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$350,000
2 Beds ⋅ 1 Baths ⋅ 5103959 MLS
Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness, energy efficiency, and year-round comfort. Completed in July 2026 and designed for low-maintenance living, the home benefits from net-metered solar credits that have offset the owner’s electrical needs, including heating and cooling. Warrantied ENERGY STAR® appliances, two quiet high-efficiency mini-splits, and a continuous fresh-air ventilation system support healthy indoor air, low operating costs, and efficient climate control. Just minutes from Brattleboro Hospital, shopping, restaurants, downtown, and Interstate 91, the home also offers walking access to miles of peaceful forested hiking trails. Designed for one-level living, the first floor includes an inviting foyer, abundant natural light, an open-concept kitchen, dining, and living area, a primary bedroom and full bath, and a large pantry with a washer and dryer. The cozy loft offers flexible space for a second bedroom, office, studio, or guests. Southeast-facing windows and double glass doors open to a rear deck overlooking the Connecticut River Valley. Enjoy autumn foliage, mountain views, classic winter landscapes, colorful sunrises, and warm-weather privacy from mature maple, oak, and locust trees. The poured-concrete walk-out basement is plumbed for radiant heat and includes two windows and double glass doors, offering potential for a workshop, recreation room, studio, guest suite, or possible efficiency apartment, subject to local approvals. The backyard offers room for gardens and outdoor enjoyment. Solar credits are available for purchase separately, creating an exceptional opportunity for long-term energy savings. Every major design decision reflects quality, durability, energy performance, and ease of living. Whether as a year-round residence, Vermont retreat, or simplified one-level home, this home offers thoughtful design, modern comfort, and long-term value.

203 Fairview St, Brattleboro
$299,000
3 Beds ⋅ 2 Baths ⋅ 5103897 MLS
Looking for your first home, ready to downsize, or seeking single level living? This one is for you. Set in a peaceful rural location near the end of a quiet dead end road, this single level ranch offers comfort, privacy, and great potential on 6.5+ acres just outside the village of West Brattleboro. Enjoy an in ground swimming pool with a pool house and bathroom - perfect for summer relaxation. High speed internet keeps you connected, a reliable Buderus boiler provides heat and hot water, and most windows have been updated to double glazed vinyl for improved efficiency. Inside, the layout is practical and inviting. Enter from the attached 24x24 two car garage into a substantial mudroom/laundry room - a huge perk in Vermont. The kitchen offers ample workspace and storage, opening to the dining and living areas with a wall of west facing windows. The living room fireplace is an ideal candidate for a woodstove insert, offering efficient heat with the ambiance of a traditional hearth. Off the central living area are three bedrooms, including a primary bedroom with full bath. Two additional bedrooms - or office/studio/workout spaces - plus a second full bath complete the floor plan. Outside, there’s room to garden, play, and enjoy the land. The price reflects the opportunity for a new owner to perform work and updates to build meaningful equity while enjoying a cozy home in a rural setting close to everyday necessities. Minutes from Memorial Park, trail networks, shopping, schools, the hospital, and I 91, this property delivers outstanding value at a competitive price. Don’t let it get away.

68 E Bonnyvale Ln, Brattleboro
$289,000
4 Beds ⋅ 2 Baths ⋅ 5103506 MLS
This in town 4 bedroom, 2 bath home offers the perfect blend of comfort, convenience and versatility. Ideally located close to town amenities, this property provides easy access to shopping, dining, services, schools, parks and everyday essentials while offering a spacious place to call home. Inside you’ll find beautiful wood flooring, inviting living spaces and a layout that provides flexibility for both living and working. With four bedrooms there is plenty of space for family and overnight guests while the large open finished attic can be turned into a number of uses. Perhaps a studio, exercise room, meditation space, the uses are only limited by your imagination. The property is well suited for those looking to operate a home-based business, offering a prime location and functional space for work-from-home needs. Enjoy the outdoors on your deck or patio and if weather doesn’t cooperate, the enclosed porch is perfect for relaxing with morning coffee or an after dinner beverage. A one-car garage adds convenience while the minimal exterior maintenance allows more time to just enjoy a little down time relaxing. A rare combination of location, flexibility and affordability are just a few of the reasons to take a look at this property. Showings begin Sunday 8/9 with OPEN HOUSE 12pm-3pm.

110 Western Ave, Brattleboro
$182,000
3 Beds ⋅ 2 Baths ⋅ 5103420 MLS
Cute as a button! Everyone knows this home painted as pretty as a picture, on the corner lot at the foot of Union Hill. The owners over the years have landscaped and created a magical setting........walk to downtown, coop and the MOOVER! Previous owners did a amazing renovation after Irene. An intown, affordable, vintage home with lots of character. 48 hour notice please in respect of the tenants. No interior photos to respect tenants privacy.

23 Williams St, Brattleboro
$295,000
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
$450,000
3 Beds ⋅ 2 Baths ⋅ 5103012 MLS
Nestled in a highly desirable West Brattleboro neighborhood, this well-cared-for home offers a wonderful community lifestyle and the ease of main-level living. The first floor features three bright bedrooms and a full bath - perfect for aging in place. Inside, you'll find classic hardwood floors and a cozy fireplace warming the living room. Step outside to an incredible, private backyard deck overlooking gorgeous, mature gardens - your own peaceful retreat. The property also includes a conveniently attached garage and a fully finished basement. The finished lower level includes a generous living room with a wet bar, a half bath, and a second fireplace, ready for a propane fireplace unit. With approximately 1,250 square feet of versatile space on each level, this home is a rare find. Showings begin Saturday, August 8th, with an Open House from 10-1 p.m.

72 Green Mdw, Brattleboro
$59,000
2 Beds ⋅ 1 Baths ⋅ 5102920 MLS
Sweet little mobile home! Large mudroom or multi purpose sun room, eat in kitchen separated from the living room with open shelving. Two bedrooms, the larger used to be two smaller bedrooms which could become that again if you need 3 bedrooms, otherwise a great bedroom with a sitting area, and a second bedroom at the end! Stackable washer/dryer in the bathroom. A large shed is great for storage, plenty of room in the yard for flowers or veggies, and you even have your own private beach on the Whetstone Brook! Comer take a look! Must be park approved!

9 Village Dr, Brattleboro
$198,000
5102764 MLS
It doesn't get better than this! Stunning! Over 3.25 acres in a neighborhood with a wait list, well known hiking trails, near cross country skiing, country club and minutes to downtown. There are 2 lots, the front being mostly wooded with some clearing started and the rear lot with an old horse meadow, stone wall and a bit of height for potential views. Not only is there road frontage on Pleasant Valley, but a right of way to take you to the rear lot. You can't miss this opportunity to join the neighborhood, become a part of something special. Don't compromise any longer, build that energy efficient, Vermont home and be the influencer for the next generation of homes.

Pleasant Valley Rd, Brattleboro
$599,000
4 Beds ⋅ 3 Baths ⋅ 5102586 MLS
This handsome Contemporary Colonial is beautifully set on over an acre of level land in the desirable Hillwinds community, w/access to 200 acres of woodland featuring 3.7 miles of trails. Designed for comfort and efficiency, the property includes 24 solar panels for substantial energy savings, 2 Tesla Powerwalls and large rear decking for outdoor living. A 24' x 24' attached garage with overhead electric doors and finished sheetrock walls provides excellent space for vehicles or a workshop. The bright, inviting interior offers spacious principal rooms, large windows throughout, and has been recently painted. A generous mudroom with terracotta and ceramic tile flooring provides access to the garage, laundry room, and half bath before leading into the open kitchen and dining area. The well-appointed kitchen features cherry cabinetry, granite countertops, stainless steel appliances and recessed lighting. The dining room offers hardwood flooring, a charming bay window with window seat, and sliders to the rear deck. The expansive living room features hardwood flooring, a fireplace with pellet stove, and sliders to the deck. A formal entry with terracotta flooring and a private office with built-in shelving and glass-fronted folding doors complete the main level. Upstairs are four spacious bedrooms. The primary suite includes two large closets and a beautifully renovated en-suite bath with a soaking tub, glass-enclosed shower, and ceramic flooring. 3 additional bedrooms offer generous closet space and share an updated full bath. One bedroom provides access to a large finished bonus room with skylights, built-in shelving, and eaves storage. The walkout lower level is mostly finished, providing space for a family room or game room, along with utility closets and a large storage room. Located in one of Southern Vermont's most sought-after neighborhoods, this exceptional home offers energy efficiency, quality finishes, abundant natural light & outstanding access to nature.

179 Hillwinds N, Brattleboro
$415,000
3 Beds ⋅ 2 Baths ⋅ 5102500 MLS
Finally! A rare offering in a neighborhood with a waiting list!! And....a rare ranch style for either aging in place or just starting out!! Nice open concept living/dining features a fireplace that has been converted to a wood stove hook up for efficient use. Private primary bath, wood floors, big mud room/ breakfast nook are some of the sweet features to look forward to. Finished basement adds family area and fitness room. Huge yard features a cute raised studio, sunny deck ad is partially fenced. Join us for an Open House Saturday, August 1st from 11 am -1 pm.

138 Wantastiquet Dr, Brattleboro
$680,000
5102102 MLS
SUPERB OPPORTUNITY to acquire one of Brattleboro’s nicest multi-family, investment properties!! Situated in one of THE BEST neighborhoods in Brattleboro, Vermont, this sweet, money-maker offers 7 units on a quiet street that is SOOO close to downtown Brattleboro. What every investor dreams of!!! Location, quality condition and build, spacious unit size, superb level, off-street parking, and public water and sewer. Many units have private entrances – wow! On-site laundry, too! It’s time to diversify, and acquiring a steady income stream is the best way forward!!! Excellent investment with superb ROI potential. LOCATION & OPPORTUNITY. This is THE ONE for you. Do NOT miss out! Private showings on request.

50 Terrace St, Brattleboro
$350,000
5100544 MLS
Discover this lovingly cared-for two-unit multi-family property, ideally located in town with convenient access to shopping, restaurants, public transportation, and everyday amenities. Each unit offers a comfortable layout featuring 2 bedrooms and 1 bathroom, making this property an excellent opportunity for owner-occupants, investors, or those seeking rental income. Pride of ownership is evident throughout, with the property having been carefully maintained over the years. Come sit on the back porch and watch the sunrise over the mountain. Whether you're looking to expand your investment portfolio or live in one unit while generating income from the other, this well-kept duplex offers convenience, versatility, and lasting value in a desirable location.

120 Western Ave, Brattleboro
$729,000
3 Beds ⋅ 3 Baths ⋅ 5100444 MLS
A rare combination of recreation & convenience in one of Brattleboro's most desirable neighborhoods. This home is designed for living & entertaining! The property sits on 1.6 acres of landscaped grounds with sweeping views of Mt. Wantastiquet showcasing spectacular sunrises & front-row views of Brattleboro's 4th of July fireworks. Tucked beside Living Memorial Park on a quiet cul-de-sac where skiing, tennis, baseball, swimming, playgrounds and year-round recreation are just steps away. Inside, oversized windows fill the home with natural light while viewing the spectacular setting. A welcoming foyer with beveled glass doors and three generous closets opens to the elegant living room with hardwood floors, propane fireplace, and expansive windows. The heart of the home is the stunning kitchen / dining area featuring ash flooring, a massive center island, custom Schrock cabinetry, granite countertops, and large sliding doors opening to the patio w/ firepit overlooking the views. Adjacent is an oversized walk-in butler's pantry offering abundant cabinetry, workspace and storage. The first floor features a guest bedroom with private en-suite bath featuring tile flooring and glass enclosed shower. Designed for entertaining, the year-round cabana room opens directly to a 2nd patio and 40x20 saltwater pool and includes a custom bar, full refrigerator, custom wine cabinet, plus an adjacent bath with concrete countertops, tile flooring and exposed brick accents. Upstairs, the primary suite offers a wall of windows framing the mountain views, a spa-inspired bath with double vanity & designer tiled rain shower, adjoining custom laundry room w/folding station, & an oversized walk-in dressing room with built-in organization. A 2nd spacious bedroom also includes a walk-in closet. Extensive updates, quality craftsmanship, beautiful outdoor living spaces, and an unbeatable location combine to create a rare offering of a truly move-in-ready home. Simply Stunning. Showings begin 7/24.

219 Hillcrest Ter, Brattleboro
$295,000
3 Beds ⋅ 1 Baths ⋅ 5100010 MLS
Timeless Character on Coveted Oak Grove Avenue! There's something special about an American Foursquare. Built for comfort and designed to stand the test of time, this quintessential early 20th-century home welcomes you with classic architecture, generous room sizes, and the warmth of original craftsmanship. Set on a desirable in-town lot along Oak Grove Avenue, this 3-bedroom home showcases beautiful hardwood floors, rich natural woodwork, and a cozy fireplace that anchors the inviting living room. The screened front porch is the perfect place to enjoy your morning coffee, greet neighbors, or unwind on warm summer evenings. Upstairs, you'll find three comfortable bedrooms and a full bath, while the unfinished attic offers exciting possibilities - whether you envision a studio, home office, playroom, or additional living space. Outside, there's room to garden, entertain, or simply enjoy the yard, along with the convenience of a one-car garage. Combining timeless character with everyday practicality, this home is just minutes from schools, the hospital, restaurants, shopping, and all the conveniences of in-town living. Come experience everything this Oak Grove Avenue gem has to offer.

136 Oak Grove Ave, Brattleboro
$250,000
2 Beds ⋅ 2 Baths ⋅ 5099429 MLS
Nestled next to Brattleboro's favorite public park, this end unit is wrapped in coveted out door space ,wrapping from the coffee deck all the way around to the back brick patio It also features a private garage with auto open, and laundry and storage neatly behind, The parking is paved with plenty of room for guests. Inside the ample galley kitchen has everything you need including a large top doing double duty as prep space and an extension of the dining room with stools to sit and sip. Just the right size for entertaining or family time, the living room is bathed in light from the large windows and the slider to the deck. A refuge from every day life, the huge main bedroom has room for a cozy chair, lots of closets and direct access to the bath. So special in it's location, so close to I91 north and south and east/west travel on RT 9, you can easily access health care, shopping, and all the fun things Vermont has to offer. Worth a visit for affordability, location and ease of lifestyle.

9 Evergreen Ln, Brattleboro
$250,000
2 Beds ⋅ 2 Baths ⋅ 5099302 MLS
This inviting 2 bedroom, 2-bathroom townhouse is located with privacy but close to Brattleboro amenities. Drive into your one car garage, in addition there is a storage area and laundry room. The second floor has a spacious living room and galley kitchen with eating nook which flows into a dining room and outdoor deck. The third level of this cozy condominium has a full sectional bathroom and 2 bedrooms with vaulted ceilings. Just next door is the Living Memorial Park offering swimming, baseball games, pickleball, skiing, skating and annual events, The popular Farmer's Market is also close by. Close to 1-91 this convenient property can be your next ....home sweet home.

11 Evergreen Ln, Brattleboro
$110,000
5099250 MLS
Nestled just behind 117 Fuller Drive, with privacy and easy access from the street, this property is the perfect spot for the tiny home you have been longing for. Water, sewer, and electric are all at the street, and the seller will help to keep the access accessible :)  The subdivision has received preliminary approval from the town, with finalization to be completed prior to sale—giving you peace of mind as you plan. Downtown Brattleboro is just about a mile away,  while everyday essentials are close by as well. Close to hospital, public transportation, schools, and shopping!  Perhaps the best perk of all? Fantastic neighbors and a rare opportunity: buyers have the option to rent the seller's ADU while building their new home, making the transition seamless and stress-free. Whether you're a first-time builder, downsizing, or a dreamer chasing simplicity, this thoughtfully positioned and convenient lot is a rare find. Come imagine the possibilities and stake your claim in wonderful Brattleboro, Vermont. Deed, taxes, and final acreage to be determined but will be at least .12 acres. NOTE- BS&L offers special tiny home loans!

117 Fuller Dr, Brattleboro
$495,000
5099165 MLS
Exceptional investment opportunity! This well maintained six-unit property is in outstanding condition and has seen numerous recent improvements, making it an attractive addition to any investment portfolio. Exterior updates include fresh paint completed last year, newer windows (approximately three years old), a newer rubber membrane roof, buried power, updated electrical, a newer hot water heater, spray foam insulation, and new cellulose insulation in the attic. The building offers six rental units, including three efficiency apartments, (2) two-bedroom units, and (1) one-bedroom unit (please note the bedroom does not have a window). Three units are currently occupied by long-term tenants. The two-bedroom and one-bedroom units each have separate electric service, while the three efficiency units are on the owner's electric meter. Heat and hot water are included for all tenants. The property also offers plenty of off-street parking with a convenient location close to shopping, the hospital, public transportation, Interstate 91, and other local amenities. A turnkey investment with many major capital improvements already completed.

1309 Putney Rd, Brattleboro
$285,000
3 Beds ⋅ 1 Baths ⋅ 5097858 MLS
Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential.

455 S Main St, Brattleboro
$465,500
5097401 MLS
Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. The building consists of four spacious 2-bedroom, 1-bath apartments, providing a desirable and consistent unit mix. Pride of ownership is evident throughout, making this a turnkey addition to any portfolio. Beyond the existing income, the property offers exciting upside with attic space that may provide opportunities for additional living area or future expansion, subject to local approvals. Ideally located in Brattleboro, tenants enjoy the convenience of a thriving downtown known for its eclectic shops, restaurants, arts scene, and year-round community events, as well as easy access to Interstate 91 and the outdoor recreation that Southern Vermont is known for. Whether you're seeking stable cash flow or long-term value-add potential, this property delivers both in one of Vermont’s most desirable communities. 3D Virtual Tours Available Upon Request.

28 Brook St, Brattleboro
$422,000
5097400 MLS
Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. The building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting pride of ownership and minimizing near-term maintenance. Located in vibrant Brattleboro, tenants enjoy easy access to the town’s eclectic mix of restaurants, coffee shops, galleries, and local events, along with convenient access to Interstate 91 and nearby outdoor recreation. Known for its strong sense of community and thriving arts scene, Brattleboro continues to attract residents seeking both small-town charm and everyday conveniences. Whether you're expanding an existing portfolio or looking for a high-yield investment in one of Southern Vermont’s most dynamic communities, this property offers strong returns and lasting appeal. 3D Virtual Tours Available Upon Request.

820 Western Ave, Brattleboro
$68,000
2 Beds ⋅ 1 Baths ⋅ 5096935 MLS
Welcome to 22 Valley Road, an affordable and easy-to-maintain 2-bedroom, 1-bath mobile home located in Brattleboro’s Tri-Park Cooperative Housing Corporation. This cozy single-level home offers a bright and refreshed interior with natural light, LED lighting, first-floor laundry hookups, and a functional layout that makes great use of the space. The kitchen features an electric range, refrigerator, freezer, and ample cabinet storage, opening nicely into the living area for everyday convenience. Outside, enjoy a level setting with off-street parking, a gravel driveway, and access to community amenities including common acreage, coin laundry, and a basketball court. The property also offers access to Whetstone Brook, nearby walking trails, and a convenient location close to Brattleboro’s shopping, dining, schools, recreation, and I-91. A great opportunity for affordable living in a convenient Brattleboro location!

22 Valley Rd, Brattleboro
$299,000
3 Beds ⋅ 1 Baths ⋅ 5096011 MLS
Welcome to a home where everyday living feels just a little more special. Offering three comfortable bedrooms and a functional, inviting layout, this property is designed for everything from quiet evenings at home to hosting family and friends. The true highlight is the incredible backyard, a rare, fully fenced, level oasis that's ready for every season of life. Fire up the grill on the spacious back deck, let the kids and pets roam freely, plant the garden you've always wanted, or gather around a fire pit under the Vermont stars. This is the kind of outdoor space buyers dream about and seldom find. In addition to the incredible yard. A fully paved driveway with room for multiple cars, space for RV's Boats and other recreational items is at your service. Located in one of Brattleboro's most convenient neighborhoods, you'll love being just minutes from vibrant downtown shops, local restaurants, schools, parks, and minutes from I-91 leaving you 30 minutes to major MA and NH Hubs. Enjoy year-round community events while still enjoying the peace and privacy of your own backyard retreat. Whether you're grabbing a morning coffee, exploring the local arts scene, or taking advantage of nearby hiking and recreation, everything you love about Brattleboro is right at your fingertips. This isn't just a place to live, it's a place to make memories. This home offers the lifestyle you've been waiting for. Don't miss your chance to experience everything this exceptional property has to offer. List Agent is related to the Sellers

48 Carriage Hill Rd, Brattleboro
$189,000
2 Beds ⋅ 2 Baths ⋅ 5095431 MLS
DESIRABLE END UNIT! Why rent when you can buy- giving you peace of mind, an opportunity for stability and building equity. Maybe you are a first-time homebuyer? Or someone who wants to downsize from a bigger house and time-consuming yard chores and projects to a simpler life. An investor? Enjoy easy, affordable, and low-maintenance living in this sweet two-bedroom, 1.5 bath townhouse. Storage space in the attic! Conveniently located 1/2 mile to downtown Brattleboro's Main Street, the food Co-op, the new Brattleboro train station and museum, and lots of fun shops and diverse restaurants. Association amenities: a fabulous in-grown pool, pickleball/tennis court. HOA dues include lovely landscaping, master insurance policy, plowing, snow-removal, and trash. A delightful community of neighbors in a very pretty setting. Sale is contingent on Sellers finding suitable housing/closing within 90 days of contract.

1 Morningside Commons, Brattleboro
$369,000
4 Beds ⋅ 2 Baths ⋅ 5095156 MLS
MAKE YOUR APPOINTMENT TODAY! A very sweet house in a desired West Brattleboro neighborhood on nice corner lot. Pull your car right into the 2-car oversized garage and enter through the enclosed porch which makes an excellent mudroom. First floor: beautifully updated kitchen with quartz countertops and cherry cabinets, a dining area that adjoins the light-filled large living room with lovely warm hardwood floors, exposed beam, an enormous picture window that allows for streaming sunshine throughout the morning. The centrally located Hearthstone woodstove adds to the appealing aesthetics of the home and provides for a secondary heat source that warms the entire home in the winter. Down the hall- a full bath and two good-sized bedrooms with wood floors. Upstairs, you will find an expansive primary bedroom, a half bath and a large office (or 4th bedroom). There is a full, poured concrete basement with bulkhead, where one of two rooms is finished and has served as a play/rec room through the years. The other room is used for storage with shelving, includes a washer and dryer, and an on-demand water heater and furnace that are only 6 years old. Outside you will enjoy a large back deck for summer grilling and relaxing. The yard provides areas for flowering trees, sun and natural shade, plantings and play. Garage roof is brand-new. Convenient location just minutes to downtown Brattleboro, or all of the West Brattleboro offerings such as hardware store. coffee shop, farm-stands, convenience store, restaurants and more. Make your appointment today!

120 Carriage Hill Rd, Brattleboro
$299,000
3 Beds ⋅ 3 Baths ⋅ 5094671 MLS
Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard—perfect for relaxing, gardening, or outdoor gatherings. Upstairs, the bedrooms offer comfortable accommodations with the opportunity to add a full bathroom in the future, allowing the home to grow with your needs. The lower level includes a separate in-law suite complete with its own private entrance and laundry area, offering flexibility for guests, multi-generational living, a home office, or potential rental income. Conveniently located, the property is less than a block from the Vermont Country Deli and within walking distance of the Brattleboro Farmers' Market, Memorial Park, and recreation fields. Easy access to Interstate 91 makes commuting simple while keeping downtown Brattleboro's shops, restaurants, arts, and entertainment just minutes away. Whether you're searching for a primary residence, an investment property, or a home with income-producing potential, this well-priced property offers an excellent opportunity.

412 Western Ave, Brattleboro
$545,000
2 Beds ⋅ 1 Baths ⋅ 5094642 MLS
Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural Vermont charm, privacy and convenience, with easy access to town. The beautiful Pleasant Valley Reservoir and the recreational opportunities provided by its protected land, trail system and class 4 road network are an underutilized outdoor paradise just down the road. The home's striking flat roof design, redwood siding, and clean mid-century modern influences create a timeless architectural aesthetic. Inside, the open concept living/dining and kitchen area is filled with natural light from the expansive windows that frame the surrounding landscape. An East/SE facing corner deck provides the perfect setting for morning coffee and sunrise views. The main level features two bedrooms and a full bath updated in 2026. The finished walkout lower level offers a spacious additional living space. The impressive gambrel barn once housed horses in its 3-5 stall lower level and has water and power. The top level of the barn is open clear span with a drive-in door ideal for vehicles and equipment storage, a wood shop, workshop, studio space or a variety of other uses including a possible second dwelling unit with applicable permits. The open land in front of the barn was once a dressage arena and provides an excellent level outdoor space for recreation, animals or agriculture. The remainder of the property includes a mix of open field, young growth forest and established yard areas surrounding the home with abundant room for large gardens and outdoor fun. Despite its peaceful country setting skiing, golf, hiking and biking are only minutes away. A rare one-of-a-kind Vermont property.

211 Pleasant Valley Rd, Brattleboro
$305,000
2 Beds ⋅ 3 Baths ⋅ 5093917 MLS
Rare opportunity to enjoy single-level living with all modern conveniences on the main floor in this magnificent condo unit. Featuring a spacious primary bedroom with a walk-in closet and full en-suite bathroom, this home offers comfort and functionality throughout. A second bedroom provides flexibility for guests, a home office, or additional living space. The open-concept kitchen and dining area features quality KitchenAid appliances and flows seamlessly into the inviting living room. An additional full bathroom, first-floor laundry, and a walkout patio complete the main level. Large windows provide an abundance of natural light throughout the home. The finished lower level offers a spacious family room with a walkout door, a convenient half bath, and an additional large unfinished area ideal for storage, a workshop, or hobby space. Only a handful of units at Morningside Commons offer this highly desirable floor plan. Enjoy all the amenities Morningside Commons has to offer, including an inground pool, tennis and pickleball courts, and beautifully maintained grounds. Leave the snow removal, lawn care, and landscaping to someone else and enjoy the ease of low-maintenance living.

136 Morningside Commons, 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
$1,350,000
5093440 MLS
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

131 133, 141 Green St, Brattleboro

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