116 Teacher Road Jamaica, VT $ 570,000
116 Teacher Road
$ 570,000
Recently Listed
Open House 5/24 12pm - 2pm
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116 Teacher Road

Jamaica, VT, 05343
$ 570,000
Bedrooms4 Baths2.1 Sq 2,359

Monthly Estimate*

$ 3,510

Listed by Carrie Mathews, Winhall Real Estate, 802-236-8458, carrie@winhallrealestate.com
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Single Family Home for sale in Jamaica, VT

for $570,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,359 square foot home was built in 1971 on a lot size of 14.4.

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.

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Open House

5/24/2026 12:00 PM - 2:00 PM
116 Teacher Road Jamaica, VT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 570,000

Bedrooms

4

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 0

Style

Cape

Lot Size

14.4

Year Built

1971

Town/City

Jamaica

County/Region

Windham

MLS | Web ID

5089829

Features
Interior
Basement Description Concrete Full Unfinished Walkout Exterior Access Basement Stairs
Interior Amenities Dining Area 1 Fireplace Furnished Kitchen/Living Living/Dining Primary BR w/ BA Natural Light Wood Stove Insert
Basement Yes
Flooring Carpet Tile Wood
Beds 4
Total Rooms 11
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General
Road Frontage TBD
Sewer Septic
Heating Propane Oil Solar Heat Pump Hot Air Wood Stove
Cooling Mini Split
Utilities Satellite
Roof Metal
Appliances Dishwasher Dryer Range Hood Electric Range Refrigerator Washer
Garage Yes
Flood Zone No
Zoning res
3/4 Baths 1
Full Baths 1
Half Baths 1
Bathrooms 3
Year Built 1971
Electric Circuit Breaker(s)
Style Cape
Stories Count 3
Construction Status Existing
Type Single Family
Auction No
Tax Year 2026
Status Detail 0
Covenants No
Construction Materials Wood Frame
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.
City Jamaica
Other Equipment Smoke Detector Wood Stove
Seasonal No
DOM 1
Price Per Sq Ft Total AG 241.63
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Exterior
Lot Features Country Setting Landscaped Secluded Ski Area Trail/Near Trail Walking Trails
Exterior Amenities Deck Gazebo Shed
Driveway Paved
Lot Size Area 14.4
Water Source Drilled Well
Garage Capacity 2
Foundation Block Concrete
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* Excluded Features
List By
Carrie Mathews

Listing Agent

Winhall Real Estate

Broker

(802) 236-8458

Phone

carrie@winhallrealestate.com

Email

Affordability Calculator

$3,510
Per Month
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Monthly Principal & Interest
$3,510
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
451920 Elementary School
452237 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
5/20/2026$570,000 Listed Price

Map


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116 Teacher Road, Jamaica, VT, 05343 is a Single Family Home for sale at $570,000 with 2,359 sqft and a lot size of 14.4. 116 Teacher Road has 4 bedrooms, 2.1 baths, and was built in 1971. The property's zip code is 05343 which is in Jamaica, VT