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
42nd St231$362,0001,206 Sq.Ft.1/24/2025Abbott Rd1942$369,8751,988 Sq.Ft.5/6/2021Acorn Ln321$270,333988 Sq.Ft.6/14/2006Adams Cross Rd211$117,0001,075 Sq.Ft.4/15/2022Akley Rd1N/AN/AN/AN/A1/31/2023Allerton Ave1732$351,1181,653 Sq.Ft.10/18/2022Ames Hill Rd4732$525,7582,306 Sq.Ft.1/29/2025Apple Tree Rd342$432,3332,294 Sq.Ft.9/12/2003Arbor Hill Cmn2422$290,1301,445 Sq.Ft.3/19/2025Arch St3N/AN/A$468,000N/AN/AAtwood St1131$250,8891,620 Sq.Ft.11/29/2012Augur Hole Rd1422$232,9001,254 Sq.Ft.9/20/2022Austine Dr1N/AN/AN/A26,499 Sq.Ft.1/27/2016Autumn Hill Dr1532$150,00059,987 Sq.Ft.2/1/2023Baker St832$259,0001,618 Sq.Ft.12/30/2022Baldwin St332$297,0001,394 Sq.Ft.9/20/2011Ballou Mountain Rd221$218,000920 Sq.Ft.10/14/2022Banks Rd332$372,3331,988 Sq.Ft.N/ABarney Hill Rd1N/AN/AN/AN/AN/ABarred Owl Ln243$643,0002,305 Sq.Ft.9/20/2016Barrows Rd1432$485,2501,910 Sq.Ft.7/24/2020Bear Hl632$366,8331,621 Sq.Ft.8/23/2024Beaver Pond Rd432$364,5002,011 Sq.Ft.8/16/2004Beech St532$286,4001,546 Sq.Ft.8/20/2021Belair Dr121N/A696 Sq.Ft.7/6/2010Belmont Ave3531$300,7393,793 Sq.Ft.10/18/2022Bennett Dr4N/AN/AN/A25,292 Sq.Ft.2/16/2016Birge St3032$276,2004,105 Sq.Ft.8/5/2022Bittersweet Ln643$415,2501,880 Sq.Ft.3/15/2024Black Mountain Rd6432$460,7572,816 Sq.Ft.4/24/2025Blakeslee St1732$318,1181,753 Sq.Ft.4/26/2023Blanche Moyse Way1N/AN/AN/A14,973 Sq.Ft.7/8/2016Bonnyvale Ln732$336,0001,408 Sq.Ft.1/22/2021Bonnyvale Rd5432$325,2274,505 Sq.Ft.5/7/2025Bradford Dr1N/AN/AN/A7,671 Sq.Ft.11/20/2020Bradley Ave432$392,6673,450 Sq.Ft.2/13/2020Brannen St342$300,6671,805 Sq.Ft.8/4/2017Brattle St2431$290,5001,402 Sq.Ft.5/9/2023Brets Rd832$411,7501,497 Sq.Ft.7/26/2024Bridge St3N/AN/AN/A7,225 Sq.Ft.8/22/2024Briggs Rd832$422,4291,385 Sq.Ft.9/11/2024Brisk Ln2N/AN/AN/A4,725 Sq.Ft.9/15/2023Broad Brook Rd122$295,0001,734 Sq.Ft.3/30/2007Brookside Dr4721$143,804878 Sq.Ft.5/23/2025Brook St1042$310,1252,450 Sq.Ft.6/6/2023Browne Ct422$391,000100,835 Sq.Ft.2/9/2022Browns Way223$487,5001,569 Sq.Ft.12/9/2019Bucklin Hill Rd231$377,0001,558 Sq.Ft.10/19/2012Bullock St652$331,1672,304 Sq.Ft.10/5/2018Burgess Way432$380,0001,305 Sq.Ft.6/22/2022Butterfield Rd1432$445,5562,206 Sq.Ft.6/7/2021Butterfly Ln362$290,0001,898 Sq.Ft.8/3/2021Butternut Hill Rd121$307,0002,032 Sq.Ft.N/AButtonwood Dr111N/A1,276 Sq.Ft.3/20/2012Camp Arden Rd422$416,0001,499 Sq.Ft.11/10/2021Canal St10342$271,8793,935 Sq.Ft.12/6/2024Cannon Rd422$359,5001,122 Sq.Ft.5/31/2022Capy Way12N/AN/A951 Sq.Ft.N/ACareer Cir532$312,0001,320 Sq.Ft.2/24/2017Carpenter Hill Rd242$417,0002,649 Sq.Ft.8/20/2021Carriage Hill Rd6232$306,8231,250 Sq.Ft.2/28/2025Cedar St3642$338,4232,459 Sq.Ft.12/1/2022Cemetary Rd1032$417,3001,654 Sq.Ft.8/18/2022Central St2042$288,4212,147 Sq.Ft.11/15/2024Chapin St1753$400,8002,972 Sq.Ft.10/4/2021Chase St1632$352,3642,128 Sq.Ft.11/1/2024Cherry St1142$347,7271,957 Sq.Ft.10/1/2021Chestnut Hl1842$434,6883,826 Sq.Ft.9/19/2023Chestnut St7042$294,5631,777 Sq.Ft.12/31/2024Chickering Dr5N/AN/AN/A11,999 Sq.Ft.9/26/2018Christie Ln332$292,6671,461 Sq.Ft.10/22/2020Church Hollow Rd632$479,0002,420 Sq.Ft.1/4/2022Church Pl342$178,0001,620 Sq.Ft.1/19/2022Church St1N/AN/AN/AN/A4/1/2014Cider Mill Hl621$358,0001,091 Sq.Ft.10/7/2024Clark Ave3832$288,8651,408 Sq.Ft.1/31/2023Clark Rd532$316,5001,289 Sq.Ft.7/29/2022Clark St3642$266,8241,767 Sq.Ft.5/27/2025Clay Dr1N/AN/A$313,000N/A3/9/2007Coach Rd432$321,0002,265 Sq.Ft.8/8/2024Collins Rd2932$393,1151,823 Sq.Ft.10/3/2022Colonial Dr1N/AN/AN/A5,302 Sq.Ft.9/30/2019Colyer Rd333$756,0002,574 Sq.Ft.7/26/2012Connecticut River Dr332$403,6671,370 Sq.Ft.12/20/2018Cooke Rd531$417,8001,517 Sq.Ft.3/25/2019Coolidge Hwy742$275,0002,128 Sq.Ft.3/6/2024Corey Cir1N/AN/A$176,000N/AN/ACorner Rd1N/AN/A$572,000N/AN/ACortland Ln232$356,0002,300 Sq.Ft.7/2/2003Cottage St842$346,1431,876 Sq.Ft.10/6/2021Cotton Mill Hl441$485,00021,966 Sq.Ft.4/30/2024Country Dr232$448,0001,664 Sq.Ft.2/28/2014Country Hl3032$368,7241,647 Sq.Ft.4/1/2025Country Ln133$345,0004,126 Sq.Ft.N/ACovey Rd1131$327,3751,520 Sq.Ft.11/21/2022Cow Path252$597,0002,308 Sq.Ft.3/10/2020Cowpath 40222$372,500551 Sq.Ft.9/14/2020Creamery Rd1N/AN/AN/AN/AN/ACrescent Dr2621$79,875837 Sq.Ft.3/26/2024Crosby St1042$301,0001,796 Sq.Ft.1/22/202530 Merrifield RdWest Chesterfield, NH 03466
Estimated Value $541,000
Living Area 2,227 SqFt
Beds 2
Baths 1.5
Year Built 1981
Property Type Single Family
Ownership Type Related
APN CHFD M:24 B:A005
Municipality CHESTERFIELD
School District Chesterfield School District
130 Farr RdWest Chesterfield, NH 03466
Estimated Value $431,000
Living Area 1,457 SqFt
Beds 3
Baths 1
Year Built 1986
Property Type Single Family
Ownership Type Individual
APN CHFD M:13-B B:C004
Municipality CHESTERFIELD
School District Chesterfield School District
680 Oxbow RdHinsdale, NH 03451
Estimated Value $247,000
Living Area 1,334 SqFt
Beds 2
Baths 2
Year Built 2011
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:034 B:016
Municipality HINSDALE
School District Hinsdale School District
10 Springbrook StHinsdale, NH 03451
Estimated Value $99,000
Living Area 924 SqFt
Beds 2
Baths 2
Year Built 1994
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:020 B:004 L:13-B
Municipality HINSDALE
School District Hinsdale School District
22 Hillcrest StHinsdale, NH 03451
Estimated Value $121,000
Living Area 1,328 SqFt
Beds 3
Baths 2
Year Built 1988
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:020 B:004 L:16-A
Municipality HINSDALE
School District Hinsdale School District
742 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
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
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
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
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
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
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
313 Oxbow RdHinsdale, NH 03451
Estimated Value $250,000
Living Area 1,568 SqFt
Beds 3
Baths 2
Year Built 2007
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:033 B:008
Municipality HINSDALE
School District Hinsdale School District
238 Route 9West Chesterfield, NH 03466
Estimated Value $416,000
Living Area 1,961 SqFt
Beds 3
Baths 2
Year Built 1972
Property Type Single Family
Ownership Type Related
APN CHFD M:14-B B:B004
Municipality CHESTERFIELD
School District Chesterfield School District
46 Meadowview RdWest Chesterfield, NH 03466
Estimated Value $677,000
Living Area 2,271 SqFt
Beds 3
Baths 2.5
Year Built 2007
Property Type Single Family
Ownership Type Multiple
APN CHFD M:14 B:A012 L:7
Municipality CHESTERFIELD
School District Chesterfield School District
60 Oak Hill RdHinsdale, NH 03451
Estimated Value $196,000
Living Area 1,296 SqFt
Beds 3
Baths 2
Year Built 2001
Property Type Manufactured Homes
Ownership Type Related
APN HNDL M:024 B:062
Municipality HINSDALE
School District Hinsdale School District