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.4/30/2025Gage St11842$213,8292,023 Sq.Ft.4/7/2025Main St21442$233,2214,583 Sq.Ft.5/30/2025Morgan St8032$237,7331,311 Sq.Ft.12/9/2024Park St8032$192,6762,051 Sq.Ft.5/16/2025South St9832$197,7003,222 Sq.Ft.5/23/2025Stream Rd10632$286,1281,771 Sq.Ft.11/18/2024All Streets in Bennington, Vermont
Abbott St4032$108,5381,163 Sq.Ft.4/23/2024Abby 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.2/3/2025Bell St1932$113,3161,070 Sq.Ft.3/13/2024Belvedere St731$220,0001,159 Sq.Ft.3/2/2023Benmont Ave5063$269,6792,822 Sq.Ft.4/29/2025Bennington 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.12/29/2023Bryce 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.12/13/2024Crescent 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.12/4/2024417 State Route 346Petersburg, NY 12138
Estimated Value $247,000
Living Area 2,964 SqFt
Beds 3
Baths 3
Year Built 1993
Property Type Rural Residence
Ownership Type Related
APN 383400 68.-2-9.23
Municipality PETERSBURG
School District Hoosick Falls Central School District
259 State Line RdEagle Bridge, NY 12057
Estimated Value $296,000
Living Area 2,124 SqFt
Beds 5
Baths 2
Year Built 1800
Property Type Rural Residence
Ownership Type Individual
APN 535089 293.-1-4
Municipality WHITE CREEK (TOV)
School District Hoosick Falls Central School District
5020 State Route 7Hoosick Falls, NY 12090
Estimated Value $265,000
Living Area 2,400 SqFt
Beds 4
Baths 3
Year Built 1905
Property Type Single Family
Ownership Type Multiple
APN 382889 48.1-3-16
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
62 Cobble Hill RdEagle Bridge, NY 12057
Estimated Value $395,000
Living Area 1,140 SqFt
Beds 3
Baths 1
Year Built 1961
Property Type Single Family
Ownership Type Individual
APN 382889 17.-3-5
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
1243 County Route 68Eagle Bridge, NY 12057
Estimated Value $207,000
Living Area 3,524 SqFt
Beds 5
Baths 2.5
Year Built 1990
Property Type Duplex 2 Units
Ownership Type Individual
APN 535089 284.-1-5
Municipality WHITE CREEK (TOV)
School District Hoosick Falls Central School District
6 Stark StHoosick Falls, NY 12090
Estimated Value $474,000
Living Area 2,460 SqFt
Beds 5
Baths 3.5
Year Built 1989
Property Type Single Family
Ownership Type Related
APN 382801 37.8-1-1.12
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
5052 State Route 67Hoosick Falls, NY 12090
Estimated Value $121,000
Living Area 600 SqFt
Beds 1
Baths 1
Year Built 1975
Property Type Single Family
Ownership Type Multiple
APN 382889 18.-1-38
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
1061 County Route 68Eagle Bridge, NY 12057
Estimated Value $200,000
Living Area 1,128 SqFt
Beds 2
Baths 1
Year Built 1900
Property Type Single Family
Ownership Type Individual
APN 535089 283.-2-25
Municipality WHITE CREEK (TOV)
School District Hoosick Falls Central School District
8 Abbott StHoosick Falls, NY 12090
Estimated Value $367,000
Living Area 1,184 SqFt
Beds 2
Baths 2
Year Built 1900
Property Type Single Family
Ownership Type Individual
APN 382801 27.15-11-19
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
10 Ball StHoosick Falls, NY 12090
Estimated Value $126,000
Living Area 1,494 SqFt
Beds 3
Baths 1
Year Built 1900
Property Type Single Family
Ownership Type Individual
APN 382801 27.15-9-12
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
1 Cross Hill RdEagle Bridge, NY 12057
Estimated Value $355,000
Living Area 2,193 SqFt
Beds 3
Baths 2
Year Built 2021
Property Type Single Family
Ownership Type Related
APN 535089 284.-1-2
Municipality WHITE CREEK (TOV)
School District Hoosick Falls Central School District
147 E Hoosick RdHoosick Falls, NY 12090
Estimated Value $330,000
Living Area 2,246 SqFt
Beds 4
Baths 2
Year Built 1810
Property Type Rural Residence
Ownership Type Related
APN 382889 38.-1-1.111
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
77 Wilder AveHoosick Falls, NY 12090
Estimated Value $175,000
Living Area 1,752 SqFt
Beds 3
Baths 1.5
Year Built 1888
Property Type Single Family
Ownership Type Individual
APN 382801 27.16-5-1
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
660 South StHoosick Falls, NY 12090
Estimated Value $177,000
Living Area 2,498 SqFt
Beds 3
Baths 2
Year Built 1880
Property Type Duplex 2 Units
Ownership Type Individual
APN 382889 48.1-3-25
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
84 Rogers AveHoosick Falls, NY 12090
Estimated Value $225,000
Living Area 1,863 SqFt
Beds 3
Baths 2.5
Year Built 1999
Property Type Single Family
Ownership Type Individual
APN 382801 37.7-6-1.22
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
655 Breese Hollow RdHoosick Falls, NY 12090
Estimated Value $277,000
Living Area 1,620 SqFt
Beds 3
Baths 2
Year Built 2001
Property Type Single Family
Ownership Type Related
APN 382889 39.-1-10.121
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District