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05343, VT - homes for sale
65 of 65 results displayed
- New
$549,000Active4 beds 3 baths2,359 sq. ft.116 Teacher Road, Jamaica, VT 05343
MLS# 5106080Listed by: WINHALL REAL ESTATE
- New
$190,000Active30.1 Acres0 Schoolhouse Road, Jamaica, VT 05343
MLS# 5105324Listed by: FOUNTAINS LAND INC. - New
$120,000Active10.2 Acres0 South Hill Road, Jamaica, VT 05343
MLS# 5105314Listed by: FOUNTAINS LAND INC. 
$875,000Pending4 beds 3 baths2,322 sq. ft.G2 Cobble Ridge Road, Winhall, VT 05340
MLS# 5105101Listed by: THE HAVEN GROUP- New
$765,000Active4 beds 3 baths2,322 sq. ft.72 Benson Fuller Road, Winhall, VT 05340
MLS# 5105009Listed by: THE HAVEN GROUP 
$299,000Active3 beds 2 baths1,296 sq. ft.170 River Road, Jamaica, VT 05343
MLS# 5104265Listed by: LOWE'S REAL ESTATE, LLC
$250,000Pending3 beds 2 baths1,224 sq. ft.270 Castle Hill Road, Jamaica, VT 05343
MLS# 5103863Listed by: LOWE'S REAL ESTATE, LLC
$499,000Active3 beds 3 baths2,584 sq. ft.1905 Turkey Mountain Road, Jamaica, VT 05343
MLS# 5103908Listed by: SOUTHERN VERMONT REALTY GROUP
$299,000Active57.76 AcresVT Route 100 South, Jamaica, VT 05343
MLS# 5103450Listed by: LOWE'S REAL ESTATE, LLC
$849,000Active4 beds 4 baths2,878 sq. ft.32 Benson Fuller Drive, Winhall, VT 05340
MLS# 5102830Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$585,000Active91.6 Acres0 Water Street, Jamaica, VT 05343
MLS# 5102573Listed by: WINHALL REAL ESTATE
$189,500Pending2 beds 1 baths893 sq. ft.1018 South Hill Road, Jamaica, VT 05343
MLS# 5102407Listed by: REAL BROKER LLC
$175,000Active3 beds 2 baths1,576 sq. ft.1372 VTRT 100 S, Jamaica, VT 05343
MLS# 5101991Listed by: MICHAEL ENGLAND REAL ESTATE
$2,350,000Active5 beds 4 baths4,752 sq. ft.6 Sunset Ridge Road, Winhall, VT 05340
MLS# 5101868Listed by: WOHLER REALTY GROUP
$99,000Active6.4 AcresWorden Road, Jamaica, VT 05343
MLS# 5101763Listed by: WINHALL REAL ESTATE
$1,450,000Active5 beds 4 baths2,974 sq. ft.494-498 Goodaleville Road, Jamaica, VT 05343
MLS# 5101688Listed by: THE HAVEN GROUP
$1,250,000Active4 beds 3 baths2,022 sq. ft.564 Goodaleville Road, Jamaica, VT 05343
MLS# 5101689Listed by: THE HAVEN GROUP
$136,000Active14 Acres182 Partridge Lane, Jamaica, VT 05343
MLS# 5101508Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$290,000Active289.12 Acres0 Black Bear Road, Jamaica, VT 05343
MLS# 5101033Listed by: FOUNTAINS LAND INC.
$260,000Active3.3 Acres0 Mountain Haunts, Winhall, VT 05340
MLS# 5099438Listed by: MICHAEL ENGLAND REAL ESTATE
$1,599,000Active6 beds 6 baths5,568 sq. ft.144 High Meadow Road, Winhall, VT 05340
MLS# 5098800Listed by: WOHLER REALTY GROUP
$219,000Active16.9 Acres00 Howe Farm Road, Jamaica, VT 05343
MLS# 5098094Listed by: SOUTHERN VERMONT REALTY GROUP
$63,000Active2 beds 1 baths672 sq. ft.2022 Route 30, Jamaica, VT 05343
MLS# 5097748Listed by: WINHALL REAL ESTATE
$480,000Active5 beds 2 baths2,194 sq. ft.3327 Route 30, Jamaica, VT 05343
MLS# 5097573Listed by: WINHALL REAL ESTATE
$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 
$495,000Active4 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
$825,000Active3 beds 3 baths2,598 sq. ft.C-4 Ridge Road, Winhall, VT 05340
MLS# 5094616Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$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
$650,000Active3 beds 4 baths2,678 sq. ft.177 Alwin Lane, Jamaica, VT 05343
MLS# 5094046Listed by: THE HAVEN GROUP- Open Sun, 11am to 1pm
$839,000Active5 beds 5 baths3,840 sq. ft.42 Blackberry Lane, Jamaica, VT 05343
MLS# 5093492Listed by: THE HAVEN 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
$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
$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
$89,900Pending4 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
$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
$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
$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
$1,100,000Active4 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 August 24, 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.