Brattleboro, VT Homes

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  $4,950,000

  • 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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  /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
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  /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 $199,440

  Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

  75 Mather Rd, Brattleboro, VT 05301
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  /33

  Est $367,892 Not Listed For Sale

  113 Stockwell Dr, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,754 Sq Ft
  • Built 1984

  113 Stockwell Dr, Brattleboro, VT 05301

  Last Sold Summary

  • 5% Above List Price
  • $200/SF
  • 4 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Victoria Woods Brattleboro Area Realty
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  /46

  $495,000

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

  214 Putney Rd, Brattleboro, VT 05301

  Step back in time and discover the enchanting potential of this distinguished 1940 Colonial, perfectly positioned to capture the spirit of Brattleboro. Perched on a generous 0.79-acre level lot, this home offers a rare blend of expansive personal space and convenient in-town living. From the moment you arrive, the classic lines, wood siding, and enduring slate roof hint at the craftsmanship of a

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  214 Putney Rd, Brattleboro, VT 05301
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  /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.

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 5, Brattleboro, VT 05301
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  $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 $1,754,418

  Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  1324 Middle 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

  • $157/SF
  • 55 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Kate Barry EXP Realty
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  $499,000

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

  23 Wilsons Woods Rd, Brattleboro, VT 05301

  Welcome to 23 Wilsons Woods Road, a meticulously maintained Colonial-style home that offers the perfect Vermont balance: total wooded privacy combined with absolute convenience. Nestled at the end of a quiet road, this property feels like a secluded retreat tucked into the forest, yet you are literally moments away from Brattleboro’s vibrant restaurants, local shops, the hospital, and a thriving

  Kate Barry EXP Realty

  23 Wilsons Woods Rd, Brattleboro, VT 05301
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  /5

  $1,875 total monthly price

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

  995 Western Ave Unit 100, Brattleboro, VT 05301

  This first floor, renovated 2-bedroom apartment is freshly painted. Amenities include an eat-in kitchen, new dishwasher and refrigerator, pantry, new or refinished flooring throughout, new bathroom, large screened porch, 1/2 garage plus parking for a second car in the driveway, separate entrance, and a large backyard with room to garden. Mowing, snow removal and heat are included. Tenant pays

  995 Western Ave Unit 100, 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 $589,667

  Last Listing Agent Flex Realty Group Flex Realty

  290 Roel 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

  • $82/SF
  • 12 Days On Market

  Last Sold Price $79,000

  Last Listing Agent Victoria Woods Brattleboro Area Realty
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  /42

  $650,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,995 Sq Ft

  299 Sunset Lake Rd, Brattleboro, VT 05301

  This exceptional 3-bedroom residence offers refined rural living with space, comfort, and stunning natural surroundings. The home features expansive open living areas, anchored by a large living room with a fireplace, creating a warm yet elegant gathering space. A newly redesigned kitchen serves as the heart of the home, perfectly suited for entertaining family and guests. Enjoy seamless

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  299 Sunset Lake Rd, Brattleboro, VT 05301
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  /17

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft
  • Townhouse for Rent

  60 Brookside Dr Unit 3, Brattleboro, VT 05301

  This warm and inviting 2-bedroom condo comes fully furnished with everything you will need to just move in and relax. The first-floor open concept kitchen/living room makes for easy entertaining while you cook dinner. Upstairs are both bedrooms and the 3/4 bathroom. This comes with a full basement that has the washer and dryer and still usable space for storage or another room. This condo is not

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  60 Brookside Dr Unit 3, 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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  /12

  Est $340,185 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

  • 3% Above List Price
  • $287/SF
  • 36 Days On Market

  Last Sold Price $331,000

  Last Listing Agent John Hatton Berkley & Veller Greenwood Country
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  /26

  $395,000

  • 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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  /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.

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 2, Brattleboro, VT 05301
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  $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 $329,470

  Last Listing Agent Kathy Dowd Bellville Realty

  7 Union St, Brattleboro, VT 05301
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  /12

  Est $570,866 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

  • 4% Below List Price
  • $175/SF
  • 20 Days On Market

  Last Sold Price $595,000

  Last Listing Agent Robert Doyle Berkley & Veller Greenwood Country
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  /41

  $429,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  387 Meadowbrook Rd, Brattleboro, VT 05301

  This West Brattleboro ranch style home is situated in that sought after "just outside of town" location with the hard-to-find combination of convenient proximity to the necessities and out the door access to walks on quiet country roads including the trails around the Pleasant Valley Reservoir just short drive up the road. The house has had two renovations in the past 20 years (2006 & 2015/16)

  Chris Long BHG Masiello Brattleboro

  387 Meadowbrook Rd, Brattleboro, VT 05301
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  /8

  $1,700 per month

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

  4 Elliot St Unit 3, Brattleboro, VT 05301

  The National, featuring this 1 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown. Coin operated Laundry is on site and off-street parking is available in the parking garage. The building is pet friendly

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 3, Brattleboro, VT 05301
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  /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 $391,838

  Last Listing Agent Kate Barry EXP Realty

  146 Sherwood Cir, Brattleboro, VT 05301
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  /3

  Est $413,009 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

  • 12% Above List Price
  • $129/SF
  • 0 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Christine Lewis Brattleboro Area Realty
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  /30

  $579,000 Under Contract

  • 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
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  /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
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  /37

  Est $406,006 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

  • 6% Below List Price
  • $301/SF
  • 16 Days On Market

  Last Sold Price $434,000

  Last Listing Agent John Redd Skihome Realty
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  /35

  $475,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,480 Sq Ft

  24 Laurel St, Brattleboro, VT 05301

  This well-maintained three-bedroom, two-bath single-family home is set on a level, fenced-in lot in a coveted neighborhood close to downtown, with convenient access to major highways. The home features radiant flooring, central air, and a finished basement offering flexible living or recreational space. A spacious kitchen provides ample cabinetry and storage, ideal for everyday living and

  Kelly Agrillo Southern Vermont Realty Group

  24 Laurel St, Brattleboro, VT 05301
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  /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 $333,000

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

  33 Frost Place, Brattleboro, VT 05301
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  /20

  Est $266,173 Not Listed For Sale

  149 Canal St, Brattleboro, VT 05301

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1899

  149 Canal St, Brattleboro, VT 05301

  Last Sold Summary

  • 21% Above List Price
  • $105/SF
  • 81 Days On Market

  Last Sold Price $220,000

  Last Listing Agent David Brown
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  /24

  $389,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  115 Country Hill, Brattleboro, VT 05301

  This lovely West Brattleboro cape is located on a quiet cul-de-sac right on the outskirts of town. Built in 2002 with a spacious design, you enter through the oversized two-car garage into a contemporary kitchen. Features include granite countertops, tile floors, an elegant backsplash, and a door leading to a private terrace, ideal for family gatherings or entertaining. The first floor has

  Kristen Ziter Taylor Brattleboro Area Realty

  115 Country Hill, Brattleboro, VT 05301
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  /24

  $22,000 Sold Apr 01, 2026

  97 Glen St, Brattleboro, VT 05301

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft
  • Built 1968

  Last Sold Summary

  • 26% Below List Price
  • $32/SF
  • 36 Days On Market

  Last Listing Agent Angela Sherman Brattleboro Area Realty

  97 Glen St, Brattleboro, VT 05301
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  /31

  Est $332,878 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

  • 1% Below List Price
  • $239/SF
  • 38 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Christine Lewis Brattleboro Area Realty
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  $599,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 4,060 Sq Ft

  141 Piney Brook Way, Brattleboro, VT 05301

  Set on 12 acres of wooded privacy in desirable Marlboro, this spacious and versatile property offers comfort, flexibility, and stunning natural surroundings. The main home features 3 bedrooms, a large family room and first-floor laundry, offering plenty of room for a growing household, guests, or multi-generational living. Cozy up by the wood stove on chilly evenings, and enjoy the peace of mind

  Desiree Stango Berkley & Veller Greenwood Country

  141 Piney Brook Way, Brattleboro, VT 05301
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  /27

  $285,000 Sold Dec 10, 2025

  91 Carriage Hill Rd, Brattleboro, VT 05301

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1975

  Last Sold Summary

  • 5% Below List Price
  • $312/SF
  • 41 Days On Market

  Current Estimated Value $285,301

  Last Listing Agent Rebecca Seymour Brattleboro Area Realty

  91 Carriage Hill Rd, Brattleboro, VT 05301
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  /26

  Est $293,157 Not Listed For Sale

  240 S Main St, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 1,948 Sq Ft
  • Built 1865

  240 S Main St, Brattleboro, VT 05301

  Last Sold Summary

  • 9% Below List Price
  • $166/SF
  • 18 Days On Market

  Last Sold Price $323,000

  Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country
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  /34

  $389,000 Pending

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  137 Pleasant Valley Rd, Brattleboro, VT 05301

  This is a rare opportunity to own a piece of Pleasant Valley road in west Brattleboro Vermont. A solid Timberframe, designed and built in 2019 with sustainability and long term affordability as the guiding factors. This 650 square foot home is just enough to provide comfortable living with its high ceiling and extravagant windows, without having to heat and maintain extraneous space. With its

  Christine Lewis Brattleboro Area Realty

  137 Pleasant Valley Rd, Brattleboro, VT 05301
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  /18

  $335,000 Sold Jul 30, 2025

  138 Cedar St, Brattleboro, VT 05301

  • 3 Beds
  • 1 Bath
  • 1,174 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Above List Price
  • $285/SF
  • 36 Days On Market

  Current Estimated Value $323,466

  Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

  138 Cedar St, Brattleboro, VT 05301
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  /14

  Est $244,452 Not Listed For Sale

  202 Canal St, Brattleboro, VT 05301

  • Studio
  • 2 Baths
  • 2,708 Sq Ft
  • Built 1910

  202 Canal St, Brattleboro, VT 05301

  Last Sold Summary

  • 16% Above List Price
  • $78/SF
  • 6 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Kevin Holmes Blue Slate Realty
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  /32

  $449,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft

  56 Lee Rd, Guilford, VT 05301

  Enjoy privacy and nature just minutes from town! This well-cared for 3 bedroom, 2 bath home sits on 4.81 acres, offering space, tranquility, and convenience. Features include a first-floor bedroom, bright and comfortable living areas, a beautiful three-season porch perfect for relaxing and taking in the peaceful setting, and a two-car garage for added storage and functionality. A great

  Claire Renaud Berkley & Veller Greenwood Country

  56 Lee Rd, Guilford, VT 05301

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