Brattleboro is a vibrant and eclectic town in the southeastern corner of the state, offering unique opportunities for real estate investors. Nestled along the Connecticut River and near the borders of New Hampshire and Massachusetts, the town serves as a gateway to New England. It’s close to major metropolitan areas like Boston and New York, making it an ideal destination for commuters and second-home buyers.
The town is home to many galleries, music venues, and festivals like the renowned Brattleboro Literary Festival and Strolling of the Heifers parade. This creative energy attracts a diverse population and propels demand for rental properties, commercial spaces, and boutique accommodations for artists and entrepreneurs.
With easy access to the Green Mountains, the Connecticut River, and local ski resorts, the area offers year-round recreation, supporting a growing market for short-term rentals and vacation properties. Whether you’re interested in single-family homes, rental units, or commercial projects, Brattleboro’s vibrant community, great location, and cultural richness make it a paramount location for real estate investment in Vermont.
Popular Streets in Brattleboro, Vermont
Canal St10342$271,8793,935 Sq.Ft.12/6/2024Chestnut St7042$294,5631,777 Sq.Ft.12/31/2024Guilford St7532$342,3791,667 Sq.Ft.11/20/2024Main St17142$301,1183,537 Sq.Ft.2/27/2025Marlboro Rd6832$325,5523,910 Sq.Ft.1/17/2025Morningside Cmns16622$222,9761,053 Sq.Ft.5/12/2025Putney Rd12142$378,6678,624 Sq.Ft.5/2/2025River Rd7022$328,7782,036 Sq.Ft.2/12/2025Sunset Lake Rd6732$397,9271,688 Sq.Ft.4/12/2024Western Ave21042$358,7782,740 Sq.Ft.6/11/2025All Streets in Brattleboro, Vermont
Sycamore St832$355,0001,753 Sq.Ft.6/10/2024Tater Ln121$333,0002,000 Sq.Ft.N/ATechnology Dr9N/AN/AN/A62,333 Sq.Ft.3/31/2022Terrace St675$587,6674,543 Sq.Ft.1/6/2006Thayer Ridge Rd1032$366,4001,695 Sq.Ft.8/1/2024Third Level Dr1N/AN/AN/A3,176 Sq.Ft.N/AThistle Hill Rd621$77,667889 Sq.Ft.5/5/2025Thomas Hill Rd1932$436,9171,849 Sq.Ft.7/27/2022Thomas St752$279,8572,420 Sq.Ft.4/24/2014Thorn Ln432$323,7501,679 Sq.Ft.4/16/2014Thurber Rd232$509,0001,829 Sq.Ft.6/9/2017Timber Ln1532$367,5711,434 Sq.Ft.11/18/2024Tkaczyk Farm Rd154$442,0002,400 Sq.Ft.N/ATown Crier Dr4N/AN/AN/A10,766 Sq.Ft.1/29/2021Town Hill Rd622$334,8001,636 Sq.Ft.9/27/2021Trailer Park Dr1N/AN/AN/AN/AN/ATrail Rd431$88,250924 Sq.Ft.4/26/2018Trillium Way243$767,5002,879 Sq.Ft.9/22/2017Tucker Reed Rd432$352,0001,430 Sq.Ft.9/12/2012Tudor Ln931$241,4441,177 Sq.Ft.5/3/2022Tyler Hill Rd132$343,0001,488 Sq.Ft.11/23/2005Tyler St1433$469,3852,422 Sq.Ft.5/1/2025Union St532$307,0001,475 Sq.Ft.7/14/2023University Way3N/AN/AN/A1,720 Sq.Ft.9/29/2023Upper Dummerston Rd5432$458,0382,129 Sq.Ft.5/16/2025Upper Forest St742$316,5712,248 Sq.Ft.1/11/2023Upper Houghton Rd252$443,0001,453 Sq.Ft.N/AUppr Dummerston Rd4N/AN/AN/AN/AN/AUrsa Ridge Rd432$682,7501,968 Sq.Ft.11/4/2024Us Route 5342$494,0003,637 Sq.Ft.2/28/2005Valgar St332$242,5002,720 Sq.Ft.6/28/2019Valley St5631$113,4001,015 Sq.Ft.5/30/2025Vandewater Rd155$946,0003,960 Sq.Ft.N/AVermont Ave1232$414,4292,087 Sq.Ft.6/21/2024Vernon St2921$369,3339,418 Sq.Ft.5/19/2023Village Dr2721$80,269813 Sq.Ft.7/16/2024Vine St1342$299,0771,433 Sq.Ft.10/3/2022Wagon Dr222$78,000791 Sq.Ft.4/14/2025Walker Pl152$340,0002,170 Sq.Ft.6/30/2021Walnut St832$306,0004,220 Sq.Ft.5/8/2024Wantastiquet Dr3332$367,8711,535 Sq.Ft.11/27/2024Washington St3642$302,0832,171 Sq.Ft.4/23/2025Water Ln232$274,000924 Sq.Ft.10/30/2018Waubanong Rd622$361,5002,129 Sq.Ft.10/9/2019Weatherhead Hollow Rd1N/AN/AN/AN/AN/AWellington Rd6N/AN/A$270,00056,264 Sq.Ft.1/14/2022Western Ave21042$358,7782,740 Sq.Ft.6/11/2025Westgate Dr432$319,5001,559 Sq.Ft.5/15/2018West Rd131$391,0001,330 Sq.Ft.10/5/2021West St6232$301,7721,849 Sq.Ft.4/17/2023Wheeler Rd1832$234,5291,335 Sq.Ft.3/20/2024Whetstone Dr1932$304,6251,494 Sq.Ft.6/13/2025Whetstone Rd432$329,7501,914 Sq.Ft.6/2/2017Whipple St442$340,7502,280 Sq.Ft.3/11/2020Whitaker Farm Rd433$424,7502,120 Sq.Ft.8/8/2022White Birch Ave231$373,5001,591 Sq.Ft.2/25/2005Whitney Pl221$331,0001,039 Sq.Ft.N/AWickopee Hill Rd3N/AN/AN/AN/AN/AWildwood Dr521$84,600831 Sq.Ft.5/27/2024Williams St4631$254,9141,458 Sq.Ft.3/19/2025Williamsville Rd111$274,000420 Sq.Ft.6/6/2017Williston St1053$345,3332,604 Sq.Ft.4/25/2024Willow St641$295,1671,600 Sq.Ft.8/31/2022Wilsons Woods Rd2532$328,1201,513 Sq.Ft.5/9/2024Winchester Rd243$482,5002,284 Sq.Ft.5/19/2005Winding Hill Rd3121$99,414938 Sq.Ft.3/26/2025Windward Dr1921$113,167879 Sq.Ft.11/5/2020Winsor Dr231$235,0001,046 Sq.Ft.8/30/2024Winter Ct632$266,3331,271 Sq.Ft.7/19/2024Winter St1931$287,5791,260 Sq.Ft.8/15/2023Woodvale Rd731$82,571908 Sq.Ft.12/30/2019Woodys Dr632$378,0001,958 Sq.Ft.7/27/2017W River Rd5N/AN/AN/AN/AN/AYeaw Rd211$457,0002,266 Sq.Ft.4/7/1989Yorkshire Cir931$283,4441,044 Sq.Ft.6/14/2021654 Plain RdHinsdale, NH 03451
Estimated Value $297,000
Living Area 1,584 SqFt
Beds 3
Baths 1.5
Year Built 1989
Property Type Single Family
Ownership Type Individual
APN HNDL M:030 B:084
Municipality HINSDALE
School District Hinsdale School District
336 Gulf RdWest Chesterfield, NH 03466
Estimated Value $229,000
Living Area 1,726 SqFt
Beds 2
Baths 1
Year Built 1776
Property Type Unknown
Ownership Type Individual
APN CHFD M:15 B:B007
Municipality CHESTERFIELD
School District Chesterfield School District
103 Herrick RdWest Chesterfield, NH 03466
Estimated Value $503,000
Living Area 2,221 SqFt
Beds 4
Baths 1
Year Built 1800
Property Type Single Family
Ownership Type Related
APN CHFD M:15 B:A015
Municipality CHESTERFIELD
School District Chesterfield School District
10 Keene DrHinsdale, NH 03451
Estimated Value $93,000
Living Area 1,080 SqFt
Beds 3
Baths 2
Year Built 2001
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:024 B:110 L:49
Municipality HINSDALE
School District Hinsdale School District
25 Middle Oxbow RdHinsdale, NH 03451
Estimated Value $276,000
Living Area 960 SqFt
Beds 3
Baths 1.5
Year Built 1966
Property Type Single Family
Ownership Type Individual
APN HNDL M:029 B:069
Municipality HINSDALE
School District Hinsdale School District
364 Gulf RdWest Chesterfield, NH 03466
Estimated Value $574,000
Living Area 2,677 SqFt
Beds 3
Baths 2.5
Year Built 1994
Property Type Single Family
Ownership Type Corporate
APN CHFD M:15 B:A006
Municipality CHESTERFIELD
School District Chesterfield School District
25 Hastings CirHinsdale, NH 03451
Estimated Value $248,000
Living Area 900 SqFt
Beds 2
Baths 1
Year Built 1973
Property Type Single Family
Ownership Type Corporate
APN HNDL M:030 B:025
Municipality HINSDALE
School District Hinsdale School District
100 Middle Oxbow RdHinsdale, NH 03451
Estimated Value $261,000
Living Area 1,532 SqFt
Beds 3
Baths 2
Year Built 1990
Property Type Manufactured Homes
Ownership Type Mixed
APN HNDL M:033 B:022
Municipality HINSDALE
School District Hinsdale School District
261 Route 9West Chesterfield, NH 03466
Estimated Value $512,000
Living Area 1,606 SqFt
Beds 3
Baths 2
Year Built 1953
Property Type Single Family
Ownership Type Individual
APN CHFD M:14-B B:A006
Municipality CHESTERFIELD
School District Chesterfield School District
554 Oxbow RdHinsdale, NH 03451
Estimated Value $234,000
Living Area 960 SqFt
Beds 3
Baths 1.5
Year Built 2001
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:037 B:009 L:2
Municipality HINSDALE
School District Hinsdale School District
152 N Hinsdale RdChesterfield, NH 03443
Estimated Value $384,000
Living Area 1,265 SqFt
Beds 2
Baths 2
Year Built 2000
Property Type Single Family
Ownership Type Related
APN CHFD M:24 B:C017
Municipality CHESTERFIELD
School District Chesterfield School District
24 Hastings CirHinsdale, NH 03451
Estimated Value $309,000
Living Area 1,739 SqFt
Beds 3
Baths 1.5
Year Built 1969
Property Type Single Family
Ownership Type Individual
APN HNDL M:030 B:012
Municipality HINSDALE
School District Hinsdale School District
106 Meetinghouse RdHinsdale, NH 03451
Estimated Value $343,000
Living Area 1,320 SqFt
Beds 2
Baths 1
Year Built 1958
Property Type Single Family
Ownership Type Individual
APN HNDL M:029 B:082
Municipality HINSDALE
School District Hinsdale School District
133 Mountain RdWest Chesterfield, NH 03466
Estimated Value $567,000
Living Area 3,913 SqFt
Beds 4
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Individual
APN CHFD M:25 B:A002 L:41
Municipality CHESTERFIELD
School District Chesterfield School District
869 Gulf RdWest Chesterfield, NH 03466
Estimated Value $204,000
Living Area 981 SqFt
Beds 2
Baths 1
Year Built 1956
Property Type Single Family
Ownership Type Individual
APN CHFD M:14-C B:C002
Municipality CHESTERFIELD
School District Chesterfield School District
23 Bittersweet LnWest Chesterfield, NH 03466
Estimated Value $629,000
Living Area 1,834 SqFt
Beds 3
Baths 2
Year Built 1950
Property Type Single Family
Ownership Type Multiple
APN CHFD M:14-A B:A001
Municipality CHESTERFIELD
School District Chesterfield School District