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
John St732$234,2861,288 Sq.Ft.6/5/2024Joslin Hill Rd242$275,0001,638 Sq.Ft.12/28/2015Justin Ave432$252,5001,315 Sq.Ft.8/23/2023Kings Way722$216,5001,245 Sq.Ft.5/2/2024Knapp Dr632$193,1671,261 Sq.Ft.5/7/2024Knoll Crest Ln531$245,6001,505 Sq.Ft.5/15/2024Kocher Dr4N/AN/AN/A33,420 Sq.Ft.3/24/2020Krause Rd633$471,5001,912 Sq.Ft.4/8/2014Lafayette St831$182,1251,220 Sq.Ft.12/2/2022Laura Ln432$268,7501,213 Sq.Ft.1/4/2023Ledgehill Rd1N/AN/AN/A16,236 Sq.Ft.N/ALeonard St1831$241,1181,354 Sq.Ft.8/8/2023Lincoln St2331$194,6001,464 Sq.Ft.10/17/2023Linden St332$163,6671,514 Sq.Ft.2/18/2022Little League Rd1N/AN/AN/A880 Sq.Ft.N/ALittle Pond Ln221$250,0001,152 Sq.Ft.N/ALovers Ln3N/AN/AN/AN/AN/ALower East Rd1632$331,8131,572 Sq.Ft.11/2/2023Lucas Ln532$340,2001,767 Sq.Ft.5/4/2018Lyons St1032$202,3331,613 Sq.Ft.11/2/2023Main St21442$233,2214,583 Sq.Ft.5/30/2025Mansion Dr2N/AN/AN/AN/A12/30/2020Maple Grove Rd2632$256,8401,298 Sq.Ft.3/13/2025Maple St2432$219,1251,662 Sq.Ft.2/23/2024Margaret La1N/AN/AN/AN/A9/12/2024Margaret Ln842$364,5001,998 Sq.Ft.11/6/2024Marian Ln342$319,0001,570 Sq.Ft.11/13/2024Marilyn St332$289,0002,088 Sq.Ft.8/10/2001Matteson Rd1132$366,0001,585 Sq.Ft.12/16/2021Mccall St1442$191,0711,882 Sq.Ft.11/3/2023Mccullough Rd1N/AN/AN/AN/AN/AMcintosh Ln732$389,7142,082 Sq.Ft.8/31/2020Mckinley St1242$201,0001,644 Sq.Ft.6/9/2022Meadow Brook Dr943$540,6672,803 Sq.Ft.11/8/2024Merson St1531$250,7141,414 Sq.Ft.3/9/2023Metcalfe Dr121$175,000756 Sq.Ft.N/AMetcalfe Rd132$220,0001,352 Sq.Ft.10/18/2024Michaels Dr1132$371,8181,903 Sq.Ft.12/2/2024Middle Pownal Rd5532$270,1631,434 Sq.Ft.12/17/2024Monument Ave7743$484,6673,243 Sq.Ft.5/21/2025Monument Cir1143$674,4004,067 Sq.Ft.10/18/2024Morgan St8032$237,7331,311 Sq.Ft.12/9/2024Morse Rd12N/AN/AN/A12,658 Sq.Ft.12/20/2022Mortimer St264$288,0002,821 Sq.Ft.2/7/2020Moses Farm Rd1N/AN/AN/AN/AN/AMoss Dr153$462,0004,225 Sq.Ft.N/AMountain Mobile Home Pa1N/AN/AN/AN/A7/13/2007Mountain Mobile Home Park2322$146,957893 Sq.Ft.1/7/2020Mountain Rd632$261,6671,443 Sq.Ft.6/29/2023Mountain View Rd2132$113,111970 Sq.Ft.8/30/2023Mount Anthony Rd18N/AN/A$113,000N/A1/31/2025Mt Anthony Rd1132$420,33313,893 Sq.Ft.5/20/2024Murphy Rd9N/AN/A$166,500N/A8/15/2024Nathan Dr521$165,0001,011 Sq.Ft.N/ANational Forest Rd121$270,0001,784 Sq.Ft.12/7/2005N Branch St7N/AN/A$184,000N/A9/2/2022Nelson Rd631$131,20016,772 Sq.Ft.2/26/2022Niles Rd832$248,8571,583 Sq.Ft.1/10/2025Northside Dr5131$211,90913,349 Sq.Ft.2/14/2025North St6253$243,2143,710 Sq.Ft.4/3/2025Norton St1132$217,3641,462 Sq.Ft.6/25/2024N Terrace Dr1N/AN/A$224,000N/AN/AOakes St2731$192,1111,060 Sq.Ft.7/1/2024Oak Ridge Ln332$172,3331,292 Sq.Ft.3/2/2023Observatory St832$260,5001,707 Sq.Ft.10/21/2022Old Harbour Rd1N/AN/AN/AN/AN/AOrchard Rd1531$228,8896,330 Sq.Ft.5/29/2018Ore Bed Rd3N/AN/AN/AN/AN/AOutwater Rd432$321,5001,895 Sq.Ft.6/6/2023Overlea Rd2531$219,6361,290 Sq.Ft.10/28/2022Pace Rd521$241,8001,342 Sq.Ft.12/11/2024Paddock Pl222$182,0001,149 Sq.Ft.6/7/2013Pageant St3632$264,1391,460 Sq.Ft.9/11/2023Park St8032$192,6762,051 Sq.Ft.5/16/2025Peaceful Way1N/AN/AN/AN/A12/31/2012Peaks Pine Rd731$230,4001,158 Sq.Ft.5/13/2024Peaks Pine Ter232$154,000951 Sq.Ft.4/23/2007Pent Rd321$194,6671,099 Sq.Ft.9/16/2005Percy Rd331$195,3331,244 Sq.Ft.N/APerformance Dr2N/AN/AN/A59,613 Sq.Ft.1/8/2015Phylis Ln5N/AN/AN/A11,617 Sq.Ft.10/11/2024Pine Cir2132$322,3811,528 Sq.Ft.6/28/2024Pine Rd432$294,0001,584 Sq.Ft.6/21/2022Pippin Knl732$457,8572,255 Sq.Ft.7/12/2019Pleasant St4164$300,5363,745 Sq.Ft.2/14/2025Pleasant Valley Rd1832$386,4622,310 Sq.Ft.11/13/2024Pratt St743$241,2862,194 Sq.Ft.7/21/2023Prospect St1932$288,0001,747 Sq.Ft.5/30/2025Pucker Hill Rd532$281,2501,411 Sq.Ft.2/11/2022Putnam St4432$234,2501,569 Sq.Ft.12/12/2024Quarry Rd532$418,0001,944 Sq.Ft.3/29/2024Quiet Acres Rd532$150,2001,125 Sq.Ft.9/28/1999Red Clover Ln222$369,0001,508 Sq.Ft.4/26/2024Red Mill Campground Rd21N/A$182,500535 Sq.Ft.12/19/2019Red Pine Rd443$537,2503,090 Sq.Ft.9/11/2020Reed Dr332$207,6671,928 Sq.Ft.7/20/2018Regwood Dr942$377,0001,712 Sq.Ft.5/14/2021Rice Ln2432$346,4501,853 Sq.Ft.5/20/2025Richards Dr331$215,0001,453 Sq.Ft.N/ARiver Rd222$249,5001,141 Sq.Ft.N/A160 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
61 Wilder AveHoosick Falls, NY 12090
Estimated Value $175,000
Living Area 1,761 SqFt
Beds 3
Baths 2
Year Built 1900
Property Type Single Family
Ownership Type Individual
APN 382801 27.15-9-4
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
75 Abbott StHoosick Falls, NY 12090
Estimated Value $94,000
Living Area 1,220 SqFt
Beds 3
Baths 1
Year Built 1879
Property Type Single Family
Ownership Type Related
APN 382801 27.11-8-12
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
432 Johnson Hill RdHoosick Falls, NY 12090
Estimated Value $315,000
Living Area 2,187 SqFt
Beds 4
Baths 1
Year Built 1900
Property Type Single Family
Ownership Type Related
APN 382889 28.-1-1
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District
32 Oak StHoosick Falls, NY 12090
Estimated Value $158,000
Living Area 1,000 SqFt
Beds 2
Baths 1
Year Built 1988
Property Type Single Family
Ownership Type Related
APN 382801 27.16-3-1
Municipality HOOSICK FALLS
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
1081 County Route 68Eagle Bridge, NY 12057
Estimated Value $200,000
Living Area 1,390 SqFt
Beds 2
Baths 1
Year Built 1955
Property Type Single Family
Ownership Type Individual
APN 535089 283.-2-21
Municipality WHITE CREEK (TOV)
School District Hoosick Falls Central School District
18 Rogers AveHoosick Falls, NY 12090
Estimated Value $215,000
Living Area 1,586 SqFt
Beds 4
Baths 1
Year Built 1916
Property Type Single Family
Ownership Type Multiple
APN 382801 37.7-1-34
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
322 Johnson Hill RdHoosick Falls, NY 12090
Estimated Value $382,000
Living Area 1,539 SqFt
Beds 3
Baths 1.5
Year Built 1865
Property Type Rural Residence
Ownership Type Individual
APN 382889 28.-1-30.1
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
69 Wilder AveHoosick Falls, NY 12090
Estimated Value $185,000
Living Area 2,176 SqFt
Beds 4
Baths 2
Year Built 1900
Property Type Duplex 2 Units
Ownership Type Related
APN 382801 27.15-9-7
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
37 Albany StHoosick Falls, NY 12090
Estimated Value $327,000
Living Area 1,906 SqFt
Beds 3
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Related
APN 382889 27.8-1-52
Municipality HOOSICK (TOV)
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
136 Rogers AveHoosick Falls, NY 12090
Estimated Value $340,000
Living Area 2,006 SqFt
Beds 4
Baths 2.5
Year Built 1990
Property Type Single Family
Ownership Type Related
APN 382801 37.8-1-3.114
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
1 Abbott St ExtHoosick Falls, NY 12090
Estimated Value $274,000
Living Area 1,485 SqFt
Beds 4
Baths 1.5
Year Built 1950
Property Type Single Family
Ownership Type Multiple
APN 382801 27.15-10-17
Municipality HOOSICK FALLS
School District Hoosick Falls Central School District
73 Johnson Hill RdHoosick Falls, NY 12090
Estimated Value $261,000
Living Area 1,848 SqFt
Beds 3
Baths 2
Year Built 1865
Property Type Single Family
Ownership Type Related
APN 382889 28.-1-22.21
Municipality HOOSICK (TOV)
School District Hoosick Falls Central School District