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
Old Green River Rd221$215,000834 Sq.Ft.10/21/2020Old Guilford Rd2831$287,6361,372 Sq.Ft.9/5/2023Old Hogback Rd121N/A998 Sq.Ft.7/25/2013Old Rd2N/AN/A$263,000N/A12/22/2021Olive St632$372,7501,464 Sq.Ft.6/29/2018Olson Dr632$482,1671,815 Sq.Ft.12/20/2021Omega Dr1N/AN/AN/A11,680 Sq.Ft.N/AOrchard Rd443$588,5003,226 Sq.Ft.12/3/2010Orchard St4843$489,6102,437 Sq.Ft.8/4/2023Organ St1042$293,1001,880 Sq.Ft.12/4/2024Overlook Dr433$460,2501,759 Sq.Ft.7/31/2003Packer Corners Rd421$232,5001,345 Sq.Ft.9/20/2024Palmeto Dr232$338,0001,404 Sq.Ft.7/13/2018Park Elm St1N/AN/AN/AN/AN/APark Pl5N/AN/AN/A2,685 Sq.Ft.9/9/2021Parkside Ave731$276,5711,151 Sq.Ft.10/3/2022Parsons Rd421$411,7501,128 Sq.Ft.8/7/2012Partridge Rd832$388,8571,725 Sq.Ft.11/5/2024Peachtree Ln543$567,2503,369 Sq.Ft.1/3/2019Pearl St1342$310,6362,041 Sq.Ft.7/21/2023Pellet St632$293,6671,389 Sq.Ft.5/28/2019Perry Rd432$374,3331,453 Sq.Ft.9/25/2020Peterson Ln232$275,5001,699 Sq.Ft.11/20/2009Pike Rd221$167,000912 Sq.Ft.N/APine St2742$298,3041,769 Sq.Ft.5/2/2025Piney Brook Way344$617,0003,440 Sq.Ft.1/5/2021Pleasant St1142$296,2862,161 Sq.Ft.8/18/2023Pleasant Valley Rd1832$503,3572,141 Sq.Ft.5/1/2024Pond Dr242$346,0001,580 Sq.Ft.8/26/2015Pond Rd1732$419,8001,845 Sq.Ft.10/10/2019Pool Farm Rd132$323,0002,037 Sq.Ft.4/30/2021Poplar Cmns922$399,4441,736 Sq.Ft.6/3/2022Potters Hill Rd133$781,0002,977 Sq.Ft.3/4/2024Prospect Ct331$313,6671,494 Sq.Ft.5/1/2019Prospect St1843$343,4382,775 Sq.Ft.12/22/2023Prospect View Dr533$386,5001,896 Sq.Ft.10/29/2024Putnam Dr332$323,3332,072 Sq.Ft.4/3/2020Putney Rd12142$378,6678,624 Sq.Ft.5/2/2025Quails Hill Rd1632$520,6252,583 Sq.Ft.4/16/2025Randall Dr531$201,0001,108 Sq.Ft.10/21/2024Rath Dr1N/AN/AN/AN/AN/ARaven Rd331$429,3332,098 Sq.Ft.12/1/2010Record Dr1221$102,000986 Sq.Ft.6/14/2024Red Oak Rdg521$393,7501,900 Sq.Ft.3/28/2012Red Tail Ln332$297,5001,351 Sq.Ft.11/12/2024Reed Hill Rd2N/AN/A$266,000N/AN/AReed St153$261,0003,292 Sq.Ft.10/26/2005Regina Vis632$379,5001,584 Sq.Ft.7/28/2016Reservoir Rd632$94,500892 Sq.Ft.2/1/2024Retting Pl253$297,0002,793 Sq.Ft.N/AReynolds Dr453$220,2501,593 Sq.Ft.3/17/2021Rice Farm Rd132$478,0001,540 Sq.Ft.N/ARiver Rd7022$328,7782,036 Sq.Ft.2/12/2025Riverside Dr331$245,000100,959 Sq.Ft.12/30/2004Riverview St362$237,0002,080 Sq.Ft.12/9/2005Robin Way1221$264,0001,332 Sq.Ft.12/24/2024Roel Rd521$360,0001,195 Sq.Ft.7/27/2023Route 93032$296,9091,499 Sq.Ft.10/14/2024Royal Rd174N/A4,417 Sq.Ft.N/ASaw Mill Rd1N/AN/A$300,000N/A2/16/2023School Rd111$317,0001,008 Sq.Ft.N/ASchool St553$401,5002,474 Sq.Ft.11/3/2022Scott Rd322$299,0001,149 Sq.Ft.8/30/2005Senator Gannett Dr1N/AN/AN/A4,861 Sq.Ft.9/30/2014Serkin Rd343$354,0001,778 Sq.Ft.9/28/2018Shadow Lawn332$356,0001,820 Sq.Ft.4/15/2022Shearer Hill Rd1942$631,1672,229 Sq.Ft.10/25/2024Sherwood Cir4232$317,5611,255 Sq.Ft.5/29/2024Shore Dr342$441,000792 Sq.Ft.9/9/2022Signal Hill Dr932$356,8751,728 Sq.Ft.10/1/2019Slate Rock Rd1532$380,8571,766 Sq.Ft.4/4/2023Snow Mountain Ln332$411,0001,913 Sq.Ft.8/22/2023Sodom Rd332$408,6671,784 Sq.Ft.5/23/2016Southern Ave1332$297,6251,468 Sq.Ft.11/30/2022South Rd1432$416,7141,888 Sq.Ft.11/4/2022South St5232$450,7692,493 Sq.Ft.12/20/2024Spalding Hill Rd132$573,0002,234 Sq.Ft.N/ASpeno Ct731$306,7141,270 Sq.Ft.10/3/2024Spring St422$251,0001,877 Sq.Ft.7/6/2006Spring Tree Rd822$280,0003,824 Sq.Ft.12/1/2022Spruce St2842$364,9292,229 Sq.Ft.1/7/2025Stafford Farm Hill Rd1N/AN/AN/A4,465 Sq.Ft.3/28/2003Stark Rd1032$495,2861,887 Sq.Ft.5/3/2021Staver Rd443$674,0003,475 Sq.Ft.11/10/2021Stearns Rd221$527,5001,804 Sq.Ft.10/4/2017Stewart Pl442$325,0001,715 Sq.Ft.9/6/2012Stickney Brook Rd221$288,0001,207 Sq.Ft.11/7/2017Stockwell Dr1532$320,3641,285 Sq.Ft.4/1/2025Stone Boat Row332$369,5001,913 Sq.Ft.7/6/2017Stonewall Dr1821$87,333930 Sq.Ft.3/14/2024Stony Hill Rd133$476,0003,165 Sq.Ft.11/6/2020Strand Ave532$307,8001,643 Sq.Ft.8/1/2024Stratton Hill Rd521$153,200691 Sq.Ft.10/28/2019Strawberry Hl243$535,5002,857 Sq.Ft.11/8/2024Summit Cir1932$514,6929,478 Sq.Ft.5/1/2025Sunny Acres Rd2131$285,5241,270 Sq.Ft.4/27/2023Sunset Lake Rd6732$397,9271,688 Sq.Ft.4/12/2024Susan Lynn Ln932$360,1111,260 Sq.Ft.3/13/2024Sutherland Rd242$288,5001,313 Sq.Ft.N/ASweet Pond Rd232$457,5001,061 Sq.Ft.6/14/2022595 Brattleboro RdHinsdale, NH 03451
Estimated Value $338,000
Living Area 1,764 SqFt
Beds 3
Baths 2
Year Built 1949
Property Type Single Family
Ownership Type Individual
APN HNDL M:019 B:006
Municipality HINSDALE
School District Hinsdale School District
37 Gateway DrHinsdale, NH 03451
Estimated Value $102,000
Living Area 924 SqFt
Beds 3
Baths 1
Year Built 1979
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:024 B:110 L:56
Municipality HINSDALE
School District Hinsdale School District
188 Monument RdHinsdale, NH 03451
Estimated Value $322,000
Living Area 1,386 SqFt
Beds 4
Baths 2
Year Built 1977
Property Type Single Family
Ownership Type Individual
APN HNDL M:024 B:096
Municipality HINSDALE
School District Hinsdale School District
34 Mountain RdWest Chesterfield, NH 03466
Estimated Value $300,000
Living Area 550 SqFt
Beds 1
Baths 1
Year Built 1920
Property Type Single Family
Ownership Type Corporate
APN CHFD M:14-C B:B003
Municipality CHESTERFIELD
School District Chesterfield School District
26 Meadowview RdWest Chesterfield, NH 03466
Estimated Value $667,000
Living Area 2,753 SqFt
Beds 3
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Related
APN CHFD M:14 B:A012 L:4
Municipality CHESTERFIELD
School District Chesterfield School District
625 Plain RdHinsdale, NH 03451
Estimated Value $289,000
Living Area 1,466 SqFt
Beds 3
Baths 1
Year Built 1880
Property Type Single Family
Ownership Type Individual
APN HNDL M:030 B:038
Municipality HINSDALE
School District Hinsdale School District
5 Keene DrHinsdale, NH 03451
Estimated Value $106,000
Living Area 672 SqFt
Beds 2
Baths 1
Year Built 1974
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:024 B:110 L:44
Municipality HINSDALE
School District Hinsdale School District
141 Old Ferry RdWest Chesterfield, NH 03466
Estimated Value $732,000
Living Area 3,629 SqFt
Beds 4
Baths 3
Year Built 2006
Property Type Single Family
Ownership Type Corporate
APN CHFD M:13 B:A008
Municipality CHESTERFIELD
School District Chesterfield School District
725 Plain RdHinsdale, NH 03451
Estimated Value $244,000
Living Area 1,134 SqFt
Beds 3
Baths 2.5
Year Built 2010
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:034 B:001 L:5
Municipality HINSDALE
School District Hinsdale School District
23 Merrifield RdWest Chesterfield, NH 03466
Estimated Value $579,000
Living Area 2,736 SqFt
Beds 3
Baths 2.5
Year Built 1990
Property Type Single Family
Ownership Type Individual
APN CHFD M:24 B:B001
Municipality CHESTERFIELD
School District Chesterfield 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
43 Asgard RdWest Chesterfield, NH 03466
Estimated Value $409,000
Living Area 1,526 SqFt
Beds 3
Baths 1
Year Built 1978
Property Type Single Family
Ownership Type Multiple
APN CHFD M:14 B:A009
Municipality CHESTERFIELD
School District Chesterfield School District
690 Oxbow RdHinsdale, NH 03451
Estimated Value $350,000
Living Area 1,062 SqFt
Beds 2
Baths 2
Year Built 1973
Property Type Single Family
Ownership Type Individual
APN HNDL M:034 B:015
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
19 Paddock DrHinsdale, NH 03451
Estimated Value $96,000
Living Area 876 SqFt
Beds 2
Baths 1
Year Built 1995
Property Type Manufactured Homes
Ownership Type Individual
APN HNDL M:024 B:015 L:7
Municipality HINSDALE
School District Hinsdale School District
66 Meadowview RdWest Chesterfield, NH 03466
Estimated Value $677,000
Living Area 2,870 SqFt
Beds 4
Baths 2.5
Year Built 2003
Property Type Single Family
Ownership Type Related
APN CHFD M:14 B:A012 L:9
Municipality CHESTERFIELD
School District Chesterfield School District