Brattleboro, VT Homes

• 

  

  /2

  $370,000

  • 5 Beds
  • 4 Baths
  • 3,002 Sq Ft

  10 Birge St, Brattleboro, VT 05301

  Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

  Christine Lewis Brattleboro Area Realty

  10 Birge St, Brattleboro, VT 05301
• 

  

  

  /56

  $240,000

  Sold Aug 29, 2025

  67 Morningside Commons, Guilford, VT 05301

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Above List Price
  • $227/SF
  • 19 Days On Market

  Current Estimated Value $237,691

  Last Listing Agent Sally Fegley BHG Masiello Brattleboro

  67 Morningside Commons, Guilford, VT 05301
• 

  

  

  /16

  Est $250,998

  Not Listed For Sale

  23 Winter Ct, Brattleboro, VT 05301

  • 3 Beds
  • 1.5 Baths
  • 1,343 Sq Ft
  • Built 1968

  23 Winter Ct, Brattleboro, VT 05301

  Last Sold Summary

  • 11 Days On Market
• 

  

  

  /51

  $899,800

  $49K PRICE DROP

  • 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
• 

  

  

  /10

  $145,000

  Sold Jan 06, 2026

  680 W River Rd, Brattleboro, VT 05301

  • Land
  • 8 Acres
  • $18,125 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 148 Days On Market

  Last Listing Agent Chris Long BHG Masiello Brattleboro

  680 W River Rd, Brattleboro, VT 05301
• 

  

  /49

  Est $396,734

  Not Listed For Sale

  125 Pine St, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 1,901 Sq Ft
  • Built 1918

  125 Pine St, Brattleboro, VT 05301

  Last Sold Summary

  • 49 Days On Market
• 

  

  /44

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft

  380 S Main St, Brattleboro, VT 05301

  Charming and conveniently located, this inviting home is situated less than one mile from the heart of Brattleboro Village. Offering 3–4 bedrooms, including a first-floor bedroom for added flexibility, the home features a practical mudroom entry and a bright, sun-filled dining porch just off the kitchen. The basement provides a dedicated workshop area, laundry space, and ample additional storage.

  Jessica Citera Cummings & Co

  380 S Main St, Brattleboro, VT 05301
• 

  

  /60

  $625,000

  Sold Oct 03, 2025

  49 Tyler St, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 2,731 Sq Ft
  • Built 1880

  Last Sold Summary

  • 14% Below List Price
  • $229/SF
  • 65 Days On Market

  Current Estimated Value $613,714

  Last Listing Agent Karen Hoppe Berkley & Veller Greenwood Country

  49 Tyler St, Brattleboro, VT 05301
• 

  

  /21

  Est $246,690

  Not Listed For Sale

  91 Pine St, Brattleboro, VT 05301

  • 3 Beds
  • 1.5 Baths
  • 1,252 Sq Ft
  • Built 1880

  91 Pine St, Brattleboro, VT 05301

  Last Sold Summary

  • 31 Days On Market
• 

  

  /45

  $329,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,218 Sq Ft

  119 Forest St, Brattleboro, VT 05301

  Great location in the heart of Brattleboro. This 3-bedroom, 1-bathroom Jewel of a home is as efficient as it is charming. Very well maintained, with gorgeous maple floors, built-ins, original natural woodwork, elegant marble countertops, and an open kitchen/dining/living space that shines with a southern exposure. Snug little wood stove adds to the uplifting spirit in this home. Large upstairs

  Kristen Ziter Taylor Brattleboro Area Realty

  119 Forest St, Brattleboro, VT 05301
• 

  

  /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 $558,990

  Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

  441 Guilford St, Brattleboro, VT 05301
• 

  

  /25

  Est $251,747

  Not Listed For Sale

  88 Washington St, Brattleboro, VT 05301

  • 3 Beds
  • 1 Bath
  • 1,033 Sq Ft
  • Built 1925

  88 Washington St, Brattleboro, VT 05301

  Last Sold Summary

  • 14 Days On Market
• 

  

  /3

  $125,000

  $50K PRICE DROP

  • Land
  • 1.75 Acres
  • $71,429 per Acre

  0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301

  Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what morecould 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

  Christine Lewis Brattleboro Area Realty

  0 Fort Dummer Heights Unit 4934976, 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 $400,259

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

  156 Sherwood Cir, Brattleboro, VT 05301
• 

  

  /27

  Est $241,659

  Not Listed For Sale

  10 Washington St, Brattleboro, VT 05301

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • Built 1870

  10 Washington St, Brattleboro, VT 05301

  Last Sold Summary

  • 10 Days On Market
• 

  

  /37

  $795,000

  • 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 almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails 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

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, 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
• 

  

  /39

  Est $504,567

  Not Listed For Sale

  101 Washington St, Brattleboro, VT 05301

  • 5 Beds
  • 2.5 Baths
  • 2,823 Sq Ft
  • Built 1905

  101 Washington St, Brattleboro, VT 05301

  Last Sold Summary

  • 121 Days On Market
• 

  

  /35

  $329,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,480 Sq Ft

  408 Old Guilford Rd, Brattleboro, VT 05301

  This is the first time this home is being offered for sale. Owned and maintained by the same owner for the past 46 years! This home is hidden from the road. Enter via the Right of Way and the land opens up into a lovely private, garden filled yard. This property abuts the Fort Dummer State Park, so you've got miles of trails in your back yard! The ranch style living offers an open concept

  Victoria Woods Brattleboro Area Realty

  408 Old Guilford Rd, 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 $391,499

  Last Listing Agent Stephanie Peduzzi-Baker Brattleboro Area Realty

  111 Bonnyvale Rd, Brattleboro, VT 05301
• 

  

  /26

  Est $428,565

  Not Listed For Sale

  109 Washington St, Brattleboro, VT 05301

  • 4 Beds
  • 2.5 Baths
  • 3,080 Sq Ft
  • Built 1871

  109 Washington St, Brattleboro, VT 05301

  Last Sold Summary

  • 87 Days On Market
• 

  

  /18

  $285,000

  $35K PRICE DROP

  • 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
• 

  

  /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 $223,801

  Last Listing Agent Sue Beaudet EXP Realty

  9 Garden Dr, Brattleboro, VT 05301
• 

  

  /31

  Est $233,153

  Not Listed For Sale

  39 Clark St, Brattleboro, VT 05301

  • 4 Beds
  • 1 Bath
  • 1,592 Sq Ft
  • Built 1880

  39 Clark St, Brattleboro, VT 05301

  Last Sold Summary

  • 31 Days On Market
• 

  

  /10

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,139 Sq Ft

  108 Morningside Commons, Brattleboro, VT 05301

  Take a deep breath...enjoy your free time...sit back and wait for the walks to be clear, the lawn mowed and the flowers to bloom...without lifting a finger! Take a dip in the clear waters of the fenced, private pool or have a game of friendly tennis or pickleball! No clean up there either! The best of the best! Top floor, end unit 2nd floor deck for looking down at the world, and windows

  Christine Lewis Brattleboro Area Realty

  108 Morningside Commons, Brattleboro, VT 05301
• 

  

  /48

  $391,000

  Sold Apr 07, 2026

  58-60 Frost Place, Brattleboro, VT 05301

  • 6 Beds
  • 2 Baths
  • 2,048 Sq Ft
  • Built 1930

  Last Sold Summary

  • 6% Below List Price
  • $191/SF
  • 142 Days On Market

  Last Listing Agent Lily Gautot Greenwald Realty Group

  58-60 Frost Place, Brattleboro, VT 05301
• 

  

  /22

  Est $248,674

  Not Listed For Sale

  95 Frost St, Brattleboro, VT 05301

  • 4 Beds
  • 1 Bath
  • 1,146 Sq Ft
  • Built 1870

  95 Frost St, Brattleboro, VT 05301

  Last Sold Summary

  • 23 Days On Market
• 

  /2

  $80,000

  $10K PRICE DROP

  • Land
  • 1.97 Acres
  • $40,609 per Acre

  24 Summit Cir, West Brattleboro, VT 05301

  Gorgeous building lot nestled into a prime development on a wooded hillside in Southern Vermont. The 1.97 wooded lot is minutes to downtown Brattleboro, yet private and rural!

  Claire Renaud Berkley & Veller Greenwood Country

  24 Summit Cir, West 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 $334,261

  Last Listing Agent Christine Lewis Brattleboro Area Realty

  64 Meadowbrook Rd, Brattleboro, VT 05301
• 

  

  /20

  Est $379,359

  Not Listed For Sale

  203 Elliot St, Brattleboro, VT 05301

  • 3 Beds
  • 3.5 Baths
  • 2,012 Sq Ft
  • Built 1880

  203 Elliot St, Brattleboro, VT 05301

  Last Sold Summary

  • 2 Days On Market
• 

  

  /32

  $175,000

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

  9 Evergreen Ln, Brattleboro, VT 05301

  Discover a rare opportunity at 9 Evergreen in Brattleboro, VT. This 2-bedroom, 2-bathroom end unit condo is a blank canvas awaiting your creative vision. While the property requires a full renovation, the heavy lifting has already been done; the interior has been completely cleared out and is clean, making it truly ready for a straightforward and efficient transformation. The end unit position

  Kate Barry EXP Realty

  9 Evergreen Ln, 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 $394,780

  Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

  155 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /41

  Est $338,301

  Not Listed For Sale

  196 Fairview St, Brattleboro, VT 05301

  • 5 Beds
  • 2 Baths
  • 1,714 Sq Ft
  • Built 1890

  196 Fairview St, Brattleboro, VT 05301

  Last Sold Summary

  • 5 Days On Market
• 

  

  /28

  $325,000

  $25K PRICE INCREASE

  • 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
• 

  

  /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 $919,802

  Last Listing Agent Robert Doyle Berkley & Veller Greenwood Country

  65 Hillwinds N, Brattleboro, VT 05301
• 

  

  /35

  Est $304,988

  Not Listed For Sale

  31 Pleasant St, Brattleboro, VT 05301

  • 1 Bed
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1884

  31 Pleasant St, Brattleboro, VT 05301

  Last Sold Summary

  • 9 Days On Market
• 

  /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
• 

  

  /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 $396,149

  Last Listing Agent Christine Lewis Brattleboro Area Realty

  36 Spruce St, Brattleboro, VT 05301
• 

  

  /39

  Est $366,057

  Not Listed For Sale

  95 Maple St, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 1,970 Sq Ft
  • Built 1890

  95 Maple St, Brattleboro, VT 05301

  Last Sold Summary

  • 4 Days On Market
• 

  

  /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

Showing Results 81 - 120, Page 3 of 18