Step into an 1880s Victorian re-imagined for the 21st century. Located moments from downtown Brattleboro, this 3-bedroom, 3-bath home blends historic craftsmanship with a cutting-edge deep-energy retrofit. Enjoy easy access to shops, dining, the Amtrak station, and the Retreat Trails from a peaceful, residential setting. Unlike typical historic renovations, this property underwent a from-the-studs rebuild in 2018, serving as a pilot for high-performance building science. It is now fully electric and fossil-fuel free, featuring : Air-to-water heat pump for heating/cooling and an Energy Recovery Ventilation (ERV) system for superior indoor air quality. The home also has a super-insulated, airtight building envelope ensuring year-round comfort and efficiency, with a durable standing seam roof equipped with solar panels. The interior honors its heritage while embracing sustainable, modern design, using eco- friendly materials: copper countertops, natural linoleum flooring, and Energy Star appliances. Modern mechanical systems and smart features throughout, you get turn-key Peace of Mind.: Every major system-from insulation to infrastructure-is new, offering a rare level of durability in a vintage home. 81 Chapin Street is more than a renovation; it’s a blueprint for the future. For those seeking environmental responsibility without sacrificing historic charm, this is a truly unique opportunity.
Set among a row of classic “painted ladies” on picturesque Chapin Street, this gracious Victorian home offers timeless charm just a short stroll from a vibrant downtown. A welcoming front yard with picket fencing and a stone walkway sets the tone, while the rear yard is fenced and features a large covered porch with access to the 2 car garage, which includes overhead storage. Enter through the expansive covered porch into a formal foyer, where period lighting, a powder room, and a handsome original staircase immediately showcase the home’s historic character. The front parlor features a bay window and distinctive bullseye molding, while the formal dining room is equally impressive with its own bay windows and a handsome fireplace with an elegant mantle and surround (has a woodstove insert). The spacious country kitchen is warm and inviting, offering cherry cabinetry, large sun-filled windows, and beautiful wood flooring. A flexible first-floor bedroom or family room includes an en suite bath and direct access to a covered rear porch—ideal for guests or easy single-level living. Upstairs, a generous landing with rear staircase leads to a spacious primary bedroom featuring a large en suite bath and convenient laundry. Two additional well-proportioned bedrooms offer excellent closet space, along with a dedicated office. Additional features include a full basement and walk-up attic, providing abundant storage or expansion potential. Rich with period details—from exquisite woodwork and original doors to classic lighting and flooring—this gracious Victorian is a true beauty, seamlessly blending historic elegance with everyday comfort. Showings begin 5/19/26.
BLACK MOUNTAIN ESTATES - where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1 mile from I-91, with ease of access to cultural & recreational opportunities, shopping, dining, & medical care. Nestled on 33 acres of pristine Vermont landscape, this premier neighborhood is thoughtfully designed, offering a vibrant community center w/ library, fireplace lounge, fitness center, full kitchen, & outdoor patio w/ fire pit. Outdoor recreational amenities incl. pickleball, bocce, shuffleboard, & horseshoes—perfect for staying active & social. Enjoy the ease of HOA-managed services & a lifestyle designed for freedom & fulfillment. Each home is single-story & ADA-compliant, offering ease, accessibility, & long-term comfort. Designed w/ energy efficiency in mind, these residences feature building materials & floor plans that minimize energy usage-providing a healthier, more affordable way to live. PRICED FROM $475,000 - $585,000. HOMES OFFER at least 5 rooms – kitchen, living, dining, primary BR w/ en-suite BA, & bonus room for office/study or guest BR – 2 BA’s, & a 1-car garage. UPGRADED HOMES OFFER: 2-car garage, sunroom, expanded living & guest rms, & larger yard. Some special touches that make BME homes beautiful & comfortable: finished 1 or 2-car garage; marble & porcelain tile; radiant floor heat; porch, private backyard, patio; marble sunken-floor showers & vanities; multi-zone heat & A/C; cherry cabinetry; granite countertops; walk-in closets; high-efficiency appliances & lighting. DO NOT MISS THIS OPPORTUNITY. Even if you are not quite ready to commit, reach out right away and ask to have your name put on the waiting list!
Tucked away on a quiet dead-end street just moments from downtown Brattleboro, this bright and inviting 3 bedroom, 1.5 bath Colonial offers the perfect blend of comfort, character, and convenience. A spacious mudroom provides a practical and welcoming entry, leading to a thoughtfully laid out interior featuring first-floor laundry, a large living room with flexible space for a home office, and a formal dining room highlighted by a generous window overlooking the private backyard. Hardwood maple floors run throughout, and four recently installed mini-splits provide efficient heating and cooling year-round. Outside, enjoy a beautifully maintained setting with established perennial gardens, raised beds, and a charming tree swing, along with a large rear deck ideal for entertaining or relaxing, an outdoor shed for additional storage, and a paved driveway and fully fenced yard. With its peaceful location and easy access to local shops, dining, and amenities, 16 Willow Street offers an exceptional place to call home. Close to Interstate 91, Mass border, hospitals, skiing, outdoor recreation and so much more! This is a must see! OPEN HOUSE ON SATURDAY, APRIL 25TH FROM 10AM-12PM.
Built in 2004 in this much-loved neighborhood, on a desirable one-way cul-de-sac, beautifully maintained, sits this 3-bedroom, 3-bath home. The first floor has a beautiful, large, eat-in kitchen, dining room, 1/2 bath, and access to a very spacious and inviting 16x16 deck ideal for family gatherings or entertaining, and a real sense of privacy. On the second floor, there is a primary bedroom with an ensuite bath, two more bedrooms, and another full bath. The basement is sure to impress, 22 x 19 and finished. This home has gorgeous hardwood flooring, tile, and carpet upstairs. There is a spacious two-car garage. Conveniently located, less than 10 minutes to vibrant downtown and 5 min to I-91. Enjoy country living with the convenience of town amenities minutes away.
Speno Court—one of Brattleboro’s most sought after neighborhoods—is a quiet, dead end street tucked between the beloved “Tree Streets” and just a short walk from downtown. With effortless access to over 9 miles of Retreat Farm trails, this tastefully remodeled home offers the perfect blend of convenience, comfort, and charm. Natural light fills the home through large picture windows and second floor dormers, while various species of hardwood flooring throughout create a bright, cheerful feel. The spacious kitchen features granite counters, Cherry shelving, a Catalpa wood bar, and stainless appliances. It opens directly into an expansive great room—designed as a combined dining and family space—offering excellent flow and energy for gatherings of any size. On the other side of the kitchen, the formal living room adds another inviting space, complete with a fireplace, built ins, and a large picture window. A ¾ bath and two additional rooms—currently used as a bedroom and an office—round out the first floor, providing flexibility for guests, work from home needs, or single level living. Upstairs, you’ll find two generous bedrooms and a spacious full bath. The primary bedroom includes a dreamy walk in closet that feels like a rare luxury at this price point. A full basement with newer 200 amp electrical service adds storage and utility, while the large, attached 2 car garage includes fantastic stand up storage space above. Homes like this don’t come along every day. Make your move and schedule your viewing today! Showings begin 5/16/26.
This meticulously maintained Cape-style home in Brattleboro, Vermont offers the perfect blend of classic charm and modern efficiency. Recent high-value improvements include a brand-new roof, upgraded 200 amp electrical service, and a dedicated electric vehicle (EV) charger. The 3 bedrooms plus office space, 2 bathrooms, dining room, and living room provide enough space to suit many options. Enjoy year-round comfort with a newly installed mini-split heating and cooling system, complemented by a cozy gas fireplace. Inside, the home features 1,686 square feet of living space with warm natural woodwork, hardwood floors, and tile finishes. Set on a level lot, the property includes a private patio and storage shed, ideal for outdoor living and convenience. Located directly across from the hospital and close to sidewalks, shops, and local amenities, this home offers the perfect turn key property in the heart of Brattleboro. Schedule a showing today!
Nestled in the sought-after Orchard Street neighborhood, this beautiful townhouse offers bright, sun-filled living spaces and a serene wooded backdrop. The rear deck extends into the backyard, creating the peaceful feeling of living in a private treehouse retreat.
First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big bedrooms and full bath up! The full basement has room for a workshop, storage or game room. Drive and carport are paved for easy maintenance. Huge shed in the back for storage or lawn care tools. Just what you have been waiting for!
Time to think of the garden! This sweet home has a huge level back yard just right for flowers, veggies and fruit trees. There is still time to get the jump on planting your favorite things! There is a primary suite on the 1st floor including laundry so there is total first floor living if you need/want it. The traditional cape 2 beds and a bath up are private for family or guests....The living room us huge and sports a fireplace at the end (sellers have not used it), the formal dining has great light and can set 6....the kitchen has lovely cherry cabinets and lots and lots of counter top for baking and every day meals. No mud season here! This lovely well cared for home is waiting for a new owner.
Lovely level lot, close to schools, hospital, shopping, State park and downtown. The best of everything, and BRAND NEW!!! Be the the envy of all your friends, with this wonderful, open concept, one level home. Primary bedroom on one end with an ensuite for privacy! New, shiny appliances, good sized island for cooking or hanging out and both a tub and a walk in shower. Special in so many ways, easy to show.
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.
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
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.
Charming and conveniently located, this inviting home is situated less than one mile from the heart of Brattleboro Village. Offering 3–4 bedrooms, including a first-floor bedroom for added flexibility, the home features a practical mudroom entry and a bright, sun-filled dining porch just off the kitchen. The basement provides a dedicated workshop area, laundry space, and ample additional storage. Set on a manageable 0.09-acre lot, the property is bordered by mature trees along the rear for added privacy, while the open yard offers excellent potential for gardens and outdoor enjoyment. A cozy screened-in porch tucked behind the house creates the perfect retreat for relaxing during the warmer months.
Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard to care for. Near down town,, MOOVER route, hospital and all the other good stuff. Quite, level short street, with easy access. Come join the neighborhood! Only the first floor is available to show on first showing. Please have all buyers qualified before requesting an appointment.
There is plenty of space to garden to your heart’s content! A place to sit under mature trees for the pleasant sound of a babbling brook, and peaceful views into a quiet woods bordered by a rambling old stone wall. With almost an acre of land, this 1941 five room, country cape has an open floor plan for kitchen, dining and living room, wood beams and a friendly wood stove. There is a first floor bedroom and full bathroom. The dormered upstairs has a bedroom with a large studio/workroom beyond. The breezeway connects the house to a two car garage with loft storage. A shed behind the garage offers handy space for wood, equipment and tools. This West Brattleboro location is just four miles from downtown Brattleboro on a paved town maintained road. Access to Interstate 91 is two miles away. Showings by appointment start on Thursday May 7, 2026.
Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders to the back for grilling and a living room with a picture window to the front yard, you can tuck in and enjoy. Half of the lower level is finished and is perfect for a den, at home office or playroom. Plenty of storage in the unfinished portion, so stock up on those sale items! Please be prequalified before making an appointment to view.
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