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.5/1/2020742 Brattleboro RdHinsdale, NH 03451
Estimated Value $281,000
Living Area 1,440 SqFt
Beds 3
Baths 1
Year Built 1964
Property Type Single Family
Ownership Type Related
APN HNDL M:024 B:056
Municipality HINSDALE
School District Hinsdale School District
329 Oxbow RdHinsdale, NH 03451
Estimated Value $220,000
Living Area 992 SqFt
Beds 2
Baths 1
Year Built 1955
Property Type Single Family
Ownership Type Individual
APN HNDL M:033 B:010
Municipality HINSDALE
School District Hinsdale School District
124 Herrick RdWest Chesterfield, NH 03466
Estimated Value $546,000
Living Area 2,288 SqFt
Beds 3
Baths 2
Year Built 2003
Property Type Single Family
Ownership Type Individual
APN CHFD M:14 B:B012 L:3
Municipality CHESTERFIELD
School District Chesterfield School District
72 Spaulding Hill RdWest Chesterfield, NH 03466
Estimated Value $448,000
Living Area 1,901 SqFt
Beds 2
Baths 2
Year Built 1983
Property Type Single Family
Ownership Type Multiple
APN CHFD M:14-C B:D018
Municipality CHESTERFIELD
School District Chesterfield School District
148 Oxbow RdHinsdale, NH 03451
Estimated Value $117,000
Living Area 692 SqFt
Beds 2
Baths 1
Year Built 1965
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:029 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
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
622 Gulf RdWest Chesterfield, NH 03466
Estimated Value $498,000
Living Area 2,324 SqFt
Beds 3
Baths 1.5
Year Built 2006
Property Type Single Family
Ownership Type Individual
APN CHFD M:15 B:A016
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
226 Route 9West Chesterfield, NH 03466
Estimated Value $575,000
Living Area 2,173 SqFt
Beds 4
Baths 2.5
Year Built 1959
Property Type Single Family
Ownership Type Mixed
APN CHFD M:14-B B:B001
Municipality CHESTERFIELD
School District Chesterfield School District
314 Monument RdHinsdale, NH 03451
Estimated Value $300,000
Living Area 1,430 SqFt
Beds 2
Baths 1.5
Year Built 1980
Property Type Single Family
Ownership Type Individual
APN HNDL M:029 B:012
Municipality HINSDALE
School District Hinsdale School District
83 Meetinghouse RdHinsdale, NH 03451
Estimated Value $258,000
Living Area 1,664 SqFt
Beds 4
Baths 1
Year Built 1959
Property Type Single Family
Ownership Type Related
APN HNDL M:029 B:060
Municipality HINSDALE
School District Hinsdale School District
12 Gateway DrHinsdale, NH 03451
Estimated Value $90,000
Living Area 994 SqFt
Beds 3
Baths 2
Year Built 1986
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:024 B:110 L:12
Municipality HINSDALE
School District Hinsdale School District
159 Oxbow RdHinsdale, NH 03451
Estimated Value $206,000
Living Area 973 SqFt
Beds 3
Baths 1
Year Built 1839
Property Type Single Family
Ownership Type Individual
APN HNDL M:029 B:016
Municipality HINSDALE
School District Hinsdale School District
73 Mountain RdWest Chesterfield, NH 03466
Estimated Value $490,000
Living Area 2,256 SqFt
Beds 3
Baths 2
Year Built 2006
Property Type Single Family
Ownership Type Individual
APN CHFD M:14-C B:C011 L:2
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