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.
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.
The Best of Both Worlds! A Home with Room to Grow and Income Potential! Looking for a property that offers more than just a place to call home? Welcome to 224-226 Branch Street, where comfortable living meets incredible versatility! This single-family home features a spacious backyard, a back deck perfect for relaxing or entertaining, and a storage shed for all your outdoor essentials. The expansive yard offers plenty of room for gardening, recreation, pets, or simply enjoying your own outdoor space. But what truly sets this property apart is the converted barn featuring an apartment that is currently rented! Imagine the possibilities of having a separate rental space to help offset your mortgage, accommodate extended family, or potentially create your own home office, studio, or workshop. Whether you’re looking for a primary residence with additional income potential, a multigenerational living arrangement, or simply a property with extra space to pursue your passions, this unique offering provides flexibility that’s hard to find. Live in the house, enjoy the yard, and let the possibilities of the barn work for you!
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!
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!
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.
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!
Well-maintained four-unit property ideally located in downtown Bennington. This versatile multi-family offering features just the right amount of yard space for outdoor enjoyment, along with ample off-street parking. The property includes two one-bedroom units, one two-bedroom unit, and one spacious four-bedroom unit, providing a flexible mix of rental options. With a strong rental history and varied unit sizes, this property is well-suited for continued use as an investment property or for an owner-occupant seeking the ability to adjust housing needs over time. Rent increase in October was updated.
Secure a smart, low-maintenance income property featuring four well-kept units—two 2-bedroom and two 1-bedroom—on a dead-end road. This is turnkey living for tenants and hassle-free ownership for you. Three of the four units have dedicated washer/dryer hookups and each unit is fully separated utilities (electric, gas or oil, hot water), so tenants manage their own bills and turnover is smooth. With reliable, long-term renters in place, enjoy immediate cash flow and minimal management effort. The private setting offers privacy and minimal traffic, while consistent occupancy make this an ideal buy-and-hold investment. Don’t miss this rare opportunity to own a dependable, income-producing asset in an out of the way location.
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.
Historic Downtown Bennington Commercial Property – Endless Possibilities! Discover a rare opportunity to own a piece of Bennington’s history! Built in 1840 and listed on the historic registry, this distinctive three-story property offers exceptional potential in a premier Main Street location, just steps from the Four Corners intersection of Main Street and Route 7. Currently operating as a law office, the property offers flexibility for a variety of commercial uses, including professional offices, medical or wellness practices, entrepreneurial ventures, or an investment property. The second and third floors present exciting possibilities for residential conversion, with potential for two separate apartments or a spacious two-story townhouse, subject to applicable zoning, permitting, and historic preservation requirements. Enjoy outstanding visibility, steady traffic exposure, and convenient walkability in the heart of downtown Bennington. Whether you're an investor, business owner, or visionary looking to create something special, this historic property offers a unique opportunity to bring your ideas to life in a location that’s hard to beat!
Exceptional investment opportunity in downtown Bennington! This income-producing multi-family property features eight apartments across two buildings, offering a versatile mix of four 2-bedroom/1-bath units and four 3-bedroom/1-bath units. With eight rental units and an additional unimproved 0.26-acre lot, this property offers investors an opportunity to build long-term wealth while exploring future value-enhancement possibilities. Three apartments have undergone updates/renovation within the past two years, providing a solid foundation for continued investment and potential rental growth. Ideally situated just off Main Street, the property benefits from convenient access to downtown Bennington's shops, restaurants, services, and amenities. A rare opportunity to acquire a substantial multi-unit investment with room to maximize its potential in a desirable downtown location.
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.
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