116 Teacher Road, Jamaica, VT 05343

• 4 beds |
• 3 baths |
• 3,747 sqft

Property 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 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.

Listing Status:

Active

Date Added:

May 20, 2026

Data Last Updated:

May 25, 2026 at 3:14AM

Listing Office:

Winhall Real Estate : 802-297-1550

Listing Agent:

Carrie Mathews : 802-236-8458 : carrie@winhallrealestate.com

MLS ID:

5089829

Interior

• General: Dining Area1 FireplaceFurnishedKitchen/LivingLiving/DiningPrimary BR w/ BANatural LightWood Stove Insert
• Appliances: DishwasherDryerRange HoodElectric RangeRefrigeratorWasher
• Basement: ConcreteFullUnfinishedWalkoutExterior AccessBasement Stairs
• Flooring: CarpetTileWood
• A/C: Mini Split
• Heating: PropaneOilSolarHeat PumpHot AirWood Stove

Exterior

• General: DeckGazeboShed
• Style: Cape

Construction

• Roofing: Metal
• General: Wood FrameBlockConcrete

Location

• Road/Access: Dead EndPublic Maintained Road
• County: Windham

Lot

• Driveway: Paved
• Zoning: res

Utilities

• Utilities: Satellite
• Water: Drilled Well
• Sewer: Septic