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
Hillcrest Ter2432$415,2271,927 Sq.Ft.8/12/2024Hillwinds1443$635,3852,670 Sq.Ft.9/29/2022Hillwinds Rd2732$501,6002,070 Sq.Ft.4/8/2025Hinesburg Rd5832$396,1201,865 Sq.Ft.11/6/2024Holstein Pl1N/AN/AN/A18,234 Sq.Ft.N/AHome St731$300,0001,329 Sq.Ft.8/20/2024Homestead Pl842$315,6671,670 Sq.Ft.10/22/2024Horton Pl642$269,0001,924 Sq.Ft.2/5/2018Hosea Fisher Ln131$352,0001,940 Sq.Ft.10/6/2015Houghton Rd131$344,0001,270 Sq.Ft.11/9/2000Howard St332$358,3331,874 Sq.Ft.5/17/2022Howland Rd1N/AN/AN/AN/A11/4/2006Hughes Rd342$486,0002,475 Sq.Ft.N/AHunt Ave652$248,5001,883 Sq.Ft.1/13/2017Indian Pipe Rd432$407,5002,192 Sq.Ft.4/25/2011Industrial Pkwy1N/AN/AN/AN/A6/16/2010Ivy Ln342$383,5001,866 Sq.Ft.7/22/2024Jackson Rd332$435,0001,938 Sq.Ft.9/7/1988Jacksonville Stage Rd411$201,000700 Sq.Ft.1/10/2025Jelly Mill Hl132$342,000880 Sq.Ft.N/AJelly Mill Rd332$328,0001,373 Sq.Ft.7/19/2024Jenckes Rd163$813,0004,959 Sq.Ft.N/AJenny Ln732$453,8002,276 Sq.Ft.2/15/2024John Seitz Dr13N/AN/AN/A27,635 Sq.Ft.3/6/2023Josh Rd432$356,5001,801 Sq.Ft.1/7/2025Judd Rd133$426,0002,532 Sq.Ft.4/12/2021Juniper Ridge Rd833$604,8752,749 Sq.Ft.7/12/2024Justin Holden Dr1N/AN/AN/A102,851 Sq.Ft.N/AJust So Ln333$563,0002,305 Sq.Ft.8/19/2016Karen Dr532$314,0001,906 Sq.Ft.1/27/2022Kathan Meadow Rd1N/AN/AN/AN/A10/16/2000Kelly Rd242$599,0001,610 Sq.Ft.N/AKettle Hole Rd1N/AN/AN/AN/AN/AKing Ave332$267,0001,364 Sq.Ft.N/AKipling Rd2932$565,7272,120 Sq.Ft.1/14/2022Knapp Rd111$206,000572 Sq.Ft.8/16/2003Kyle Rd532$259,2001,160 Sq.Ft.7/28/2022Lake Rd23N/A$413,500902 Sq.Ft.N/ALamson St232$297,0001,434 Sq.Ft.2/4/2015Landmark Hill Dr553$338,5004,414 Sq.Ft.8/15/2019Larkin St443$316,0002,169 Sq.Ft.7/11/2024Larrabee Rd233$436,0002,052 Sq.Ft.7/20/2023Laurel St1532$344,0711,788 Sq.Ft.11/29/2024Lawrence St431$316,0001,528 Sq.Ft.10/27/2021Lawton Dr1832$313,1181,341 Sq.Ft.1/27/2025Ledgewood Hts Rd1N/AN/AN/A1,275 Sq.Ft.N/ALeft Bank Way342$266,3331,866 Sq.Ft.12/30/2019Legate Ln231$336,0001,140 Sq.Ft.8/2/2019Leverwood Ln221$209,500715 Sq.Ft.N/ALevi Howard Rd432$355,5002,085 Sq.Ft.11/12/2024Lexington Ave2432$290,7501,391 Sq.Ft.3/8/2021Lincoln Way132$299,0001,864 Sq.Ft.N/ALinden St2733$388,0004,946 Sq.Ft.2/20/2025Locust St942$338,7781,908 Sq.Ft.8/14/2023Lost Mile Rd422$391,5001,825 Sq.Ft.7/18/2024Lower Dover Rd1832$396,2672,003 Sq.Ft.6/1/2021Lower Houghton Rd141$308,0001,919 Sq.Ft.8/23/2012Lucier Rd732$375,0001,657 Sq.Ft.N/ALyman Hill Rd1N/AN/AN/AN/A6/25/2002Lynwood Dr2422$96,167897 Sq.Ft.4/24/2024Lyons St132$351,0001,765 Sq.Ft.5/17/2021Macintosh Ln443$537,7502,195 Sq.Ft.12/4/2020Main St17142$301,1183,537 Sq.Ft.2/27/2025Maple St4142$324,0001,965 Sq.Ft.8/30/2024Marlboro Ave3732$300,4321,287 Sq.Ft.5/21/2025Marlboro Rd6832$325,5523,910 Sq.Ft.1/17/2025Martel Way331$245,000959 Sq.Ft.8/8/2016Mather Rd1332$433,9091,959 Sq.Ft.5/31/2024Meadowbrook Rd5932$382,8243,195 Sq.Ft.8/25/2023Meeting House Ln1933$486,8132,376 Sq.Ft.7/7/2023Melchen Rd643$529,7501,655 Sq.Ft.6/6/2024Melendy Hill Rd333$372,5001,080 Sq.Ft.11/27/2009Melrose St1141$314,4292,503 Sq.Ft.11/1/2017Memorial Park Dr1N/AN/AN/A29,365 Sq.Ft.N/AMercury Dr3N/AN/AN/A9,240 Sq.Ft.12/10/2004Metcalf Ln332$387,0001,265 Sq.Ft.9/25/2018Metcalf Rd242$632,0002,570 Sq.Ft.6/1/2022Middle Rd3432$490,8752,043 Sq.Ft.5/31/2024Miller Rd1532$419,5452,488 Sq.Ft.11/4/2024Molly Stark Trl121$114,000936 Sq.Ft.8/1/2012Moonlight Ln233$671,0002,692 Sq.Ft.1/24/2025Moore Ct1N/AN/AN/A3,960 Sq.Ft.N/AMoreland Ave2342$279,1901,847 Sq.Ft.12/13/2024Morningside Cmns16622$222,9761,053 Sq.Ft.5/12/2025Moss Hollow Rd1232$371,4441,811 Sq.Ft.9/24/2021Mountain Home Park1932$95,667979 Sq.Ft.12/22/2022Mountain Rd531$385,5001,093 Sq.Ft.4/18/2013Mountain View Ave831$283,6671,345 Sq.Ft.9/11/2020Myrtle St1442$393,1432,347 Sq.Ft.12/22/2021Neringa Rd1N/AN/A$1,039,000N/A12/8/2020New England Dr1632$371,5001,682 Sq.Ft.10/30/2024Noahs Ln4N/AN/AN/A5,684 Sq.Ft.3/31/2022North St853$475,6253,097 Sq.Ft.10/1/2019Oak Crst442$416,5001,926 Sq.Ft.12/16/2024Oak Grove Ave4232$314,1621,905 Sq.Ft.10/13/2023Oak Hill Rd332$342,3331,796 Sq.Ft.3/12/2021Oak St3053$405,1673,121 Sq.Ft.6/28/2024Obryan Dr3N/AN/AN/A11,927 Sq.Ft.8/31/2018Old County Rd521$312,0001,403 Sq.Ft.7/21/1987Old Ferry Rd2432$487,00035,695 Sq.Ft.10/1/2024226 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
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
6 Cedar StHinsdale, NH 03451
Estimated Value $94,000
Living Area 936 SqFt
Beds 2
Baths 1.5
Year Built 1986
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:020 B:004 L:21-D
Municipality HINSDALE
School District Hinsdale School District
775 Plain RdHinsdale, NH 03451
Estimated Value $285,000
Living Area 840 SqFt
Beds 2
Baths 2
Year Built 1980
Property Type Single Family
Ownership Type Individual
APN HNDL M:034 B:007
Municipality HINSDALE
School District Hinsdale School District
33 Meadowview RdWest Chesterfield, NH 03466
Estimated Value $774,000
Living Area 3,058 SqFt
Beds 4
Baths 2.5
Year Built 2004
Property Type Single Family
Ownership Type Related
APN CHFD M:14 B:A012 L:15
Municipality CHESTERFIELD
School District Chesterfield 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
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
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
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
23 Pond RdHinsdale, NH 03451
Estimated Value $404,000
Living Area 1,416 SqFt
Beds 3
Baths 1
Year Built 2000
Property Type Single Family
Ownership Type Individual
APN HNDL M:020 B:051
Municipality HINSDALE
School District Hinsdale School District
92 Meadowview RdWest Chesterfield, NH 03466
Estimated Value $651,000
Living Area 2,130 SqFt
Beds 3
Baths 2
Year Built 2010
Property Type Single Family
Ownership Type Related
APN CHFD M:14 B:A012 L:18
Municipality CHESTERFIELD
School District Chesterfield School District
3 Park DrHinsdale, NH 03451
Estimated Value $86,000
Living Area 728 SqFt
Beds 2
Baths 1
Year Built 1981
Property Type Manufactured Homes
Ownership Type Related
APN HNDL M:024 B:110 L:28
Municipality HINSDALE
School District Hinsdale School District
10 Pierce RdHinsdale, NH 03451
Estimated Value $223,000
Living Area 1,000 SqFt
Beds 2
Baths 1
Year Built 1964
Property Type Single Family
Ownership Type Individual
APN HNDL M:024 B:049
Municipality HINSDALE
School District Hinsdale School District
39 Meetinghouse RdHinsdale, NH 03451
Estimated Value $213,000
Living Area 672 SqFt
Beds 2
Baths 1
Year Built 1949
Property Type Single Family
Ownership Type Individual
APN HNDL M:029 B:049
Municipality HINSDALE
School District Hinsdale 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
672 Oxbow RdHinsdale, NH 03451
Estimated Value $480,000
Living Area 2,386 SqFt
Beds 3
Baths 2
Year Built 2008
Property Type Rural Residence
Ownership Type Individual
APN HNDL M:034 B:017
Municipality HINSDALE
School District Hinsdale School District