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.5/13/2025All Streets in Brattleboro, Vermont
Cross St222$415,0001,354 Sq.Ft.10/29/2012Culbertson Dr133N/A2,579 Sq.Ft.3/12/1999Darien St232$288,0001,092 Sq.Ft.10/27/2017Day Rd253$604,0002,657 Sq.Ft.N/ADeacon Pl342$475,3332,460 Sq.Ft.8/8/2018Deepwood Park4632$123,4571,024 Sq.Ft.1/26/2024Deer Park Rd921$463,6251,744 Sq.Ft.3/20/2023Depot St7N/AN/AN/A6,145 Sq.Ft.11/1/2024Dickinson Rd932$563,0001,882 Sq.Ft.N/ADogwood Dr1N/AN/A$135,000N/A4/20/2015Draper Ln722$205,0001,082 Sq.Ft.9/4/2020Dummer Ave274$360,0003,120 Sq.Ft.1/1/1992Dupre Dr221$291,000503,358 Sq.Ft.10/13/2015Dutton Farm Rd132$466,0001,849 Sq.Ft.N/ADylan Rd3N/AN/AN/A31,688 Sq.Ft.4/16/2019East-West Rd132$389,0001,792 Sq.Ft.11/13/2001Eaton Ave932$418,5712,068 Sq.Ft.8/30/2022Ebby Dr353$245,0001,633 Sq.Ft.6/12/2020Edgewood Dr631$80,167877 Sq.Ft.4/20/2016Edward Hts2132$322,0001,584 Sq.Ft.5/1/2024Eels Ct131$181,000835 Sq.Ft.3/18/2002Eli Way1N/AN/A$355,000N/AN/AEllingwood Rd132$361,0001,512 Sq.Ft.5/24/2019Elliot St6653$278,3912,771 Sq.Ft.4/1/2025Elliot Ter352$247,0002,234 Sq.Ft.3/21/2023Elm St853$283,0003,147 Sq.Ft.5/30/2018E Orchard St3N/AN/AN/AN/AN/AEstabrook St441$220,0001,211 Sq.Ft.12/31/2018Estey Cir832$293,2501,304 Sq.Ft.12/21/2017Estey St1252$307,6001,865 Sq.Ft.6/30/2022Ethan Hl343$504,3332,368 Sq.Ft.9/23/2020Evergreen Ln822$244,8571,248 Sq.Ft.10/7/2022Experiment Way1N/AN/AN/AN/AN/AFairground Rd1342$266,80027,831 Sq.Ft.11/12/2021Fairly Wild Way1N/AN/A$408,000N/AN/AFairview St2132$317,6001,742 Sq.Ft.2/28/2025Fairview Vlg Dr1N/AN/AN/A16,477 Sq.Ft.N/AFalls Brook Rd14N/A$252,000496 Sq.Ft.N/AFarmhouse Sq242N/A2,505 Sq.Ft.N/AFay Boyden Rd5N/AN/A$314,200N/A11/23/2020Fisch Rd22N/A$382,000600 Sq.Ft.N/AFlat St11N/AN/AN/A12,413 Sq.Ft.3/19/2021Fleisher Ln2N/AN/AN/AN/AN/AForest St832$301,6672,098 Sq.Ft.7/15/2024Fort Dummer Hts342$431,0002,345 Sq.Ft.12/30/2021Fox Farm Rd832$466,2001,925 Sq.Ft.11/3/2020Franklin Rd1N/AN/AN/A756 Sq.Ft.N/AFriendship Rd332$348,6671,903 Sq.Ft.10/22/2020Frog Hl243$552,0002,135 Sq.Ft.8/26/2021Frost Pl1042$360,5001,850 Sq.Ft.11/29/2022Frost St2753$309,1182,811 Sq.Ft.11/21/2024Fuller Dr2731$288,7201,402 Sq.Ft.11/4/2022Garden Dr332$276,3331,593 Sq.Ft.3/15/2022Garfield Dr3N/AN/A$77,0008,349 Sq.Ft.N/AGates Pond Rd2N/AN/A$739,000N/AN/AGateway Farm Rd333$471,0002,390 Sq.Ft.10/10/2003Generous St821$282,2861,307 Sq.Ft.11/9/2016Gibson Rd354$771,0003,178 Sq.Ft.5/31/2012Gingko Ln132N/A1,600 Sq.Ft.11/9/1999Glen Orne Dr3N/AN/AN/A25,519 Sq.Ft.3/30/2020Glen St2821$123,615943 Sq.Ft.5/20/2024Goldfinch Ln341$296,3331,854 Sq.Ft.10/25/2023Goodenough Rd1632$426,7861,779 Sq.Ft.7/31/2020Grant Rd343$608,6672,594 Sq.Ft.4/1/2024Greenhill Pkwy2532$355,4171,603 Sq.Ft.8/27/2024Greenleaf St2532$336,0001,596 Sq.Ft.6/12/2024Green Meadow Rd2232$386,1821,801 Sq.Ft.7/19/2023Green Mountain Camp Rd432$560,0002,449 Sq.Ft.5/9/2025Green River Rd5432$359,1221,679 Sq.Ft.1/7/2025Green St4843$326,0652,424 Sq.Ft.4/11/2024Grove St1843$331,0002,433 Sq.Ft.3/15/2023Gsp Dr4N/AN/AN/A9,868 Sq.Ft.12/15/2015Guilford Center Rd4N/AN/AN/AN/AN/AGuilford St7532$342,3791,667 Sq.Ft.11/20/2024Gulf Rd422$395,3331,262 Sq.Ft.9/19/2024Hague Rd421$257,750846 Sq.Ft.N/AHale Rd1732$381,8462,103 Sq.Ft.7/12/2023Halifax Pike Rd3N/AN/AN/AN/A3/28/2017Halladay Brook Rd732$394,2001,494 Sq.Ft.8/4/2023Hall Farm Rd132$681,0002,390 Sq.Ft.N/AHall Rd143$772,0003,598 Sq.Ft.2/28/2018Hamilton Rd1232$394,3331,732 Sq.Ft.12/20/2021Hampshire Cir931$310,4441,163 Sq.Ft.1/15/2015Hanson Rd1932$309,3681,487 Sq.Ft.5/1/2025Hardwood Way1N/AN/AN/A5,566 Sq.Ft.9/27/2013Harris Ave1432$385,0832,270 Sq.Ft.6/1/2022Harris Dr421$217,7501,358 Sq.Ft.7/22/2011Harris Pl422$365,0005,313 Sq.Ft.9/21/2022Harvest Hill Rd432$308,6671,825 Sq.Ft.5/10/2024Haskell Dr232$421,0001,724 Sq.Ft.9/30/2019Hatch School Rd1732$419,538244,295 Sq.Ft.11/23/2022Hayes Rd121$239,000864 Sq.Ft.N/AHemlock Hill Rd542$408,6001,912 Sq.Ft.10/9/2015Hescock Rd632$781,5001,918 Sq.Ft.7/2/2013Hidden Lake Rd133N/A915 Sq.Ft.9/12/2019High Bridge Rd232$286,0001,577 Sq.Ft.7/21/2023Highland St2632$312,1541,657 Sq.Ft.9/1/2022Highlawn Rd1632$352,5001,895 Sq.Ft.2/28/2019High St5453$344,3713,007 Sq.Ft.8/7/2024Higley Hill Rd432$400,6672,649 Sq.Ft.5/1/202014 Pierce RdHinsdale, NH 03451
Estimated Value $208,000
Living Area 1,177 SqFt
Beds 2
Baths 1.5
Year Built 1958
Property Type Single Family
Ownership Type Individual
APN HNDL M:024 B:048
Municipality HINSDALE
School District Hinsdale School District
663 Plain RdHinsdale, NH 03451
Estimated Value $320,000
Living Area 2,601 SqFt
Beds 3
Baths 3
Year Built 1870
Property Type Triplex 3 Units
Ownership Type Individual
APN HNDL M:030 B:076
Municipality HINSDALE
School District Hinsdale School District
654 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
17 Oak Hill RdHinsdale, NH 03451
Estimated Value $323,000
Living Area 1,196 SqFt
Beds 3
Baths 2
Year Built 1998
Property Type Single Family
Ownership Type Individual
APN HNDL M:024 B:106
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
11 Keene DrHinsdale, NH 03451
Estimated Value $88,000
Living Area 924 SqFt
Beds 2
Baths 1
Year Built 1984
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:024 B:110 L:50
Municipality HINSDALE
School District Hinsdale School District
36 Emerson DrHinsdale, NH 03451
Estimated Value $266,000
Living Area 960 SqFt
Beds 3
Baths 1
Year Built 1988
Property Type Single Family
Ownership Type Individual
APN HNDL M:030 B:050
Municipality HINSDALE
School District Hinsdale School District
9 Hillcrest StHinsdale, NH 03451
Estimated Value $127,000
Living Area 1,296 SqFt
Beds 3
Baths 2
Year Built 2003
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:020 B:004 L:3-A
Municipality HINSDALE
School District Hinsdale School District
779 Brattleboro RdHinsdale, NH 03451
Estimated Value $404,000
Living Area 1,598 SqFt
Beds 3
Baths 2
Year Built 1976
Property Type Single Family
Ownership Type Individual
APN HNDL M:024 B:004
Municipality HINSDALE
School District Hinsdale School District
18 Old Ferry RdWest Chesterfield, NH 03466
Estimated Value $593,000
Living Area 2,002 SqFt
Beds 3
Baths 2
Year Built 1987
Property Type Single Family
Ownership Type Multiple
APN CHFD M:13-B B:C006
Municipality CHESTERFIELD
School District Chesterfield School District
15 Pierce RdHinsdale, NH 03451
Estimated Value $242,000
Living Area 1,232 SqFt
Beds 3
Baths 2
Year Built 2001
Property Type Manufactured Homes
Ownership Type Multiple
APN HNDL M:024 B:035
Municipality HINSDALE
School District Hinsdale School District
214 Mountain RdWest Chesterfield, NH 03466
Estimated Value $1,144,000
Living Area 1,718 SqFt
Beds 4
Baths 2
Year Built 1983
Property Type Duplex 2 Units
Ownership Type Mixed
APN CHFD M:25-A B:A002
Municipality CHESTERFIELD
School District Chesterfield School District
2 Homestretch DrHinsdale, NH 03451
Estimated Value $99,000
Living Area 1,140 SqFt
Beds 2
Baths 2
Year Built 2001
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:024 B:055 L:1-W
Municipality HINSDALE
School District Hinsdale 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
1 Hastings CirHinsdale, NH 03451
Estimated Value $292,000
Living Area 1,200 SqFt
Beds 2
Baths 2
Year Built 1972
Property Type Single Family
Ownership Type Individual
APN HNDL M:025 B:024
Municipality HINSDALE
School District Hinsdale School District
452 Brattleboro Rd #454Hinsdale, NH 03451
Estimated Value $232,000
Living Area 1,047 SqFt
Beds 3
Baths 1
Year Built 1970
Property Type Single Family
Ownership Type Individual
APN HNDL M:014 B:032
Municipality HINSDALE
School District Hinsdale School District