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Bennington County, VT - homes for sale
59 of 59 results displayed
$17,000Active1 Acres326A Bergabhang Drive, Stamford, VT 05352
MLS# 5075991Listed by: DEERFIELD VALLEY REAL ESTATE
$125,000Active1.45 AcresL/O River Road, Winhall, VT 05340
MLS# 5075425Listed by: THE HAVEN GROUP
$625,000Active170 Acres0 Suncrest Road, Rupert, VT 05775
MLS# 5075271Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$500,000Active21.2 Acres56 Lower Taylor Hill Road, Winhall, VT 05340
MLS# 5074721Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$450,000Pending1.18 Acres97 North Branch Road #H4, Winhall, VT 05340
MLS# 5073906Listed by: STRATTON REAL ESTATE
$375,000Active1.23 Acres0 Winhall Hollow Road #Lot 23 Ravenwood, Winhall, VT 05340
MLS# 5073717Listed by: WOHLER REALTY GROUP
$450,000Active10.26 Acres4.1 Pearl Buck Drive, Winhall, VT 05340
MLS# 5073637Listed by: WOHLER REALTY GROUP
$35,000Active1 Acres0 Barber Pond Road, Pownal, VT 05261
MLS# 5073107Listed by: MAPLE LEAF REAL ESTATE
$2,500,000Active227 Acres00 VT Route 11, Peru, VT 05152
MLS# 5072898Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$175,000Active2.26 Acres0 Stratton Gardens Road #Lot 23, Winhall, VT 05340
MLS# 5072896Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$2,190,000Active1.16 Acres301 Northside Drive, Bennington, VT 05201
MLS# 5072776Listed by: TPW REAL ESTATE
$139,000Active1.62 Acres0 Lower Taylor Hill Road, Winhall, VT 05340
MLS# 5072280Listed by: MICHAEL ENGLAND REAL ESTATE
$95,000Active1 Acres41 Moose Hollow Road, Winhall, VT 05340
MLS# 5070793Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$69,000Active8 Acres1337 Chunks Brook Road, Sandgate, VT 05250
MLS# 5070480Listed by: DEREK GREENE
$125,000Active2.9 Acres311 Beechwood Lane #19, Peru, VT 05152
MLS# 5070443Listed by: BROMLEY REAL ESTATE
$249,000Active17.6 Acres88 Cedar Lane #5, Peru, VT 05152
MLS# 5053318Listed by: WINHALL REAL ESTATE
$400,000Active8.01 Acres248 French Hollow Road #1, Winhall, VT 05340
MLS# 5068233Listed by: WOHLER REALTY GROUP
$160,000Active2.9 AcresLot 21 Sunderland Hill Road, Sunderland, VT 05250
MLS# 5069111Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$28,000Active2.3 Acres00 Heartwellville View Road #38/39, Readsboro, VT 05350
MLS# 5068949Listed by: FLEX REALTY
$14,000Active1.2 Acres00 Heartwellville View Road #32, Readsboro, VT 05350
MLS# 5068954Listed by: FLEX REALTY
$27,999Active2.4 Acres00 Heartwellville View Road #34/35, Readsboro, VT 05350
MLS# 5068956Listed by: FLEX REALTY
$19,999Active1.5 AcresLebensdorf Lane, Readsboro, VT 05350
MLS# 5068765Listed by: OWNERENTRY.COM- $400,000Active8.01 Acres
248 French Hollow Road, Winhall, VT 05340
MLS# 5068233Listed by: WOHLER REALTY GROUP 
$109,000Active17 Acres00 Bill T Drive, Readsboro, VT 05350
MLS# 5068152Listed by: DEERFIELD VALLEY REAL ESTATE
$385,000Pending41.1 Acres00 Ross Road, Winhall, VT 05340
MLS# 5067562Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$14,999Pending1 AcresOberhugel Road, Readsboro, VT 05350
MLS# 5067787Listed by: OWNERENTRY.COM
$425,000Active3 Acreslot A Frost Pond Road, Dorset, VT 05251
MLS# 5067701Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$425,000Active3 Acreslot B Frost Pond Road, Dorset, VT 05251
MLS# 5067704Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$65,000Active2.38 Acres0 Sunset Hill Road, Pownal, VT 05261
MLS# 5067472Listed by: EDGE REALTY VERMONT
$74,900Active5.3 Acres00 Heartwellville View Road #64/65/66/69/70, Readsboro, VT 05350
MLS# 5066003Listed by: FLEX REALTY
$29,000Active1.2 Acres00 Oberdorf Road #Lot 276, Stamford, VT 05352
MLS# 5064834Listed by: SOUTHERN VERMONT REALTY GROUP
$120,000Pending20 Acres1319 Vail Road, Bennington, VT 05201
MLS# 5062033Listed by: MAPLE LEAF REAL ESTATE
$85,000Active9.74 Acres1 & 2 Joy Lane, Arlington, VT 05250
MLS# 5058622Listed by: WOHLER REALTY GROUP
$59,000Active0.29 Acres420 Burgess Road, Bennington, VT 05201
MLS# 5056952Listed by: PERROTT REALTY
$2,300,000Active67 Acres215 VT Route 30, Dorset, VT 05251
MLS# 5056222Listed by: WOHLER REALTY GROUP
$9,999Pending1.2 AcresAlpendorf Avenue, Readsboro, VT 05350
MLS# 5055680Listed by: OWNERENTRY.COM
$65,000Active17.3 Acres0 Hidden Valley Road, Shaftsbury, VT 05262
MLS# 5055076Listed by: PERROTT REALTY
$249,000Active3.42 Acres0 Havoc Hill Road, Dorset, VT 05253
MLS# 5052809Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$895,000Active24.08 AcresA Windsor Road, Manchester, VT 05255
MLS# 5051011Listed by: WOHLER REALTY GROUP
$1,500,000Active38.57 Acres500 Nims Road #Lot 2, Dorset, VT 05251
MLS# 5049329Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$342,000Active28.5 Acres11 Old County Road, Landgrove, VT 05148
MLS# 5048222Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$99,000Active1 Acres88A Sylvan Ridge Road, Winhall, VT 05340
MLS# 5047790Listed by: STRATTON REAL ESTATE
$1,950,000Active7 Acres720 North Branch Street, Bennington, VT 05201
MLS# 5047411Listed by: TPW REAL ESTATE
$27,500Active1.2 Acres0 Bergrucken Lane #6-377, Stamford, VT 05352
MLS# 5044034Listed by: SOUTHERN VERMONT REALTY GROUP
$780,000Pending663.95 Acres0 West Sandgate/ Sandgate Road, Sandgate, VT 05250
MLS# 5042174Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$175,000Active15.49 Acres00 Silk Road, Bennington, VT 05201
MLS# 5040464Listed by: OWNERENTRY.COM
$135,000Active1.36 Acres0 Stratton View Road #62-63, Winhall, VT 05340
MLS# 5036986Listed by: MICHAEL ENGLAND REAL ESTATE
$65,000Active0.74 Acres0 Stratton View Road #58, Winhall, VT 05340
MLS# 5036988Listed by: MICHAEL ENGLAND REAL ESTATE
$65,000Active1.02 Acres0 Stratton View Road #59, Winhall, VT 05340
MLS# 5036984Listed by: MICHAEL ENGLAND REAL ESTATE
$195,000Active40 Acres0 Alden Lane #Land Lot 18, Sunderland, VT 05250
MLS# 5025318Listed by: WOHLER REALTY GROUP
$360,000Active2 Acres100 Back Nine Bluff, Manchester, VT 05254
MLS# 5013982Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$399,500Active2.7 Acres2937 Dorset West Road, Dorset, VT 05251
MLS# 5013651Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$575,000Active99.31 Acres000 Route 11, Peru, VT 05152
MLS# 5012880Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$179,000Active0.2 Acres10 Partridge Hill #Lot 10, Manchester, VT 05255
MLS# 4999931Listed by: WOHLER REALTY GROUP
$35,000Pending1.7 Acres159 Oberdorf Road, Readsboro, VT 05350
MLS# 5037699Listed by: MAPLE LEAF REAL ESTATE
$115,000Active2.9 AcresLot 3 Route 11/30, Winhall, VT 05340
MLS# 4963233Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$475,000Active12.82 Acres22 Morse Road, Bennington, VT 05201
MLS# 5030488Listed by: TPW REAL ESTATE
$199,000Pending55.1 Acres0 Andrea Drive #parcel id 00PR32025R; 00PR32023R, Stamford, VT 05352
MLS# 4985234Listed by: ALTON + WESTALL REAL ESTATE AGENCY, LLC
$215,000Active4.46 AcresOA East Manchester Road, Manchester, VT 05255
MLS# 5031411Listed by: EXP REALTY
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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 February 20, 2026
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© 2023 - 2026 ERA Franchise Systems LLC. All rights reserved. ERA Franchise Systems LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. ERA, ERA Real Estate powered, and their respective logos are registered service marks of ERA Franchise Systems LLC. Each office is independently owned and operated.
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.
© 2023 - 2026 ERA Franchise Systems LLC. All rights reserved. ERA Franchise Systems LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. ERA, ERA Real Estate powered, and their respective logos are registered service marks of ERA Franchise Systems LLC. Each office is independently owned and operated.