Brattleboro, VT Homes

• 

  

  

  /16

  Est $228,500 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,343 Sq Ft

  23 Winter Ct, Brattleboro, VT 05301

  23 Winter Ct, Brattleboro, VT 05301
• 

  

  

  /37

  $849,000

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on 11 acres of landscaped grounds with lawns, stone walls, gardens, and woodland in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
• 

  

  

  /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
• 

  

  

  /24

  Est $300,017 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,514 Sq Ft

  94 Fuller Dr, Brattleboro, VT 05301

  94 Fuller Dr, Brattleboro, VT 05301
• 

  

  

  /29

  $310,000

  • 4 Beds
  • 2 Baths
  • 2,408 Sq Ft

  78-80 Central St, Brattleboro, VT 05301

  MOTIVATED SELLER: Charming Two-Unit Multi-Family on Quiet In-Town Street – Ideal for Investors or Owner-Occupants! Tucked away on a peaceful side street yet just minutes from shopping, dining, and public transportation, this two-family property offers the perfect blend of convenience and comfort. The current owners have updated all the electrical in both units. Each unit features spacious,

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  78-80 Central St, 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
• 

  

  /21

  Est $251,939 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,252 Sq Ft

  91 Pine St, Brattleboro, VT 05301

  91 Pine St, Brattleboro, VT 05301
• 

  

  /58

  $568,000

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft

  192 Western Ave, Brattleboro, VT 05301

  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

  Claire Renaud Berkley & Veller Greenwood Country

  192 Western Ave, 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
• 

  

  /25

  Est $259,033 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,033 Sq Ft

  88 Washington St, Brattleboro, VT 05301

  88 Washington St, Brattleboro, VT 05301
• 

  

  /25

  $189,000

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  22 Chestnut St Unit 1, Brattleboro, VT 05301

  Welcome to 22 Chestnut Street, Unit #1 — a charming and fully furnished first-floor condo nestled in the lovely Chestnut Street neighborhood. This spacious 2-bedroom, 1-bath unit features a thoughtfully updated bathroom with a clawfoot tub and separate shower, a cozy mudroom entryway, and a sunny side porch that conveys with the unit — perfect for morning coffee or evening relaxation. The kitchen

  Erica Reynolds Southern Vermont Realty Group

  22 Chestnut St Unit 1, 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
• 

  

  /27

  Est $249,824 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft

  10 Washington St, Brattleboro, VT 05301

  10 Washington St, Brattleboro, VT 05301
• 

  

  /20

  $279,900

  • 4 Beds
  • 2 Baths
  • 1,733 Sq Ft

  1177 Western Ave, Brattleboro, VT 05301

  So much to offer! This 4 bedroom 2 bath has plenty of room for all! It features a large kitchen with lots of counter space and the laundry tucked in for easy access while you cook and bake. The deck overlooks the lower yard where the solar panels live and the perfect spot for the above ground swimming pool (needs a liner). Huge lot, lots of off street parking and on the MOOVER line for non

  Christine Lewis Brattleboro Area Realty

  1177 Western Ave, 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
• 

  

  /17

  Est $329,118 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,927 Sq Ft

  18 Central St, Brattleboro, VT 05301

  18 Central St, Brattleboro, VT 05301
• 

  /2

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  109 Central St, Brattleboro, VT 05301

  Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard

  Christine Lewis Brattleboro Area Realty

  109 Central St, 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
• 

  

  /31

  Est $205,261 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,592 Sq Ft

  39 Clark St, Brattleboro, VT 05301

  39 Clark St, Brattleboro, VT 05301
• 

  

  /30

  $629,000

  • 4 Beds
  • 2 Baths
  • 2,656 Sq Ft

  204 Meeting House Ln, Brattleboro, VT 05301

  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

  Desiree Stango Berkley & Veller Greenwood Country

  204 Meeting House Ln, 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
• 

  

  /18

  Not Listed For Sale

  • Studio
  • 1,683 Sq Ft

  60 Clark St, Brattleboro, VT 05301

  60 Clark St, Brattleboro, VT 05301
• 

  /2

  $90,000

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft

  93 Clark St, Brattleboro, VT 05301

  An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please,

  Christine Lewis Brattleboro Area Realty

  93 Clark St, Brattleboro, VT 05301
• 

  

  /38

  $239,000 Sold Aug 14, 2025

  • 1,056 Sq Ft
  • $226/SF
  • 13 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1988

  81 Morningside Commons, Guilford, VT 05301

  The moment you step into this condo, you notice its unique features and feel a sense of calm. In the living room, you’ll enjoy the “Anywhere” ethanol fireplace for its ambience and extra heat - with no connections, venting or emissions to worry about! The kitchen has been carefully redone, with expanded cabinetry and improvements to the layout and lighting, including a custom display cabinet and

  Victoria Woods Brattleboro Area Realty

  81 Morningside Commons, Guilford, VT 05301
• 

  

  /33

  Est $256,684 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,722 Sq Ft

  87 Clark St, Brattleboro, VT 05301

  87 Clark St, Brattleboro, VT 05301
• 

  /2

  $89,000

  • 4 Beds
  • 3 Baths
  • 2,108 Sq Ft

  321 Williams St, Brattleboro, VT 05301

  Great opportunity for starting or expanding your investment portfolio. Good rental income and affordable property. Nice location. Good parking for tenants and private porches. Minimal yard maintenance.

  Susan Bellville Bellville Realty

  321 Williams St, Brattleboro, VT 05301
• 

  

  /39

  $329,000 Sold Aug 14, 2025

  • 1,713 Sq Ft
  • $192/SF
  • 24 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1920

  158 Clark Ave, Brattleboro, VT 05301

  Lovingly refurbished and full of timeless charm, this two bedroom, one bathroom Arts and Crafts bungalow offers bright, comfortable living within a mile from Brattleboro Memorial Hospital and both the middle and high schools. Set on a beautifully level lot, the home features a welcoming enclosed porch, a covered outdoor dining area perfect for three-season enjoyment, and a built-in one-car garage

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  158 Clark Ave, Brattleboro, VT 05301
• 

  

  /22

  Est $247,020 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,146 Sq Ft

  95 Frost St, Brattleboro, VT 05301

  95 Frost St, Brattleboro, VT 05301
• 

  

  /51

  $899,800

  • 5 Beds
  • 8 Baths
  • 7,430 Sq Ft

  925 Hinesburg Rd, Brattleboro, VT 05301

  Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

  Christine Lewis Brattleboro Area Realty

  925 Hinesburg Rd, Brattleboro, VT 05301
• 

  

  /46

  $668,000 Sold Aug 12, 2025

  • 2,226 Sq Ft
  • $300/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1985

  395 Hillwinds Rd, Brattleboro, VT 05301

  Turnkey Home in Sought-After Hillwinds! Located in the desirable Hillwinds neighborhood and nestled among the trees, your dream home awaits! This charming and functional home offers open, sun-filled living spaces, softwood floors, and abundant storage. The kitchen is a cook’s dream, featuring granite countertops, a gas stove, farmhouse sink, and a unique pull-out cabinet on wheels for added

  Desiree Stango Berkley & Veller Greenwood Country

  395 Hillwinds Rd, Brattleboro, VT 05301
• 

  

  /20

  Est $387,253 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,012 Sq Ft

  203 Elliot St, Brattleboro, VT 05301

  203 Elliot St, Brattleboro, VT 05301
• 

  

  /60

  $895,000

  • 3 Beds
  • 3 Baths
  • 2,258 Sq Ft

  266 Ursa Ridge Rd, Dummerston, VT 05301

  This home is living art, tucked away at the end of the road of lovely homes & hundreds of acres ridgetop, yet only 10 minutes from downtown Brattleboro. Built by a craftsman this home is gracious & energy efficient. Building materials have been harvested from it's 51-1/2 acre woodland. Rooms are thoughtfully designed awash with natural light. Walk up the covered, stone walkway to enter the

  Randi Ziter Brattleboro Area Realty

  266 Ursa Ridge Rd, Dummerston, VT 05301
• 

  

  /28

  $180,000 Sold Aug 12, 2025

  • 1,531 Sq Ft
  • $118/SF
  • 70 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1941

  316 Putney Rd, Brattleboro, VT 05301

  Convenient Location & Low Maintenance Living! Enjoy easy access to shopping, public transportation and waterfront with scenic trails. The backyard is just the right size for enjoying nature and a little fresh air. This charming home combines classic character with practical updates featuring a standing seam roof, vinyl windows and aluminum siding. Inside, the home radiates its original charm

  Kristen Ziter Taylor Brattleboro Area Realty

  316 Putney Rd, Brattleboro, VT 05301
• 

  

  /41

  Est $334,808 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,714 Sq Ft

  196 Fairview St, Brattleboro, VT 05301

  196 Fairview St, Brattleboro, VT 05301
• 

  

  /18

  $309,900

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft

  164 Chestnut St, Brattleboro, VT 05301

  Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders

  Christine Lewis Brattleboro Area Realty

  164 Chestnut St, Brattleboro, VT 05301
• 

  

  /22

  $336,000 Sold Aug 12, 2025

  • 1,104 Sq Ft
  • $304/SF
  • 63 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1968

  62 Lawton Dr, Brattleboro, VT 05301

  Everything deserves a second chance, and this home found the right owner to love and recreate it in a stunning new life. Anyone who has looked at this home in the past few years, has to come back to see the shine....the fresh new look....the simplicity of move right in. Not only is this home refreshed stem to stern, it has new windows, siding, shingles, kitchen, bath.....and on and on! Tuck

  Christine Lewis Brattleboro Area Realty

  62 Lawton Dr, Brattleboro, VT 05301
• 

  

  /17

  Est $278,112 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,320 Sq Ft

  155 Maple St, Brattleboro, VT 05301

  155 Maple St, Brattleboro, VT 05301
• 

  

  /23

  $1,150,000

  • 6,442 Sq Ft

  69-71 Elliot St, Brattleboro, VT 05301

  Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

  Erica Reynolds Southern Vermont Realty Group

  69-71 Elliot St, Brattleboro, VT 05301
• 

  

  /5

  $100,000 Sold Aug 11, 2025

  • 700 Sq Ft
  • $143/SF
  • 19 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1966

  39 Brookside Dr Unit 7, Brattleboro, VT 05301

  Ready for a redo, this home is priced right for anyone who is handy with freshening, light carpentry (flooring) and other minor skills. Worth the effort to find an affordable option to renting or living with Mom! 48 hour a must for notice. This condo is located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park.

  Christine Lewis Brattleboro Area Realty

  39 Brookside Dr Unit 7, Brattleboro, VT 05301
• 

  

  /35

  Est $313,728 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,560 Sq Ft

  31 Pleasant St, Brattleboro, VT 05301

  31 Pleasant St, Brattleboro, VT 05301

Showing Results 81 - 120, Page 3 of 18