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7 Union St, Brattleboro
$341,000
4 Beds ⋅ 3 Baths ⋅ 5071411 MLS
Cheerful, comfortable and cozy! Built in 1903 this nine room, three level home has four bedrooms, and a full bathroom on each level. The hilltop setting gives the back deck a treehouse feel! The light filled kitchen has walnut butcher block counters, a maple hardwood floor, a vintage sink, a coffee/tea nook and glass sliding doors to the deck. The kitchen opens to the dining/living room. A walnut bookcase with floor to ceiling shelves, and windows that invite you to sit and enjoy the easterly and southerly woodsy views. The first floor has a bedroom with ensuite bathroom. First floor has maple hard wood floors with radiant heat for cozy warmth. Upstairs there are three bedrooms, a full bathroom, a walk in closet, built in linen cabinets, maple hardwood floors, and stairs to insulated attic storage. The lower level has radiant floor heat, a laundry room, a full bathroom, a storage closet. There is a large pleasant room 15' x 20', perfect for a studio, a family room, a home office, a game room. The walk out access has a pet door that leads to a fenced back yard. Four zone heating for comfort. New Trex deck, plumbing and oil tank give ease of mind. This handy location has Crowell Park across the street, Green Street School just beyond. Downtown Brattleboro is nearby for restaurants, music, movie theater, library, cafes, a hardware store and a soon to be completed Amtrak train station! Interstate 91 is just up the road. Showings begin on 12/7/25 by appointment.

7 Union St, Brattleboro

65 Cedar St, Brattleboro
$339,000
4 Beds ⋅ 2 Baths ⋅ 5093467 MLS
Step into a world of artistic whimsy and historic allure at 65 Cedar Street, a property overflowing with character, magic, and boundless potential. Nestled in an ideal location with an entrance to the beloved Retreat Trails, this unique home offers an enchanting escape from the everyday. Outside, the property is embraced by beautiful, mature gardens cultivated over time in a spirit of enchanting "benign neglect" where nature and romance intertwine to create a storybook setting that will capture your heart from the moment you arrive. Inside, you will find a spacious layout featuring 4 bedrooms and 2 full baths spread across 2,250 square feet of versatile living space. The home has been thoroughly cleaned out and deep-cleaned, presenting a pristine, blank canvas with exceptional, rock-solid "bones" ready for its next chapter. Fine historic details anchor the home, from rich wood floors to timeless built-ins. At the heart of the home sits a magnificent centerpiece: a vintage Vermont Iron Stove Works stove, radiating authentic New England warmth and charm. The footprint continues to impress with a bright, beautiful sunroom perfect for morning coffee, a large attached 2-car garage providing excellent storage, and a expansive bonus space tucked away in the finished attic. This property is being offered in "as-is" condition and does not include appliances, making it the ultimate dream project for those looking to invest sweat equity into a truly remarkable historic home. Bring your vision to finish the cosmetic upgrades and unlock the true grandeur of this whimsical masterpiece. OPEN HOUSE SUNDAY, JUNE 14TH | 12:00 PM – 2:00 PM Come experience the magic and explore the incredible potential of this one-of-a-kind home in person!

65 Cedar St, Brattleboro

144 Belmont Ave, Brattleboro
$339,000
3 Beds ⋅ 2 Baths ⋅ 5064544 MLS
Adorable 4-Square with tons of charm and built-ins in a great location! Welcome to this beautifully cared for 3-bedroom, 2-bath classic 4-square home, full of warmth, character, and timeless details. From the moment you step inside, you’ll fall in love with the original woodwork, custom built-ins, and light-filled spaces that make this home truly special. The inviting front porch leads into a spacious living area with hardwood floors and period charm throughout. The updated kitchen blends modern convenience with historic character and flows easily into the dining room, perfect for entertaining. Upstairs, you’ll find three comfortable bedrooms and a full bath. Enjoy the private backyard, ideal for relaxing or gardening. Located in a highly sought-after neighborhood, just minutes from parks, shops, and restaurants — this home has it all: character, comfort, and convenience. Recent Improvements & Upgrades include, New windows (2016), New back deck (2016), Shed repairs (2016), Paved driveway (2017), Kitchen renovation + new bathroom (2020), Updated front porch with storage benches (2020), Outdoor electrical work and added lamppost (2021), New stone walkway (2023), New toilet and vanity in upstairs bath (2024), New hot water heater (2025) and New oil tank. Delayed showings to begin on 10/11/25 with Open House 1-3. Sale subject to the Sellers securing suitable housing.

144 Belmont Ave, Brattleboro

290 Guilford St, Brattleboro
$335,000
3 Beds ⋅ 2 Baths ⋅ 5065553 MLS
This meticulously maintained 3-bedroom, 2-bath ranch surprises with its spacious layout and thoughtfully designed interior. The kitchen is a dream for those who love to cook, featuring quartz countertops, slate flooring, solid hardwood soft-close cabinetry, a dedicated baking station, and access to the nearly 700 sq. ft. back deck—perfect for entertaining. The open main living area features beautiful Red Oak flooring throughout. The expansive primary suite offers a peaceful retreat with a large slider to the deck and an oversized en suite bath with a custom tile shower. Downstairs, enjoy a large family or recreation room with a built-in bar and separate laundry area. Recent upgrades include energy-efficient mini split heating and cooling units and a Tesla Powerwall, adding year-round comfort and energy independence to the home’s already impressive sustainable features. A 3.5 kW roof-mounted solar array and two PV hot water panels provide domestic hot water, backed by grid power and an electric water heater. Two pellet stoves offer additional efficient heating options. Outside, you’ll find mature perennial and vegetable gardens, a tranquil brook, and a cozy fire pit. With access to conserved hiking trails and located just 0.4 miles from Living Memorial Park, this move-in-ready home blends modern efficiency with the best of Vermont living. Delayed showings until the Open House Saturday Oct 18th 10am-12pm

290 Guilford St, Brattleboro

75 Moreland Ave, Brattleboro
$330,000
5106434 MLS
On offer is this tidy, three-unit multi-family home, located in a tranquil residential neighborhood on Moreland Avenue. Originally designed as a multi-family, the three units have identical floor plans with good layout flow. Each 2-bedroom unit has a large eat-in kitchen with pantry, a dining room with French doors opening to the living room and the bonus of a generous, three-season, enclosed front-porch. Each unit features the original handsome wood trim and doors, gleaming hard wood floors, good closet space, and many huge windows filling the place with glorious natural light. There are separate electric meters and boilers for each unit. Additional bonuses are the two-car garage, a small but sweet yard with trees including two pear trees, and a good basement. Great investment opportunity or owner occupied income property. Currently, the first floor is rented with a lease while the second and third floor units are vacant. Great location near high school, hospital, shopping and I-91. Property is being sold "as is". Sale is subject to license to sell. Please Note: Unit 3's pantry is unfinished. Showings begin Saturday 8/29. OPEN HOUSES Saturday 12pm-2pm and Sunday 10am-12pm.

75 Moreland Ave, Brattleboro

255 Guilford St, Brattleboro
$330,000
3 Beds ⋅ 2 Baths ⋅ 5088378 MLS
Looking for your first home — or ready to downsize? THIS ONE IS FOR YOU! Ideally located just outside the bustle of town yet close to everyday conveniences, this efficient ranch with daylight basement comes with a fantastic 24' x 24' detached garage — perfect for hobbyists, collectors, or simply keeping vehicles protected. Set on a half acre and minutes from Memorial Park, shopping, schools, the hospital, and I 91, this property delivers tremendous value at a competitive price point. The main level features an expansive kitchen that opens to the dining/living room and flows onto a massive 36' x 11' deck — ideal for entertaining or relaxing outdoors. A primary bedroom with adjoining full-bath, and an additional bedroom or office complete the first floor. The lower level adds even more flexibility with a third bedroom or office with adjoining ¾-bath, a large family room, a mudroom entry, and a utility/laundry room. There’s room to play, garden, and enjoy the outdoors, all while benefiting from an efficient footprint and an easy, open floor plan. With a great location, versatile layout, and standout garage, this home checks all the boxes. Don’t let it get away. Showings begin 5/17/26

255 Guilford St, Brattleboro

184 Carriage Hill Rd, Brattleboro
$325,000
3 Beds ⋅ 2 Baths ⋅ 5091277 MLS
Perfectly situated at the top of the hill on highly desirable Carriage Hill in West Brattleboro, this delightful yellow ranch offers the perfect blend of neighborhood comfort and exceptional curb appeal, accented by a lovely stone pathway and beautiful exterior gardens. Step out back to discover your own private oasis featuring a spacious wooden deck with a gorgeous overhead pergola, custom built-in bench seating, and an attached screened-in porch that looks out over a lush green backyard complete with a handy storage shed. Inside, the home boasts a bright, expansive living room with durable flooring and a mini-split system for efficient year-round comfort. The generous eat-in kitchen features warm wood cabinetry with vibrant turquoise accent shelving, tile flooring, and a large window overlooking the serene backyard. Comfortable bedrooms with unique, colorful accent walls and a dedicated home office or study space under a cheerful blue ceiling provide a highly versatile layout. Complete with two functional bathrooms including one full bath with a tub/shower combo and a second featuring a retro blue shower stall—this home is ready for its next chapter. Come see all this West Brattleboro gem has to offer at our upcoming open house on Sunday, May 31st from 2:00 PM to 4:00 PM!

184 Carriage Hill Rd, Brattleboro

1644 Upper Dummerston, Brattleboro
$325,000
2 Beds ⋅ 2 Baths ⋅ 5090888 MLS
Found It! Live all on one level and tuck the guests in upstairs! The kitchen is modern with lots of counter top for the bakers and cookie makers, The laundry lives next to the kitchen and there is a second bath for visitors and guests. The sweet spot is the huge living room with a wood stove insert in the lovely fireplace. Mini-splits are already up and running for help with both heating and cooling and a bank of solar helps with energy cost for years to come! There is a sweet level easy access side yard, with gardens and layers of woodland for privacy and hiking. Plenty of room to build a garage but there are some nice storage sheds already waiting for the mower and other accoutrements. Minutes to town, near the West River and lots of hiking trails. Private, affordable, cute as a button!

1644 Upper Dummerston, Brattleboro

91 Sunny Acres Rd, Brattleboro
$325,000
3 Beds ⋅ 3 Baths ⋅ 5064191 MLS
Lovely and updated, very low maintenance, clean, 3-bedroom, 3-bath home on .22 acre. HARDWOOD floors throughout! The kitchen is fabulous with granite countertops and island with soft-close drawers and GE appliances. The 3 bathrooms are completely renovated and attractive as well. Tons of south-facing sunlight and passive solar! Most windows have been replaced, including the french door to deck. A HUGE added bonus is the large and versatile 630 sq. ft finished "family/recreation room" with a 3/4 bath in the basement with direct entry to/from the two-car garage (or down the circular stairs from main floor). There is a newer Mini-split and hot water heater (2022) and a cozy propane stove in this space. This comfortable area has served as a longer-term living space for family as well as a very comfortable private area for visiting guests. The house has easy-maintenance vinyl siding and a 10-year-old roof in excellent shape. The front and back decks are in tip-top condition. The property is in located in a friendly neighborhood, close to the middle and high school and approximately a mile to the Fort Dummer State Park trails. Very convenient location to hospital, downtown, shops and more.

91 Sunny Acres Rd, Brattleboro

197 Western Ave, Brattleboro
$320,000
5090264 MLS
Excellent opportunity to own a well-maintained and fully occupied 3-unit investment property in the heart of Brattleboro. Located in-town with convenient access to shopping, restaurants, entertainment, and everyday amenities, this property offers strong in-place income with additional upside potential. The building consists of two 2-bedroom units and one spacious 3-bedroom unit and has been consistently rented. Strong income-producing property with attractive investor returns. Tenants pay their own heat and electric, helping to keep operating expenses low and improving overall investment performance. This is a rare opportunity to acquire a stable, income-producing property in one of Southern Vermont’s most desirable rental markets.

197 Western Ave, Brattleboro

11 Culbertson Dr, Brattleboro
$320,000
5 Beds ⋅ 4 Baths ⋅ 5058015 MLS
Located in the heart of Brattleboro walking distance to the farmer’s market and the expansive Living Memorial Park, this unique home has many options. Open up one doorway and it could be a 4 bedroom home plus an in-law studio. Or, keep it as 3 separate units – a 3 bedroom home, 1 bedroom apartment, and a very large and elegant studio apartment. It currently functions as an active Air BnB and could also be an owner occupied Bed and Breakfast. The current setup for Air BnB is bringing in $54,000 per year of income. There are some light commercial use possibilities as well with parking for six cars. Two fireplaces, beautiful wood floors, custom built ins, and a second floor balcony plus abundant natural lighting give a cozy feel and a storybook charm. Public water and sewer are a nice bonus. This is the former home of famous bridge player and author Ely Culbertson. Located on a quiet dead end street with only one other home, this is a very private location backing to deep woods and a forest trail with a swimming hole just steps away in the Whetstone Brook. The yard is beautifully landscaped with perennial, herb, and vegetable gardens. Less than 2 miles to Interstate 91, hospital, and downtown Brattleboro's shops and restaurants. Enjoy year round recreation in every direction. There are numerous waterways and hiking trails to enjoy plus world class skiing at Mt. Snow and Stratton mountains. Owner would consider financing a portion of the sale with a sizeable downpayment.

11 Culbertson Dr, Brattleboro

44 Brook St, Brattleboro
$319,000
4 Beds ⋅ 2 Baths ⋅ 5076763 MLS
Charming 4-Bedroom Home in the Heart of Town Welcome to this beautifully updated single-family home offering a perfect blend of classic charm and modern comfort. Conveniently located in town, this home is just minutes from the hospital, schools, shopping, and public transportation — ideal for families and commuters alike. Step inside to find freshly painted interiors, gleaming hardwood floors, and brand-new carpeting throughout. The spacious layout includes 4 bedrooms, 1 full bath, and 1 half bath, providing plenty of space for everyone. The updated kitchen features all new appliances, making it ready for your culinary creations. Enjoy relaxing on the enclosed front porch, perfect for morning coffee or evening reading, or entertain guests on the rear deck overlooking the yard. The single-car garage adds convenience and extra storage space. This move-in-ready home is a must-see — all the work has been done for you!

44 Brook St, Brattleboro

69 Carriage Hill Rd, Brattleboro
$317,000
3 Beds ⋅ 1 Baths ⋅ 5099340 MLS
Welcome to this lovingly maintained 3-bedroom, 1-bath ranch located in the sought-after Carriage Hill neighborhood of West Brattleboro. Where affordability & opportunity come together in this move-in ready home. Whether you're taking the exciting step into homeownership or searching for a home that lets you spend less time on upkeep and more time enjoying life. The open-concept, light filled living room and eat-in kitchen create a comfortable, welcoming space that feels like home the moment you walk in. South facing windows fill the living room with an abundance of natural light, creating a bright and inviting atmosphere throughout the day. Just off the kitchen, step onto the back deck overlooking the spacious, fenced-in backyard. Mature trees provide natural shade and privacy, while the property extends well into the woods with established walking trails, offering a setting to explore and enjoy nature right from your own backyard. Back inside, you'll find three comfortable bedrooms and a full bath, all conveniently located on the main level. The partially finished basement adds valuable living space with a versatile bonus room, a rec room or office space, and a spacious utility area, providing flexibility for hobbies, fitness space, or additional storage. Thoughtfully cared for over the years, this home offers peace of mind with a roof that's approximately seven years old and a hot water heater that's just two years old. Additional features include town water and sewer, a paved driveway, and a functional layout designed for today's lifestyle. Enjoy easy access to shopping, local restaurants, coffee shops, Brattleboro Memorial Hospital, Interstate 91, public transportation, schools, and countless everyday conveniences, all while coming home to the peaceful charm of an established neighborhood. ** OPEN HOUSE ** Sunday, July 19th 11AM to 1PM.

69 Carriage Hill Rd, Brattleboro

117 Oak Grove Ave, Brattleboro
$315,250
3 Beds ⋅ 1 Baths ⋅ 5089873 MLS
Located in one of the area’s most desirable and close-knit neighborhoods, this beautifully preserved 1929 home blends timeless character with thoughtful updates. Featuring hardwood floors, natural woodwork, custom built-ins, classic wainscoting, and a welcoming mudroom, the home retains the charm and craftsmanship buyers love. The open and inviting first floor offers generous living space and a formal dining room, complemented by a retro-inspired kitchen full of personality. Just off the living room, the enclosed south-facing porch with newer windows may become your favorite place to relax and unwind. Upstairs offers 3 bedrooms, a bright and cheerful bath, and access to an incredible attic space with exciting potential for a studio, yoga room, office, or expanded living area. Outside, the landscaping is a delightful surprise, featuring striking artistic bluestone details and a peaceful water feature that create a private, zen-like setting rarely found in town. This is a wonderful opportunity to own a character-filled home in a neighborhood known for its quality homes, strong sense of community, and convenient access to restaurants, shopping, and local amenities.

117 Oak Grove Ave, Brattleboro

458 Williams St, Brattleboro
$315,000
5084518 MLS
Located just minutes from I-91 and downtown Brattleboro, the former WKVT radio station offers a unique opportunity to own a well maintained commercial property. Tucked into a quiet neighborhood with close proximity to the activity of Western Avenue, this 3,240 SF building strikes an ideal balance between accessibility and privacy, making it well-suited for a variety of professional, creative, or service-based uses. The two-level layout provides flexibility and functionality. The upper level features five private offices, multiple storage areas and closets, two bathrooms, a welcoming entry/reception area, and a kitchenette making it well suited for a range of uses including administrative operations or client-facing businesses. The lower level, previously home to radio station operations, includes five additional offices along with a bathroom, utility room, and storage space, offering potential for collaborative workspace, production, or specialized use. Constructed in 2003, the building benefits from modern systems including central A/C, public water and sewer, high-speed internet availability, and a standby generator system to support continuous operations. On-site parking adds convenience for both staff and visitors. Set on a 4.3-acre parcel with frontage on Whetstone Brook, the property offers a natural, attractive setting rarely found with commercial properties. The building is positioned above the brook, providing a sense of separation and privacy while remaining close to major routes and downtown amenities. A strong option for businesses seeking a move-in-ready location with room to grow in Southern Vermont.

458 Williams St, Brattleboro

70 Arbor Hill Commons Unit 14, Brattleboro
$315,000
2 Beds ⋅ 2 Baths ⋅ 5080289 MLS
Welcome to Arbor Hill- a 55 and older community of thoughtfully designed and cared for condominiums. Enter the inviting "Bluebell" building on the ground level and take either the stairs or the elevator to the second/top floor. Down the quiet hall you will find the beautiful unit #14. This delightful unit has seen recent renovations totaling $51K+ since 2023, including new flooring and a soft-color professional paintjob throughout. Both of the decks have been upgraded with composite planks, the new deck awnings were added and railings have been replaced. Additionally, the condo has several new appliances such as washer/dryer, dishwasher and air conditioners. Even more, there are new toilets, and 2 Larson storm doors. This gorgeous open-concept home offers a desirable floorplan that has a gentle ease-of-flow and plenty of room for all of your furniture. Soak up the morning sunshine in front of your large easterly-facing windows or on one of two balconies. The kitchen is bright and cheery and open to the dining area. The living room is large and light. #14 features a sizable main bedroom with its own full bath and a walk-in closet. There's a second bedroom with a balcony access. Across the hall you'll find a 3/4 bath with walk-in shower and a separate laundry room. The Bluebell building shares a big exercise room and a comfortable and attractive social/meeting room. Arbor Hill has great management so there is less to worry about, and you'll delight in more time for yourself and others. The grounds are nicely landscaped for added appeal. All of this and centrally located to all that Brattleboro has to offer. Come take a look at what comfortable, convenient and low-maintenance living looks like. Association fees: $375.00/mnth includes heat and hot water, water and sewer costs, and BB interior maintenance. $502.00/mnth includes exterior maintenance, plowing, landscaping, reserves. (w/in the $502.00 is a $67.00 special assessment to fall off at end of 2026)

70 Arbor Hill Commons Unit 14, Brattleboro

30 Lexington Ave, Brattleboro
$300,000
3 Beds ⋅ 1 Baths ⋅ 5103014 MLS
Welcome to this charming, well maintained ranch built with character, exceptional functionality, and comfort on a desirable dead end street. Classic curb appeal and the timeless design allow for first-floor living with spacious living and dining areas. It is flooded with natural light from the oversized windows and features original hardwood trim, solid wood doors, built-ins, and vintage light fixtures. Currently carpeted, but beautiful oak floors are underneath. The sunroom is welcoming and bright, offering the perfect space for an artist or an afternoon retreat while connecting with nature. The floor plan includes 3 bedrooms all of which look out to the expansive, level backyard. The vintage bathroom has warm accents, featuring original cream tiles with delicate pink surrounding the tub and shower, along with a laundry chute to the basement. The outside is impressive with a large open backyard offering endless possibilities for entertaining, gardening, recreation, or future outdoor additions. There is a charming rustic outbuilding that is the perfect garden shed or potential workshop. An oversized one-car garage connects to the home via a comfortable breezeway. There's an expansive full basement with cold storage room and flexibility for hobbies or a workshop. This home is rich in character yet full of opportunity for the next special owners to add their touches. Very close to the hospital, shopping, schools, bus route, and I-91.

30 Lexington Ave, Brattleboro

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