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
Riverside Dr932$312,4291,688 Sq.Ft.10/16/2024River St2132$192,1332,373 Sq.Ft.7/24/2023Road Park4032$101,475939 Sq.Ft.1/10/2025Roaring Branch Ln1N/AN/AN/AN/AN/ARobinson Ave2931$248,3451,374 Sq.Ft.3/14/2025Rockmair Rdg543$400,5002,252 Sq.Ft.8/14/2019Rockwood St1732$218,3531,172 Sq.Ft.8/4/2020Rocky Ln2042$289,3751,752 Sq.Ft.2/24/2023Roizin Rd442$445,7502,510 Sq.Ft.10/22/2015Rollin St1131$222,2001,422 Sq.Ft.8/26/2024Rosemont St132$300,0001,500 Sq.Ft.N/ARussett Dr832$315,8751,797 Sq.Ft.4/11/2025Rutter Rd2132$258,4761,426 Sq.Ft.5/24/2023Safford St4642$229,9111,926 Sq.Ft.3/5/2024Saunders Dr331$178,667912 Sq.Ft.N/ASawmill Rd1122$255,6001,262 Sq.Ft.4/4/2025Sawyer Dr431$189,7501,156 Sq.Ft.9/27/2023School St3343$227,0006,149 Sq.Ft.9/27/2024Scott St942$210,1431,684 Sq.Ft.3/14/2025Searles Crossing Rd331$169,3331,286 Sq.Ft.12/29/2020Seminary Ln433$476,5002,680 Sq.Ft.1/15/2025Settlers Rd1031$268,2001,463 Sq.Ft.8/8/2019Shady Ln731$191,2861,103 Sq.Ft.7/10/2024Sharon Dr443$409,2502,731 Sq.Ft.8/16/2024Shawmut St221$147,000640 Sq.Ft.8/25/2010Shields Dr11N/AN/AN/A17,452 Sq.Ft.7/30/2021Short St542$228,4001,694 Sq.Ft.1/30/2023Silk Rd2532$360,0531,873 Sq.Ft.3/21/2025Silver St2942$257,4623,101 Sq.Ft.7/31/2024Simon Ln221$238,500845 Sq.Ft.2/16/2016Skiparee Rd251N/A3,763 Sq.Ft.N/ASkytop Dr611$139,667597 Sq.Ft.2/6/2020Smiths Way521$82,250800 Sq.Ft.6/1/2023Soule St931$198,1111,269 Sq.Ft.5/30/2019Southshire Dr2143$534,4212,854 Sq.Ft.9/8/2023South St9832$197,7003,222 Sq.Ft.5/23/2025Springhill Rd1232$370,0911,803 Sq.Ft.4/23/2024Spring St1042$211,9001,905 Sq.Ft.4/16/2025Spur Rd722$354,0001,678 Sq.Ft.2/7/2014S Stream Rd2N/AN/AN/AN/AN/AStark St1342$266,1821,730 Sq.Ft.6/17/2021Stocklee Ln333$289,3332,156 Sq.Ft.4/15/2005Stonehedge Dr1833$439,2352,506 Sq.Ft.2/4/2025Stream Rd10632$286,1281,771 Sq.Ft.11/18/2024Streamway432$350,5001,926 Sq.Ft.6/30/2023Strohmaier Rd732$299,1671,477 Sq.Ft.3/27/2023Sugar Maple Ln432$360,5001,880 Sq.Ft.7/23/2021Sunset Dr1232$243,2861,290 Sq.Ft.11/1/2023Sunset Trailer Park1021$170,000976 Sq.Ft.2/2/2019Sweets Ln331$210,500966 Sq.Ft.10/14/2016Sweets Mhp1721$158,438879 Sq.Ft.12/6/2024Sycamore Rd621$168,667794 Sq.Ft.4/29/2022Tel Cir432$272,5001,435 Sq.Ft.10/22/2024Tel Rd2131$231,5241,203 Sq.Ft.5/15/2025Terrace Dr543$503,4002,389 Sq.Ft.1/5/2017Thunder Rd232$396,5002,199 Sq.Ft.7/18/2014Tinkham831$210,5001,367 Sq.Ft.1/25/2013Tori Ln421$151,250796 Sq.Ft.5/27/2022Tower Rd532$279,0001,780 Sq.Ft.10/24/2024Town Line Rd431$231,7501,122 Sq.Ft.10/21/2022Townline Rd1832$366,2502,054 Sq.Ft.10/20/2022Townsend Dr221$162,000894 Sq.Ft.7/13/2020Transport Dr231$194,0002,094 Sq.Ft.9/23/1996Union St6542$240,5102,328 Sq.Ft.10/22/2024Us Route 75832$258,1672,236 Sq.Ft.2/28/2025Vail Rd3332$275,2001,584 Sq.Ft.4/30/2024Valentine Ln233$220,0001,880 Sq.Ft.1/29/2021Valentine Pl252$233,0001,500 Sq.Ft.8/9/2006Valentine St763$264,2862,543 Sq.Ft.1/13/2022Valley View Dr433$519,7502,345 Sq.Ft.4/15/2020Veterans Memorial Dr2N/AN/AN/A33,887 Sq.Ft.N/AVillage Ln333$508,0002,400 Sq.Ft.2/28/2024Vt Route 92321$243,3681,065 Sq.Ft.3/10/2025Wade Rd332$340,6671,689 Sq.Ft.4/28/2017Waite Dr531$171,800956 Sq.Ft.6/18/2004Walloomsac Rd6532$404,8242,756 Sq.Ft.5/20/2025Walts Way131$229,0001,200 Sq.Ft.3/27/2018Warn St531$204,4001,165 Sq.Ft.3/29/2021Washing Brook Rd631$234,8331,475 Sq.Ft.7/31/2024Washington Ave3142$266,2222,403 Sq.Ft.10/26/2022Watershed Rd431$283,0001,283 Sq.Ft.8/29/2017Webb St1742$218,3331,822 Sq.Ft.2/9/2024Weeks St2532$269,6801,708 Sq.Ft.5/21/2024West Rd5043$439,2963,465 Sq.Ft.7/30/2024Westside Dr432$279,7501,709 Sq.Ft.7/31/2020West St1632$249,6001,254 Sq.Ft.4/9/2025Westwood Dr332$277,6671,429 Sq.Ft.6/27/1994Whipstock Rd932$295,8751,766 Sq.Ft.5/13/2016White Birches5221$103,346921 Sq.Ft.4/14/2025Whiteoak Dr232$346,5001,246 Sq.Ft.N/AWillow Brook Dr1N/AN/AN/AN/A3/17/2017Willow Rd3932$245,6251,427 Sq.Ft.9/8/2023Woodford City Rd121$262,0001,320 Sq.Ft.7/20/2023Woodford Rd1931$173,6671,414 Sq.Ft.7/22/2024Woodland Dr432$306,2501,804 Sq.Ft.7/30/2024Woodward Dr331$229,3331,367 Sq.Ft.8/31/20054 Estabrook AveHoosick Falls, NY 12090
Estimated Value $217,000
Living Area 1,760 SqFt
Beds 3
Baths 1.5
Year Built 1870
Property Type Single Family
Ownership Type Mixed
APN 382801 27.19-7-30
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
20354 State Route 22Petersburg, NY 12138
Estimated Value $145,000
Living Area 832 SqFt
Beds 2
Baths 1
Year Built 1942
Property Type Single Family
Ownership Type Individual
APN 383400 68.-2-36
Municipality PETERSBURG
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
94 Ball St ExtHoosick Falls, NY 12090
Estimated Value $184,000
Living Area 1,056 SqFt
Beds 3
Baths 1
Year Built 1972
Property Type Single Family
Ownership Type Individual
APN 382889 27.16-11-2
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
5032 State Route 7Hoosick Falls, NY 12090
Estimated Value $203,000
Living Area 880 SqFt
Beds 2
Baths 1
Year Built 1962
Property Type Single Family
Ownership Type Individual
APN 382889 48.1-3-18
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
15 Congress StHoosick Falls, NY 12090
Estimated Value $214,000
Living Area 1,232 SqFt
Beds 4
Baths 1
Year Built 1850
Property Type Single Family
Ownership Type Multiple
APN 382801 27.16-7-5
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
15 Munsell StHoosick Falls, NY 12090
Estimated Value $148,000
Living Area 1,192 SqFt
Beds 3
Baths 1.5
Year Built 1900
Property Type Single Family
Ownership Type Individual
APN 382801 27.11-9-2
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
669 South StHoosick Falls, NY 12090
Estimated Value $257,000
Living Area 1,571 SqFt
Beds 4
Baths 1
Year Built 1850
Property Type Single Family
Ownership Type Related
APN 382889 48.1-4-7
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
405 Hill RdHoosick Falls, NY 12090
Estimated Value $459,000
Living Area 1,886 SqFt
Beds 4
Baths 1
Year Built 1934
Property Type Rural Residence
Ownership Type Individual
APN 382889 37.-4-7
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
29 Ball St ExtHoosick Falls, NY 12090
Estimated Value $139,000
Living Area 1,224 SqFt
Beds 5
Baths 1
Year Built 1917
Property Type Single Family
Ownership Type Individual
APN 382801 27.16-4-2
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
10 Richmond AveHoosick Falls, NY 12090
Estimated Value $281,000
Living Area 2,231 SqFt
Beds 4
Baths 1.5
Year Built 1939
Property Type Single Family
Ownership Type Corporate
APN 382801 27.19-7-13
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
346 Johnson Hill RdHoosick Falls, NY 12090
Estimated Value $352,000
Living Area 1,680 SqFt
Beds 2
Baths 2
Year Built 1990
Property Type Single Family
Ownership Type Individual
APN 382889 28.-1-26.124
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
5155 State Route 7Hoosick Falls, NY 12090
Estimated Value $446,000
Living Area 2,304 SqFt
Beds 4
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Related
APN 382889 48.-1-5.23
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
53 Ball St ExtHoosick Falls, NY 12090
Estimated Value $206,000
Living Area 1,352 SqFt
Beds 3
Baths 1
Year Built 1988
Property Type Single Family
Ownership Type Related
APN 382801 27.20-1-28
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
15 Saratoga StHoosick Falls, NY 12090
Estimated Value $144,000
Living Area 968 SqFt
Beds 3
Baths 2
Year Built 1978
Property Type Single Family
Ownership Type Individual
APN 382801 27.11-6-2
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
402 South StHoosick Falls, NY 12090
Estimated Value $304,000
Living Area 960 SqFt
Beds 2
Baths 1
Year Built 2007
Property Type Single Family
Ownership Type Individual
APN 382889 58.-2-1.15
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District