Brattleboro, VT Homes

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  /60

  $3,800,000

  $2M PRICE DROP

  • 4 Beds
  • 8 Baths
  • 16,736 Sq Ft

  1950 Collins Rd, Brattleboro, VT 05301

  Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

  

  Margretta Fischer

  Wohler Realty Group

  (802) 317-7158

  1950 Collins Rd, Brattleboro, VT 05301
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  /14

  $4,550 Per Month

  • 3 Beds
  • 2 Baths
  • 3,236 Sq Ft
  • Condo for Rent

  63-73 Main St Unit A, Brattleboro, VT 05301

  Property Id: 2534919This spacious loft is truly one of a kind! It comes fully furnished and has been carefully renovated to preserve the timeless character of the historic building while seamlessly incorporating premium, modern upgrades.You can have the best of both worlds with tranquil views of the Connecticut River and Wantastiquet Mountain while still being conveniently located

  (802) 490-3143

  63-73 Main St Unit A, Brattleboro, VT 05301
• 

  

  

  /17

  $200,000

  Sold Jan 16, 2026

  75 Mather Rd, Brattleboro, VT 05301

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft
  • Built 1959

  Last Sold Summary

  • 4% Below List Price
  • $278/SF
  • 6 Days On Market

  Current Estimated Value $199,851

  Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

  75 Mather Rd, Brattleboro, VT 05301
• 

  

  

  /33

  Est $374,174

  Not Listed For Sale

  145 Marlboro Ave, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 2,313 Sq Ft
  • Built 1940

  145 Marlboro Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 50 Days On Market
• 

  

  

  /26

  $395,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  135 Country Hill, Brattleboro, VT 05301

  Built in 2004 in this much-loved neighborhood, on a desirable one-way cul-de-sac, beautifully maintained, sits this 3-bedroom, 3-bath home. The first floor has a beautiful, large, eat-in kitchen, dining room, 1/2 bath, and access to a very spacious and inviting 16x16 deck ideal for family gatherings or entertaining, and a real sense of privacy. On the second floor, there is a primary bedroom with

  Neil Goldberg Brattleboro Area Realty

  135 Country Hill, Brattleboro, VT 05301
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  /30

  $1,300

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  210 Elliot St Unit 3, Brattleboro, VT 05301

  210 Elliot St Unit 3, Brattleboro, VT 05301
• 

  

  /54

  $1,743,600

  Sold Sep 30, 2025

  1324 Middle Rd, Brattleboro, VT 05301

  • 7 Beds
  • 7.5 Baths
  • 8,718 Sq Ft
  • Built 2005

  Last Sold Summary

  • 50% Below List Price
  • $200/SF
  • 274 Days On Market

  Current Estimated Value $1,691,580

  Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  1324 Middle Rd, Brattleboro, VT 05301
• 

  

  /36

  Est $397,502

  Not Listed For Sale

  711 Western Ave, Brattleboro, VT 05301

  • 6 Beds
  • 3 Baths
  • 2,232 Sq Ft
  • Built 1920

  711 Western Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 9 Days On Market
• 

  

  /37

  $595,000

  • 3 Beds
  • 3 Baths
  • 2,172 Sq Ft

  171 Green Meadow, Brattleboro, VT 05301

  Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef’s kitchen with ample counter space and a spacious pantry with an integrated dining area—perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor living

  Thomas Dahlin Berkley & Veller Greenwood Country

  171 Green Meadow, Brattleboro, VT 05301
• 

  

  /18

  $1,800

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  611 S Main St Unit Brattleboro, Brattleboro, VT 05301

  Quite Neighborhood, Walking distance to shopping. Close to State Park and walking trails. Short drive to the farmers market and Parks. Located within walking distance to Brattleboro Memorial hospital.

  611 S Main St Unit Brattleboro, Brattleboro, VT 05301
• 

  

  /46

  $450,000

  Sold May 15, 2026

  214 Putney Rd, Brattleboro, VT 05301

  • 4 Beds
  • 2.5 Baths
  • 2,756 Sq Ft
  • Built 1940

  Last Sold Summary

  • 9% Below List Price
  • $163/SF
  • 46 Days On Market

  Current Estimated Value $494,200

  Last Listing Agent Keith Nowak Four Seasons Sotheby's Int'l Realty

  214 Putney Rd, Brattleboro, VT 05301
• 

  

  /26

  Est $126,819

  Not Listed For Sale

  1149 Western Ave, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 1,873 Sq Ft
  • Built 1869

  1149 Western Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 215 Days On Market
• 

  

  /46

  $625,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 2,520 Sq Ft

  143 Hillwinds Rd, Brattleboro, VT 05301

  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

  Christine Lewis Brattleboro Area Realty

  143 Hillwinds Rd, Brattleboro, VT 05301
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  /11

  $1,700 Per Month

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

  4 Elliot St Unit 2, Brattleboro, VT 05301

  Corner apartment in downtown Brattleboro in the National is located on the corner of Elliot and Main Street. This one-bedroom apartment is in a secure building, laundry facilities on site, with parking down the street in the parking garage. Pets are welcome with an extra pet fee. PICTURES ARE VIRTUALLY STAGED- APARTMENT IS NOT FURNISHED

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 2, Brattleboro, VT 05301
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  /60

  $570,000

  Sold Jul 31, 2025

  290 Roel Rd, Brattleboro, VT 05301

  • 2 Beds
  • 2.5 Baths
  • 2,599 Sq Ft
  • Built 1991

  Last Sold Summary

  • 5% Below List Price
  • $219/SF
  • 79 Days On Market

  Current Estimated Value $583,333

  Last Listing Agent Flex Realty Group Flex Realty

  290 Roel Rd, Brattleboro, VT 05301
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  /40

  Not Listed For Sale

  965 Western Ave, Brattleboro, VT 05301

  • 4 Beds
  • 3 Baths
  • 2,358 Sq Ft
  • Built 1840

  965 Western Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 55 Days On Market
• 

  

  /22

  $400,000

  $5K PRICE INCREASE

  • 4 Beds
  • 4 Baths
  • 2,182 Sq Ft

  39 Williston St, Brattleboro, VT 05301

  One of a kind!Although this home would indeed make a very special single family, this property has many other options on offer! The owner has built a sustainable and popular AirB&B business with many quality repeat patrons bringing in unparalleled owner-occupied income.( Numbers available upon request).The wonderfully sympathetic renovation of this property includes the beautiful front room

  Christine Lewis Brattleboro Area Realty

  39 Williston St, Brattleboro, VT 05301
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  /9

  $1,450 Per Month

  • Studio
  • 1 Bath
  • 425 Sq Ft
  • Bright Studio Apartment - Brattleboro, VT. $1450/month, 425 sq.ft. ALL UTILITIES INCLUDED- Availa...

  47 Flat St Unit 402, Brattleboro, VT 05301

  Welcome to Dewitt Block, Unit #402– Fully renovated studio apartment with 3/4 bathroom, available for rent in downtown Brattleboro– Located on the top floor, no neighbors above– Large windows, high ceilings, stainless steel appliances– Utilities included (electric, heat, hot water and AC)– Secure building with security cameras on property– On site shared laundry

  47 Flat St Unit 402, Brattleboro, VT 05301
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  /40

  $781,000

  Sold Sep 19, 2025

  1194 Ames Hill Rd, Brattleboro, VT 05301

  • 3 Beds
  • 5 Baths
  • 2,663 Sq Ft
  • Built 1944

  Last Sold Summary

  • 2% Below List Price
  • $293/SF
  • 33 Days On Market

  Last Listing Agent Keith Nowak Four Seasons Sotheby's Int'l Realty

  1194 Ames Hill Rd, Brattleboro, VT 05301
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  /26

  Not Listed For Sale

  1 Wildwood Dr, West Brattleboro, VT 05301

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft
  • Built 1977

  1 Wildwood Dr, West Brattleboro, VT 05301

  Last Sold Summary

  • 12 Days On Market
• 

  

  /31

  $475,000

  Under Contract

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

  30 Chapin St, Brattleboro, VT 05301

  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

  Robert Doyle Berkley & Veller Greenwood Country

  30 Chapin St, Brattleboro, VT 05301
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  /16

  $2,200 Per Month

  • 2 Beds
  • 1 Bath
  • 1,525 Sq Ft
  • Apartment for Rent

  80 Central St, Brattleboro, VT 05301

  This second floor, two-bedroom apartment in town on a quiet side street. This unit has had some updates to the kitchen and bathroom, along with fresh paint throughout. The rooms have amazing sunlight throughout the day and enjoy the evenings on your enclosed porch. This is close to shopping, public transportation and schools. Rent does not include any utilities. Photos are virtually staged,

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  80 Central St, Brattleboro, VT 05301
• 

  

  /36

  $341,000

  Sold Jan 27, 2026

  7 Union St, Brattleboro, VT 05301

  • 4 Beds
  • 3 Baths
  • 1,668 Sq Ft
  • Built 1903

  Last Sold Summary

  • 10% Above List Price
  • $204/SF
  • 3 Days On Market

  Current Estimated Value $328,575

  Last Listing Agent Kathy Dowd Bellville Realty

  7 Union St, Brattleboro, VT 05301
• 

  

  /12

  Est $339,726

  Not Listed For Sale

  2812 River Rd, Brattleboro, VT 05301

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 2008

  2812 River Rd, Brattleboro, VT 05301

  Last Sold Summary

  • 36 Days On Market
• 

  

  /27

  $475,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,246 Sq Ft

  81 Chapin St, Brattleboro, VT 05301

  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

  John Hatton Berkley & Veller Greenwood Country

  81 Chapin St, Brattleboro, VT 05301
• 

  

  /13

  $1,800 Per Month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  100 Clark St Unit 2, Brattleboro, VT 05301

  100 Clark St Unit 2, Brattleboro, VT 05301
• 

  

  /60

  $489,000

  Sold May 13, 2026

  23 Wilsons Woods Rd, Brattleboro, VT 05301

  • 4 Beds
  • 3.5 Baths
  • 2,312 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Below List Price
  • $212/SF
  • 35 Days On Market

  Current Estimated Value $499,255

  Last Listing Agent Kate Barry EXP Realty

  23 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /12

  Est $626,944

  Not Listed For Sale

  58 Oak St, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 3,400 Sq Ft
  • Built 1867

  58 Oak St, Brattleboro, VT 05301

  Last Sold Summary

  • 20 Days On Market
• 

  

  /27

  $399,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,464 Sq Ft

  28 Wilsons Woods Rd, Brattleboro, VT 05301

  Immaculate and well-cared-for, open-concept 4-bedroom, 3-bath ranch offers easy one-level living. Move-in ready, the home features an updated kitchen with quartz countertops, farmhouse sink, and stainless steel appliances. Freshly painted bedrooms and bamboo flooring throughout create a bright and inviting interior that blends modern style with everyday comfort. The home is equipped with two heat

  Cassandra Ehrlich BHG Masiello Brattleboro

  28 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /10

  $1,700 Per Month

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

  114 Main St Unit 37, Brattleboro, VT 05301

  Newly Renovated apartment. Located on the 3rd floor of 114 Main Street, this apartment has its own washer and dryer in the unit. Heat is included and pets are welcome. A nice big window with views of downtown allows so much sunlight into the space. Dedicated free parking can be used at the 215 Main Street tenant parking lot. Apartment is not furnished, photos are virtually staged.

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  114 Main St Unit 37, Brattleboro, VT 05301
• 

  

  /37

  $375,000

  Sold Jun 16, 2025

  146 Sherwood Cir, Brattleboro, VT 05301

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft
  • Built 1998

  Last Sold Summary

  • 7% Above List Price
  • $230/SF
  • 66 Days On Market

  Current Estimated Value $394,010

  Last Listing Agent Kate Barry EXP Realty

  146 Sherwood Cir, Brattleboro, VT 05301
• 

  

  /3

  Est $399,925

  Not Listed For Sale

  394 Canal St, Brattleboro, VT 05301

  • Studio
  • 2 Baths
  • 2,863 Sq Ft
  • Built 1930

  394 Canal St, Brattleboro, VT 05301

  Last Sold Summary

  • 0 Days On Market
• 

  

  /39

  $399,900

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,339 Sq Ft

  16 Willow St, Brattleboro, VT 05301

  Tucked away on a quiet dead-end street just moments from downtown Brattleboro, this bright and inviting 3 bedroom, 1.5 bath Colonial offers the perfect blend of comfort, character, and convenience. A spacious mudroom provides a practical and welcoming entry, leading to a thoughtfully laid out interior featuring first-floor laundry, a large living room with flexible space for a home office, and a

  Jamie Watson BHG Masiello Keene

  16 Willow St, Brattleboro, VT 05301
• 

  

  /15

  $2,200 Per Month

  • 2 Beds
  • 1 Bath
  • 1,525 Sq Ft
  • Apartment for Rent

  78 Central St, Brattleboro, VT 05301

  This first floor, two-bedroom apartment in town on a quiet side street. This unit has had some updates to the kitchen and bathroom, along with fresh paint throughout. The rooms have amazing sunlight throughout the day and enjoy the evenings on your enclosed porch. This is close to shopping, public transportation and schools. Rent does not include any utilities. Photos are virtually staged,

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  78 Central St, Brattleboro, VT 05301
• 

  /2

  $80,000

  Sold Dec 19, 2025

  Lot #3 Peachtree Ln, Brattleboro, VT 05301

  • Land
  • 4.27 Acres
  • $18,735 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 50 Days On Market

  Last Listing Agent Desiree Stango Berkley & Veller Greenwood Country

  Lot #3 Peachtree Ln, Brattleboro, VT 05301
• 

  

  /37

  Est $433,291

  Not Listed For Sale

  94 Brets Rd, Brattleboro, VT 05301

  • 3 Beds
  • 2.5 Baths
  • 1,444 Sq Ft
  • Built 2001

  94 Brets Rd, Brattleboro, VT 05301

  Last Sold Summary

  • 16 Days On Market
• 

  

  /39

  $389,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,163 Sq Ft

  44 Cedar St, Brattleboro, VT 05301

  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

  Desiree Stango Berkley & Veller Greenwood Country

  44 Cedar St, Brattleboro, VT 05301
• 

  

  /7

  $2,200 Per Month

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

  4 Elliot St Unit 5, Brattleboro, VT 05301

  Corner apartment in downtown Brattleboro in the National is located on the corner of Elliot and Main Street. This two-bedroom apartment is in a secure building, laundry facilities on site, with parking down the street in the parking garage. Pets are welcome with an extra pet fee. PICTURES ARE VIRTUALLY STAGED - APARTMENT IS NOT FURNISHED

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 5, Brattleboro, VT 05301
• 

  

  /33

  $386,250

  Sold Jun 12, 2025

  33 Frost Place, Brattleboro, VT 05301

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft
  • Built 1880

  Last Sold Summary

  • 3% Below List Price
  • $239/SF
  • 49 Days On Market

  Current Estimated Value $345,166

  Last Listing Agent Keith Nowak Four Seasons Sotheby's Int'l Realty

  33 Frost Place, Brattleboro, VT 05301
• 

  

  /31

  Est $333,863

  Not Listed For Sale

  47 Sherwood Cir, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1995

  47 Sherwood Cir, Brattleboro, VT 05301

  Last Sold Summary

  • 38 Days On Market

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