Bennington Vermont Real Estate

Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer. Current tenants keep their units up well.

Centrally located renovated Bennington duplex, with backyard and garage. This duplex can generate an annual net operating income of ~$23k+ at current numbers (~10.5%), producing robust returns from cash flow and not speculation! Owner performed renovations since acquiring, including to heating systems, plumbing, and gut renovation of the upstairs 2br (currently rented for $1,400). Unit 1 on the ground floor is spacious 3br ~1,250 square feet with backyard access, eat in kitchen, desirable layout, and would make a perfect owners' unit if the intention is to owner occupy and cover your mortgage and make extra income (current rent is $1,709 and tenant is on a month-to-month lease). his is a significant opportunity to acquire in-demand housing in Bennington ahead of the historic $54million Bennington Highschool mixed use redevelopment down the street (one of the largest redevelopments in state history), and the start of a falling rate environment that should lead to organic price appreciation independent of the strong cash flow. Listing Broker is a member of the LLC selling the property.

Low maintenance duplex in Bennington. Offering good rental history and income. 2 -3 bedroom units, newer systems, vinyl siding and more. Walking distance to town. schools and recreation.

Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a prime spot to establish or expand your business. Upstairs, you’ll find a generously sized 2-3 bedroom, 1 bathroom apartment spanning approximately 1,250 square feet. Whether you choose to live above your business or rent it out for additional income, the upper-level unit offers comfort and flexibility with plenty of natural light and charm. This property is perfect for an entrepreneur looking to live and work in the same location or an investor seeking strong rental potential in a vibrant downtown setting.

A wonderful investment opportunity in the desirable village of North Bennington! This income-producing property with three units has been well kept and updated over the years - most recently with a brand new roof. Two of the three-bedroom units have been freshly renovated and all are currently occupied with a strong rental history. Two of the units have two stories, giving it a townhouse feel, while the one-level unit is perfect for accessibility. All include laundry hook-ups for convenience. There is also ample parking for tenants and guests. Across the street is the lovely Paran Creek, and you're not far from Lake Paran. Great dining and shopping is well within walking distance. With the strong need for housing in the area, you can't go wrong with owning your very own rental property! Don't miss out on this one.

Charming Downtown Victorian - Income Opportunity Meets Timeless Style Tucked behind the classic facade of this downtown Bennington gem lies an incredible opportunity-for homeowners and investors alike. Located in the heart of downtown on a street known for both professional and residential appeal, this Victorian-style duplex offers versatility, character, and reliable income potential. Each unit-one upstairs, one downstairs-offers over 1,140 square feet of well-maintained and tastefully furnished living space. All utilities are separate for each unit. Currently operating as a successful Airbnb with consistent 5-star reviews, this property is truly turnkey, ready to welcome guests or new owners immediately. The upstairs unit features three bedrooms, making it perfect for a family looking to live comfortably while generating income from the lower-level rental. Alternatively, continue operating both units as short-term rentals and enjoy a steady stream of income from the area's many visitors, skiers, foliage seekers, and Bennington College families alike. Just steps from shops, restaurants, and local attractions, this location couldn’t be more ideal for guests or residents who want to experience the charm of downtown Bennington on foot.

Great investment opportunity! This 3 Unit building consists of one, one bedroom unit and two, two bedroom units. The possibilities and flexibility are a real upside. With minimal work the units will be ready to rent out and you'll be able to select your own tenants. One heating system so owner is responsible for heat in it's current configuration. The large lot has potential for additional structures if the town approves. Large wooded section of the property and out of town living, while still being just a few minutes away from downtown Bennington.

Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs. Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable bedrooms. Recent energy-efficient upgrades include newer windows, oil tank, insulation, and high-efficiency heating system, helping to keep utility expenses low while enhancing year-round comfort. The property offers separate utilities, off-street parking, private outdoor space, and a strong rental history with consistent cash flow. Whether you're looking to live in one unit and rent the other or add a solid asset to your investment portfolio, this two-family checks all the boxes. Don't miss this rare opportunity for affordable in-town living with excellent long-term upside!

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.

An exceptional opportunity to own a prominent historic Victorian property currently configured for income production in the heart of Bennington. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible use and strong upside potential as a multifamily or mixed-use investment. The main building features multiple well-appointed residential-style suites, many with fireplaces, along with generous common areas that lend themselves well to apartment or extended-stay configurations. A separate on-site restaurant space is leased to a successful Thai restaurant providing additional income stream. Recent zoning approvals allow for a variety of residential and mixed-use options, including multifamily conversion, restaurant, bar/lounge, and catering uses. The property is well maintained with updated systems and a proven operating history, offering buyers the ability to reposition, convert, or continue income operations. Located within the Village of Bennington, just blocks from downtown shops, dining, and cultural attractions, and convenient to Manchester, Williamstown, and the Berkshires. This offering is cross-listed with commercial MLS to reflect its flexibility, income potential, and redevelopment opportunities.