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

  1950 Collins Rd, Brattleboro, VT 05301
• 

  

  

  /12

  $1,600

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  1063 Marlboro Rd Unit 2, Brattleboro, VT 05301

  West Brattleboro quiet area owned parking and porch

  1063 Marlboro Rd Unit 2, 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 $204,281

  Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

  75 Mather Rd, Brattleboro, VT 05301
• 

  

  

  /29

  Est $351,202

  Not Listed For Sale

  64 Meadowbrook Rd, Brattleboro, VT 05301

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

  64 Meadowbrook Rd, Brattleboro, VT 05301

  Last Sold Summary

  • 16 Days On Market
• 

  

  

  /32

  $495,000

  • 3,882 Sq Ft

  1309 Putney Rd, Brattleboro, VT 05301

  Exceptional investment opportunity! This well maintained six-unit property is in outstanding condition and has seen numerous recent improvements, making it an attractive addition to any investment portfolio. Exterior updates include fresh paint completed last year, newer windows (approximately three years old), a newer rubber membrane roof, buried power, updated electrical, a newer hot water

  Kerry Mulverhill

  1309 Putney Rd, Brattleboro, VT 05301
• 

  

  /21

  $2,100

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Townhouse for Rent

  240 Fairview St, Brattleboro, VT 05301

  Comfortable spacious freshly renovated and updated 2 bedroom duplex. 1st floor living and dining, large kitchen, 2nd floor 2 bedrooms, office/sitting, bathroom. Laundry in warm dry basement. TV & high speed WiFi. Large front porch, big backyard, parking for 1 car. Friendly safe neighborhood with lots of mature trees & greenery. 5 minute walk to hiking trails and hospital. 1 mile to downtown.

  240 Fairview St, 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 $1,741,095

  Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  1324 Middle Rd, Brattleboro, VT 05301
• 

  

  /37

  Est $443,230

  Not Listed For Sale

  880 Green River Rd, Brattleboro, VT 05301

  • 3 Beds
  • 1 Bath
  • 1,608 Sq Ft
  • Built 1983

  880 Green River Rd, Brattleboro, VT 05301

  Last Sold Summary

  • 48 Days On Market
• 

  

  /32

  $475,000

  $75K PRICE DROP

  • 4,116 Sq Ft

  33 Oak St, Brattleboro, VT 05301

  This is a rare opportunity to take over a multi-family project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the

  Kate Barry EXP Realty

  33 Oak St, Brattleboro, VT 05301
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  /16

  $2,200 Per Month

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

  78 Central St Unit 78, 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

  78 Central St Unit 78, Brattleboro, VT 05301
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  /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 $473,146

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

  214 Putney Rd, Brattleboro, VT 05301
• 

  

  /25

  Est $342,774

  Not Listed For Sale

  6 Willow St, Brattleboro, VT 05301

  • 4 Beds
  • 1.5 Baths
  • 1,503 Sq Ft
  • Built 1928

  6 Willow St, Brattleboro, VT 05301

  Last Sold Summary

  • 42 Days On Market
• 

  /2

  $245,000

  Under Contract

  • 2,148 Sq Ft

  69 Grove St, Brattleboro, VT 05301

  69 Grove Street is a pleasant 2 unit home just a short walk from vibrant downtown. Each unit features 2 bedrooms, bath, living room and kitchen with wide board flooring and replacement windows. The first floor unit has a covered front porch, pantry and W&D hookups in the basement. The second floor apartment has an additional room (office), W&D hookups, decking and a rear staircase. Recent

  Robert Doyle Berkley & Veller Greenwood Country

  69 Grove St, Brattleboro, VT 05301
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  /13

  $2,200 Per Month

  • 2 Beds
  • 1 Bath
  • 1,545 Sq Ft
  • House for Rent

  78 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,

  78 Central St, Brattleboro, VT 05301
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  /35

  $391,000

  Sold Jun 25, 2026

  76 Belmont Ave, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,686 Sq Ft
  • Built 1915

  Last Sold Summary

  • 9% Above List Price
  • $232/SF
  • 4 Days On Market

  Current Estimated Value $356,342

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

  76 Belmont Ave, Brattleboro, VT 05301
• 

  

  /26

  Est $335,292

  Not Listed For Sale

  157 Pine St, Brattleboro, VT 05301

  • 3 Beds
  • 1.5 Baths
  • 1,435 Sq Ft
  • Built 1890

  157 Pine St, Brattleboro, VT 05301

  Last Sold Summary

  • 22 Days On Market
• 

  

  /25

  $139,000

  $20K PRICE DROP Under Contract

  • 1 Bed
  • 1 Bath
  • 592 Sq Ft

  219 High St Unit 3, Brattleboro, VT 05301

  Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share

  Kristen Ziter Taylor Brattleboro Area Realty

  219 High St Unit 3, Brattleboro, VT 05301
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  /10

  $2,400 Per Month

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

  114 Main St Unit 31, Brattleboro, VT 05301

  Newly renovated third floor two bedroom apartment with a large window with in-town views. Access to everything you need within a few blocks. Enjoy the downtown scene with restaurants and breweries right on the same block. This one room apartment has its own washer and dryer in the unit. Pictures are virtually staged, apartment is not furnished.

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  114 Main St Unit 31, Brattleboro, VT 05301
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  /56

  $538,000

  Sold Jul 21, 2026

  1041 Church Hollow Rd, Brattleboro, VT 05301

  • 4 Beds
  • 2.5 Baths
  • 2,567 Sq Ft
  • Built 1987

  Last Sold Summary

  • $210/SF
  • 2 Days On Market

  Current Estimated Value $560,545

  Last Listing Agent Kathy Dowd Bellville Realty

  1041 Church Hollow Rd, Brattleboro, VT 05301
• 

  

  /29

  Est $378,090

  Not Listed For Sale

  28 Greenleaf St, Brattleboro, VT 05301

  • 2 Beds
  • 1.5 Baths
  • 1,620 Sq Ft
  • Built 2006

  28 Greenleaf St, Brattleboro, VT 05301

  Last Sold Summary

  • 10 Days On Market
• 

  

  /26

  $1,350,000

  • 7,660 Sq Ft

  131,133,141 Green St, Brattleboro, VT 05301

  What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very

  Susan Bellville Bellville Realty

  131,133,141 Green St, Brattleboro, VT 05301
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  /9

  $1,700 Per Month

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

  4 Elliot St Unit 11, Brattleboro, VT 05301

  In town, one bedroom apartment, with bright sunlit rooms. The apartment has a combined kitchen and living room, with a separate bedroom. Coin operated laundry is on site, trash removal, and a secure building. Pet friendly building, Photos are virtually staged and apartment is not furnished.

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 11, Brattleboro, VT 05301
• 

  

  /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 $564,437

  Last Listing Agent Flex Realty Group Flex Realty

  290 Roel Rd, Brattleboro, VT 05301
• 

  

  /27

  Est $487,154

  Not Listed For Sale

  32 Christie Ln, Brattleboro, VT 05301

  • 3 Beds
  • 2.5 Baths
  • 2,832 Sq Ft
  • Built 1985

  32 Christie Ln, Brattleboro, VT 05301

  Last Sold Summary

  • 12 Days On Market
• 

  

  /27

  $319,000

  $20K PRICE DROP Under Contract

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  117 Oak Grove Ave, Brattleboro, VT 05301

  Located in one of the area’s most desirable and close-knit neighborhoods, this beautifully preserved 1929 home blends timeless character with thoughtful updates. Featuring hardwood floors, natural woodwork, custom built-ins, classic wainscoting, and a welcoming mudroom, the home retains the charm and craftsmanship buyers love. The open and inviting first floor offers generous living space and a

  Liz LaVorgna Brattleboro Area Realty

  117 Oak Grove Ave, 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
• 

  

  /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
• 

  

  /48

  Est $315,256

  Not Listed For Sale

  52 Belmont Ave, Brattleboro, VT 05301

  • 3 Beds
  • 1.5 Baths
  • 1,300 Sq Ft
  • Built 1924

  52 Belmont Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 57 Days On Market
• 

  

  /22

  $399,000

  • 9 Beds
  • 4 Baths
  • 3,286 Sq Ft

  19 Canal St, Brattleboro, VT 05301

  Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an

  Karen Hoppe Berkley & Veller Greenwood Country

  19 Canal 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 $335,460

  Last Listing Agent Kathy Dowd Bellville Realty

  7 Union St, Brattleboro, VT 05301
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  /60

  Not Listed For Sale

  7 Deepwood Park, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1987

  7 Deepwood Park, Brattleboro, VT 05301

  Last Sold Summary

  • 204 Days On Market
• 

  

  /40

  $490,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,182 Sq Ft

  160 Akley Rd, Guilford, VT 05301

  Here's an open concept, post and beam beauty located on a quiet country road just outside West Brattleboro. Walk through the covered porch into the welcome foyer, where there's plenty of closet space for coats and gear, then enter the main home. The post and beam construction highlights the bright and open spaces. The chef's kitchen is complete with ample cabinet areas, granite counter tops, full

  Bill Hickok Berkley & Veller Greenwood Country

  160 Akley Rd, Guilford, 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 $495,495

  Last Listing Agent Kate Barry EXP Realty

  23 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /10

  Not Listed For Sale

  42-44 Canal St, Brattleboro, VT 05301

  42-44 Canal St, Brattleboro, VT 05301

  Last Sold Summary

  • 2 Days On Market
• 

  /2

  $350,000

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 3,312 Sq Ft

  573 S Main St, Brattleboro, VT 05301

  Just around the corner! From the middle and high school, Oak groveelementary! Pop around the corner for all the high school games,exercise at the track. Interstate is minutes away for easy access towork or play! One apartment is over 1,000 square feet so tons of roomfor owner occupancy! 2 nice front porches. Worth looking at for eitheryour own home or as an investment. Masks

  Christine Lewis Brattleboro Area Realty

  573 S Main 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
• 

  

  /23

  Not Listed For Sale

  8 Deepwood Park, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 880 Sq Ft
  • Built 2024

  8 Deepwood Park, Brattleboro, VT 05301

  Last Sold Summary

  • 118 Days On Market
• 

  

  /8

  $48,000

  $4K PRICE DROP

  • Land
  • 6.1 Acres
  • $7,869 per Acre

  0 Cooke Rd, Brattleboro, VT 05301

  Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

  Victoria Woods Brattleboro Area Realty

  0 Cooke Rd, Brattleboro, VT 05301
• 

  

  /14

  $120,000

  Sold Apr 28, 2026

  60 Brookside Dr Unit 1, Brattleboro, VT 05301

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

  Last Sold Summary

  • $171/SF
  • 6 Days On Market

  Current Estimated Value $121,295

  Last Listing Agent Morriah Adams BHG Masiello Brattleboro

  60 Brookside Dr Unit 1, Brattleboro, VT 05301
• 

  

  /41

  Est $536,517

  Not Listed For Sale

  441 Guilford St, Brattleboro, VT 05301

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

  441 Guilford St, Brattleboro, VT 05301

  Last Sold Summary

  • 48 Days On Market

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