Brattleboro Vermont Real Estate

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.

Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers an excellent opportunity for both investors and owner-occupants. 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. One of these renovated units is currently occupied, while the remaining vacant unit is truly turn-key and ready for immediate occupancy or lease-up at market rates. Unit 2 also benefits from a recently installed water heater. The property currently has two occupied units, providing immediate cash flow, with one vacant unit offering flexibility for an owner-occupant or additional rental income. 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!

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).

This charming Victorian 3 family blends classic architecture, strong rental potential, and an exceptional opportunity for a new owner to build equity. Period details greet you at every turn—decorative exterior brackets, turned porch columns, tall windows, rich wood trim, and a welcoming front porch that sets the tone for the character inside. Well cared for and boasting great bones, the property is primed for a new owner to build upon its historic interior features and bring fresh vibrancy to the living spaces. The first floor unit showcases some of the home’s most impressive original elements, including a beautifully preserved tin ceiling, an authentic butler’s pantry, hardwood flooring, pocket doors, and natural woodwork. With a generous seven room layout, wraparound porch access, and abundant natural light, it’s an ideal option for an owner occupant. The second floor unit mirrors the first with the same spacious seven room floor plan, offering excellent rental appeal. The third floor apartment has a more modern, airy, attic style feel and features a private south facing deck—perfect for tenants seeking a unique, sun filled space. Kitchens and baths throughout the property are clean and functional, and as reflected in the photos, they present a prime opportunity for modernization—allowing the next owner to refresh the spaces and significantly enhance long term value. Set on a compact lot, the home offers a landscaped front yard and ample off street parking discreetly tucked at the rear of the property. Each apartment has separate mechanical systems, with tenants responsible for their own utilities. Conveniently located near downtown, schools, shopping, and transportation, this Victorian 3 family combines timeless character with meaningful potential—ideal for investors or owner occupants looking to build equity while enjoying the charm of a classic New England home.

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.

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.

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.

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.

Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser. Seller is doing a 1031 exchange. 48 hour notice to show, mask up please!

Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an exceptional occupancy history with very little vacancy. The building has been well maintained and features newer windows, vinyl siding, two oil tanks, and two boilers. Tenants pay their own electric while the owner covers heat, water, sewer, and taxes. Conveniently located just moments from downtown shopping, restaurants, entertainment, and public transportation, the property is ideally situated to support continued strong rental demand. A unique opportunity to acquire a proven income-producing property with a long track record of stable occupancy and excellent cash flow potential.

This is a rare opportunity to take over a multi-family project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the complex will offer roughly 11,183 square feet of high-demand housing. The financial incentives currently lined up for this project are significant. The sale includes access to VHIP funds : 8 original units $130,000 and the 5 new units $187,500. Additionally, there is a $125,000 Downtown State Tax Credit that can be used directly or sold to a bank at 90% face value, plus an estimated $60,000 in weatherization incentives. A recent appraisal supports a strong finished value, offering a clear path to equity for an investor. Located in a neighborhood with high rental demand and a low vacancy rate, this property is in an ideal location and could also be renovated one stage at a time so that units could go live and start generating cash flow. A lot of leg work has already been done, and the entire community wants to see this building come alive again with residents. This part of Brattleboro is thriving and this is truly the opportunity to take the worst house in the best neighborhood and turn it into affordable housing that generates a positive return. All project documents, including architect plans and both as-is and as-complete appraisals, are available in a shared Drive file. Please note that proof of funds or a commercial pre-approval is required before scheduling a showing or receiving the full data room.

Attention Investors & 1031 Exchange Buyers! A premier, turn-key investment opportunity is now available in the high-demand Brattleboro rental market. Offered at $540,000, this massive, stately 6-unit multifamily building delivers immediate, fully stabilized cash flow from day one. With a robust gross monthly income of $7,675 and an outstanding gross annual income of $92,100, this property is a proven portfolio foundational asset. The property features a rock-solid financial track record with an annual net operating income (NOI) of $33,756.41, representing an exceptional 6.25% un-leveraged Cap Rate and a highly competitive 5.86 Gross Rent Multiplier (GRM). All 6 units are currently fully occupied by seasoned tenants, with all security deposits transferring securely to the new owner at closing. The asset stands out for its exceptional location and structural layout. Situated in a prime, highly walkable in-town location, it sits just minutes from vibrant downtown Brattleboro shops, dining, transit, and major local employers—positioning this building for historically near-zero vacancy rates. Operationally, the building runs like a well-oiled machine. Streamlined infrastructure is already in place with separate tenant communications and established, reliable local vendor accounts (including Dead River for fuel delivery, Mastaler Cleaning for common area upkeep, and Goodenough for weekly trash service). The structural footprint includes a solid brick facade, convenient off-street parking for multiple tenant vehicles, a secure consolidated front porch mailbox station, and coded keyless entry to the basement utility area. Whether you are seeking to execute a strict tax-deferred exchange or expand your passive income portfolio, this stabilized multifamily building offers predictable yields with clear operational upside to push rents over time. Financial disclosures and itemized expense sheets are ready for review.

Great income producing properties! Rent out the 2 apartments over the garage while you live in the adorable 2-story home. Or, finish the house renovations and rent all 3. Located on a quiet side street in this beloved neighborhood, you are in close proximity to the Retreat trails, which offer extensive hiking, and close to our vibrant downtown, a short walk away. The adorable 1,600-square-foot home has 3 bedrooms and 2 baths. The light-filled, open-concept kitchen/dining area is inviting and spacious. Upstairs needs finishing, but there are vaulted ceilings and an abundance of light from the many skylights. Pretty stone paths, widespread gardens, open decks, and a level, private sunny lawn. Above the two-car garage are two rental units—one occupied and one vacant—offering immediate income, strong potential for investors, and appreciation for homeowners. One unit is a two-bedroom, one-bath, and the other is a one-bedroom, one-bath. The home needs some finishing work, but this is an unbeatable opportunity, and your work will be well worth it. *The income/expenses are only for the 2 garage apartments.

What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very pleasant lawn space. An investment with nothing major to put on the "to-do" list. Separate 2 bedroom carriage house, with garage, would be fantastic for owner quarters