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Bennington town, VT - homes for sale
84 of 84 results displayed
- New
$200,000Active58.1 Acres1073 Chapel Road, Bennington, VT 05201
MLS# 5087361Listed by: PREFERRED PROPERTIES
- New
Listed by BHGRE$499,000Active6 beds 6 baths9,000 sq. ft.425 Main Street, Bennington, VT 05201
MLS# 5087015Listed by: BHG MASIELLO BRATTLEBORO - New
$295,500Active3 beds 2 baths1,365 sq. ft.341 Chester Knoll Drive, Bennington, VT 05201
MLS# 5086769Listed by: MAPLE LEAF REAL ESTATE - New
$235,000Active5 beds 2 baths1,860 sq. ft.205 County Street, Bennington, VT 05201
MLS# 5086669Listed by: PERROTT REALTY - New
$299,000Active3 beds 2 baths1,640 sq. ft.56 Hildur Hill, Bennington, VT 05201
MLS# 5086658Listed by: MAHAR MCCARTHY REAL ESTATE - New
$325,000Active6 beds 3 baths2,476 sq. ft.343 Safford Street, Bennington, VT 05201
MLS# 5086322Listed by: FOUR CORNER PROPERTIES LLC - New
$275,000Active3 beds 2 baths1,526 sq. ft.302 Prospect Street, Bennington, VT 05201
MLS# 5086287Listed by: HOFFMAN REAL ESTATE - New
$237,700Active3 beds 2 baths1,222 sq. ft.117 Putnam Street, Bennington, VT 05202-1
MLS# 5086250Listed by: PERROTT REALTY - New
$219,900Active2 beds 1 baths1,075 sq. ft.1083 Main Street, Bennington, VT 05201
MLS# 5086144Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP - New
$325,000Active1 beds 2 baths1,120 sq. ft.113 South Street #302, Bennington, VT 05201
MLS# 5086029Listed by: HOFFMAN REAL ESTATE - New
$55,000Active0.51 Acres24 Asa's Way, Bennington, VT 05201
MLS# 5086022Listed by: MAHAR MCCARTHY REAL ESTATE - New
$55,000Active0.48 Acres29 Asa's Way, Bennington, VT 05201
MLS# 5086024Listed by: MAHAR MCCARTHY REAL ESTATE - New
$235,000Active3 beds 2 baths1,300 sq. ft.340 Pleasant Street, Bennington, VT 05201
MLS# 5085882Listed by: REAL BROKER LLC - New
$199,900Active3 beds 2 baths1,176 sq. ft.2 Hamlin Avenue, Bennington, VT 05201
MLS# 5085771Listed by: FOUR CORNER PROPERTIES LLC - New
$579,000Active3 beds 2 baths2,501 sq. ft.856 Matteson Road, Bennington, VT 05201
MLS# 5085559Listed by: MAPLE LEAF REAL ESTATE 
$275,000Active2 beds 1 baths1,104 sq. ft.124 ALBE Drive, Bennington, VT 05201
MLS# 5085209Listed by: MAHAR MCCARTHY REAL ESTATE
$65,000Pending9.24 Acres0 Evergreen Drive, Bennington, VT 05201
MLS# 5084875Listed by: MAPLE LEAF REAL ESTATE
$324,900Active3 beds 2 baths1,900 sq. ft.2 Pine Road, Bennington, VT 05201
MLS# 5084585Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$339,900Active3 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 2 baths1,934 sq. ft.508 Barney Road, Bennington, VT 05201
MLS# 5084270Listed by: PERROTT REALTY
$395,000Active3 beds 2 baths1,556 sq. ft.231 Washington Avenue, Bennington, VT 05201
MLS# 5084174Listed by: MAHAR MCCARTHY REAL ESTATE
$295,000Active3 beds 1 baths1,344 sq. ft.951 gage Street, Bennington, VT 05201
MLS# 5083898Listed by: PERROTT REALTY
$219,000Active4 beds 1 baths1,127 sq. ft.20 Sage Street, Bennington, VT 05257
MLS# 5083528Listed by: EXP REALTY
$239,500Pending3 beds 2 baths1,280 sq. ft.38 Cyr Court, Bennington, VT 05201
MLS# 5083155Listed by: MAPLE LEAF REAL ESTATE
$259,000Active3 beds 1 baths1,056 sq. ft.1808 East Road, Bennington, VT 05201
MLS# 5082307Listed by: EXP REALTY
$525,000Active3 beds 3 baths3,182 sq. ft.4 Stonehedge Drive, Bennington, VT 05201
MLS# 5082188Listed by: MAHAR MCCARTHY REAL ESTATE
$275,000Active-- beds -- baths1,680 sq. ft.318 North Street, Bennington, VT 05201
MLS# 5081898Listed by: HOFFMAN REAL ESTATE
$289,000Active6 beds 2 baths2,520 sq. ft.111-113 Booth Terrace, Bennington, VT 05201
MLS# 5081825Listed by: EXP REALTY
$997,000Active0.53 Acres153 Northside Drive, Bennington, VT 05201
MLS# 5081713Listed by: FOUR CORNER PROPERTIES LLC
$235,000Active4 beds 2 baths1,652 sq. ft.209 Grove Street, Bennington, VT 05201
MLS# 5081606Listed by: MAHAR MCCARTHY REAL ESTATE
$295,000Active4 beds 2 baths2,206 sq. ft.116-118 South Branch Street, Bennington, VT 05201
MLS# 5081518Listed by: MAHAR MCCARTHY REAL ESTATE
$295,000Active4 beds 2 baths2,022 sq. ft.124 South Branch Street, Bennington, VT 05201
MLS# 5081521Listed by: MAHAR MCCARTHY REAL ESTATE
$375,000Active3 beds 2 baths1,748 sq. ft.695 Dermody Road, Bennington, VT 05201
MLS# 5081523Listed by: MAHAR MCCARTHY REAL ESTATE
$199,000Active2 beds 3 baths1,156 sq. ft.106 Park Street #2, Bennington, VT 05201
MLS# 5081071Listed by: MAPLE LEAF REAL ESTATE
$220,000Pending54 Acres399 Bard Road, Bennington, VT 05201
MLS# 5081020Listed by: PREFERRED PROPERTIES
$350,000Pending2 beds 2 baths1,190 sq. ft.527 Jennings Brook Drive, Bennington, VT 05201
MLS# 5080868Listed by: MAPLE LEAF REAL ESTATE
$350,000Pending2 beds 2 baths1,190 sq. ft.525 Jennings Brook Drive, Bennington, VT 05201
MLS# 5080662Listed by: MAPLE LEAF REAL ESTATE
$350,000Pending2 beds 2 baths1,190 sq. ft.523 Jennings Brook Drive, Bennington, VT 05201
MLS# 5080506Listed by: MAPLE LEAF REAL ESTATE
$159,900Pending2 beds 2 baths852 sq. ft.432 South Street #B-2, Bennington, VT 05201
MLS# 5080471Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$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
$265,000Pending4 beds 2 baths1,882 sq. ft.13 Hall Street, Bennington, VT 05257
MLS# 5080292Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$350,000Active4 beds 3 baths2,530 sq. ft.93 Russett Drive, Bennington, VT 05201
MLS# 5080194Listed by: MAHAR MCCARTHY REAL ESTATE
$370,000Active3 beds 2 baths1,463 sq. ft.303 Prospect Street, Bennington, VT 05201
MLS# 5080054Listed by: MAPLE LEAF REAL ESTATE
$289,000Active7 beds 6 baths5,712 sq. ft.136 North Street, Bennington, VT 05201
MLS# 5079239Listed by: EXP REALTY
$165,000Active2 beds 1 baths806 sq. ft.415 County Street, Bennington, VT 05201
MLS# 5079018Listed by: FOUR CORNER PROPERTIES LLC
$215,000Pending2 beds 1 baths938 sq. ft.55 Eden Way #3B, Bennington, VT 05201
MLS# 5078623Listed by: MAPLE LEAF REAL ESTATE
$199,000Active4 beds 2 baths1,980 sq. ft.210 Division Street, Bennington, VT 05201
MLS# 5078485Listed by: MAPLE LEAF REAL ESTATE
$355,000Active4 beds 2 baths2,108 sq. ft.149 Jewett Drive, Bennington, VT 05201
MLS# 5077814Listed by: MAPLE LEAF REAL ESTATE
$395,000Pending-- beds -- baths4,646 sq. ft.307 North Street, Bennington, VT 05201
MLS# 5077752Listed by: EXP REALTY
$269,000Active2 beds 1 baths2,500 sq. ft.626 Main Street, Bennington, VT 05201
MLS# 5061443Listed by: MAHAR MCCARTHY REAL ESTATE
$55,000Pending3 beds 1 baths1,254 sq. ft.1488 Morgan Street, Bennington, VT 05201
MLS# 5075687Listed by: R.H. THACKSTON & COMPANY
$1,495,000Active7 beds 6 baths6,392 sq. ft.16 West Road, Bennington, VT 05201
MLS# 5075253Listed by: MAHAR MCCARTHY REAL ESTATE
$100,000Active3 beds 1 baths1,508 sq. ft.109 Evergreen Drive, Bennington, VT 05201
MLS# 5074746Listed by: EXP REALTY
$269,900Active3 beds 2 baths900 sq. ft.2092 N Bennington Road, Bennington, VT 05257
MLS# 5074418Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$98,999Active2 beds 2 baths825 sq. ft.78 Ethans Way, Bennington, VT 05201
MLS# 5073749Listed by: EXP REALTY
$359,900Active3 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
$975,000Active-- beds -- baths8,888 sq. ft.124 Elm Street, Bennington, VT 05201
MLS# 5072098Listed by: TPW REAL ESTATE
$299,000Active4 beds 2 baths2,000 sq. ft.207 Silver Street, Bennington, VT 05201
MLS# 5070659Listed by: PERROTT REALTY
$230,000Active3 beds 1 baths1,092 sq. ft.113 Main Street, Bennington, VT 05201
MLS# 5068744Listed by: MAPLE LEAF REAL ESTATE
$649,000Active3 beds 3 baths2,715 sq. ft.58 Mount Anthony Road, Bennington, VT 05201
MLS# 5067086Listed by: MAHAR MCCARTHY REAL ESTATE
$695,000Active3 beds 3 baths2,868 sq. ft.134 Monument Avenue, Bennington, VT 05201
MLS# 5065403Listed by: MAHAR MCCARTHY REAL ESTATE
$198,000Pending5 beds -- baths2,201 sq. ft.317 Pleasant Street, Bennington, VT 05201
MLS# 5065393Listed by: SUGARHOUSE 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.
$349,000Active3 beds 2 baths1,829 sq. ft.89 Merson Street, Bennington, VT 05201
MLS# 5064108Listed by: MAHAR MCCARTHY REAL ESTATE
$329,000Active4 beds 2 baths1,728 sq. ft.103 Norton Street, Bennington, VT 05201
MLS# 5062804Listed by: MAHAR MCCARTHY REAL ESTATE
$625,000Active3 beds 2 baths1,416 sq. ft.682 Fox Hill Road, Bennington, VT 05201
MLS# 5061356Listed by: HOFFMAN REAL ESTATE
$645,000Active3 beds 2 baths1,535 sq. ft.704 Fox Hill Road, Bennington, VT 05201
MLS# 5061361Listed by: HOFFMAN REAL ESTATE
$59,000Active0.29 Acres420 Burgess Road, Bennington, VT 05201
MLS# 5056952Listed by: PERROTT REALTY
$295,000Active4 beds 2 baths1,792 sq. ft.254 Union Street, Bennington, VT 05201
MLS# 5055054Listed by: MAHAR MCCARTHY REAL ESTATE
$96,906Active2 beds 2 baths777 sq. ft.10 Cassie Lane, Bennington, VT 05201-0000
MLS# 5050693Listed by: EXP REALTY
$96,406Active2 beds 2 baths777 sq. ft.32 Cassie Lane, Bennington, VT 05201
MLS# 5050696Listed by: EXP REALTY
$96,906Active2 beds 2 baths777 sq. ft.41 Audrey Lane, Bennington, VT 05201
MLS# 5050698Listed by: EXP REALTY
$219,500Active3 beds 1 baths1,254 sq. ft.14 Robinson Avenue, Bennington, VT 05201
MLS# 5049236Listed by: MAHAR MCCARTHY REAL ESTATE
$365,000Active4 beds 2 baths1,735 sq. ft.19 Royal Street, Bennington, VT 05257
MLS# 5048567Listed by: MAPLE LEAF REAL ESTATE
$1,950,000Active7 Acres720 North Branch Street, Bennington, VT 05201
MLS# 5047411Listed by: TPW REAL ESTATE
$139,000Pending4 beds 1 baths1,262 sq. ft.101 Morgan Street, Bennington, VT 05201
MLS# 5045703Listed by: PERROTT REALTY
$1,950,000Active9 beds 7 baths6,956 sq. ft.1086 West Road, Bennington, VT 05201
MLS# 5074314Listed by: MAHAR MCCARTHY REAL ESTATE
$145,000Active15.49 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 May 7, 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.