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Bennington County, VT - land & lots for sale
76 of 76 results displayed
- New
$500,000Active2.48 Acres691 Indian Paint Brush Road #E-13R and E-14R, Winhall, VT 05340
MLS# 5111789Listed by: 42 NORTH LP
- New
$95,000Active9.68 Acres390 Fairview Street, Bennington, VT 05201
MLS# 5111395Listed by: FOUR CORNER PROPERTIES LLC - New
$865,000Active18.3 Acres00 Pine Tree Lane, Manchester, VT 05255
MLS# 5111347Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY - New
$85,000Active10 Acres0 Ladd Road, Pownal, VT 05261
MLS# 5111157Listed by: HOFFMAN REAL ESTATE - New
$55,000Active7.1 Acres0 Route 153, Rupert, VT 05768
MLS# 5111140Listed by: NEW ENGLAND LAKESIDE REALTY 
$53,000Active0.51 Acres24 Asa's Way, Bennington, VT 05257
MLS# 5086022Listed by: MAHAR MCCARTHY REAL ESTATE
$975,000Active69.3 Acres437 Pratt Road, Pownal, VT 05261
MLS# 5110570Listed by: MAPLE LEAF REAL ESTATE
$45,000Pending3.67 Acres0 Grapevine Lane, Pownal, VT 05261
MLS# 5109674Listed by: MAHAR MCCARTHY REAL ESTATE
$60,000Active5 Acres0 Sunderland Hill Road, Sunderland, VT 05250
MLS# 5107454Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$190,000Active3.8 Acres148 VT Route 30, Winhall, VT 05340
MLS# 5107343Listed by: TPW REAL ESTATE
$240,000Active10.06 Acres0 Stratton Gardens Road #10a, 10b,, Winhall, VT 05340
MLS# 5107127Listed by: MICHAEL ENGLAND REAL ESTATE
$695,000Active117 AcresNorth Pownal Road #002 232, Pownal, VT 05261
MLS# 5107042Listed by: ALTON + WESTALL REAL ESTATE AGENCY, LLC
$85,000Active2.8 Acres0 West Mountain Road, Shaftsbury, VT 05262
MLS# 5106931Listed by: EXP REALTY
$108,000Active1 Acres0 Sylvan Ridge Road #Lot 25, Winhall, VT 05340
MLS# 5106244Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$245,000Active3 Acres0 Fox Lane #lot 3, Dorset, VT 05251
MLS# 5105566Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$239,000Active5.35 Acres01 Old Depot Road, Arlington, VT 05250
MLS# 5105515Listed by: TPW REAL ESTATE
$20,000Active1.2 Acres0 Bergrucken Lane #6-377, Stamford, VT 05352
MLS# 5105218Listed by: SOUTHERN VERMONT REALTY GROUP
$675,000Active80.5 Acres221 Landgrove Road, Landgrove, VT 05148
MLS# 5105190Listed by: MARY MITCHELL MILLER REAL ESTATE
$15,500Active1.2 Acres00 Heartwellville View Road #38, Readsboro, VT 05350
MLS# 5104818Listed by: FLEX REALTY
$15,500Active1.1 Acres00 Heartwellville View Road #39, Readsboro, VT 05350
MLS# 5104821Listed by: FLEX REALTY
$39,500Active2.1 Acres00 Heartwellville View Road #65 & 66, Readsboro, VT 05350
MLS# 5104824Listed by: FLEX REALTY
$19,500Active1.1 Acres00 Heartwellville View Road #69, Readsboro, VT 05350
MLS# 5104828Listed by: FLEX REALTY
$19,500Active1 Acres00 Heartwellville View Road #70, Readsboro, VT 05350
MLS# 5104829Listed by: FLEX REALTY
$58,000Active0.48 Acres33 Asa's Way #16, Bennington, VT 05257
MLS# 5104588Listed by: MAPLE LEAF REAL ESTATE
$595,000Active23.62 Acres3213 West Road, Bennington, VT 05201
MLS# 5104539Listed by: MAHAR MCCARTHY REAL ESTATE
$115,000Active1 Acres75 Sylvan Ridge Road, Winhall, VT 05340
MLS# 5104082Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$75,000Active11.2 Acres0 Mount Anthony Road, Bennington, VT 05201
MLS# 5102718Listed by: MAHAR MCCARTHY REAL ESTATE
$49,000Active0.21 Acres2 Belvedere Street, Bennington, VT 05201
MLS# 5102053Listed by: PERROTT REALTY
$105,000Active30.8 Acres0 Old Gale Hill Road, Glastenbury, VT 05262
MLS# 5099471Listed by: PERROTT REALTY
$260,000Active3.3 Acres0 Mountain Haunts, Winhall, VT 05340
MLS# 5099438Listed by: MICHAEL ENGLAND REAL ESTATE
$20,000Active0.99 Acres0 Route 30, Winhall, VT 05340
MLS# 5099207Listed by: MICHAEL ENGLAND REAL ESTATE
$59,900Active0.92 Acres14 The Lane, Stamford, VT 05352
MLS# 5098536Listed by: MONARCH REALTY
$229,000Active10 Acres468 Skyboro Road, Pownal, VT 05261
MLS# 5097950Listed by: BISHOP WEST REAL ESTATE, INC.
$125,000Active1.18 Acres510 Center Street, Pownal, VT 05261
MLS# 5097453Listed by: MAPLE LEAF REAL ESTATE
$1,425,000Active38 AcresB Prospect Street, Manchester, VT 05254
MLS# 5094369Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$88,000Active5.77 Acres0 East Road, Shaftsbury, VT 05262
MLS# 5094032Listed by: HOFFMAN REAL ESTATE
$374,900Active2.31 Acres0 Wall Street #Lot 2 & 3, Winhall, VT 05340
MLS# 5093473Listed by: THE HAVEN GROUP
$69,900Active2.25 Acres0 Brambley Lane, Bennington, VT 05201
MLS# 5092066Listed by: HOFFMAN REAL ESTATE
$1,295,000Active52.61 Acres00 Montgomery Road, Pownal, VT 05261
MLS# 5092084Listed by: ALTON + WESTALL REAL ESTATE AGENCY, LLC
$145,000Active3 Acres530 Finbars Forest Road, Manchester, VT 05255
MLS# 5090186Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$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
$53,000Active0.48 Acres29 Asa's Way, Bennington, VT 05257
MLS# 5086024Listed by: MAHAR MCCARTHY REAL ESTATE
$99,900Pending2.6 Acres0 Kesick Swamp Road, Sunderland, VT 05250
MLS# 5085683Listed by: KW VERMONT - BRENDA JONES REAL ESTATE GROUP
$64,000Pending13.01 Acres3 W Hill Drive, Readsboro, VT 05350
MLS# 5085630Listed by: DEREK GREENE
$750,000Active279.97 Acres0 Klondike Road, Stamford, VT 05352
MLS# 5085248Listed by: UNITED COUNTRY REAL ESTATE MIKE JARVIS GROUP INC
$85,000Active1.2 Acres23 Moose Hollow Road #40, Winhall, VT 05340
MLS# 5083719Listed by: WINHALL REAL ESTATE
$150,000Active4 Acres0 Rocky Lane, Dorset, VT 05253
MLS# 5082777Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$997,000Active0.53 Acres153 Northside Drive, Bennington, VT 05201
MLS# 5081713Listed by: FOUR CORNER PROPERTIES LLC
$198,000Active54 Acres399 Bard Road, Bennington, VT 05201
MLS# 5081020Listed by: PREFERRED PROPERTIES
$825,000Active77.6 AcresWinhall Hollow Road, Winhall, VT 05340
MLS# 5079556Listed by: WOHLER REALTY GROUP
$495,000Active28 Acres00 VT Route 11, Peru, VT 05152
MLS# 5077214Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$1,900,000Active199 Acres00 VT Route 11, Peru, VT 05152
MLS# 5077219Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$450,000Active21.2 Acres56 Lower Taylor Hill Road, Winhall, VT 05340
MLS# 5074721Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$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
$2,395,000Active227 Acres00 VT Route 11, Peru, VT 05152
MLS# 5072898Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$150,000Active2.26 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
$139,000Pending1.62 Acres0 Lower Taylor Hill Road, Winhall, VT 05340
MLS# 5072280Listed by: MICHAEL ENGLAND REAL ESTATE
$90,000Active1 Acres41 Moose Hollow Road, Winhall, VT 05340
MLS# 5070793Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$115,000Active2.9 Acres311 Beechwood Lane #19, Peru, VT 05152
MLS# 5070443Listed by: BROMLEY REAL ESTATE
$400,000Active8.01 Acres248 French Hollow Road #1, Winhall, VT 05340
MLS# 5068233Listed by: WOHLER REALTY GROUP
$299,000Active9.3 Acres1347 Morse Hill Road #Lot 12-A, Dorset, VT 05253
MLS# 5069660Listed by: THE HAVEN GROUP
$23,999Active2.4 Acres00 Heartwellville View Road #34/35, Readsboro, VT 05350
MLS# 5068956Listed by: FLEX REALTY
$19,999Pending1.5 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 
$79,000Active17 Acres00 Bill T Drive, Readsboro, VT 05350
MLS# 5068152Listed by: DEERFIELD VALLEY REAL ESTATE
$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.
$1,200,000Active60 Acres215 VT Route 30, Dorset, VT 05251
MLS# 5056222Listed by: WOHLER REALTY GROUP
$1,500,000Active38.57 Acres500 Nims Road #Lot 2, Dorset, VT 05251
MLS# 5049329Listed by: JOSIAH ALLEN REAL ESTATE, INC.
$245,000Active28.5 Acres11 Old County Road, Landgrove, VT 05148
MLS# 5048222Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$145,000Pending15.49 Acres00 Silk Road, Bennington, VT 05201
MLS# 5040464Listed by: OWNERENTRY.COM
$399,500Active2.7 Acres2937 Dorset West Road, Dorset, VT 05251
MLS# 5013651Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$115,000Active2.9 AcresLot 3 Route 11/30, Winhall, VT 05340
MLS# 4963233Listed by: JOSIAH ALLEN REAL ESTATE, INC.
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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 October 2, 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.