Brattleboro, VT Homes

• 

  

  

  /24

  $210,000

  Pending

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft

  40 Brookside Dr Unit 6, Brattleboro, VT 05301

  Rare to find an in-town condo with a waterfront view like this! Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the tranquil Whetstone Brook. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement with washer/dryer hookup and extra storage. The entire interior has been freshly painted,

  Angela Sherman Brattleboro Area Realty

  40 Brookside Dr Unit 6, Brattleboro, VT 05301
• 

  

  

  /40

  $447,700

  Sold Dec 08, 2025

  10 Ethan Hill, Brattleboro, VT 05301

  • 3 Beds
  • 2.5 Baths
  • 2,399 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $187/SF
  • 7 Days On Market

  Current Estimated Value $462,528

  Last Listing Agent John Mcpherson Berkley & Veller Greenwood Country

  10 Ethan Hill, Brattleboro, VT 05301
• 

  

  

  /35

  Est $360,577

  Not Listed For Sale

  25 Strand Ave, Brattleboro, VT 05301

  • 3 Beds
  • 1 Bath
  • 1,488 Sq Ft
  • Built 1880

  25 Strand Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 11 Days On Market
• 

  

  

  /5

  $250,000

  $20K PRICE DROP

  • 2,112 Sq Ft

  556 S Main St, Brattleboro, VT 05301

  New beginnings! Just right to live in one side, fix the other and have the tenant pay for your new lifestyle or have a family duplex and lie with extended family. the north side is vacant, needs renovation, and the south side has a tenant that will transfer with the building. Corner lot, yard, off street parking. Easy to see north unit, but otherwise a 48 hour notice to show.

  Christine Lewis Brattleboro Area Realty

  556 S Main St, Brattleboro, VT 05301
• 

  

  

  /50

  $659,000

  Sold Sep 29, 2025

  86 Stark Rd, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 2018

  Last Sold Summary

  • $412/SF
  • 4 Days On Market

  Current Estimated Value $643,478

  Last Listing Agent Victoria Woods Brattleboro Area Realty

  86 Stark Rd, Brattleboro, VT 05301
• 

  

  /39

  Not Listed For Sale

  30 Crosby St, Brattleboro, VT 05301

  • 4 Beds
  • 5 Baths
  • 2,660 Sq Ft
  • Built 1940

  30 Crosby St, Brattleboro, VT 05301

  Last Sold Summary

  • 89 Days On Market
• 

  

  /36

  $325,000

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,216 Sq Ft

  6 Sycamore St, Brattleboro, VT 05301

  Located in one of Brattleboro’s desirable neighborhoods, this inviting 4-bedroom home offers a comfortable layout, great natural light, and convenient access to schools, parks, trails, shopping, and downtown amenities. The bright living room features a large bay window that fills the space with natural sunlight, while the kitchen offers ample cabinet space and overlooks the backyard. With two

  Wendie Wright Coldwell Banker LIFESTYLES - Hanover

  6 Sycamore St, Brattleboro, VT 05301
• 

  

  /39

  $395,000

  Sold Nov 20, 2025

  105 Chestnut St, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 2,715 Sq Ft
  • Built 1895

  Last Sold Summary

  • $145/SF
  • 10 Days On Market

  Current Estimated Value $399,393

  Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

  105 Chestnut St, Brattleboro, VT 05301
• 

  

  /31

  Est $329,348

  Not Listed For Sale

  473 Williams St, Brattleboro, VT 05301

  • 2 Beds
  • 1.5 Baths
  • 1,760 Sq Ft
  • Built 1990

  473 Williams St, Brattleboro, VT 05301

  Last Sold Summary

  • 4 Days On Market
• 

  

  /34

  $78,000

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  22 Valley St, Brattleboro, VT 05301

  Welcome to 22 Valley Road, an affordable and easy-to-maintain 2-bedroom, 1-bath mobile home located in Brattleboro’s Tri-Park Cooperative Housing Corporation. This cozy single-level home offers a bright and refreshed interior with natural light, LED lighting, first-floor laundry hookups, and a functional layout that makes great use of the space. The kitchen features an electric range,

  Grayson VanHendrick Flex Realty

  22 Valley St, Brattleboro, VT 05301
• 

  

  /27

  $450,000

  Sold Jul 09, 2026

  81 Chapin St, Brattleboro, VT 05301

  • 3 Beds
  • 3 Baths
  • 1,246 Sq Ft
  • Built 1849

  Last Sold Summary

  • 9% Below List Price
  • $361/SF
  • 50 Days On Market

  Current Estimated Value $467,860

  Last Listing Agent John Hatton Berkley & Veller Greenwood Country

  81 Chapin St, Brattleboro, VT 05301
• 

  

  /37

  Est $287,002

  Not Listed For Sale

  625 Western Ave, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,341 Sq Ft
  • Built 1900

  625 Western Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 7 Days On Market
• 

  

  /59

  $675,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 2,245 Sq Ft

  442 Josh Rd, Brattleboro, VT 05301

  These spectacular 64 acres are located in one of the area's most romantically pastoral settings with open fields offering a mesmerizing view of Mount Monadnock, all of which is protected by a view easement. Set back at the end of a quiet dirt road and lined by stone walls, with boundary points marked by white quartz boulders, this renovated 1825 post-and-beam farmhouse combines classic

  Neil Goldberg Brattleboro Area Realty

  442 Josh Rd, Brattleboro, VT 05301
• 

  

  /12

  $79,000

  Sold Dec 11, 2025

  13 Winding Hill Rd, West Brattleboro, VT 05301

  • 2 Beds
  • 2 Baths
  • 1,222 Sq Ft
  • Built 1988

  Last Sold Summary

  • $65/SF
  • 2 Days On Market

  Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

  13 Winding Hill Rd, West Brattleboro, VT 05301
• 

  

  /33

  Est $432,853

  Not Listed For Sale

  55 Thayer Ridge Rd, Brattleboro, VT 05301

  • 3 Beds
  • 3 Baths
  • 1,716 Sq Ft
  • Built 1968

  55 Thayer Ridge Rd, Brattleboro, VT 05301

  Last Sold Summary

  • 57 Days On Market
• 

  

  /51

  $499,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,874 Sq Ft

  41 Chapin St, Brattleboro, VT 05301

  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

  Kristen Ziter Taylor Brattleboro Area Realty

  41 Chapin St, Brattleboro, VT 05301
• 

  

  /30

  $497,408

  Sold Apr 10, 2026

  204 Meeting House Ln, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 2,656 Sq Ft
  • Built 1970

  Last Sold Summary

  • 14% Below List Price
  • $187/SF
  • 230 Days On Market

  Current Estimated Value $507,787

  Last Listing Agent Desiree Stango Berkley & Veller Greenwood Country

  204 Meeting House Ln, Brattleboro, VT 05301
• 

  

  /27

  Est $413,754

  Not Listed For Sale

  22 Howard St, Brattleboro, VT 05301

  • 4 Beds
  • 1.5 Baths
  • 1,994 Sq Ft
  • Built 1940

  22 Howard St, Brattleboro, VT 05301

  Last Sold Summary

  • 7 Days On Market
• 

  

  /40

  $339,000

  Under Contract

  • 4 Beds
  • 2 Baths
  • 2,250 Sq Ft

  65 Cedar St, Brattleboro, VT 05301

  Step into a world of artistic whimsy and historic allure at 65 Cedar Street, a property overflowing with character, magic, and boundless potential. Nestled in an ideal location with an entrance to the beloved Retreat Trails, this unique home offers an enchanting escape from the everyday. Outside, the property is embraced by beautiful, mature gardens cultivated over time in a spirit of enchanting

  Kate Barry EXP Realty

  65 Cedar St, Brattleboro, VT 05301
• 

  

  /25

  $365,000

  Sold May 26, 2026

  85 Stockwell Dr, Brattleboro, VT 05301

  • 5 Beds
  • 3 Baths
  • 2,254 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $162/SF
  • 156 Days On Market

  Current Estimated Value $365,562

  Last Listing Agent Christine Lewis Brattleboro Area Realty

  85 Stockwell Dr, Brattleboro, VT 05301
• 

  

  /40

  Not Listed For Sale

  43 Williston St, Brattleboro, VT 05301

  • 4 Beds
  • 4 Baths
  • 3,628 Sq Ft
  • Built 1890

  43 Williston St, Brattleboro, VT 05301

  Last Sold Summary

  • 177 Days On Market
• 

  

  /32

  $429,000

  $70K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 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 mile

  Dan Normandeau Berkley & Veller Greenwood Country

  77 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /30

  $330,000

  Sold Aug 07, 2025

  116 Edward Heights, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 2,146 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Above List Price
  • $154/SF
  • 56 Days On Market

  Current Estimated Value $339,290

  Last Listing Agent Stephanie Wilde

  116 Edward Heights, Brattleboro, VT 05301
• 

  

  /40

  Est $710,770

  Not Listed For Sale

  43 Tyler St, Brattleboro, VT 05301

  • 4 Beds
  • 3 Baths
  • 3,137 Sq Ft
  • Built 1870

  43 Tyler St, Brattleboro, VT 05301

  Last Sold Summary

  • 7 Days On Market
• 

  /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, only

  Christine Lewis Brattleboro Area Realty

  93 Clark St, Brattleboro, VT 05301
• 

  

  /38

  $425,000

  Sold Jun 30, 2026

  32 Marlboro Ave, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1949

  Last Sold Summary

  • $221/SF
  • 0 Days On Market

  Current Estimated Value $335,718

  Last Listing Agent Andie Fusco Four Seasons Sotheby's Int'l Realty

  32 Marlboro Ave, Brattleboro, VT 05301
• 

  

  /40

  Est $507,932

  Not Listed For Sale

  7 Chase St, Brattleboro, VT 05301

  • 5 Beds
  • 3 Baths
  • 3,113 Sq Ft
  • Built 1840

  7 Chase St, Brattleboro, VT 05301

  Last Sold Summary

  • 87 Days On Market
• 

  

  /57

  $300,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,522 Sq Ft

  69 Carriage Hill Rd, Brattleboro, VT 05301

  **Includes 1-Year Home Warranty** Welcome to this lovingly maintained 3-bedroom, 1-bath ranch located in the sought-after Carriage Hill neighborhood of West Brattleboro. Where affordability & opportunity come together in this move-in ready home. Whether you're taking the exciting step into homeownership or searching for a home that lets you spend less time on upkeep and more time enjoying life.

  Isabella Luhrs BHG Masiello Keene

  69 Carriage Hill Rd, Brattleboro, VT 05301
• 

  

  /45

  $93,000

  Sold Mar 31, 2026

  26 Lynwood Dr, Brattleboro, VT 05301

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1985

  Last Sold Summary

  • 19% Below List Price
  • $92/SF
  • 35 Days On Market

  Last Listing Agent Jon Tourville

  26 Lynwood Dr, Brattleboro, VT 05301
• 

  

  /38

  Est $364,644

  Not Listed For Sale

  106 Western Ave, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 2,061 Sq Ft
  • Built 1924

  106 Western Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 25 Days On Market
• 

  

  /37

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  412 Western Ave, Brattleboro, VT 05301

  Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard—perfect for

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  412 Western Ave, Brattleboro, VT 05301
• 

  

  /26

  $714,000

  Sold Oct 06, 2025

  29 Canal St, Brattleboro, VT 05301

  • 18 Beds
  • 8 Baths
  • 4,932 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Below List Price
  • $145/SF
  • 135 Days On Market

  Last Listing Agent Michael Gilman 3GEN Real Estate Inc

  29 Canal St, Brattleboro, VT 05301
• 

  

  /38

  Est $394,673

  Not Listed For Sale

  24 Oak Crest Unit 1, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,715 Sq Ft
  • Built 1920

  24 Oak Crest Unit 1, Brattleboro, VT 05301

  Last Sold Summary

  • 76 Days On Market
• 

  

  /27

  $295,000

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  136 Oak Grove Ave, Brattleboro, VT 05301

  Timeless Character on Coveted Oak Grove Avenue!There's something special about an American Foursquare. Built for comfort and designed to stand the test of time, this quintessential early 20th-century home welcomes you with classic architecture, generous room sizes, and the warmth of original craftsmanship.Set on a desirable in-town lot along Oak Grove Avenue, this 3-bedroom home showcases

  Liz LaVorgna Brattleboro Area Realty

  136 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /29

  $250,000

  Sold Feb 12, 2026

  78-80 Central St, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 2,408 Sq Ft
  • Built 1920

  Last Sold Summary

  • 29% Below List Price
  • $104/SF
  • 133 Days On Market

  Last Listing Agent Peggy Winchester ACORN REAL ESTATE GROUP LLC

  78-80 Central St, Brattleboro, VT 05301
• 

  

  /27

  Est $526,073

  Not Listed For Sale

  39 Western Ave, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1890

  39 Western Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 61 Days On Market
• 

  

  /54

  $899,000

  $501K PRICE DROP Under Contract

  • 4 Beds
  • 4.5 Baths
  • 4,908 Sq Ft

  131 Stark Rd, Brattleboro, VT 05301

  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,

  Christine Lewis Brattleboro Area Realty

  131 Stark Rd, Brattleboro, VT 05301
• 

  

  /34

  $310,000

  Sold Sep 26, 2025

  35 Hillcrest Terrace, Brattleboro, VT 05301

  • 3 Beds
  • 2.5 Baths
  • 1,025 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Above List Price
  • $302/SF
  • 8 Days On Market

  Current Estimated Value $321,834

  Last Listing Agent Morriah Adams BHG Masiello Brattleboro

  35 Hillcrest Terrace, Brattleboro, VT 05301
• 

  

  /18

  Est $331,688

  Not Listed For Sale

  48 Speno Ct, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1950

  48 Speno Ct, Brattleboro, VT 05301

  Last Sold Summary

  • 21 Days On Market
• 

  

  /26

  $349,900

  $45K PRICE DROP Under Contract

  • 3,240 Sq Ft

  458 Williams St, Brattleboro, VT 05301

  458 Williams Street, formerly the WKVT headquarters, presents an opportunity for buyers exploring potential residential or mixed-use conversion in a convenient Brattleboro location. The 3,240 SF building is currently configured for office use across two levels, with more than 10 individual rooms, multiple bathrooms, and an existing kitchenette. This layout may lend itself to reconfiguration

  Neil Goldberg Brattleboro Area Realty

  458 Williams St, Brattleboro, VT 05301

Showing Results 161 - 200, Page 5 of 18