An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please, only fully qualified with either proof of funds or a bank rehab loan prequel letter. Pets, so flexibility is needed for showing.
Opportunity to live and invest in upgrades for your new home.
Set in a fantastic, highly sought-after neighborhood, this home is ideally located directly across from Oak Grove School, just around the corner from the Little League field, and within one mile of the hospital, middle and high schools, Interstate 91, and Brattleboro’s vibrant downtown shops and restaurants. This 4-bedroom, 1.5-bath Cape Cod–style home offers a quick closing opportunity and solid potential. Upstairs, you’ll find two generously sized bedrooms with freshly painted walls, gleaming hardwood floors, and a conveniently located half bath between them. The first floor features two additional bedrooms and a full bath, with all bedrooms offering ample closet space. The sun-filled living room boasts a cozy wood-burning fireplace, while the kitchen provides abundant cabinet and counter space. Relax and unwind on the inviting three-season porch—perfect for warm summer evenings. Outside, the spacious backyard offers plenty of room for gardening and outdoor enjoyment, and the garage includes an additional storage room. A full basement provides excellent storage space and includes a washer and dryer. A brand-new oil furnace was installed in January 2026. With great bones and just a few cosmetic updates, this home has the potential to truly shine. Enjoy the convenience of a prime location less than two hours from Boston and Albany, 3.5 hours from New York City, and 4 hours from Montreal. So many plusses—don’t miss this opportunity! **If you drive by - The address is 49 Clark Avenue. Do not get confused with Clark Street which is in a different area of town.**
Enjoy a spacious kitchen that flows seamlessly into a large living area with open views of Mount Wantastiquet. This single-level ranch offers four generously sized bedrooms and a full bath, making it ideal for those seeking one-floor living and efficient heating. A cozy woodstove in the living area helps offset heating costs while adding warmth and charm. Hardwood flooring, a beautifully tiled shower, claw-foot tub, pantry, built-ins, vintage 1950s kitchen counter, and authentic hardware showcase the home’s timeless character. Ample storage throughout and a full, dry basement add comfort and practicality. Offered as an estate sale and sold as is, this property presents a wonderful opportunity to personalize a solid home in an inspiring location. With great bones and mountain views, a little paint and attention will go a long way. Showings begin Sunday, March 8th, by appointment.
Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great West Brattleboro location. The homes sit unseen approximately 500 feet back on a private driveway from the public road. The houses need a fair amount of repair and remodeling to get them in good condition. The main house is a cape style home with open concept kitchen/dining/living room, full bath, and 2 bedroom on the first floor with 2 bedrooms on the second floor. a large green house stands directly adjacent to the house. The 2nd home is smaller and features a large room on the main floor with kitchen area, living room and bath. Upstairs is a spacous loft bedroom. An unfinished room off the main level was added to become a hot-tub room. This 2nd house would make a nice guesthouse, office, studio or possible long term rental or AirBnb rental. A large garage structure was started but never finished. A common outdoor wood boiler was used to heat both houses and the greenhouse previously but the boiler needs repair/replacement. Several acres have been cleared on the lot. The remaining forest has some marketable timber. The property can also be accessed via a deeded right of way from Goodenough Rd. The property could be perfect for someone seeking a large private parcel of land. It may also be attractive to developers looking to build a road and develop multiple house sites.
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.
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.
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!
The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy here. Along with the bedroom, there is laundry and full bath on the first floor. The attached 2 car garage keeps you out of the weather, tidy and dry. An amazingly level lot is great for gardening or games. And, you are on pavement, no mud season here! Easy to get to the mountains or Brattleboro and beyond. This is a must see for those long in the market, looking for just the right home.
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.
Enjoy privacy and nature just minutes from town! This well-cared for 3 bedroom, 2 bath home sits on 4.81 acres, offering space, tranquility, and convenience. Features include a first-floor bedroom, bright and comfortable living areas, a beautiful three-season porch perfect for relaxing and taking in the peaceful setting, and a two-car garage for added storage and functionality. A great opportunity to enjoy country living with easy access to town amenities. OPEN HOUSE SATURDAY 3/21 11AM - 1PM.
This well-maintained three-bedroom, two-bath single-family home is set on a level, fenced-in lot in a coveted neighborhood close to downtown, with convenient access to major highways. The home features radiant flooring, central air, and a finished basement offering flexible living or recreational space. A spacious kitchen provides ample cabinetry and storage, ideal for everyday living and entertaining. Two bedrooms are located on the main level, while the second-floor primary suite offers vaulted ceilings and added privacy. Outdoor highlights include a 16’ x 20’ Trex deck, a bluestone walkway, and a large driveway bordered by a stone wall. A detached one-car garage with a carport adds functionality. Enjoy proximity to the Retreat Trails and Harris Hill Ski Jump, combining comfort, convenience, and an exceptional location.
Welcome to 23 Wilsons Woods Road, a meticulously maintained Colonial-style home that offers the perfect Vermont balance: total wooded privacy combined with absolute convenience. Nestled at the end of a quiet road, this property feels like a secluded retreat tucked into the forest, yet you are literally moments away from Brattleboro’s vibrant restaurants, local shops, the hospital, and a thriving arts scene. The standout feature of this residence is the thoughtfully designed addition, which serves as a premier mother-in-law suite or guest wing. This expansive space offers flexible multi-generational living without compromise, featuring its own eat-in kitchen and sitting area, and the high-end luxury of radiant floor heating for year-round comfort. With direct access to a private deck and open patio, it is a seamless blend of indoor-outdoor living. The home’s exceptional layout includes 4 bedrooms and 4 bathrooms, providing a natural flow that is perfect for both entertaining and quiet daily life. High standards of maintenance are evident throughout, including recent roof renovations and pristine mechanical systems. Whether you are relaxing on the classic covered wraparound porch or hosting a dinner on the beautiful rear deck, the serene surroundings provide a sense of total calm. This move-in-ready property offers the comfort and quality lifestyle Vermont is known for—quality construction, modern upgrades, and a location that puts the very best of Brattleboro right at your fingertips. Open House April 12th 12pm-2pm
Step back in time and discover the enchanting potential of this distinguished 1940 Colonial, perfectly positioned to capture the spirit of Brattleboro. Perched on a generous 0.79-acre level lot, this home offers a rare blend of expansive personal space and convenient in-town living. From the moment you arrive, the classic lines, wood siding, and enduring slate roof hint at the craftsmanship of a bygone era. Inside, the home spans a spacious 2,756 square feet, featuring four bedrooms plus bonus room and three bathrooms that provide ample room for family, guests, or creative pursuits. While the interiors are ready for a thoughtful restoration, the home's historic character serves as a beautiful canvas for your vision. This is a unique opportunity to breathe new life into a property with significant provenance, preserving its architectural soul while infusing it with modern comforts and your own personal style.The true magic of this property lies in its setting. Imagine waking up to sweeping, picturesque views of the West River Meadows, a daily reminder of Vermont's natural beauty right from your back yard. Despite this serene visual escape, you are just a short, pleasant walk from the vibrant heartbeat of downtown Brattleboro, where local shops, dining, and community events await. This residence offers the best of both worlds: a private, historic retreat with the convenience of a walkable, connected lifestyle. There are extensive berry bushes, a vegetable garden, and perennials growing on the property. Don't miss this rare opportunity.
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. Open House: Saturday, April 11, 11am-1pm.
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!
Welcome to Hillwinds and this lovely colonial. With 200 acres of conserved land and trails behind and a wonderful meadow view in the front, this house truly feels a part of the landscape. The main house has four bedrooms and two and a half baths and invites you to step right into your new life in this well cared for and lovingly maintained home. The gardens are in, the drive paved and the garden shed with power is standing ready. The sweet sun room is a nice addition to the living area, just off the kitchen/family room so a great place to expand when entertaining in the warmer months. It overlooks the very peaceful conservancy and is a special place for a quiet read or fun games in the rain. No worries of power outages here with both a gas generator and the new Tesla Powerwall! Above the garage is a versatile space that can be used as a studio, guest room, mother-in-law suite, or a study boasting a mini-split, refrigerator, and three-quarter bath. Enjoy the fire pit in the evening, under the stars. Watch the bluebirds at the birdhouses as they raise their families, the chipmunks that scurry, and the turkeys in the meadow. This is a wonderful neighborhood. Make it yours. Open house Saturday, April 11th 11am - 1pm
Beautifully sited on 1.9 acres just off Greenhill Parkway, this tastefully modernized 1940s cape blends architectural pedigree with thoughtful, high end updates. Designed by noted architect James Britton of Greenfield, MA - a contemporary of Royal Barry Wills and long admired for his classic New England forms - the home retains its classic original character, while offering a fully refreshed interior. The 4 BR, 3 BA layout includes a full width living room with wood burning fireplace, a handsome dining room with built-in corner cabinets and a massive, x-pane window overlooking the backyard. The kitchen is a standout, featuring Crown Point beaded frame cabinetry, heated encaustic tile floors, Zellige tile walls, a Liebherr refrigerator, Miele propane cooktop, KitchenAid double ovens, and a custom Pella hydraulic lift awning window - ideal for outdoor entertaining. Rounding out the first floor is a beautifully executed mudroom/laundry created between the kitchen and attached 2 car garage, a private and comfortable den, a spacious formal entry hall, and updated powder room. All bathrooms have been fully renovated with Waterworks fixtures and Toto washlet toilets; two with custom tile showers, heated tile floors, and Visual Comfort lighting. A spacious suite above the garage offers flexibility for a primary bedroom or in law arrangement, offering new solid oak flooring, a walk-in closet, and a decadent bathroom with soaking tub and separate shower. The location is exceptional, being an easy walk to downtown and the park, and privately tucked into an unusually large lot; and with unique, direct access to over 9 miles of trails via a path along the lower edge of the property. A rare combination of history, craftsmanship, and modern comfort in one of Brattleboro’s most desirable neighborhoods. The home also comes with original 1944 blueprints and historical materials from the Norton family; the property’s first owners.
Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer with skylight, entry closet and stained-glass windows. Adjacent, opens into a warm, spacious family room with cherry wainscoting, a gas stone fireplace, curved architectural accents and mud room access. The formal living room features a brick fireplace and is surrounded by classic post & beam architecture and stained glass windows. The open kitchen & dining area are ideal for entertaining and impress with cherry cabinetry, quartz countertops, stainless appliances, and sliders to an expansive deck with serene views. A den, half bath, and laundry closet complete the main level. Upstairs offers four bedrooms, including a stunning primary suite with cathedral ceiling, triple closets, fireplace, and Palladian windows. There is a tucked-away guest room that enjoys a private ¾ bath. The finished lower level includes a generous game room with wet bar, half bath, propane stove, & TV area—pool table included! A detached 2-car garage with storage, a garden shed, and timeless craftsmanship throughout make this a truly rare offering.
Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has Italian ceramic countertops & butcher block, including a dinette with southern light. With an open concept living/dining arrangement, the living room has lovely radiant wood stove heat. The adjacent dining area is drenched in sunlight. The home affords views of the West River Valley and Green Mountain vistas as far as Hogback Mountain. The first floor offers a fabulous great room, 2 fireplaces, an office, a sun room with hot tub, a laundry room and decks for admiring the sunrises and sunsets. The second floor is exceptional with three expansive primary en suites and two more rooms perfect for study, meditation, or extra bedrooms if needed. The two car garage has plenty of room for a workshop and the landscape features stone walking paths, wildflowers, perennials, pear trees as well as an in-ground pool. Brattleboro offers that small town charm with culture everywhere, from our music center, the Brattleboro Museum and Art Center, galleries, cafes, and more. Convenient to ski mountains & easy access to Boston and NYC. The next owner will truly be fortunate! Showings start Friday, April 10th by appointment.
Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of room for everyone in five bedrooms (and of course 7 bathrooms), a choice of large or cozy living rooms and an office to work from home. Toast your toes at either fireplace or soap stone wood stove. Invite your circle of friends to yoga, parties or create a media room in the huge, finished walk-out basement family room, plumbed and wired for a second kitchen, with ½ bath, easily converted to extended family suite. 47x21 bonus room with skylights and ample windows overlooking the grounds is perfect for play/gym space, artist studio, etc. 3 car detached heated, finished garage/workshop with storage above. Create a cross-country ski track for moonlight nights. Watch for fireflies in the meadows and see the forest creatures explore their world. A one-of-a-kind property with so much to love; solid, expansive architecture, two staircases, windows everywhere, gleaming wood floors and well positioned, dimmable lighting, bringing together classic and fun, this home was designed for those who love organization with oodles of storage space. The heart of Vermont is here!
Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now is the time to write your own story...and live in your own Hundred Acre Wood....only this one is grown up with 103 acres, 35 acres of open meadow, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect location...minutes to town, the interstate and all you need for any lifestyle... you are tucked away in the gentle rolling meadows of home. High speed internet is available for home workers or streamers. The small touches are amazing, marble sink toppers from Dartmouth College and dramatic imported faucets tipping the scale of lovely. Delicate adz work in the original wing is amazing and a rarity and the slate floor entry with an inlaid heart to greet you every time you come home is a warm gift from the owner. A huge real cook kitchen with professional Garland range, commercial fridge and soapstone tops galore will tease you into your finest meal ever. Dig deep, find the child who dreamed of the Hundred Acre Wood, and step foot into that dream, in the lovely, comforting hills and meadows of Vermont. Come home for a lifetime. *Age of home is the best estimate seller has.
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