Bennington is a charming New England town that is steeped in history and surrounded by natural beauty. Its strategic location, cultural richness, and affordability contribute to its growing appeal, which has not gone unnoticed among homebuyers, renters, and investors. One of Bennington's advantages is its location in southern Vermont. It’s close to major metropolitan areas like Albany, New York, and Boston, making it an appealing destination for commuters and remote workers who desire a quieter, more affordable lifestyle.
Historic landmarks like the Bennington Battle Monument and Old First Church attract history enthusiasts and tourists all year-round. The local arts scene which includes galleries, theaters, and craft fairs, enhances the town’s vibrancy and supports vacation rental opportunities.
Surrounded by the Green Mountains, the town offers a wealth of outdoor activities all year round, boosting the demand for short-term rental properties. Property prices remain relatively low when compared to larger cities, offering investors a chance to enter the market at a manageable price point with the potential for steady appreciation.
Popular Streets in Bennington, Vermont
Branch St14332$215,2301,588 Sq.Ft.4/25/2025Burgess Rd9331$230,5321,484 Sq.Ft.4/30/2025Chapel Rd13231$207,5525,644 Sq.Ft.3/31/2025East Rd11131$249,5202,836 Sq.Ft.6/27/2025Gage St11842$213,8292,023 Sq.Ft.6/2/2025Main St21442$233,2214,583 Sq.Ft.6/6/2025Morgan St8032$237,7331,311 Sq.Ft.12/9/2024Park St8032$192,6762,051 Sq.Ft.5/16/2025South St9832$197,7003,222 Sq.Ft.6/13/2025Stream Rd10632$286,1289,244 Sq.Ft.11/18/2024All Streets in Bennington, Vermont
Abbott St4032$108,5381,163 Sq.Ft.5/30/2025Abby Ln1N/AN/AN/AN/AN/AAdams St1132$238,0001,843 Sq.Ft.6/15/2021Airport Rd842$168,1671,372 Sq.Ft.8/25/2014Albe Dr2132$261,4761,381 Sq.Ft.9/12/2023Andre Ln531$247,4001,110 Sq.Ft.3/6/2025Andrian Dr332$202,6671,400 Sq.Ft.N/AAnthony Dr1432$245,2861,410 Sq.Ft.11/8/2024Applegate Dr1N/AN/AN/AN/A7/27/2016Apple Hill Rd1632$373,2312,233 Sq.Ft.2/13/2025Appletree Ln243$365,0002,157 Sq.Ft.7/18/2007Arthurs Dr331$158,333979 Sq.Ft.7/20/2023Astrachan Dr632$297,6001,597 Sq.Ft.3/29/2024Audrey Ln322$125,3331,134 Sq.Ft.4/24/2013Austin Hill Rd1133$389,1002,153 Sq.Ft.8/19/2024Austin Hill Rd At Bard Rd1N/AN/AN/AN/AN/AAutumn Acres1232$289,6671,454 Sq.Ft.7/16/2024Baker Dr1222$164,0001,189 Sq.Ft.12/9/2024Bank St1343$424,6672,321 Sq.Ft.6/7/2022Barber St832$237,8751,301 Sq.Ft.11/22/2024Barbs Way332$206,0001,476 Sq.Ft.9/1/2015Bard Rd1032$352,2001,719 Sq.Ft.3/19/2019Barney Rd1931$209,8671,270 Sq.Ft.11/9/2023Beach Rd1821$252,778976 Sq.Ft.6/8/2022Beaudoin Ln342$376,0003,075 Sq.Ft.N/ABecks Dr243$430,5001,977 Sq.Ft.1/20/2015Bedrock Rd2N/AN/A$177,0002,304 Sq.Ft.2/24/2012Beech St7731$205,7861,482 Sq.Ft.6/11/2025Bell St1932$113,3161,070 Sq.Ft.3/13/2024Belvedere St731$220,0001,159 Sq.Ft.3/2/2023Benmont Ave5063$269,6792,822 Sq.Ft.6/10/2025Bennington Byp731$253,8002,038 Sq.Ft.10/31/2022Bennington Plz1N/AN/AN/AN/AN/ABennington Rd1332$266,2868,594 Sq.Ft.8/17/2023Bennington Sq3N/AN/AN/A50,317 Sq.Ft.4/14/2020Bennington Town1N/AN/AN/AN/AN/ABennington Vlg1N/AN/AN/AN/AN/ABerard St143$273,0002,401 Sq.Ft.N/ABickford Hollow Rd233$265,0001,225 Sq.Ft.10/21/1992Birch Dr632$302,1671,648 Sq.Ft.2/2/2011Birch Rd821$207,6251,025 Sq.Ft.7/27/2012Bird Hl1N/AN/AN/AN/AN/ABlackberry Ln742$379,8331,997 Sq.Ft.9/13/2024Bluestone Rd943$474,8002,988 Sq.Ft.8/7/2024Booth Ter832$206,0001,450 Sq.Ft.11/6/2023Boudreau Ln132N/A1,048 Sq.Ft.N/ABowen Rd1422$183,2867,573 Sq.Ft.1/24/2023Bradford St3432$213,5451,564 Sq.Ft.3/5/2025Bradley Dr1432$259,0771,333 Sq.Ft.7/11/2022Brambley Ln631$212,6001,043 Sq.Ft.3/25/2020Branch St14332$215,2301,588 Sq.Ft.4/25/2025Bridge St332$282,3331,155 Sq.Ft.6/21/2004Broken Pines Dr421$276,3331,440 Sq.Ft.10/24/2003Brookside Dr532$181,5001,104 Sq.Ft.11/30/2017Browning Pl531$177,4001,322 Sq.Ft.6/20/2025Bryce Rd1N/AN/AN/AN/A7/8/2010Buckley Dr731$243,0001,303 Sq.Ft.3/8/2016Burgess Rd9331$230,5321,484 Sq.Ft.4/30/2025Camp Rd821$198,000826 Sq.Ft.7/28/2023Cardinal Ln732$382,4292,003 Sq.Ft.5/1/2020Caroline Dr931$216,62511,893 Sq.Ft.1/21/2022Carpenter Hill Rd3832$340,7142,015 Sq.Ft.12/12/2024Carpenter Ln331$230,3331,239 Sq.Ft.3/19/2021Carver St622$105,333915 Sq.Ft.7/2/2001Cassie Ln622$86,833868 Sq.Ft.5/13/2024Catamount Ln454$533,7503,558 Sq.Ft.12/20/2021Center St4232$254,7381,253 Sq.Ft.8/27/2024Chandler Way333$634,0003,255 Sq.Ft.9/16/2013Chapel Rd13231$207,5525,644 Sq.Ft.3/31/2025Charles St631$174,6671,148 Sq.Ft.3/8/2024Chester Knoll Dr3332$240,7271,368 Sq.Ft.3/6/2025Chimes St531$197,4001,082 Sq.Ft.7/23/2021Church Ln233$362,0002,053 Sq.Ft.10/8/2021City Stream Rd322$282,0001,192 Sq.Ft.8/4/2022Clyde St532$247,6001,309 Sq.Ft.8/17/2006Coleville Rd4132$299,2501,784 Sq.Ft.11/21/2022Colgate Hts1N/AN/AN/AN/A4/21/2023College Dr1N/AN/AN/AN/AN/ACongress St1142$232,7271,699 Sq.Ft.4/13/2021Convent Ave2632$289,4581,720 Sq.Ft.7/10/2024Coolidge Ave1831$198,3891,244 Sq.Ft.8/12/2024Corcorans Way431$207,7501,126 Sq.Ft.5/3/2018Corey Ln1232$272,0831,328 Sq.Ft.7/25/2024Cortland Ln332$376,0002,206 Sq.Ft.3/22/2002Coulter St1132$289,4551,718 Sq.Ft.1/12/2024Country Club Dr1N/AN/AN/AN/A12/20/2006County St6542$203,1172,665 Sq.Ft.5/7/2025Cow Path Ln1N/AN/AN/AN/AN/ACrahan Way134$499,0002,460 Sq.Ft.N/ACrescent Blvd3032$339,1483,129 Sq.Ft.6/20/2025Crescent Ln221$253,000800 Sq.Ft.12/12/2008Crestwood Dr832$337,0003,702 Sq.Ft.3/30/2023Crossover Rd1931$239,0001,393 Sq.Ft.10/25/2024Cross Rd432$282,7501,560 Sq.Ft.8/16/2024Cross St1331$194,6921,237 Sq.Ft.9/29/2017Cutler St542$246,4002,192 Sq.Ft.7/15/2022Cyr Ct3232$241,9061,352 Sq.Ft.7/20/2022Darling St731$207,0001,096 Sq.Ft.5/29/2020Depot St4242$220,7004,649 Sq.Ft.7/2/2024Dermody Rd3032$253,1431,643 Sq.Ft.12/4/2024620 South StHoosick Falls, NY 12090
Estimated Value $184,000
Living Area 972 SqFt
Beds 2
Baths 1
Year Built 1986
Property Type Residential Vacant Land
Ownership Type Related
APN 382889 48.-1-18
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
415 N Hemlock LnWilliamstown, MA 01267
Estimated Value $563,000
Living Area 2,073 SqFt
Beds 3
Baths 3
Year Built 1988
Property Type Condominium
Ownership Type Related
APN WILL M:128.0 B:0042 L:0415.0
Municipality WILLIAMSTOWN
School District Mount Greylock School District
4947 State Route 7Hoosick Falls, NY 12090
Estimated Value $191,000
Living Area 1,105 SqFt
Beds 3
Baths 1
Year Built 1800
Property Type Single Family
Ownership Type Individual
APN 382889 48.1-1-2
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
328 North StWilliamstown, MA 01267
Estimated Value $360,000
Living Area 1,344 SqFt
Beds 3
Baths 1.5
Year Built 1900
Property Type Single Family
Ownership Type Individual
APN WILL M:128.0 B:0904
Municipality WILLIAMSTOWN
School District Mount Greylock School District
817 N Hoosac RdWilliamstown, MA 01267
Estimated Value $337,000
Living Area 1,432 SqFt
Beds 3
Baths 1.5
Year Built 1949
Property Type Single Family
Ownership Type Multiple
APN WILL M:118.0 B:0061
Municipality WILLIAMSTOWN
School District Mount Greylock School District
20289 State Route 22Petersburg, NY 12138
Estimated Value $122,000
Living Area 1,080 SqFt
Beds 2
Baths 1
Year Built 1951
Property Type Single Family
Ownership Type Individual
APN 383400 68.-1-7
Municipality PETERSBURG
78 Summer StWilliamstown, MA 01267
Estimated Value $581,000
Living Area 1,889 SqFt
Beds 2
Baths 1
Year Built 1951
Property Type Single Family
Ownership Type Multiple
APN WILL M:117.0 B:0125
Subdivision Charles E Bridges
School District Mount Greylock School District
44 Mountain View StWilliamstown, MA 01267
Estimated Value $301,000
Living Area 1,458 SqFt
Beds 2
Baths 1
Year Built 1955
Property Type Single Family
Ownership Type Individual
APN WILL M:126.0 B:0903
Municipality WILLIAMSTOWN
School District Mount Greylock School District
128 White Oaks RdWilliamstown, MA 01267
Estimated Value $328,000
Living Area 1,355 SqFt
Beds 2
Baths 2
Year Built 1850
Property Type Single Family
Ownership Type Related
APN WILL M:117.0 B:0020
Municipality WILLIAMSTOWN
School District Mount Greylock School District
179 Breese Hollow RdHoosick Falls, NY 12090
Estimated Value $243,000
Living Area 1,134 SqFt
Beds 2
Baths 2
Year Built 2002
Property Type Single Family
Ownership Type Trust
APN 382889 58.-2-3
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
50 May StWilliamstown, MA 01267
Estimated Value $658,000
Living Area 2,670 SqFt
Beds 4
Baths 2
Year Built 1932
Property Type Single Family
Ownership Type Individual
APN WILL M:118.0 B:0019
Municipality WILLIAMSTOWN
School District Mount Greylock School District
351 South StHoosick Falls, NY 12090
Estimated Value $372,000
Living Area 1,760 SqFt
Beds 2
Baths 3
Year Built 1973
Property Type Single Family
Ownership Type Related
APN 382889 58.-2-22
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
20346 State Route 22Petersburg, NY 12138
Estimated Value $234,000
Living Area 1,316 SqFt
Beds 3
Baths 1
Year Built 1947
Property Type Single Family
Ownership Type Individual
APN 383400 68.-2-34
Municipality PETERSBURG
School District Hoosick Falls Central School District
23 Sand Springs RdWilliamstown, MA 01267
Estimated Value $308,000
Living Area 1,358 SqFt
Beds 3
Baths 1.5
Year Built 1989
Property Type Single Family
Ownership Type Related
APN WILL M:116.0 B:0024
Municipality WILLIAMSTOWN
School District Mount Greylock School District
1139 N Hoosac RdWilliamstown, MA 01267
Estimated Value $253,000
Living Area 1,012 SqFt
Beds 2
Baths 1
Year Built 1929
Property Type Single Family
Ownership Type Related
APN WILL M:127.0 B:0137
Municipality WILLIAMSTOWN
School District Mount Greylock School District
57 Harrison AveWilliamstown, MA 01267
Estimated Value $296,000
Living Area 1,188 SqFt
Beds 3
Baths 1
Year Built 1948
Property Type Single Family
Ownership Type Individual
APN WILL M:117.0 B:0013
Municipality WILLIAMSTOWN
School District Mount Greylock School District