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.

Turnkey Two-Unit Investment Opportunity in a Prime Downtown Location! This beautifully renovated duplex is perfect for a first-time investor or owner-occupant looking to build equity while generating income. The property features a two-bedroom unit and a one-bedroom unit, both thoughtfully updated and well maintained. The first-floor unit has been fully renovated, including an updated kitchen, new bathroom, new flooring, and updated electrical. The second-floor unit has also been refreshed with new flooring and fresh paint throughout, creating a clean and inviting living space. Major exterior improvements include new siding, new windows, and a repaired roof, offering peace of mind for years to come. Located in a great downtown setting close to shops, restaurants, and local amenities, the property is currently occupied by wonderful tenants, making it an easy addition to any investment portfolio. Whether you’re looking to live in one unit and rent the other or expand your rental holdings, this move-in ready duplex is an excellent opportunity. Listing agent owned.

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.

Located downtown, this three-unit building it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. The property includes an unfinished space with the potential to add an additional unit, offering great investment upside. Recent updates include a brand-new roof installed this year. Shared driveway with MLS #5057052; seller is seeking to sell both properties together. Listing agent is related to the seller.

Well located three-unit property in downtown Bennington offering a strong opportunity for both investors and owner occupants. Two of the three units are currently occupied by long-term tenants in good standing, providing immediate and reliable income. The third and smallest unit has been intentionally left vacant for the past couple of months while the owner completed improvements, creating an ideal opportunity for a first-time homebuyer or owner occupant using FHA, VA, or other low down payment financing. This allows a buyer to live in one unit while the rental income from the other two helps offset expenses. The location on Union Street places you close to downtown amenities including shops, restaurants, schools, and everyday conveniences. Whether you are looking to begin building equity while living on-site or expand your investment portfolio, this well positioned multi-family property offers flexibility and income potential.

Downtown mixed-use investment opportunity located on North Street near the Four Corners intersection of Routes 7 and 9 in the heart of Bennington. The property features six total units, including four residential apartments (three two-bedroom units and one one-bedroom unit) and two street-level commercial storefronts with direct North Street frontage providing strong visibility for retail, office, or service uses. The building extends deep into the lot with rear access from the back of the property and is conveniently located near public parking. Located within Bennington’s Downtown (D) zoning district supporting mixed residential and commercial uses and maintaining active street-level commercial space along North Street. Current rents present potential upside for investors through future lease adjustments, operational improvements, or updates over time. Income and expense information available to qualified buyers.

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!

This three-unit building features one unit per floor and is ideally located downtown. Set back from the road, it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. Highlights include a large back deck, a spacious partially fenced yard, and a shared driveway with MLS #5057051. The seller prefers to sell both properties together. Listing agent is related to the seller.

Exceptional mixed-use opportunity in Bennington’s MU-2 District offering flexibility for investors, owner-occupants, or live/work configurations. Sale includes both 307 North Street and 307.5 North Street, two separate buildings situated on one 0.70-acre parcel with strong visibility and approximately 150 feet of frontage along North Street (VT Route 7). The front building (c. 1840) offers approximately 3,446 square feet and is currently configured for professional office use with multiple private offices, meeting rooms, reception area, kitchen space, and updated mechanical systems including a high-efficiency boiler, providing potential for continued commercial use or residential conversion (subject to approvals). The detached rear building is a 3-bedroom, 1-bath home of approximately 1,200 square feet with separate utilities, offering income or owner-occupancy potential. Zoned Mixed Use #2 to allow a variety of residential and commercial uses, this property presents a rare opportunity for flexible use and future value-add in a highly accessible Bennington 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.

An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main building is configured with multiple residential-style suites, many with fireplaces, plus generous common areas suited for multifamily conversion, extended-stay residential use, or other permitted residential layouts. A separate on-site restaurant space is currently leased, providing additional income tied strictly to the real estate. The property is well maintained with updated systems and offers buyers the opportunity to reposition or convert the asset to meet residential or investment objectives. This offering conveys the real estate only. No hospitality or lodging business operations, financial records, future reservations, brand name, website, licenses, or goodwill are included or transferable with this sale. A separate commercial offering is available for buyers interested in acquiring the property together with an operating hospitality business. Walkable to downtown Bennington shops, dining, and cultural attractions, and convenient to Manchester, Williamstown, and the Berkshires.