Properties Near 556 South Main Street Brattleboro, VT

Just around the corner! From the middle and high school, Oak grove elementary! Pop around the corner for all the high school games, exercise at the track. Interstate is minutes away for easy access to work or play! One apartment is over 1,000 square feet so tons of room for owner occupancy! 2 nice front porches. Worth looking at for either your own home or as an investment. Masks please. Owner is a licensed appraiser and is doing a 1031 exchange. 48 hour notice to show.

The current owner is occupying as a single family and therefore there are no filings on lead paint. Should new owner decide to return to rentals, the reports would need to be newly filed. only 1st floor unit is available to show on first showing. Current owner does not have a rental history. Please have your buyer fully qualified before requesting a showing.

Excellent opportunity to own a three-unit investment property in a fabulous location. Enjoy being near the well-known Little League field — grab a hot dog and catch a game. Conveniently located near public transportation, the hospital, shopping, restaurants, schools, and other local amenities. The property offers a great yard set back from the road, providing both privacy and usable outdoor space. A large barn accommodates up to two vehicles and offers excellent additional storage potential. The home features low-maintenance vinyl siding, plenty of off-street parking, and strong investment potential for both owner-occupants and investors alike. Each unit has its own private entrance and separate electric service, adding convenience for tenants and ease of management for owners.

458 Williams Street, formerly the WKVT headquarters, presents an opportunity for buyers exploring potential residential or mixed-use conversion in a convenient Brattleboro location. The 3,240 SF building is currently configured for office use across two levels, with more than 10 individual rooms, multiple bathrooms, and an existing kitchenette. This layout may lend itself to reconfiguration depending on a buyer’s plans, whether for multi-unit housing, live/work spaces, or continued commercial use. Built in 2003, the structure offers the advantage of more modern construction compared to many conversion properties, with central A/C, public water and sewer, high-speed internet availability, and a standby generator system already in place. On-site parking is established, which is an important consideration for any future use. The property sits on 4.3 acres with frontage along Whetstone Brook, providing a natural setting and additional land area that could be incorporated into future plans. The building itself is set above the brook, offering privacy and separation from the surrounding area. Located in a commercial zoning district just minutes from I-91 and downtown Brattleboro, the property offers flexibility for a range of potential uses. Buyers should perform their own due diligence regarding zoning, permitting, and feasibility of any intended conversion.

Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass windows, and glowing wood floors. First floor has a bedroom option and a full bathroom, there's a full bathroom on each floor! Plenty of room for everyone with three more bedrooms and a bathroom on the second floor. There is an additional room on the second floor with separate entrance that would make a great office, and the third floor offers an in-law potential with a one bedroom studio apartment. There are two furnaces and two oil tanks, one for the first floor, one for the second floor, and a propane wall unit for the third floor.

This handsome two unit home is located on desirable Pleasant Street and includes a large yard with plenty of parking. Each unit is 2 bedrooms, bath, living room and kitchen and they feature softwood flooring, bulls eye molding, replacement windows, decking and a covered front porch. Tenant pays for Electric and Heat and each unit has new Buderus boilers. W&D hookup up and Coin washer and dryer in the basement for the lower apartment. Landlord pays common space electric (front porch, basement and common hallway).

Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers an excellent opportunity for investors. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. All three units are currently occupied, providing immediate cash flow. Unit 2 also benefits from a recently installed water heater. Enjoy peace of mind with separate utilities, state lead compliance, vinyl siding, and several replacement windows. Located in a highly walkable area—just steps from downtown, grocery stores, the hospital, and public transit—this property combines low maintenance with strong income potential. The spacious 2-bedroom units feature bright living areas and comfortable bedroom sizes, while the 1-bedroom unit offers a cozy, efficient layout. Each unit is thoughtfully designed to maximize natural light and functional living space. Off-street parking included. With major updates already completed—including vinyl siding, selective window replacements, and recent interior renovations—this property is designed for low-overhead management. The separate utility configuration allows tenants to manage their own heating and electric costs, further simplifying ownership. Don't miss this opportunity to own a high-quality multifamily property in one of Brattleboro's most convenient locations. Schedule your showing today!

New beginnings! Just right to live in one side, fix the other and have the tenant pay for your new lifestyle or have a family duplex and lie with extended family. the north side is vacant, needs renovation, and the south side has a tenant that will transfer with the building. Corner lot, yard, off street parking. Easy to see north unit, but otherwise a 48 hour notice to show.

69 Grove Street is a pleasant 2 unit home just a short walk from vibrant downtown. Each unit features 2 bedrooms, bath, living room and kitchen with wide board flooring and replacement windows. The first floor unit has a covered front porch, pantry and W&D hookups in the basement. The second floor apartment has an additional room (office), W&D hookups, decking and a rear staircase. Recent improvements include a new boiler, full attic insulation and new oil tanks. Tenant pays for Heat, Electric, Water & Sewer.