116 Teacher Rd

Jamaica, VT 05343

$570,000
Price
4
Beds
2,359 Sq. Ft.
$242 / Sq. Ft.
2,359
Sq. Ft.
$242
per Sq. Ft.
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Description

Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time residence. Conveniently located just 20 minutes from Stratton Mountain and Mount Snow. The south-facing home features...Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time residence. Conveniently located just 20 minutes from Stratton Mountain and Mount Snow. The south-facing home features bright, open living and dining spaces with large picture windows showcasing beautiful views in every direction. A fieldstone hearth with wood stove creates a warm and inviting atmosphere for entertaining, while the kitchen offers abundant storage. The main level includes three bedrooms, a ¾ bath, and a sun-filled mudroom/sunroom with wall-to-wall windows and its own propane stove. Upstairs, the spacious primary suite or bunk room retreat includes a full bath, cedar walk-in closet, and mountain views. The basement with half bath, and attached 2-car garage provide excellent storage, workshop, recreation, or future living space potential. Outside, enjoy expansive lawns, meadows, a screened gazebo, private trails, mature forest, stone walls from an old homestead, and a year-round creek. Endless hiking, snowmobiling, ATV riding, and outdoor adventure await right from the property. Energy-efficient upgrades include owned REC solar panels, owned Tesla backup batteries, Daikin heat pumps and mini splits, rebuilt chimney, generator-ready setup, multiple heating options, and high-speed Starlink internet with mesh coverage. Tucked at the end of a town-maintained dead-end road, this is a rare opportunity to own a true Vermont escape.
  1. Listed by Carrie Mathews • Winhall Real Estate

Property Details for 116 Teacher Road

Zoning
res
LISTING UPDATED: 05/21/2026 02:42 PM

Property Details for 116 Teacher Road

StatusActive
MLS #5089829
Days on Market13
Taxes$6,413 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1971
Lot Size14.40 AC / 627,264 SF
CountyWindham County
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Location

Listing Courtesy of Winhall Real Estate
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Building Information for 116 Teacher Road

Stories3Year Built1971Building Size-Lot Size14.40 AC / 627,264 SF

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$3,375 per month

30 year fixed, 6.36% Interest

Principal and Interest

$2,840

Property Taxes

$534

HOA Dues

$0

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Property Information for 116 Teacher Road

Summary
Location and General Information
  • City: Jamaica
  • County: VT-Windham
  • Directions: From Route 100 take Henderson Road, up the hill, the road will bend to the left and there turns into Teacher Road. Continue to the dead end.
  • Latitude: 43.068726215767498
  • Longitude: -72.755253754631042
  • Road Frontage: TBD
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05343
Taxes and HOA Information
  • SPAN Number: 32410110141
  • Tax Year: 2026
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Paved
Property
Lot Information
  • Lot Features: Country Setting, Landscaped, Secluded, Ski Area, Trail/Near Trail, Walking Trails
  • Lot Size Acres: 14.4
  • Total Finished Area: 2359.0
  • Above Grade Finished Area: 2359.0
  • Above Grade Finished Area Source: Public Records
  • Above Grade Unfinished Area: 0.0
  • Below Grade Finished Area: 0.0
  • Below Grade Finished Area Source: Public Records
  • Below Grade Unfinished Area: 1388.0
  • BelowGradeUnfinishedAreaSource: Public Records
  • Lot Size Square Feet: 627264.0
  • Total Area: 3747.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Resort: Yes
  • Surveyed: Unknown
  • Year Built: 1971
Utilities
  • Electric: Circuit Breaker(s)
  • Sewer: Septic
  • Water Source: Drilled Well
  • Utilities: Satellite
  • Internet: Satellite Internet
Interior and Exterior Features
Exterior Features
  • Color: Shale
  • Construction Materials: Wood Frame
  • Roof: Metal
Interior Features
  • Appliances: Dishwasher, Dryer, Range Hood, Electric Range, Refrigerator, Washer
  • Basement: Yes
  • Basement Access Type: Walkout
  • Basement Description: Concrete, Full, Unfinished, Walkout, Exterior Access, Basement Stairs
  • Flooring: Carpet, Tile, Wood
  • Heating: Propane, Oil, Solar, Heat Pump, Hot Air, Wood Stove
  • Cooling: Mini Split
  • Total Stories: 3
  • Rooms Total: 11
  • Bathrooms Full: 1
  • Bathrooms Half: 1
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 1
  • Bedrooms Total: 4
  • Bathrooms Total: 3

Property History for 116 Teacher Road

DateEvent & SourcePriceAppreciation
May 20, 2026

Listed (Active)

New England Real Estate Network #5089829

$570,000—
Feb 14, 2023

Sold (Public Record)

Public Record #1506252086

$385,000—
Feb 14, 2023

Sold

New England Real Estate Network #4937663

$385,000—
DateEvent & SourcePrice
05/20/2026

Listed (Active)

New England Real Estate Network #5089829

$570,000
02/14/2023

Sold (Public Record)

Public Record #1506252086

$385,000
02/14/2023

Sold

New England Real Estate Network #4937663

$385,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 116 Teacher Road

Taxable ValueLand$51,300Additions$182,300Total$233,600
Tax Record2024$6,029 ($502 / month)
Home Facts
Beds4Baths1Total Finished SqFt2,360 SqFtAbove Grade Finished SqFt2,360 SqFtStories1Lot Size627,264 SqFtStyleSingle Family ResidenceYear Built1970CountyWINDHAMAPN(101) 00P-11Fireplace TypeHas Fireplace

Schools near 116 Teacher Road

This home is within West River Valley Modified Union Education District #72a.
Rating
School
Type
Grades
Distance
Leland & Gray Uhsd #34
Public - 6 to 12
Rating
School
Distance
Leland & Gray Uhsd #34
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 116 Teacher Road, Jamaica, VT 05343

116 Teacher Road is a single family home for sale in Jamaica, VT 05343. This property was listed for sale on May 20, 2026 by Winhall Real Estate, it's currently listed at $570,000. It has been on the market for a total of 13 days and was last sold on February 14, 2023. This listing's school districts are West River Valley Modified Union Education District #72b, West River Valley Modified Union Education District #72a. Nearby schools include Leland & Gray Uhsd #34. 116 Teacher Road is a 4-bed, 3-bath, 2,359 sqft single family home built in 1971.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Winhall Real Estate

Copyright 2026 PrimeMLS, 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 PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 06/03/2026 12:58 AM