cassie Ln, 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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