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05343, VT - homes for sale
54 of 54 results displayed
- Coming Soon
$1,599,000Coming Soon6 beds 6 baths144 High Meadow Road, Winhall, VT 05340
MLS# 5098800Listed by: WOHLER REALTY GROUP
- New
$219,000Active16.9 Acres00 Howe Farm Road, Jamaica, VT 05343
MLS# 5098094Listed by: SOUTHERN VERMONT REALTY GROUP - New
$63,000Active2 beds 1 baths672 sq. ft.2022 Route 30, Jamaica, VT 05343
MLS# 5097748Listed by: WINHALL REAL ESTATE - New
$480,000Active5 beds 2 baths2,194 sq. ft.3327 Route 30, Jamaica, VT 05343
MLS# 5097573Listed by: WINHALL REAL ESTATE - New
$1,500,000Active7 beds 8 baths8,364 sq. ft.251 Pratt Bridge Road, Jamaica, VT 05343
MLS# 5097566Listed by: WINHALL REAL ESTATE 
$140,000Active1 beds 1 baths400 sq. ft.2074 VT RT 30, Jamaica, VT 05343
MLS# 5097088Listed by: MICHAEL ENGLAND REAL ESTATE- $140,000Active1 beds 1 baths400 sq. ft.
2074 VTRT 30 Route, Jamaica, VT 04343
MLS# 5097088Listed by: MICHAEL ENGLAND REAL ESTATE 
$515,000Active4 beds 3 baths2,115 sq. ft.367 Stratton Gate Road, Jamaica, VT 05343
MLS# 5097042Listed by: CUMMINGS & CO
$3,995,000Active4 beds 6 baths5,500 sq. ft.816 Black Bear Road, Jamaica, VT 05343
MLS# 5096846Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$1,475,000Active2 beds 2 baths1,601 sq. ft.691 Black Bear Road, Jamaica, VT 05343
MLS# 5095401Listed by: WINHALL REAL ESTATE
$195,000Active4.86 Acres1036 Dalewood Road, Jamaica, VT 05343
MLS# 5094902Listed by: WINHALL REAL ESTATE
$50,000Active28 Acresnon Pikes Falls Road #000H-3, Jamaica, VT 05343
MLS# 5094910Listed by: WINHALL REAL ESTATE
$559,000Active4 beds 3 baths2,000 sq. ft.155 Pratt Bridge Road, Jamaica, VT 05343
MLS# 5094845Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$449,000Active3 beds 3 baths1,980 sq. ft.163 Howe Farm Road, Jamaica, VT 05343
MLS# 5094647Listed by: LOWE'S REAL ESTATE, LLC
$45,000Active1 Acres0 Edie Lane #68, Jamaica, VT 05343
MLS# 5094562Listed by: WINHALL REAL ESTATE
$45,000Active1 Acres0 West Hill Road #39, Jamaica, VT 05343
MLS# 5094563Listed by: WINHALL REAL ESTATE
$2,500Active0.18 Acres0 Clayton Lane, Jamaica, VT 05343
MLS# 5094564Listed by: WINHALL REAL ESTATE
$575,000Pending4 beds 4 baths1,211 sq. ft.9 Beaver Pond Lane, Jamaica, VT 05343
MLS# 5094302Listed by: THE HAVEN GROUP
$650,000Active3 beds 4 baths2,678 sq. ft.177 Alwin Lane, Jamaica, VT 05343
MLS# 5094046Listed by: THE HAVEN GROUP
$839,000Active5 beds 5 baths3,840 sq. ft.42 Blackberry Lane, Jamaica, VT 05343
MLS# 5093492Listed by: THE HAVEN GROUP
$495,000Active3 beds 3 baths1,344 sq. ft.994 West Jamaica Road, Jamaica, VT 05343
MLS# 5093205Listed by: WOHLER REALTY GROUP
$86,000Active6.2 Acres1297 River Road, Jamaica, VT 05343
MLS# 5093083Listed by: BRATTLEBORO AREA REALTY
$139,000Active5 Acres14 Sugar Lot Lane, Jamaica, VT 05343
MLS# 5092583Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$1,295,000Active5 beds 4 baths3,040 sq. ft.4427 West Hill Road South, Jamaica, VT 05343
MLS# 5090616Listed by: WINHALL REAL ESTATE
$798,000Active3 beds 5 baths3,100 sq. ft.52 High Meadow Road #11, Winhall, VT 05155
MLS# 5090546Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$1,100,000Active5 beds 5 baths4,453 sq. ft.6 Old Ridge Road, Winhall, VT 05340
MLS# 5090234Listed by: WOHLER REALTY GROUP
$1,225,000Active4 beds 3 baths3,357 sq. ft.153 High Meadow Road, Winhall, VT 05340
MLS# 5090036Listed by: WOHLER REALTY GROUP
$595,000Active4 beds 2 baths1,430 sq. ft.9 Mountain Acres Road, Jamaica, VT 05343
MLS# 5089830Listed by: WINHALL REAL ESTATE
$215,000Active2 beds 1 baths691 sq. ft.8581 Vermont Route 30 #B, Jamaica, VT 05343
MLS# 5089602Listed by: THE HAVEN GROUP
$110,000Active2 beds 2 baths1,040 sq. ft.1940 VT RT 30, Jamaica, VT 05343
MLS# 5089414Listed by: MICHAEL ENGLAND REAL ESTATE
$899,000Active5 beds 4 baths4,000 sq. ft.178 High Meadow Road, Winhall, VT 05340
MLS# 5088923Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$850,000Active5 beds 4 baths3,218 sq. ft.4880 Pikes Falls Road, Jamaica, VT 05343
MLS# 5088809Listed by: MICHAEL ENGLAND REAL ESTATE
$720,000Active4 beds 3 baths2,317 sq. ft.B2 Maple Ridge Road, Winhall, VT 05340
MLS# 5085195Listed by: MICHAEL ENGLAND REAL ESTATE
$89,900Active4 beds 2 baths1,902 sq. ft.206 Smith Road, Jamaica, VT 05343
MLS# 5082980Listed by: BRATTLEBORO AREA REALTY
$1,450,000Active201.4 AcresForrester Road, Jamaica, VT 05343
MLS# 5082418Listed by: LOWE'S REAL ESTATE, LLC- Open Sat, 10am to 12pm
$460,000Active3 beds 2 baths1,888 sq. ft.57 Oak Lane, Jamaica, VT 05343
MLS# 5081124Listed by: MICHAEL ENGLAND REAL ESTATE 
$195,000Active1.2 Acres4769 Pikes Falls Road, Jamaica, VT 05143
MLS# 5080889Listed by: EXP REALTY
$1,399,999Active6 beds 4 baths3,800 sq. ft.121 High Meadow Road, Winhall, VT 05340-9999
MLS# 5080413Listed by: LISTWITHFREEDOM.COM
$325,000Active4 beds 2 baths2,520 sq. ft.29 Pikes Falls Road, Jamaica, VT 05343
MLS# 5078084Listed by: WINHALL REAL ESTATE
$500,000Active71 Acres00 Turkey Mountain Road, Jamaica, VT 05343
MLS# 5077252Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$85,000Active1 Acres000F-320 Bourbon Run, Jamaica, VT 05343
MLS# 5076157Listed by: MICHAEL ENGLAND REAL ESTATE
$8,200,000Active6 beds 10 baths10,763 sq. ft.557 Trager Road, Jamaica, VT 05343
MLS# 5076041Listed by: WOHLER REALTY GROUP
$899,000Active4 beds 3 baths3,252 sq. ft.E1 Rock Ridge Road, Winhall, VT 05340
MLS# 5075528Listed by: THE HAVEN GROUP
$340,000Active12.05 Acres101 Catherine Road, Jamaica, VT 05343
MLS# 5074686Listed by: STRATTON REAL ESTATE
$450,000Active10.26 Acres4.1 Pearl Buck Drive, Winhall, VT 05340
MLS# 5073637Listed by: WOHLER REALTY GROUP
$57,000Active2 beds 1 baths844 sq. ft.2036 VT RT 30, Jamaica, VT 05343
MLS# 5072288Listed by: MICHAEL ENGLAND REAL ESTATE
$210,000Active35 Acres00 Route 100, Jamaica, VT 05343
MLS# 5070790Listed by: SOUTHERN VERMONT REALTY GROUP
$35,000Pending1 AcresBourbon Run Road, Jamaica, VT 05343
MLS# 5067790Listed by: OWNERENTRY.COM
$475,000Active30 Acres00 West Hill Road South, Jamaica, VT 05343
MLS# 5065110Listed by: SOUTHERN VERMONT REALTY GROUP
$1,140,000Active4 beds 3 baths4,193 sq. ft.70 Hunter Lane, Jamaica, VT 05343
MLS# 5060615Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$1,040,000Active5 beds 5 baths3,363 sq. ft.1189 Cole Pond Road, Jamaica, VT 05343
MLS# 5060071Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$178,000Active8 Acres4441 Route 30, Jamaica, VT 05343
MLS# 5067302Listed by: THE HAVEN GROUP
$120,000Active4.68 Acres8559 VT Route 30 #Lots 2 & 3, Jamaica, VT 05343
MLS# 5076767Listed by: WINHALL REAL ESTATE
$2,399,000Active4 beds 5 baths3,569 sq. ft.662 Howe Farm Road, Jamaica, VT 05343
MLS# 4972272Listed by: FOUR SEASONS SOTHEBY'S INT'L 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 July 10, 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.