Properties Near 318 North Street Bennington, VT

An investment gem or owner-occupied standout in the heart of Bennington, this renovated property features three distinct units, each offering the privacy and feel of a single-family home. Unlike traditional stacked apartments, all three units boast a two-story layout with 2 bedrooms and 1 full bath, ensuring no neighbors above or below. Each features modern finishes, bright living spaces, and a thoughtful flow between the main floor living area and the second-floor bedrooms. The "crown jewel" of the property is the beautifully converted two-story barn; this detached third unit offers total independence and opens up to its own beautiful, private backyard—a rare luxury for a multi-family setup.

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!

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!

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!

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.

Exceptional opportunity to own a beautifully maintained duplex in the heart of Bennington. Each spacious unit offers 3BR and 1.5BA, featuring warm wood floors, generous living space, and thoughtful layouts that appeal to both tenants and owner-occupants alike. Renovated and updated through the years, the property has been meticulously cared for and has an organized, efficient setup throughout. Both units benefit from separate utilities, dedicated basement and attic storage, and four off-street parking spaces—rare and valuable amenities that enhance everyday livability and long-term investment performance. Ideally located just minutes from downtown Bennington, enjoy convenient access to local shops, dining, and community amenities. Commuters will appreciate being approximately one hour to Albany Airport and 3 hours to NYC and Boston. A turnkey, low-maintenance asset with strong fundamentals, flexibility, and future upside—this is a standout opportunity in today’s market.

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.

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.

This beautifully renovated 2-unit home by JDN Properties offers 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 residence with a luxurious upstairs primary suite and kitchenette, use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize rental income with separate 1-bedroom and 2-bedroom units, this property is designed to adapt to your lifestyle. Each unit is equipped with independent Utilities, ensuring privacy and convenience. The estimated monthly rental income ranges from $2,200 to $2,600, based on current market conditions. Located in a tranquil village neighborhood, within walking distance of downtown Bennington’s vibrant shops and restaurants, and just two blocks from Southwestern Vermont Medical Center. The iconic Elm Street Market is close by, while Bennington College is only a short four-mile drive away. Recent renovations include fresh paint and new flooring throughout, creating a modern and inviting atmosphere. The downstairs living room features a passthrough countertop to the eat-in kitchen, enhancing the open-concept design. All kitchen cabinets and appliances are brand new. Upstairs, the apartment boasts a bright and airy open kitchen with kitchen island storage, and a picture window overlooking a deep backyard and a scenic brook, a tributary of the Walloomsac River. The large carpeted bedroom and full bathroom face the front of the house, providing comfort and privacy. Both furnaces have recently received new hot water mixing valves and have been professionally inspected and serviced, ensuring reliable performance. The property also offers two off-street parking spaces in front, with ample additional street parking available for guests. This charming home blends modern amenities with a desirable location, making it an exceptional opportunity for buyers seeking versatility and value.

A must see, well-kept 2-unit property offering flexibility for owner-occupants or investors. The main-level unit features 3 bedrooms, a full bath, a spacious eat-in kitchen with new cabinets, and a laundry room with washer and dryer. The upstairs unit offers 1 bedroom, a full bath, eat-in kitchen, and a cozy living room with hardwood floors. Exterior features include a nice, level backyard, 2 covered parking spaces under a large carport, and an additional 2-car garage/barn with workshop space, shed access, and a large open upper level for storage or potential additional use. Ideal for multi-generational living, income producing investment, or easily converted back to a single family residence. Move-in ready!

Downtown Bennington duplex with income in place and upside potential. The lower unit has been completely renovated, featuring a new kitchen, updated bathroom, and new flooring throughout. Exterior and structural improvements include a repointed foundation, fully sided exterior, new roof, and a gravel driveway. Bennington continues to see investment, revitalization, and ongoing redevelopment in the downtown and surrounding areas, enhancing the long-term appeal of this location. Known for its walkable downtown, the area offers local eateries, cafes, shops, and everyday conveniences right nearby. Ideal for an owner-occupant or investor, this manageable multifamily offers easy access to the New York and is just a short drive to Mount Snow, MASS MoCA, and the cultural and recreational attractions of Williamstown and the surrounding Berkshires.

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.

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.

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.