welcomehome-nh.com Search Results

Price Improvement! Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures the historic essence of Vermont with its chestnut beams, wide plank flooring and stylish yet unpretentious design. Interior features offer the perfect balance of grandeur and intimacy with oversized windows that bathe the rooms in natural light, 3 fireplaces and authentic lighting. The kitchen is a culinary haven with state-of-the-art appliances and stunning Brazilian countertops, providing ample workspace and an eat-in area. The first floor also offers a formal dining room, a guest/primary suite with a private entrance and laundry, an office, and it's completed by a sitting room where the current owners gather around the piano. Upstairs you'll find a generous primary suite, two bedrooms, and one with a connecting room, an ideal playroom or office. The walk-out basement is partially finished with a workout room, laundry room and abundant storage. The house includes high-speed fiber internet and a whole-house generator. The attached 2-car garage is heated and a second heated detached 2-car garage with a finished loft above is perfect for playing pool and foosball with family & friends. Relaxation comes easily by the inviting in-ground pool overlooking tranquil woodlands, the stone-terraced landscape and native wildlife. This special property is nestled in a friendly community on a country road, adjacent to 367 acres of protected land with trails perfect for hiking, biking and snowshoeing. Just 2 hrs to Boston, 3.5 hrs to NYC with direct Amtrak to NYC. Easy drive to ski mountains.

4 Beds ⋅ 4 Baths ⋅ 5088064 MLS

Price Improvement! Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures the historic essence of Vermont with its chestnut beams, wide plank flooring and stylish yet unpretentious design. Interior features offer the perfect balance of grandeur and intimacy with oversized windows that bathe the rooms in natural light, 3 fireplaces and authentic lighting. The kitchen is a culinary haven with state-of-the-art appliances and stunning Brazilian countertops, providing ample workspace and an eat-in area. The first floor also offers a formal dining room, a guest/primary suite with a private entrance and laundry, an office, and it's completed by a sitting room where the current owners gather around the piano. Upstairs you'll find a generous primary suite, two bedrooms, and one with a connecting room, an ideal playroom or office. The walk-out basement is partially finished with a workout room, laundry room and abundant storage. The house includes high-speed fiber internet and a whole-house generator. The attached 2-car garage is heated and a second heated detached 2-car garage with a finished loft above is perfect for playing pool and foosball with family & friends. Relaxation comes easily by the inviting in-ground pool overlooking tranquil woodlands, the stone-terraced landscape and native wildlife. This special property is nestled in a friendly community on a country road, adjacent to 367 acres of protected land with trails perfect for hiking, biking and snowshoeing. Just 2 hrs to Boston, 3.5 hrs to NYC with direct Amtrak to NYC. Easy drive to ski mountains.

390 Pleasant Valley Rd, Brattleboro

$800,000

Professional office building in the heart of downtown Brattleboro situated on 1.14 acres and perched on the bank above the Connecticut River with its owned paved parking and outstanding views from nearly every office/room of the River and Mt. Wantastiquet beyond. Currently the home of a bank on the main level (and separate ATM building in front) and various professional offices and healthcare providers on the upper and lower levels. Undoubtedly some of the most desirable office space in town due to the location and walls of glass and vistas they provide. There is vacant space at present allowing an owner user to occupy the space. The property also offers tremendous outdoor space for its tenants to utilize. The building sits well back from main street but has great visibility and is an impressive structure in great overall condition. Keypad code electronic entry allows tenants keyless 24-hour access. Passenger elevator to all floors. Main systems have been updated and maintained. Ideal as an owner-occupied business location with income, an investor looking for a quality income property OR for a 1031 Exchange target property. At full occupancy with market rents applied it will be an impressive rate of return on investment. Financials available upon request and execution of an NDA.

5049010 MLS

Professional office building in the heart of downtown Brattleboro situated on 1.14 acres and perched on the bank above the Connecticut River with its owned paved parking and outstanding views from nearly every office/room of the River and Mt. Wantastiquet beyond. Currently the home of a bank on the main level (and separate ATM building in front) and various professional offices and healthcare providers on the upper and lower levels. Undoubtedly some of the most desirable office space in town due to the location and walls of glass and vistas they provide. There is vacant space at present allowing an owner user to occupy the space. The property also offers tremendous outdoor space for its tenants to utilize. The building sits well back from main street but has great visibility and is an impressive structure in great overall condition. Keypad code electronic entry allows tenants keyless 24-hour access. Passenger elevator to all floors. Main systems have been updated and maintained. Ideal as an owner-occupied business location with income, an investor looking for a quality income property OR for a 1031 Exchange target property. At full occupancy with market rents applied it will be an impressive rate of return on investment. Financials available upon request and execution of an NDA.

201-205 Main St, Brattleboro

$790,000

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.

4 Beds ⋅ 4 Baths ⋅ 5082195 MLS

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.

104 Juniper Ridge Rd, Brattleboro

$750,000

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, rolling meadows, 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.

4 Beds ⋅ 5 Baths ⋅ 5064709 MLS

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, rolling meadows, 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.

131 Stark Rd, Brattleboro

$726,500

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.

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

$615,000

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 25th 11am - 1pm

5 Beds ⋅ 4 Baths ⋅ 5082786 MLS

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 25th 11am - 1pm

143 Hillwinds Rd, Brattleboro

$609,000

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.

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

$595,000

Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and oversized wavy glass windows that bathe the interior in natural light. The 1st floor is bright and inviting, with a sun-filled dining room and a living room featuring a propane insert for warmth and ambiance. For accessibility, there is a 1st floor full bathroom and bedroom with historic curved wall. The gracious staircase brings you to a reading nook on the landing, 3 bedrooms, and a full bath with a clawfoot tub. The large laundry room offers flexibility to double as a studio, craft, or hobby space. The property also features two accessory apartments, offering excellent income potential or space for guests or extended family. A detached barn has storage above, and plenty off-street parking. The yard has been extensively and thoughtfully landscaped with lush, low-maintenance perennials, stone patios, and garden pathways. A private sauna nestled among the gardens creates a peaceful retreat a after a busy day. This exceptional property is a rare find—gracefully blending history, function, and opportunity in one of Brattleboro’s most coveted locations. Being offered as a single family home.

5 Beds ⋅ 4 Baths ⋅ 5103977 MLS

Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and oversized wavy glass windows that bathe the interior in natural light. The 1st floor is bright and inviting, with a sun-filled dining room and a living room featuring a propane insert for warmth and ambiance. For accessibility, there is a 1st floor full bathroom and bedroom with historic curved wall. The gracious staircase brings you to a reading nook on the landing, 3 bedrooms, and a full bath with a clawfoot tub. The large laundry room offers flexibility to double as a studio, craft, or hobby space. The property also features two accessory apartments, offering excellent income potential or space for guests or extended family. A detached barn has storage above, and plenty off-street parking. The yard has been extensively and thoughtfully landscaped with lush, low-maintenance perennials, stone patios, and garden pathways. A private sauna nestled among the gardens creates a peaceful retreat a after a busy day. This exceptional property is a rare find—gracefully blending history, function, and opportunity in one of Brattleboro’s most coveted locations. Being offered as a single family home.

58 Oak St, Brattleboro

$590,000

This exceptional 3-bedroom residence offers refined rural living with space, comfort, and stunning natural surroundings. The home features expansive open living areas, anchored by a large living room with a fireplace, creating a warm yet elegant gathering space. A newly redesigned kitchen serves as the heart of the home, perfectly suited for entertaining family and guests. Enjoy seamless indoor-outdoor living from the wrap-around deck, where sweeping views provide a peaceful backdrop for morning coffee or evening relaxation. The property also includes a separate apartment space, ideal for hosting extended family or guests while maintaining privacy. The 10.01 acres include a greenhouse, established garden space, and acres of usable land offering tranquility, privacy, and endless possibilities. A rare opportunity to own a luxury rural retreat with views, versatility, and timeless appeal.

3 Beds ⋅ 3 Baths ⋅ 5074103 MLS

This exceptional 3-bedroom residence offers refined rural living with space, comfort, and stunning natural surroundings. The home features expansive open living areas, anchored by a large living room with a fireplace, creating a warm yet elegant gathering space. A newly redesigned kitchen serves as the heart of the home, perfectly suited for entertaining family and guests. Enjoy seamless indoor-outdoor living from the wrap-around deck, where sweeping views provide a peaceful backdrop for morning coffee or evening relaxation. The property also includes a separate apartment space, ideal for hosting extended family or guests while maintaining privacy. The 10.01 acres include a greenhouse, established garden space, and acres of usable land offering tranquility, privacy, and endless possibilities. A rare opportunity to own a luxury rural retreat with views, versatility, and timeless appeal.

299 Sunset Lake Rd, Brattleboro

$580,000

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.

4 Beds ⋅ 3 Baths ⋅ 5082239 MLS

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.

11 Strawberry Hl, Brattleboro

$570,000

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!

2 Beds ⋅ 2 Baths ⋅ 5086838 MLS

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!

84 Magnolia Dr, Brattleboro

$568,000

Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising authenticity. Bonus: the home includes generous unfinished space—brimming with potential for additional living area, studio, or guest suite. This property is a true gem with room to make it your own.

3 Beds ⋅ 2 Baths ⋅ 5084454 MLS

Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising authenticity. Bonus: the home includes generous unfinished space—brimming with potential for additional living area, studio, or guest suite. This property is a true gem with room to make it your own.

192 Western Ave, Brattleboro

$550,000

What will the next life be for this iconic property? From popular and innovative hair salon to successful dental practice to a 4 unit family complex….pick your use!!! Owner occupied business…roomy apartments…small business complex…this multi use property has been renovated in the last few years with nice kitchens and baths..and has been used essentially as a single family with a huge yard, paved parking and easy access. Some permits may be required but it is a great base to start a new investment

5076291 MLS

What will the next life be for this iconic property? From popular and innovative hair salon to successful dental practice to a 4 unit family complex….pick your use!!! Owner occupied business…roomy apartments…small business complex…this multi use property has been renovated in the last few years with nice kitchens and baths..and has been used essentially as a single family with a huge yard, paved parking and easy access. Some permits may be required but it is a great base to start a new investment

72 Landmark Hill Dr, Brattleboro

$528,000

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

5091758 MLS

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

25-27 Gingko Ln, Brattleboro

$525,000

Here's an open concept, post and beam beauty located on a quiet country road just outside West Brattleboro. Walk through the covered porch into the welcome foyer, where there's plenty of closet space for coats and gear, then enter the main home. The post and beam construction highlights the bright and open spaces. The chef's kitchen is complete with ample cabinet areas, granite counter tops, full pantry to hold all your cooking needs, and an island for easy sit downs or work space for entertaining. The kitchen flows to the living-dining room, with windows galore and doors that lead out to the deck. The Jotul woodstove anchors the space and will keep you warm on cold winter nights. On the second floor you'll find spacious bedrooms with a 3/4 bath and the main bedroom suite featuring an extra large bath that includes a shower and spa tub. Then upstairs to the bonus rooms with cathedral ceilings, perhaps a home office or study or just a quiet place to relax. There's a full walkout basement that could be finished if you need more space. Outside there are fruit trees, garden space, and almost 14 acres to explore, with Broad Brook flowing through the property. An excellent opportunity for comfortable country living within minutes of town.

3 Beds ⋅ 3 Baths ⋅ 5096932 MLS

Here's an open concept, post and beam beauty located on a quiet country road just outside West Brattleboro. Walk through the covered porch into the welcome foyer, where there's plenty of closet space for coats and gear, then enter the main home. The post and beam construction highlights the bright and open spaces. The chef's kitchen is complete with ample cabinet areas, granite counter tops, full pantry to hold all your cooking needs, and an island for easy sit downs or work space for entertaining. The kitchen flows to the living-dining room, with windows galore and doors that lead out to the deck. The Jotul woodstove anchors the space and will keep you warm on cold winter nights. On the second floor you'll find spacious bedrooms with a 3/4 bath and the main bedroom suite featuring an extra large bath that includes a shower and spa tub. Then upstairs to the bonus rooms with cathedral ceilings, perhaps a home office or study or just a quiet place to relax. There's a full walkout basement that could be finished if you need more space. Outside there are fruit trees, garden space, and almost 14 acres to explore, with Broad Brook flowing through the property. An excellent opportunity for comfortable country living within minutes of town.

160 Akley Rd, Brattleboro

$525,000

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.

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

$497,408

Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive yard offers ample space for gardening, play, or simply enjoying the outdoors. Inside, a striking brick chimney creates a natural separation between the kitchen and the dining/sitting area. A cozy wood stove, nestled at the chimney’s base, adds character and warmth to the home. The spacious living room provides plenty of space for relaxing or entertaining. Offering three comfortable bedrooms & a primary bathroom. A few steps down from the main level reveals an additional oversized room and a full bathroom featuring a jetted tub. The basement includes a laundry area and ample space for a home office, playroom, or storage. Off the kitchen, sliding glass doors open to a beautiful gated deck—ideal for entertaining or enjoying peaceful moments outside, surrounded by nature. This thoughtfully designed split-level home offers the ease of minimal stairs while providing distinct living areas across different levels. Whether you're looking for tranquility, space, or functionality, this home checks all the boxes.

4 Beds ⋅ 2 Baths ⋅ 5052046 MLS

Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive yard offers ample space for gardening, play, or simply enjoying the outdoors. Inside, a striking brick chimney creates a natural separation between the kitchen and the dining/sitting area. A cozy wood stove, nestled at the chimney’s base, adds character and warmth to the home. The spacious living room provides plenty of space for relaxing or entertaining. Offering three comfortable bedrooms & a primary bathroom. A few steps down from the main level reveals an additional oversized room and a full bathroom featuring a jetted tub. The basement includes a laundry area and ample space for a home office, playroom, or storage. Off the kitchen, sliding glass doors open to a beautiful gated deck—ideal for entertaining or enjoying peaceful moments outside, surrounded by nature. This thoughtfully designed split-level home offers the ease of minimal stairs while providing distinct living areas across different levels. Whether you're looking for tranquility, space, or functionality, this home checks all the boxes.

204 Meetinghouse Ln, Brattleboro

$495,000

Beautifully maintained, 1880s, in-town Victorian blends timeless elegance with modern comfort. The large, light-filled kitchen combines with an open, cathedral ceiling dining area inviting the gathering of family and friends. The renovated kitchen has granite, stainless steel appliances, and laundry area. Soaring, 9 ft ceilings create light-filled rooms. Elegance of timeless design and detailed wood trimmed finishes are throughout with crafted moldings framing arched and stain glass windows, custom fireplace mantles and functionally flexible built-ins. Enjoy the old-world charm of two covered porches. The expansive first floor has lovely potential for those wanting first floor accommodations. An ornately crafted staircase rises gracefully to the second floor with four bedrooms, two full baths and the continuation of flooding sunlight. The outdoors offers gorgeous stonework, lush perennial plantings and a magical patio. So close to downtown’s Brattleboro Museum, Art Center, Galleries, Cafes, and more! Convenient to ski mountains and ready access to Boston and NY City. Visit this beloved, period home to experience a world of gentle elegance.

4 Beds ⋅ 3 Baths ⋅ 5087925 MLS

Beautifully maintained, 1880s, in-town Victorian blends timeless elegance with modern comfort. The large, light-filled kitchen combines with an open, cathedral ceiling dining area inviting the gathering of family and friends. The renovated kitchen has granite, stainless steel appliances, and laundry area. Soaring, 9 ft ceilings create light-filled rooms. Elegance of timeless design and detailed wood trimmed finishes are throughout with crafted moldings framing arched and stain glass windows, custom fireplace mantles and functionally flexible built-ins. Enjoy the old-world charm of two covered porches. The expansive first floor has lovely potential for those wanting first floor accommodations. An ornately crafted staircase rises gracefully to the second floor with four bedrooms, two full baths and the continuation of flooding sunlight. The outdoors offers gorgeous stonework, lush perennial plantings and a magical patio. So close to downtown’s Brattleboro Museum, Art Center, Galleries, Cafes, and more! Convenient to ski mountains and ready access to Boston and NY City. Visit this beloved, period home to experience a world of gentle elegance.

41 Chapin St, Brattleboro

$493,000

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.

3 Beds ⋅ 3 Baths ⋅ 5089156 MLS

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.

30 Chapin St, Brattleboro

$489,000

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

4 Beds ⋅ 4 Baths ⋅ 5077786 MLS

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

23 Wilsons Woods Rd, Brattleboro

$475,000

Beautifully cared-for 3 bedroom, 3 bath single family condo in a desirable small association, conveniently located near town, golf course and major road access. This spacious home features a sought after first-floor primary suite with en-suite bath, skylights that fill the home with natural light, and elegant cherry flooring throughout the main living areas. The remodeled kitchen offers modern finishes and functionality, while the family room boasts brand new carpeting for added comfort. a perfect blend of privacy, convenience, and tasteful updates in an exceptional location. Open house Sunday May 31st 11am-2pm.

3 Beds ⋅ 3 Baths ⋅ 5091438 MLS

Beautifully cared-for 3 bedroom, 3 bath single family condo in a desirable small association, conveniently located near town, golf course and major road access. This spacious home features a sought after first-floor primary suite with en-suite bath, skylights that fill the home with natural light, and elegant cherry flooring throughout the main living areas. The remodeled kitchen offers modern finishes and functionality, while the family room boasts brand new carpeting for added comfort. a perfect blend of privacy, convenience, and tasteful updates in an exceptional location. Open house Sunday May 31st 11am-2pm.

94 Brets Rd, Brattleboro

$475,000

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.

3 Beds ⋅ 2 Baths ⋅ 5073849 MLS

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.

24 Laurel St, Brattleboro

$450,000

Welcome to 44 Cedar St! A charming and inviting 3-bedroom home located in a highly desirable neighborhood. This home offers a bright and functional open-concept kitchen with a pantry and plenty of additional storage, flowing seamlessly into the main living space, filled with abundant natural light and a warm, welcoming atmosphere. The living room features a hearth and fireplace with a woodstove insert, perfect for cold winter days and nights. A convenient mudroom provides lots of storage space and helps keep everyday living organized. A half-bath is located on the first floor, while two additional bedrooms and a full bathroom are situated on the second floor, offering ideal flexibility for guests, family, or a home office. The main level also includes a spacious primary bedroom that enjoys direct access to a beautifully landscaped, fenced-in backyard—creating a private, peaceful outdoor retreat perfect for relaxing or entertaining. This versatile space can also function as an additional living area, studio, or flex space to suit your needs. Enjoy quiet mornings or unwind in the evenings on the screened-in front porch—an inviting extension of the living space perfect for relaxation. Outside, a charming pergola creates a delightful setting for entertaining, dining al fresco, or gathering with friends and family in a serene outdoor environment. This beautifully maintained home is situated just minutes from the Retreat Trails and Harris Hill Ski Jump, and within walking distance to downtown, offering the perfect blend of outdoor recreation, convenience, and small-town charm. Don’t miss the opportunity to make this warm, inviting, and truly special home your own! Showings will begin on Friday, May 8th, with an Open House on Saturday, May 9th from 11:00 AM – 2:00 PM.

3 Beds ⋅ 2 Baths ⋅ 5086268 MLS

Welcome to 44 Cedar St! A charming and inviting 3-bedroom home located in a highly desirable neighborhood. This home offers a bright and functional open-concept kitchen with a pantry and plenty of additional storage, flowing seamlessly into the main living space, filled with abundant natural light and a warm, welcoming atmosphere. The living room features a hearth and fireplace with a woodstove insert, perfect for cold winter days and nights. A convenient mudroom provides lots of storage space and helps keep everyday living organized. A half-bath is located on the first floor, while two additional bedrooms and a full bathroom are situated on the second floor, offering ideal flexibility for guests, family, or a home office. The main level also includes a spacious primary bedroom that enjoys direct access to a beautifully landscaped, fenced-in backyard—creating a private, peaceful outdoor retreat perfect for relaxing or entertaining. This versatile space can also function as an additional living area, studio, or flex space to suit your needs. Enjoy quiet mornings or unwind in the evenings on the screened-in front porch—an inviting extension of the living space perfect for relaxation. Outside, a charming pergola creates a delightful setting for entertaining, dining al fresco, or gathering with friends and family in a serene outdoor environment. This beautifully maintained home is situated just minutes from the Retreat Trails and Harris Hill Ski Jump, and within walking distance to downtown, offering the perfect blend of outdoor recreation, convenience, and small-town charm. Don’t miss the opportunity to make this warm, inviting, and truly special home your own! Showings will begin on Friday, May 8th, with an Open House on Saturday, May 9th from 11:00 AM – 2:00 PM.

44 Cedar St, Brattleboro

$450,000

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.

3 Beds ⋅ 3 Baths ⋅ 5082621 MLS

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.

81 Chapin St, Brattleboro

$450,000

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.

4 Beds ⋅ 3 Baths ⋅ 5076579 MLS

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.

214 Putney Rd, Brattleboro

$442,000

Conveniently located in Brattleboro Center, this historic three-family home offers the perfect blend of Historic charm, and modern convenience. It is an ideal opportunity for an investor seeking profitable rental income or an owner-occupant looking to live on the main level while offsetting their mortgage with two additional rental units. The first-floor unit features high ceilings, French doors, built-ins, and beautiful pine floors in the living and dining rooms. The updated kitchen includes stainless steel appliances, refaced cabinets, newer floor, newer refrigerator, dishwasher, and hood. This unit offers a spacious master en-suite, a second large bedroom, a hallway bath, a mudroom entryway and a large laundry room with ample storage. The side entrance leads to a private porch and a newer, spacious Trex deck, perfect for entertaining or relaxing while enjoying cool summer breezes. The second floor contains two additional apartments. Unit 2 includes two bedrooms and one bath w/ private covered porch and separate back entrance, while Unit 3 is a studio with a combined bedroom/living area and a spacious walk-in closet. Each unit is equipped with separate electric meters and panels. Major Improvements in the last 10 years include vinyl siding (2019), a new oil tank (2019), a water tank (2018), the Trex deck, reinforced porches & pvc railings, and numerous interior upgrades. The property also features a full basement with a workshop, four parking spaces, and a newer bicycle shed. The location is ideally situated near Main Street shopping, restaurants, the hospital, museum & art center, and the Connecticut River. It is a commuter’s dream, located in close proximity to the Brattleboro Transportation Center, the Amtrak Station, and the highway (I-91). For winter and outdoor enthusiasts, it is less than an hour from premier Southern Vermont ski resorts, including Mt. Snow, Stratton, and Bromley. Don't miss out on this amazing Opportunity!

5075240 MLS

Conveniently located in Brattleboro Center, this historic three-family home offers the perfect blend of Historic charm, and modern convenience. It is an ideal opportunity for an investor seeking profitable rental income or an owner-occupant looking to live on the main level while offsetting their mortgage with two additional rental units. The first-floor unit features high ceilings, French doors, built-ins, and beautiful pine floors in the living and dining rooms. The updated kitchen includes stainless steel appliances, refaced cabinets, newer floor, newer refrigerator, dishwasher, and hood. This unit offers a spacious master en-suite, a second large bedroom, a hallway bath, a mudroom entryway and a large laundry room with ample storage. The side entrance leads to a private porch and a newer, spacious Trex deck, perfect for entertaining or relaxing while enjoying cool summer breezes. The second floor contains two additional apartments. Unit 2 includes two bedrooms and one bath w/ private covered porch and separate back entrance, while Unit 3 is a studio with a combined bedroom/living area and a spacious walk-in closet. Each unit is equipped with separate electric meters and panels. Major Improvements in the last 10 years include vinyl siding (2019), a new oil tank (2019), a water tank (2018), the Trex deck, reinforced porches & pvc railings, and numerous interior upgrades. The property also features a full basement with a workshop, four parking spaces, and a newer bicycle shed. The location is ideally situated near Main Street shopping, restaurants, the hospital, museum & art center, and the Connecticut River. It is a commuter’s dream, located in close proximity to the Brattleboro Transportation Center, the Amtrak Station, and the highway (I-91). For winter and outdoor enthusiasts, it is less than an hour from premier Southern Vermont ski resorts, including Mt. Snow, Stratton, and Bromley. Don't miss out on this amazing Opportunity!

176 High St, Brattleboro

$439,000

This West Brattleboro ranch style home is situated in that sought after "just outside of town" location with the hard-to-find combination of convenient proximity to the necessities and out the door access to walks on quiet country roads including the trails around the Pleasant Valley Reservoir just short drive up the road. The house has had two renovations in the past 20 years (2006 & 2015/16) and offers a great floor plan, primary bedroom suite, large modern kitchen/dining room, attached two car garage, dedicated office/study, entry/mudroom and a full "sock friendly" clean/dry walk-out basement. The home also features hardwood, softwood and tile flooring, stainless kitchen appliances and a pantry closet, a first-floor laundry, lots of storage and much more. The primary suite is separated from the main house and located at the south end with outstanding privacy. Built as an addition in 2015 to the original house it boasts pine flooring, large walk-in closet, direct access to the back decks, lots of glass for natural light and an amazing bathroom with a huge custom tile shower, soaking tub, double vanity and tons of elbow room. On the outside you'll find a large full length back deck, pole barn for extra storage, outstanding lawns and landscaped grounds with plenty of room for summer cookouts and family fun. The house systems have been upgraded and improved over recent years with two mini-splits, a Buderus OHWBB 2 zone heating system, a pellet stove in the living room, a newer 200 AMP panel with a 6.4 KW ground mounted solar array that is grid tied and offsets some utility costs and is overall a very efficient home. The primary suite addition has a full basement now attached to the original foundation which adds a bonus storage area with an at grade double door making it easy to store equipment or the "toys" in dry cool space. A very well cared for home in a great location just minutes to town. Sale subject to Seller finalizing their purchase of new primary home.

4 Beds ⋅ 2 Baths ⋅ 5079663 MLS

This West Brattleboro ranch style home is situated in that sought after "just outside of town" location with the hard-to-find combination of convenient proximity to the necessities and out the door access to walks on quiet country roads including the trails around the Pleasant Valley Reservoir just short drive up the road. The house has had two renovations in the past 20 years (2006 & 2015/16) and offers a great floor plan, primary bedroom suite, large modern kitchen/dining room, attached two car garage, dedicated office/study, entry/mudroom and a full "sock friendly" clean/dry walk-out basement. The home also features hardwood, softwood and tile flooring, stainless kitchen appliances and a pantry closet, a first-floor laundry, lots of storage and much more. The primary suite is separated from the main house and located at the south end with outstanding privacy. Built as an addition in 2015 to the original house it boasts pine flooring, large walk-in closet, direct access to the back decks, lots of glass for natural light and an amazing bathroom with a huge custom tile shower, soaking tub, double vanity and tons of elbow room. On the outside you'll find a large full length back deck, pole barn for extra storage, outstanding lawns and landscaped grounds with plenty of room for summer cookouts and family fun. The house systems have been upgraded and improved over recent years with two mini-splits, a Buderus OHWBB 2 zone heating system, a pellet stove in the living room, a newer 200 AMP panel with a 6.4 KW ground mounted solar array that is grid tied and offsets some utility costs and is overall a very efficient home. The primary suite addition has a full basement now attached to the original foundation which adds a bonus storage area with an at grade double door making it easy to store equipment or the "toys" in dry cool space. A very well cared for home in a great location just minutes to town. Sale subject to Seller finalizing their purchase of new primary home.

387 Meadow Brook Rd, Brattleboro

$435,000

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.

3 Beds ⋅ 2 Baths ⋅ 5078629 MLS

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.

56 Lee Rd, Brattleboro

$425,000

Timeless Cape character, thoughtful renovations, outdoor living, and rare double lot come together at Marlboro Avenue, a standout Brattleboro offering with both charm and opportunity. This four bedroom, two bath gem has been thoughtfully renovated throughout. The flexible layout includes bedrooms and a bath with a spa shower on the first floor, two additional bedrooms and a full bath upstairs, plus a finished bonus room that is great for cozy movie nights. The other side of the basement includes laundry and workshop space, along with a separate area for storage with convenient exterior access. Hardwood floors, natural light, and craftsman touches, including built-ins in the bedrooms, bring warmth and character throughout. A new mudroom entry off the kitchen adds everyday function with custom storage and a cozy electric fireplace. Outdoor living is equally inviting, with a private deck, low-maintenance gardens, mature privacy trees, a firepit, tree house, small shed, one-car garage, and a large outbuilding offering excellent space for a workshop, storage, hobbies, or creative use. Comfort and convenience continue with recently added heat pumps for efficient heating and cooling, new roof, oil baseboard heat as the primary system, public water, public sewer, and fiber optic internet. Nearby sidewalks and close proximity to local shopping, schools, recreation, Brattleboro Memorial Hospital, downtown Brattleboro, and I-91 add to the property's appeal. The double lot offers added outdoor space and possible future opportunity. Seller's attorney confirmed the second lot is buildable, though any future use should be confirmed directly with the town. With thoughtful renovations, charming details, useful spaces, and future potential, this Brattleboro property offers a compelling blend of comfort, convenience, and possibility.

4 Beds ⋅ 2 Baths ⋅ 5090833 MLS

Timeless Cape character, thoughtful renovations, outdoor living, and rare double lot come together at Marlboro Avenue, a standout Brattleboro offering with both charm and opportunity. This four bedroom, two bath gem has been thoughtfully renovated throughout. The flexible layout includes bedrooms and a bath with a spa shower on the first floor, two additional bedrooms and a full bath upstairs, plus a finished bonus room that is great for cozy movie nights. The other side of the basement includes laundry and workshop space, along with a separate area for storage with convenient exterior access. Hardwood floors, natural light, and craftsman touches, including built-ins in the bedrooms, bring warmth and character throughout. A new mudroom entry off the kitchen adds everyday function with custom storage and a cozy electric fireplace. Outdoor living is equally inviting, with a private deck, low-maintenance gardens, mature privacy trees, a firepit, tree house, small shed, one-car garage, and a large outbuilding offering excellent space for a workshop, storage, hobbies, or creative use. Comfort and convenience continue with recently added heat pumps for efficient heating and cooling, new roof, oil baseboard heat as the primary system, public water, public sewer, and fiber optic internet. Nearby sidewalks and close proximity to local shopping, schools, recreation, Brattleboro Memorial Hospital, downtown Brattleboro, and I-91 add to the property's appeal. The double lot offers added outdoor space and possible future opportunity. Seller's attorney confirmed the second lot is buildable, though any future use should be confirmed directly with the town. With thoughtful renovations, charming details, useful spaces, and future potential, this Brattleboro property offers a compelling blend of comfort, convenience, and possibility.

32 Marlboro Ave, Brattleboro

$415,000

Outstanding investment opportunity! This well-maintained 5-unit apartment building offers strong income in a highly desirable neighborhood close to downtown, shopping, schools, and the hospital. The property features five 1-bedroom apartments and has seen some updates, including some new vinyl replacement windows, one unit fully renovated, recently painted porches, and improvements to portions of the plumbing and electrical systems. Two car garage, off-street parking, and rear yard, adding to the property's long-term appeal and rental demand. With its prime location, valuable updates, and excellent cash-flow, this is a turnkey addition to any investment portfolio or a great opportunity for an owner looking to grow their rental holdings. Don't miss your chance to own this exceptional income-producing property! No interior photos due to tenant privacy.

5100788 MLS

Outstanding investment opportunity! This well-maintained 5-unit apartment building offers strong income in a highly desirable neighborhood close to downtown, shopping, schools, and the hospital. The property features five 1-bedroom apartments and has seen some updates, including some new vinyl replacement windows, one unit fully renovated, recently painted porches, and improvements to portions of the plumbing and electrical systems. Two car garage, off-street parking, and rear yard, adding to the property's long-term appeal and rental demand. With its prime location, valuable updates, and excellent cash-flow, this is a turnkey addition to any investment portfolio or a great opportunity for an owner looking to grow their rental holdings. Don't miss your chance to own this exceptional income-producing property! No interior photos due to tenant privacy.

126 Oak Grove Ave, Brattleboro