Brattleboro, VT Homes

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  /47

  $550,000

  • 4 Beds
  • 4 Baths
  • 2,372 Sq Ft

  187 Hillwinds Rd, Brattleboro, VT 05301

  Welcome home! Four bedroom, 4-bathroom home with dedicated office space is located in one of the area’s most desirable communities. Just minutes from Brattleboro, it offers the perfect blend of convenience, comfort, and outdoor living, with walking trails right nearby. The bright, open layout is ideal for everyday living and entertaining, featuring a welcoming kitchen, dining, and living area. A

  Claire Renaud Berkley & Veller Greenwood Country

  187 Hillwinds Rd, Brattleboro, VT 05301
• 

  

  

  /11

  $2,175 per month

  • 4 Beds
  • 1 Bath
  • 1,360 Sq Ft
  • House for Rent

  123 Frost St, Brattleboro, VT 05301

  A nice house that is suitable for up to 5 occupants and conveniently located within walking distance to the shopping, restaurants and entertainment in downtown Brattleboro. Spacious kitchen includes a dishwasher and built in microwave, recently purchased stove & fridge. This unit also featuring laundry hookups and a bathtub/shower combo. This home features a first floor bedroom or office space

  123 Frost St, Brattleboro, VT 05301
• 

  

  

  /40

  $781,000 Sold Sep 19, 2025

  • 2,663 Sq Ft
  • $293/SF
  • 33 Days On Market

  • 3 Beds
  • 5 Baths
  • Built 1944

  1194 Ames Hill Rd, Brattleboro, VT 05301

  Welcome to The Appleshed. Starting as a storage structure within an old apple orchard, to a gentleman's hunting/fishing camp, to the cherished family home it is today, this property has had many lives and grown into a beloved gathering place for generations. Now it’s ready for its next chapter. Set on 63.8 acres with a babbling brook and breathtaking views of Mount Monadnock, this is a true

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  1194 Ames Hill Rd, Brattleboro, VT 05301
• 

  

  

  /26

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft

  1 Wildwood Dr, West Brattleboro, VT 05301

  1 Wildwood Dr, West Brattleboro, VT 05301
• 

  

  

  /3

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  24 Dogwood Dr, Brattleboro, VT 05301

  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

  Dan Normandeau Berkley & Veller Greenwood Country

  24 Dogwood Dr, Brattleboro, VT 05301
• 

  

  /12

  $1,850 per month

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft
  • Apartment for Rent

  1155 Putney Rd Unit 1A, Brattleboro, VT 05301

  Newly renovated second floor apt above local Restaurant. Conveniently located on the roundabout at Exit 3 of I-91. Great apartment with all new appliances, countertops, flooring, upgraded electrical and more. Easy location near shopping and restaurants. Non smokers and no pets. All utilities by tenant.

  Jim Bialowski BHG Masiello Keene

  1155 Putney Rd Unit 1A, Brattleboro, VT 05301
• 

  

  /15

  $55,000 Sold Sep 19, 2025

  • 2,090 Sq Ft
  • $26/SF
  • 432 Days On Market

  • Built 1860

  211 High St, Brattleboro, VT 05301

  Here's a great opportunity! Formerly a 2 unit multi-family, this is currently a shell ready for your finishing! This property will need everything ... heating, electrical, plumbing, exterior work and full interior finishing. Very convenient to downtown, some off street parking but nicely sited above the road. Please do NOT park in the driveway.

  A.J. Bellville Bellville Realty

  211 High St, Brattleboro, VT 05301
• 

  

  /14

  Est $248,280 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  23 Robin Way, Brattleboro, VT 05301

  23 Robin Way, Brattleboro, VT 05301
• 

  

  /3

  $560,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  162 Buttonwood Dr, Brattleboro, VT 05301

  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

  Dan Normandeau Berkley & Veller Greenwood Country

  162 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /4

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 640 Sq Ft
  • Condo for Rent

  498 Marlboro Rd Unit N37, Brattleboro, VT 05301

  Property Id: 1510783Two bedroom apartment for rent in a professionally managed apartment building in West Brattleboro, Vermont. Clean, bright, with on-site laundry and off-street parking. Rents include heat and hot water. All units are non smoking. Small pets would require approval and an additional security deposit.

  498 Marlboro Rd Unit N37, Brattleboro, VT 05301
• 

  

  /13

  $269,141 Sold Sep 12, 2025

  • 956 Sq Ft
  • $282/SF
  • 6 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1929

  81 Oak Grove Ave, Brattleboro, VT 05301

  Welcome to this delightful 2-bedroom, 1-bathroom bungalow nestled in one of the most sought-after neighborhoods! Brimming with character and warmth, this cozy home offers a perfect blend of vintage charm and modern convenience. Many upgrades including a garage makeover, storage shed, roof, back porch, and so much more. Step inside to find a bright, inviting living space with hardwood floors,

  Claire Renaud Berkley & Veller Greenwood Country

  81 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /13

  Not Listed For Sale

  0 Middle Rd, Brattleboro, VT 05301

  0 Middle Rd, Brattleboro, VT 05301
• 

  

  /3

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  161 Buttonwood Dr, Brattleboro, VT 05301

  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

  Dan Normandeau Berkley & Veller Greenwood Country

  161 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /10

  $1,650 per month

  • 1 Bed
  • 1 Bath
  • 422 Sq Ft
  • Apartment for Rent

  114 Main St Unit 33, Brattleboro, VT 05301

  Newly renovated third floor one bedroom apartment with a large window with in-town views. Access to everything you need within a fewblocks. Enjoy the downtown scene with restaurants and breweries right on the same block. This one room apartment has its own washer and dryer in the unit. Pictures are virtually staged, apartment is not furnished.

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  114 Main St Unit 33, Brattleboro, VT 05301
• 

  

  /20

  $265,000 Sold Sep 12, 2025

  • 1,178 Sq Ft
  • $225/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1970

  17 Winter Ct, Brattleboro, VT 05301

  Classic Ranch Style Home! Just starting out or thinking of downsizing? This could be the one! Nestled in a sweet neighborhood, this charming ranch offers easy one-level living just minutes from downtown shopping, schools, and recreation. Set on a manageable 0.2 acre lot, this home features a bright enclosed porch/bonus room perfect for morning coffee, reading, or relaxing year-round. Continuing

  Liz LaVorgna Berkley & Veller Greenwood Country

  17 Winter Ct, Brattleboro, VT 05301
• 

  

  /3

  Est $420,342 Not Listed For Sale

  • Studio
  • 2 Baths
  • 2,863 Sq Ft

  394 Canal St, Brattleboro, VT 05301

  394 Canal St, Brattleboro, VT 05301
• 

  

  /39

  $625,000

  • 5 Beds
  • 4 Baths
  • 3,748 Sq Ft

  58 Oak St, Brattleboro, VT 05301

  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

  Rebecca Seymour Brattleboro Area Realty

  58 Oak St, Brattleboro, VT 05301
• 

  /2

  $1,500 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  376 Western Ave Unit 1, Brattleboro, VT 05301

  Property Id: 2099462Completely renovated spacious and bright first floor apartment. Large deck. Wood stove with free wood. New Mitsubishi mini split. Close to town park, hiking trails, farmers market. Close to downtown. Off street parking and storage area.

  376 Western Ave Unit 1, Brattleboro, VT 05301
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  /60

  $868,000 Sold Sep 09, 2025

  • 3,685 Sq Ft
  • $236/SF
  • 28 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1994

  155 Hillwinds N, Brattleboro, VT 05301

  Situated in Brattleboro’s premier, rural neighborhood, this much-loved home is a masterclass in thoughtful design, meticulous construction, & refined living. A grand dbl-door foyer welcomes you into a soaring entry hall that flows seamlessly into a sunken, dbl-height ceiling LR - complete w/ granite-surround FP, custom blt-ins, & crowned by a dramatic balcony overlook. Light pours in from every

  Dan Normandeau Berkley & Veller Greenwood Country

  155 Hillwinds N, Brattleboro, VT 05301
• 

  

  /26

  Est $239,162 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  17 Evergreen Ln, Brattleboro, VT 05301

  17 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /36

  $442,500

  • 4 Beds
  • 3.5 Baths
  • 2,794 Sq Ft

  87 Orchard St, Brattleboro, VT 05301

  Pleasant and comfortable! This inviting home offers four bedrooms, three and a half bathrooms, a choice of primary bedroom with ensuite bath on the first floor or on the second. Enjoy a pleasant open flow living, kitchen and dining with hard wood floors for entertaining or hosting your next book club. The first floor offers a cheerful step saver kitchen with a pantry, gas range and views to the

  Jim Bellville Bellville Realty

  87 Orchard St, Brattleboro, VT 05301
• 

  

  /7

  $1,800 per month

  • 1 Bed
  • 1 Bath
  • 535 Sq Ft
  • Apartment for Rent

  215 Main St Unit 209, Brattleboro, VT 05301

  Recently renovated One bedroom apartment on the second floor. This one-bedroom apartment has bright sun lit rooms, with additional locking storage in the building, along with an elevator to get to the second floor for the onsite laundry facilities. This is intown living at its best. Apartment is partially furnished, just needs a bed.

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  215 Main St Unit 209, Brattleboro, VT 05301
• 

  

  /20

  $245,000 Sold Sep 05, 2025

  • 2,168 Sq Ft
  • $113/SF
  • 18 Days On Market

  • Built 1915

  14-16 Valley St, Brattleboro, VT 05301

  Perfectly situated on a quiet street close to downtown, stores, and schools, this well cared for duplex is a rare opportunity for owner-occupants or investors alike. Each spacious unit offers 3 bedrooms and 1 full bath, with a host of updates and energy-efficient upgrades throughout. Many recent upgrades include Solar panels, Finished and insulated attics, Partially finished basements, Gas

  Claire Renaud Berkley & Veller Greenwood Country

  14-16 Valley St, Brattleboro, VT 05301
• 

  

  /37

  Est $410,862 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,444 Sq Ft

  94 Brets Rd, Brattleboro, VT 05301

  94 Brets Rd, Brattleboro, VT 05301
• 

  

  /32

  $425,000

  • 3 Beds
  • 1.5 Baths
  • 1,655 Sq Ft

  155 Upper Dummerston Rd, Brattleboro, VT 05301

  Great location! This 3-bedroom Colonial, built in 1920 (when houses were well-built) on Upper Dummerston Road is up the road from the Brattleboro Country Club and its golf course, cross country skiing, trails, and the West River. On a comfortable 0.75 level acres, this property is private but only 10 minutes from the center of town. Lots of windows bring in lots of light. Generous living room,

  John Hatton Berkley & Veller Greenwood Country

  155 Upper Dummerston Rd, Brattleboro, VT 05301
• 

  

  /13

  $2,350 per month

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • Apartment for Rent

  4 Elliot St Unit 8, Brattleboro, VT 05301

  The National, featuring this 2 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown and the mountain. Coin operated Laundry is on site and off street parking is available in the parking garage. The building is pet friendly

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 8, Brattleboro, VT 05301
• 

  

  /13

  $91,000 Sold Sep 04, 2025

  • 949 Sq Ft
  • $96/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1984

  7 Stonewall Dr Unit 60159.s07, Brattleboro, VT 05301

  This is a well cared for and improved affordable home. The airy open concept of the main space makes for a feeling of spaciousness. The primary bedroom has direct access to the full bath and laundry. The attached enclosed porch offers additional seasonal living space, The large corner lot offers good garden space and storage in the good sized storage shed.

  David Brown Berkley & Veller Greenwood Country

  7 Stonewall Dr Unit 60159.s07, Brattleboro, VT 05301
• 

  

  /20

  Est $257,429 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  149 Canal St, Brattleboro, VT 05301

  149 Canal St, Brattleboro, VT 05301
• 

  

  /44

  $475,000

  • 4 Beds
  • 3 Baths
  • 3,314 Sq Ft

  76 Spruce St, Brattleboro, VT 05301

  Sweet! The perfect location...intown...backing up to the retreat trail system...and has a beautiful front porch and private back deck. This has been a much loved home, ready for a new generation to create their own music and harmony of life. The rooms are large, comfortable with lots of windows, real wood paneling reflecting the era, high ceilings, enough room to work from home (even an office

  Christine Lewis Brattleboro Area Realty

  76 Spruce St, Brattleboro, VT 05301
• 

  

  /12

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 790 Sq Ft
  • Apartment for Rent

  4 Elliot St Unit 6, Brattleboro, VT 05301

  The National, featuring this 2 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown and the mountain. Coin operated Laundry is on site and off street parking is available in the parking garage. The building is pet friendly

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 6, Brattleboro, VT 05301
• 

  

  /10

  $54,000 Sold Sep 03, 2025

  • Land
  • 0.25 Acre
  • $216,000 per Acre

  • 387 Days On Market

  203 Fairview St, Brattleboro, VT 05301

  In-town lots are few and far between these days but are such a great option! Design your own low inpact, energy efficient home, your dream home! This is your spot! This neighborhood is friendly and convenient to schools, Memorial Park, shopping, hospitals and just minutes to 91. The .25 acre lot is cleared and ready to go with easy access to town water and sewer. House site is set back from the

  Rebecca Seymour Brattleboro Area Realty

  203 Fairview St, Brattleboro, VT 05301
• 

  

  /30

  Not Listed For Sale

  • 8 Beds
  • 4 Baths
  • 3,854 Sq Ft

  100 Frost St, Brattleboro, VT 05301

  100 Frost St, Brattleboro, VT 05301
• 

  

  /18

  $425,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,074 Sq Ft

  36 Spruce St, Brattleboro, VT 05301

  New Price! $25,000.00 price drop and a revised offering... If you saw this home before you want to take a second look! The 2nd floor is now vacant! ..and ready for owner occupancy. The basement, barn and lower building are empty and ready for all YOUR stuff. Plenty of undercover storage for boats, special vehicles or lots of other toys. A workshop? Home is just right for 2 family use or

  Christine Lewis Brattleboro Area Realty

  36 Spruce St, Brattleboro, VT 05301
• 

  

  /56

  $240,000 Sold Aug 29, 2025

  • 1,056 Sq Ft
  • $227/SF
  • 19 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1988

  67 Morningside Commons, Guilford, VT 05301

  From the rhododendron, orange day lily and morning glories in front of this condo to the herb and flower garden in the rear and with everything in between, this condo speaks "lovely". Completely updated and immaculately maintained. Kitchen features stylish cabinets, Corian counter tops, all Whirlpool stainless steel appliances and a double oven. The hanging wrought iron pot holder and fruit

  Sally Fegley BHG Masiello Brattleboro

  67 Morningside Commons, Guilford, VT 05301
• 

  

  /31

  Est $352,160 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  47 Sherwood Cir, Brattleboro, VT 05301

  47 Sherwood Cir, Brattleboro, VT 05301
• 

  

  /46

  $379,000

  • 4 Beds
  • 2 Baths
  • 1,446 Sq Ft

  155 Oak Grove Ave, Brattleboro, VT 05301

  All work has been done for you on this beautiful, 1932 period home. 4 bedrooms, 2 full baths, set in a high demand, desirable neighborhood. Manicured, corner lot with classical perennial plantings, two covered porches, a slate roof, and detached double garage. There are 20+ upgraded, insulated windows, with antique reproduction filling the home with natural light. Hardwood floors predominate.

  Kristen Ziter Taylor Brattleboro Area Realty

  155 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /35

  $525,000 Sold Aug 19, 2025

  • 2,456 Sq Ft
  • $214/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  1073 Upper Dummerston Rd, Brattleboro, VT 05301

  This very Vermont country home is nestled on a peaceful, beautifully landscaped 1.5 acre lot along Upper Dummerston Road. Built with unparalleled craftsmanship by some of the region’s finest artisans, the home exudes exceptional quality throughout. At the heart of the residence is a large chef's kitchen, complete with a gas fireplace, granite countertops, solid maple cabinetry, and premium Wolf

  Thomas Dahlin Berkley & Veller Greenwood Country

  1073 Upper Dummerston Rd, Brattleboro, VT 05301
• 

  

  /38

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,950 Sq Ft

  773 Guilford St, Brattleboro, VT 05301

  773 Guilford St, Brattleboro, VT 05301
• 

  

  /30

  $400,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  1089 Marlboro Rd, Brattleboro, VT 05301

  The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Again in place is easy

  Christine Lewis Brattleboro Area Realty

  1089 Marlboro Rd, Brattleboro, VT 05301
• 

  

  /33

  $377,840 Sold Aug 19, 2025

  • 1,536 Sq Ft
  • $246/SF
  • 103 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2000

  111 Bonnyvale Rd, Brattleboro, VT 05301

  An attractive, low-maintenance, solid home in great shape in a desirable West Brattleboro country location just a few minutes to downtown! This 3 bedroom, 1.5 bath home was built in 2000. Enter through the front steps or the attached 2 car garage into the mudroom. First floor features a sweet efficient kitchen with plenty of cabinets and a movable island, a charming dining room, an attractive,

  Stephanie Peduzzi-Baker Brattleboro Area Realty

  111 Bonnyvale Rd, Brattleboro, VT 05301

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