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Bennington town, VT - homes for sale
93 of 93 results displayed
- New
$58,000Active0.48 Acres33 Asa's Way #16, Bennington, VT 05257
MLS# 5104588Listed by: MAPLE LEAF REAL ESTATE
- New
$595,000Active23.62 Acres3213 West Road, Bennington, VT 05201
MLS# 5104539Listed by: MAHAR MCCARTHY REAL ESTATE - Coming Soon
$179,000Coming Soon3 beds 2 baths130 Morgan Street, Bennington, VT 05201
MLS# 5104457Listed by: PERROTT REALTY - New
$375,000Active3 beds 2 baths1,911 sq. ft.21 Russett Drive, Bennington, VT 05201
MLS# 5104474Listed by: MAHAR MCCARTHY REAL ESTATE - New
$375,000Active3 beds 2 baths2,016 sq. ft.291 Spring Hill Road, Bennington, VT 05201
MLS# 5104363Listed by: MAPLE LEAF REAL ESTATE - New
$189,900Active3 beds 1 baths1,206 sq. ft.232 Depot Street, Bennington, VT 05201
MLS# 5103372Listed by: MAPLE LEAF REAL ESTATE - New
$349,000Active8 beds 4 baths3,637 sq. ft.710 Main Street, Bennington, VT 05201
MLS# 5102985Listed by: PERROTT REALTY - New
$389,900Active3 beds 2 baths2,098 sq. ft.185 Jewett Drive, Bennington, VT 05201
MLS# 5103003Listed by: MAHAR MCCARTHY REAL ESTATE 
$75,000Active11.2 Acres0 Mount Anthony Road, Bennington, VT 05201
MLS# 5102718Listed by: MAHAR MCCARTHY REAL ESTATE
$259,000Active2 beds 1 baths1,318 sq. ft.104 John Street, Bennington, VT 05201
MLS# 5102096Listed by: PERROTT REALTY
$49,000Active0.21 Acres2 Belvedere Street, Bennington, VT 05201
MLS# 5102053Listed by: PERROTT REALTY
$169,900Active2 beds 2 baths819 sq. ft.432 South Street #A11, Bennington, VT 05201
MLS# 5102057Listed by: FLEX REALTY
$350,000Active8 beds 4 baths2,586 sq. ft.110 Short Street, Bennington, VT 05201
MLS# 5101907Listed by: MAPLE LEAF REAL ESTATE
$365,000Active3 beds 2 baths1,588 sq. ft.12 Hall Street, Bennington, VT 05257
MLS# 5101687Listed by: MAHAR MCCARTHY REAL ESTATE
$142,900Active2 beds 1 baths784 sq. ft.60 Tori Lane, Bennington, VT 05201
MLS# 5101539Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$232,500Active3 beds 2 baths1,582 sq. ft.903 Gage Street, Bennington, VT 05201
MLS# 5101468Listed by: LAMACCHIA REALTY INC.
$250,000Active4 beds 2 baths1,458 sq. ft.301 Elm Street, Bennington, VT 05201
MLS# 5101031Listed by: HOFFMAN REAL ESTATE
$335,000Active3 beds 2 baths1,414 sq. ft.308 Crescent Boulevard, Bennington, VT 05201
MLS# 5101006Listed by: MAPLE LEAF REAL ESTATE
$275,000Pending3 beds 2 baths1,302 sq. ft.2867 Chapel Road, Bennington, VT 05201
MLS# 5100537Listed by: HOFFMAN REAL ESTATE
$249,000Active4 beds 4 baths2,144 sq. ft.250 North Street, Bennington, VT 05201
MLS# 5100263Listed by: MAHAR MCCARTHY REAL ESTATE
$595,000Active3 beds 2 baths2,379 sq. ft.1278 Harrington Road, Bennington, VT 05201
MLS# 5099405Listed by: MAHAR MCCARTHY REAL ESTATE
$265,000Active3 beds 2 baths1,688 sq. ft.128 NorthSide Drive, Bennington, VT 05201
MLS# 5099392Listed by: MAHAR MCCARTHY REAL ESTATE
$619,000Pending4 beds 3 baths2,692 sq. ft.34 Monument Avenue, Bennington, VT 05201
MLS# 5099185Listed by: EXP REALTY
$259,000Active4 beds 2 baths1,768 sq. ft.549 Houran Road, Bennington, VT 05201
MLS# 5098985Listed by: EXP REALTY
$205,000Active3 beds 2 baths1,632 sq. ft.305 Weeks Street, Bennington, VT 05201
MLS# 5098061Listed by: MAPLE LEAF REAL ESTATE
$210,000Active5 beds 2 baths2,200 sq. ft.118 Foster Drive, Bennington, VT 05201
MLS# 5098066Listed by: MAPLE LEAF REAL ESTATE
$439,000Active3 beds 3 baths2,389 sq. ft.15 Polygraphic Lane, Bennington, VT 05257
MLS# 5097821Listed by: HOFFMAN REAL ESTATE
$230,000Active3 beds 2 baths1,128 sq. ft.104 Short Street, Bennington, VT 05201
MLS# 5097604Listed by: MAPLE LEAF REAL ESTATE
$539,900Active4 beds 3 baths2,376 sq. ft.811 Middle Pownal Road, Bennington, VT 05201
MLS# 5097526Listed by: EXP REALTY
$165,000Pending2 beds 1 baths806 sq. ft.415 County Street, Bennington, VT 05201
MLS# 5097234Listed by: FOUR CORNER PROPERTIES LLC
$219,900Active3 beds 2 baths1,372 sq. ft.420 Gore Road, Bennington, VT 05201
MLS# 5097011Listed by: MAHAR MCCARTHY REAL ESTATE
$150,000Active5 beds 2 baths1,575 sq. ft.127 Dewey Street, Bennington, VT 05201
MLS# 5096965Listed by: MAPLE LEAF REAL ESTATE
$135,000Active2 beds 2 baths948 sq. ft.432 South Street #C10, Bennington, VT 05201
MLS# 5096615Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$209,900Active3 beds 2 baths1,608 sq. ft.107 Jefferson Avenue, Bennington, VT 05201
MLS# 5096450Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$264,900Active4 beds 2 baths1,146 sq. ft.109 County Street, Bennington, VT 05201
MLS# 5096457Listed by: MAPLE LEAF REAL ESTATE
$180,000Active3 beds 2 baths1,640 sq. ft.105 Hicks Avenue, Bennington, VT 05201
MLS# 5096423Listed by: MAPLE LEAF REAL ESTATE
$189,000Active4 beds 2 baths1,840 sq. ft.209 Depot Street, Bennington, VT 05201
MLS# 5096338Listed by: MAHAR MCCARTHY REAL ESTATE
$80,000Active4 beds 2 baths1,465 sq. ft.107 Lyons Street, Bennington, VT 05201
MLS# 5096159Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$480,000Active4 beds 3 baths3,312 sq. ft.498 Town Line Road, Bennington, VT 05201
MLS# 5095717Listed by: DIAMOND REALTY
$179,000Active2 beds 2 baths1,056 sq. ft.106 Park Street #9, Bennington, VT 05201
MLS# 5095599Listed by: MAHAR MCCARTHY REAL ESTATE
$249,900Active-- beds -- baths3,569 sq. ft.406-408 Gage Street, Bennington, VT 05201
MLS# 5095558Listed by: MAPLE LEAF REAL ESTATE
$299,000Active3 beds 2 baths1,829 sq. ft.89 Merson Street, Bennington, VT 05201
MLS# 5095251Listed by: MAHAR MCCARTHY REAL ESTATE
$299,000Active3 beds 2 baths1,411 sq. ft.262 Union Street, Bennington, VT 05201
MLS# 5095149Listed by: MAPLE LEAF REAL ESTATE
$499,900Active2 beds 3 baths3,105 sq. ft.193 Finley Drive, Bennington, VT 05201
MLS# 5094280Listed by: HOFFMAN REAL ESTATE
$209,000Pending4 beds 2 baths1,518 sq. ft.142 Pine Circle, Bennington, VT 05201
MLS# 5093692Listed by: MAPLE LEAF REAL ESTATE
$650,000Active5 beds 3 baths5,524 sq. ft.81 Honeysuckle Lane, Bennington, VT 05257
MLS# 5093651Listed by: MAHAR MCCARTHY REAL ESTATE
$74,900Active2.25 Acres0 Brambley Lane, Bennington, VT 05201
MLS# 5092066Listed by: HOFFMAN REAL ESTATE
$155,000Pending4 beds 2 baths2,643 sq. ft.905 County Street, Bennington, VT 05201
MLS# 5091674Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$350,000Active2 beds 2 baths1,190 sq. ft.524 Jennings Brook Drive, Bennington, VT 05201
MLS# 5090266Listed by: MAPLE LEAF REAL ESTATE
$277,700Pending2 beds 1 baths2,142 sq. ft.32 Albe Drive, Bennington, VT 05201
MLS# 5090246Listed by: MAPLE LEAF REAL ESTATE
$179,000Active3 beds 3 baths1,485 sq. ft.432 South Street #D2, Bennington, VT 05201
MLS# 5089968Listed by: EXP REALTY
$695,000Active4 beds 2 baths1,614 sq. ft.515 Quarry Road, Bennington, VT 05201
MLS# 5089246Listed by: MAPLE LEAF REAL ESTATE
$250,000Active3 beds 2 baths1,824 sq. ft.103 Jennings Brook Drive, Bennington, VT 05201
MLS# 5088382Listed by: MAHAR MCCARTHY REAL ESTATE
$219,000Active3 beds 1 baths1,047 sq. ft.99 Coolidge Avenue, Bennington, VT 05201
MLS# 5088016Listed by: MAPLE LEAF REAL ESTATE
$279,000Active3 beds 2 baths1,408 sq. ft.8 West Street, Bennington, VT 05257
MLS# 5087836Listed by: MAHAR MCCARTHY REAL ESTATE
$475,000Active12.82 Acres22 Morse Road, Bennington, VT 05201
MLS# 5087850Listed by: TPW REAL ESTATE
$180,000Active58.1 Acres1073 Chapel Road, Bennington, VT 05201
MLS# 5087361Listed by: PREFERRED PROPERTIES
Listed by BHGRE$475,000Active6 beds 6 baths9,000 sq. ft.425 Main Street, Bennington, VT 05201
MLS# 5087015Listed by: BHG MASIELLO BRATTLEBORO
$219,000Active5 beds 2 baths1,860 sq. ft.205 County Street, Bennington, VT 05201
MLS# 5086669Listed by: PERROTT REALTY
$224,000Active3 beds 2 baths1,222 sq. ft.117 Putnam Street, Bennington, VT 05202-1
MLS# 5086250Listed by: PERROTT REALTY
$209,900Active2 beds 1 baths1,075 sq. ft.1083 Main Street, Bennington, VT 05201
MLS# 5086144Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$55,000Active0.51 Acres24 Asa's Way, Bennington, VT 05201
MLS# 5086022Listed by: MAHAR MCCARTHY REAL ESTATE
$55,000Active0.48 Acres29 Asa's Way, Bennington, VT 05201
MLS# 5086024Listed by: MAHAR MCCARTHY REAL ESTATE
$215,000Active3 beds 2 baths1,300 sq. ft.340 Pleasant Street, Bennington, VT 05201
MLS# 5085882Listed by: REAL BROKER LLC
$199,900Pending3 beds 2 baths1,176 sq. ft.2 Hamlin Avenue, Bennington, VT 05201
MLS# 5085771Listed by: FOUR CORNER PROPERTIES LLC
$309,900Active3 beds 2 baths1,900 sq. ft.2 Pine Road, Bennington, VT 05201
MLS# 5084585Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$319,900Active3 beds 2 baths1,500 sq. ft.683 Water Street, Bennington, VT 05257
MLS# 5084514Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$350,000Pending2 beds 2 baths1,190 sq. ft.526 Jennings Brook Drive, Bennington, VT 05201
MLS# 5084448Listed by: MAPLE LEAF REAL ESTATE
$269,000Active3 beds 1 baths1,344 sq. ft.951 gage Street, Bennington, VT 05201
MLS# 5083898Listed by: PERROTT REALTY
$209,000Active4 beds 1 baths1,127 sq. ft.20 Sage Street, Bennington, VT 05257
MLS# 5083528Listed by: EXP REALTY
$265,000Active-- beds -- baths1,680 sq. ft.318 North Street, Bennington, VT 05201
MLS# 5081898Listed by: HOFFMAN REAL ESTATE
$997,000Active0.53 Acres153 Northside Drive, Bennington, VT 05201
MLS# 5081713Listed by: FOUR CORNER PROPERTIES LLC
$269,000Active4 beds 2 baths2,206 sq. ft.116-118 South Branch Street, Bennington, VT 05201
MLS# 5081518Listed by: MAHAR MCCARTHY REAL ESTATE
$275,000Active4 beds 2 baths2,022 sq. ft.124 South Branch Street, Bennington, VT 05201
MLS# 5081521Listed by: MAHAR MCCARTHY REAL ESTATE
$198,000Active54 Acres399 Bard Road, Bennington, VT 05201
MLS# 5081020Listed by: PREFERRED PROPERTIES
$379,000Active2 beds 2 baths1,190 sq. ft.527 Jennings Brook Drive, Bennington, VT 05201
MLS# 5080868Listed by: MAPLE LEAF REAL ESTATE
$65,000Active5.6 Acres80 Crossover Road, Bennington, VT 05201
MLS# 5080317Listed by: PERROTT REALTY
$65,000Active1.24 Acres2041 East Road, Bennington, VT 05201
MLS# 5080306Listed by: PERROTT REALTY
$395,000Pending-- beds -- baths4,646 sq. ft.307 North Street, Bennington, VT 05201
MLS# 5077752Listed by: EXP REALTY
$269,000Pending2 beds 1 baths2,500 sq. ft.626 Main Street, Bennington, VT 05201
MLS# 5061443Listed by: MAHAR MCCARTHY REAL ESTATE
$359,900Pending3 beds 2 baths1,404 sq. ft.38 Oak Ridge Lane, Bennington, VT 05201
MLS# 5073481Listed by: HOFFMAN REAL ESTATE
$2,190,000Active1.16 Acres301 Northside Drive, Bennington, VT 05201
MLS# 5072776Listed by: TPW REAL ESTATE
$950,000Active-- beds -- baths8,888 sq. ft.124 Elm Street, Bennington, VT 05201
MLS# 5072098Listed by: TPW REAL ESTATE
$230,000Active3 beds 1 baths1,092 sq. ft.113 Main Street, Bennington, VT 05201
MLS# 5068744Listed by: MAPLE LEAF REAL ESTATE
$529,000Active3 beds 3 baths2,715 sq. ft.58 Mount Anthony Road, Bennington, VT 05201
MLS# 5067086Listed by: MAHAR MCCARTHY REAL ESTATE
$399,000Active6 beds -- baths5,208 sq. ft.126 Washington Avenue, Bennington, VT 05201
MLS# 5064754Listed by: MAPLE LEAF REAL ESTATE
$35,300Pending2 beds 1 baths1,302 sq. ft.933 East Road, Bennington, VT 05201
MLS# 5064307Listed by: REALHOME SERVICES AND SOLUTIONS, INC.
$96,406Active2 beds 2 baths777 sq. ft.32 Cassie Lane, Bennington, VT 05201
MLS# 5050696Listed by: EXP REALTY
$357,500Active4 beds 2 baths1,735 sq. ft.19 Royal Street, Bennington, VT 05257
MLS# 5048567Listed by: MAPLE LEAF REAL ESTATE
$139,000Pending4 beds 1 baths1,262 sq. ft.101 Morgan Street, Bennington, VT 05201
MLS# 5045703Listed by: PERROTT REALTY
$145,000Pending15.49 Acres00 Silk Road, Bennington, VT 05201
MLS# 5040464Listed by: OWNERENTRY.COM
$199,000Pending3 beds 2 baths1,600 sq. ft.130 Morgan Street, Bennington, VT 05201
MLS# 5039510Listed by: PERROTT REALTY
$190,000Pending5 beds 2 baths1,478 sq. ft.32-34 Sage Street, Bennington, VT 05257
MLS# 5033843Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
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Copyright 2026 Prime MLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of Prime MLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated August 13, 2026
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© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.