Brattleboro, VT Homes

• 

  

  

  /41

  $545,000 Sold Jul 18, 2025

  441 Guilford St, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 2,450 Sq Ft
  • Built 1880

  Last Sold Summary

  • 1% Below List Price
  • $222/SF
  • 48 Days On Market

  Current Estimated Value $530,449

  Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

  441 Guilford St, Brattleboro, VT 05301
• 

  

  

  /24

  Est $602,812 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft

  89 Oak Grove Ave, Brattleboro, VT 05301

  89 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  

  /28

  $325,000

  • 5 Beds
  • 3 Baths
  • 2,209 Sq Ft

  16 Washington St, Brattleboro, VT 05301

  Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass

  Rebecca Seymour Brattleboro Area Realty

  16 Washington St, Brattleboro, VT 05301
• 

  

  

  /44

  $405,000 Sold Jul 28, 2025

  156 Sherwood Cir, Brattleboro, VT 05301

  • 4 Beds
  • 2.5 Baths
  • 2,132 Sq Ft
  • Built 1998

  Last Sold Summary

  • 8% Above List Price
  • $190/SF
  • 33 Days On Market

  Current Estimated Value $394,551

  Last Listing Agent Fine Homes Group International Keller Williams Realty-Metropolitan

  156 Sherwood Cir, Brattleboro, VT 05301
• 

  

  

  /16

  Est $233,232 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
• 

  /2

  $150,000

  • Land
  • 2.05 Acres
  • $73,171 per Acre

  00 Fort Dummer Heights, Brattleboro, VT 05301

  Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

  Christine Lewis Brattleboro Area Realty

  00 Fort Dummer Heights, Brattleboro, VT 05301
• 

  

  /14

  $65,000 Sold Jul 11, 2025

  4 Brookwood Dr, West Brattleboro, VT 05301

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • Built 1978

  Last Sold Summary

  • 4% Below List Price
  • $70/SF
  • 70 Days On Market

  Last Listing Agent Cassandra Ehrlich BHG Masiello Brattleboro

  4 Brookwood Dr, West Brattleboro, VT 05301
• 

  

  /21

  Est $266,304 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
• 

  

  /5

  $380,000

  • 6 Beds
  • 4 Baths
  • 3,264 Sq Ft

  25 Cottage St, Brattleboro, VT 05301

  Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

  Christine Lewis Brattleboro Area Realty

  25 Cottage St, Brattleboro, VT 05301
• 

  

  /33

  $377,840 Sold Aug 19, 2025

  111 Bonnyvale Rd, Brattleboro, VT 05301

  • 3 Beds
  • 1.5 Baths
  • 1,536 Sq Ft
  • Built 2000

  Last Sold Summary

  • 8% Above List Price
  • $246/SF
  • 103 Days On Market

  Current Estimated Value $379,298

  Last Listing Agent Stephanie Peduzzi-Baker Brattleboro Area Realty

  111 Bonnyvale Rd, Brattleboro, VT 05301
• 

  

  /25

  Est $258,413 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

  $365,000

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

  85 Stockwell Dr, Brattleboro, VT 05301

  Sweet! This 5 bedroom /3 bath home is located in one of our most sought after neighborhoods, is newly remodeled, has 2 pellet stoves for economical heat and a nice back deck. Lots of opportunities to garden, relax in a hammock or play with pets. Flexible floor plan is perfect for at home workers, multigenerational living and aging in place. Hop the MOOVER and take a ride downtown, to Memorial

  Christine Lewis Brattleboro Area Realty

  85 Stockwell Dr, Brattleboro, VT 05301
• 

  

  /26

  $207,000 Sold May 27, 2025

  9 Garden Dr, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1920

  Last Sold Summary

  • 9% Above List Price
  • $137/SF
  • 28 Days On Market

  Current Estimated Value $222,323

  Last Listing Agent Sue Beaudet EXP Realty

  9 Garden Dr, Brattleboro, VT 05301
• 

  

  /27

  Est $278,341 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft

  10 Washington St, Brattleboro, VT 05301

  10 Washington 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
• 

  

  /29

  $330,000 Sold Jul 25, 2025

  64 Meadowbrook Rd, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 1890

  Last Sold Summary

  • 3% Below List Price
  • $244/SF
  • 16 Days On Market

  Current Estimated Value $330,693

  Last Listing Agent Christine Lewis Brattleboro Area Realty

  64 Meadowbrook Rd, Brattleboro, VT 05301
• 

  

  /26

  Est $451,629 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,080 Sq Ft

  109 Washington St, Brattleboro, VT 05301

  109 Washington St, Brattleboro, VT 05301
• 

  

  /45

  $115,000

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

  26 Lynwood Dr, Brattleboro, VT 05301

  Don’t miss this unique opportunity to own a mobile home in a Vermont park with features that truly set it apart. Situated on a large lot, this home offers a full concrete foundation with a walkout basement—a rare find that provides exceptional storage, workshop space, or future finishing potential.The interior features a highly functional floor plan, with the kitchen, living room, and dining

  Jon Tourville

  26 Lynwood Dr, Brattleboro, VT 05301
• 

  

  /5

  $100,000 Sold Aug 11, 2025

  39 Brookside Dr Unit 7, Brattleboro, VT 05301

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Built 1966

  Last Sold Summary

  • $143/SF
  • 19 Days On Market

  Current Estimated Value $110,249

  Last Listing Agent Christine Lewis Brattleboro Area Realty

  39 Brookside Dr Unit 7, Brattleboro, VT 05301
• 

  

  /31

  Est $205,810 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,592 Sq Ft

  39 Clark St, Brattleboro, VT 05301

  39 Clark St, Brattleboro, VT 05301
• 

  

  /29

  $295,000 Pending

  • 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
• 

  

  /46

  $415,000 Sold Nov 07, 2025

  155 Oak Grove Ave, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 1,446 Sq Ft
  • Built 1932

  Last Sold Summary

  • 9% Above List Price
  • $287/SF
  • 7 Days On Market

  Current Estimated Value $386,904

  Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

  155 Oak Grove Ave, 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
• 

  

  /34

  $469,900

  • 5 Beds
  • 4 Baths
  • 3,064 Sq Ft

  176 High St, Brattleboro, VT 05301

  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,

  Matt Waddington Hoffman Real Estate

  176 High St, Brattleboro, VT 05301
• 

  

  /42

  $925,000 Sold Oct 01, 2025

  65 Hillwinds N, Brattleboro, VT 05301

  • 5 Beds
  • 4.5 Baths
  • 4,150 Sq Ft
  • Built 1983

  Last Sold Summary

  • 9% Above List Price
  • $223/SF
  • 5 Days On Market

  Current Estimated Value $863,129

  Last Listing Agent Robert Doyle Berkley & Veller Greenwood Country

  65 Hillwinds N, Brattleboro, VT 05301
• 

  

  /22

  Est $258,964 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,146 Sq Ft

  95 Frost St, Brattleboro, VT 05301

  95 Frost St, Brattleboro, VT 05301
• 

  

  /16

  $353,900

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  39 Atwood St, Brattleboro, VT 05301

  First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big

  Christine Lewis Brattleboro Area Realty

  39 Atwood St, Brattleboro, VT 05301
• 

  

  /18

  $410,000 Sold Nov 06, 2025

  36 Spruce St, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 2,074 Sq Ft
  • Built 1845

  Last Sold Summary

  • 9% Below List Price
  • $198/SF
  • 183 Days On Market

  Current Estimated Value $399,297

  Last Listing Agent Christine Lewis Brattleboro Area Realty

  36 Spruce St, Brattleboro, VT 05301
• 

  

  /20

  Est $431,632 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
• 

  

  /48

  $299,000

  • 5 Beds
  • 3 Baths
  • 2,360 Sq Ft

  5 Reynolds Dr, Brattleboro, VT 05301

  Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers a rare "move-in ready" opportunity for both savvy investors and owner-occupants. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. With new toilets and stainless/modern

  Kate Barry EXP Realty

  5 Reynolds Dr, Brattleboro, VT 05301
• 

  

  /14

  $250,000 Sold Oct 31, 2025

  70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Built 1995

  Last Sold Summary

  • $200/SF
  • 5 Days On Market

  Current Estimated Value $259,379

  Last Listing Agent Robert Doyle Berkley & Veller Greenwood Country

  70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301
• 

  

  /41

  Est $343,612 Not Listed For Sale

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

  196 Fairview St, Brattleboro, VT 05301

  196 Fairview 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
• 

  

  /8

  $87,000 Sold Nov 17, 2025

  00 Fisch Rd, Brattleboro, VT 05301

  • Land
  • 34.77 Acres
  • $2,502 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 7 Days On Market

  Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

  00 Fisch Rd, Brattleboro, VT 05301
• 

  

  /35

  Est $316,402 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,560 Sq Ft

  31 Pleasant St, Brattleboro, VT 05301

  31 Pleasant St, Brattleboro, VT 05301
• 

  

  /30

  $350,000

  • 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. Aging in place is easy

  Christine Lewis Brattleboro Area Realty

  1089 Marlboro Rd, Brattleboro, VT 05301
• 

  

  /46

  $668,000 Sold Aug 12, 2025

  395 Hillwinds Rd, Brattleboro, VT 05301

  • 4 Beds
  • 2.5 Baths
  • 2,226 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Above List Price
  • $300/SF
  • 7 Days On Market

  Current Estimated Value $660,918

  Last Listing Agent Desiree Stango Berkley & Veller Greenwood Country

  395 Hillwinds Rd, Brattleboro, VT 05301
• 

  

  /39

  Est $397,983 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,970 Sq Ft

  95 Maple St, Brattleboro, VT 05301

  95 Maple St, Brattleboro, VT 05301
• 

  

  /5

  $270,000

  • 6 Beds
  • 2 Baths
  • 2,112 Sq Ft

  556 S Main St, Brattleboro, VT 05301

  What a great way to start your home ownership! A tenant can help with the monthly expenses letting you build your own reserves and take a bit ofpressure off the cost of home ownership! This 2 family has two-3 bedroom units, a nice yard and off street parking. Check it out and see for yourself...please respect the 48 hour notice for tenants, mask up! No interior photos due to tenant privacy.

  Christine Lewis Brattleboro Area Realty

  556 S Main St, Brattleboro, VT 05301
• 

  /2

  $525,000 Sold May 16, 2025

  135 Upper Dummerston Rd, Brattleboro, VT 05301

  • 5 Beds
  • 3.5 Baths
  • 3,600 Sq Ft
  • Built 1910

  Last Sold Summary

  • 19% Below List Price
  • $146/SF
  • 269 Days On Market

  Current Estimated Value $539,683

  Last Listing Agent Susan LeCours Barrett & Valley Assoc. Inc

  135 Upper Dummerston Rd, Brattleboro, VT 05301

Showing Results 81 - 120, Page 3 of 18