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
Dewey St7442$253,9212,169 Sq.Ft.2/21/2025Division Pl432$148,000935 Sq.Ft.8/7/2024Division St2642$210,7201,821 Sq.Ft.5/12/2025Dove Rd421$202,0001,250 Sq.Ft.5/20/2022Dudley Pl732$113,286878 Sq.Ft.6/7/2022Duffy Dr2332$322,0451,574 Sq.Ft.3/29/2024Dustin Dr431$105,000889 Sq.Ft.10/19/2012Dutch Haven Rd221$220,0001,144 Sq.Ft.N/AEarls Dr832$216,4291,412 Sq.Ft.3/29/2013East Rd11131$249,5202,836 Sq.Ft.4/30/2025Eastside Dr332$315,3331,962 Sq.Ft.1/26/2023East St4632$248,5651,217 Sq.Ft.1/6/2023Eastview Dr942$311,3751,747 Sq.Ft.12/14/2021Eaton Rd453$367,0002,676 Sq.Ft.9/14/2007Eddy St632$116,0001,052 Sq.Ft.5/1/2019Eden Way1021$199,3001,194 Sq.Ft.4/5/2024Ed Wright Way1N/AN/AN/A2,160 Sq.Ft.9/20/2019Elm St7942$305,9712,700 Sq.Ft.5/30/2025Emma St2321$125,818811 Sq.Ft.9/8/2021Erbs Way122$288,0001,536 Sq.Ft.N/AEthans Way631$97,667901 Sq.Ft.10/13/2023Everdale Rd331$215,6671,367 Sq.Ft.12/30/1998Everett St332$277,3331,720 Sq.Ft.N/AEvergreen Dr1531$204,1431,351 Sq.Ft.1/31/2025Evergreen Ln531$216,2001,030 Sq.Ft.5/21/2021Fairview St1643$432,25032,798 Sq.Ft.10/10/2023Farley Dr1032$109,900939 Sq.Ft.12/8/2020Fillmore St3231$208,7931,278 Sq.Ft.9/27/2023Finley Dr622$389,8331,517 Sq.Ft.9/30/2024Foster Dr1032$248,9001,311 Sq.Ft.11/30/2012Fox Hill Rd3633$438,0003,020 Sq.Ft.3/8/2024Francis St143$363,0002,138 Sq.Ft.4/12/2024Franklin Ln221$212,0001,702 Sq.Ft.N/AFrank St831$193,5001,199 Sq.Ft.12/16/2022Frost Dr842$296,8751,690 Sq.Ft.8/24/2021Frost Ln331$197,3331,071 Sq.Ft.3/22/2024Fuller Rd1232$321,7001,780 Sq.Ft.4/30/2019Funny Farm Rd1N/AN/AN/AN/A12/12/2019Furnace Brook Rd1032$282,2221,538 Sq.Ft.2/6/2024Furnace Grove Rd464$461,3335,497 Sq.Ft.6/20/2018Gage Pl431$176,750973 Sq.Ft.4/18/2024Gage St11842$213,8292,023 Sq.Ft.4/7/2025Garbrooke Dr3132$267,7101,521 Sq.Ft.1/12/2024Garden Ln433$328,7501,799 Sq.Ft.11/22/2024Goodall St331$139,333823 Sq.Ft.1/10/1994Gore Rd6532$214,2201,575 Sq.Ft.2/28/2025Gore Road Park3932$148,316930 Sq.Ft.4/11/2023Grandview St4342$282,5812,016 Sq.Ft.9/5/2024Grant St953$235,0002,206 Sq.Ft.12/20/2021Greenview Dr2632$288,0402,216 Sq.Ft.12/30/2024Greenwood Dr285$550,0005,039 Sq.Ft.3/13/2007Grove St3432$223,5881,619 Sq.Ft.1/31/2025Gulley Ln431$139,667943 Sq.Ft.8/22/2023Gypsy Ln1032$376,2225,194 Sq.Ft.3/11/2022Hamilton St274$318,5002,664 Sq.Ft.3/24/2015Hamlin Ave431$178,2501,180 Sq.Ft.3/23/2023Hannaford Sq4N/AN/AN/A32,175 Sq.Ft.1/1/2000Harbour Rd2632$242,5001,264 Sq.Ft.5/8/2025Harlan Rd162N/A2,365 Sq.Ft.N/AHarmon Rd731$169,5001,351 Sq.Ft.10/31/2023Harmony Ln331$178,6671,248 Sq.Ft.5/8/1997Harrington Rd1033N/A3,827 Sq.Ft.7/28/2016Harrison Ave1132$292,3642,027 Sq.Ft.7/19/2021Harvard St942$182,0001,270 Sq.Ft.6/12/2024Harwood Dr632$267,0001,470 Sq.Ft.12/19/2014Harwood Hill Rd7532$271,7883,837 Sq.Ft.1/10/2025Hatchery Rd1N/AN/AN/AN/AN/AHewitt Dr132$337,0002,140 Sq.Ft.5/3/2006Hickory Hill Rd1N/AN/AN/AN/A10/22/2010Hickory Hl1332$250,3081,573 Sq.Ft.10/14/2022Hickory Rd921$166,333823 Sq.Ft.4/24/2024Hicks Ave1731$189,4291,278 Sq.Ft.1/31/2025Hildur Hl1032$257,6671,181 Sq.Ft.12/29/2017Hill Shadow Farm Rd743$531,0002,465 Sq.Ft.8/25/2017Hillside Rd232$219,0001,792 Sq.Ft.9/7/2011Hillside St532$263,7503,773 Sq.Ft.7/10/2017Hilltop Dr322$184,5001,244 Sq.Ft.10/23/2020Holden St452$311,0002,689 Sq.Ft.11/8/2016Honeysuckle Ln531$293,2001,228 Sq.Ft.10/13/2021Horst Rd422$224,0001,566 Sq.Ft.2/15/2012Hospital Dr5N/AN/AN/A32,880 Sq.Ft.6/1/2021Houghton Ln3432$248,3752,076 Sq.Ft.12/18/2024Houran Rd1542$347,8332,225 Sq.Ft.1/25/2024Hoyt Dr322$140,3331,009 Sq.Ft.7/26/2021Hunt St1431$248,2311,792 Sq.Ft.5/31/2024Hurley Ln632$226,6001,607 Sq.Ft.4/9/2021Hutchinson St1032$112,900911 Sq.Ft.9/25/2018Hutton St521$178,2001,149 Sq.Ft.7/12/2016Ice Pond Ln321$200,500610 Sq.Ft.N/AImperial Ave2742$243,0771,677 Sq.Ft.8/26/2022Jacks Dr422$171,2501,114 Sq.Ft.3/27/2018Jayces Way131$187,0001,465 Sq.Ft.5/18/2001Jayne Ln943$368,5561,954 Sq.Ft.11/16/2021Jefferson Ave1942$255,3162,104 Sq.Ft.9/28/2023Jefferson Hts3732$287,4051,593 Sq.Ft.3/7/2025Jennings Brook Dr2132$257,7001,625 Sq.Ft.4/10/2025Jennings Dr1732$310,2351,535 Sq.Ft.3/1/2024Jerome Dr1N/AN/AN/AN/AN/AJewett Brook Rd331$281,0001,277 Sq.Ft.5/18/1990Jewett Dr932$301,8891,344 Sq.Ft.10/14/20225 Waldron AveHoosick Falls, NY 12090
Estimated Value $156,000
Living Area 1,727 SqFt
Beds 3
Baths 1.5
Year Built 1975
Property Type Misc Res Improvement
Ownership Type Related
APN 382801 27.19-7-18
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
15 Shingle Hollow RdPetersburg, NY 12138
Estimated Value $497,000
Living Area 2,512 SqFt
Beds 4
Baths 2.5
Year Built 2000
Property Type Single Family
Ownership Type Related
APN 382889 47.-1-23
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
160 Mountain View WayHoosick Falls, NY 12090
Estimated Value $342,000
Living Area 2,050 SqFt
Beds 3
Baths 2.5
Year Built 1995
Property Type Single Family
Ownership Type Individual
APN 382889 37.-5-22
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
20769 State Route 22Petersburg, NY 12138
Estimated Value $252,000
Living Area 1,266 SqFt
Beds 2
Baths 1
Year Built 1960
Property Type Single Family
Ownership Type Individual
APN 382889 57.-2-7.21
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
1107 County Route 68Eagle Bridge, NY 12057
Estimated Value $322,000
Living Area 2,075 SqFt
Beds 3
Baths 2
Year Built 1800
Property Type Single Family
Ownership Type Individual
APN 535089 283.-2-17.1
Municipality WHITE CREEK (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
22 Congress StHoosick Falls, NY 12090
Estimated Value $159,000
Living Area 1,408 SqFt
Beds 3
Baths 1
Year Built 1890
Property Type Single Family
Ownership Type Individual
APN 382801 27.16-8-9
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
19 Rensselaer StHoosick Falls, NY 12090
Estimated Value $191,000
Living Area 924 SqFt
Beds 3
Baths 1
Year Built 1865
Property Type Single Family
Ownership Type Multiple
APN 382801 27.16-8-6
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
164 Cobble Hill RdEagle Bridge, NY 12057
Estimated Value $265,000
Living Area 1,250 SqFt
Beds 3
Baths 2
Year Built 1978
Property Type Single Family
Ownership Type Multiple
APN 382889 18.-1-1.2
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
1119 County Route 68Eagle Bridge, NY 12057
Estimated Value $233,000
Living Area 2,688 SqFt
Beds 3
Baths 1.5
Year Built 1787
Property Type Single Family
Ownership Type Individual
APN 535089 283.-2-13
Municipality WHITE CREEK (TOV)
School District Hoosick Falls Central School District
106 Mapletown RdHoosick Falls, NY 12090
Estimated Value $439,000
Living Area 1,680 SqFt
Beds 3
Baths 2
Year Built 2000
Property Type Single Family
Ownership Type Related
APN 382889 28.-1-16.16
Municipality HOOSICK (TOV)
School District Hoosick Falls Central 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
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
127 State Line RdHoosick Falls, NY 12090
Estimated Value $342,000
Living Area 1,768 SqFt
Beds 2
Baths 2
Year Built 2008
Property Type Single Family
Ownership Type Individual
APN 535089 293.-1-15
Municipality WHITE CREEK (TOV)
School District Hoosick Falls Central School District
1003 County Route 68Eagle Bridge, NY 12057
Estimated Value $141,000
Living Area 2,808 SqFt
Beds 3
Baths 2
Year Built 1775
Property Type Single Family
Ownership Type Corporate
APN 535089 283.-2-30
Municipality WHITE CREEK (TOV)
School District Hoosick Falls Central School District
1101 County Route 68Eagle Bridge, NY 12057
Estimated Value $215,000
Living Area 1,288 SqFt
Beds 2
Baths 2
Year Built 1973
Property Type Single Family
Ownership Type Individual
APN 535089 283.-2-17.2
Municipality WHITE CREEK (TOV)
School District Hoosick Falls Central School District