Jamaica, VT | 116 Teacher Road

This beautiful home in the traditional village of Wardsboro offers sweeping mountaintop views and spectacular sunsets, along with convenient access to nearby ski resorts, cross-country ski trails, VAST trails, and the town center - all just minutes away. Great for the outdoor enthusiast, this home is also well-suited for remote work, streaming, and staying connected with dedicated reliable high-speed internet for uninterrupted service. Recent improvements include an expansive kitchen with updated appliances, a new roof, windows, flooring, well pump, mini-split systems, and high-efficiency propane heating and hot water. In winter, relax by the warmth of the woodstove; during warmer months, entertain guests on the deck or around the fire pit. A finished walkout basement provides flexible space for a game room, additional living space or bedrooms. The property features a three-car garage with loft storage, a notable 16 by 20 foot antique barn, an 18 by 10 foot open shelter, and a 14 by 12 foot enclosed outbuilding ideal for storing snowmobiles and recreational gear. Ample parking accommodates visitors and trailers, while pets can enjoy a fenced yard & shelter under the Magnolia tree. The surveyed property also includes two additional lots with state-approved wastewater permits already on file, offering the opportunity to build, sell, or preserve them for added privacy.

Tucked into a tree-lined one-acre lot in Wardsboro, Vermont, this special property offers just the right amount of privacy while keeping you close to everything Southern Vermont has to offer. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property offers easy access to year-round recreation. Start the morning on the large front porch or settle onto the oversized back deck and take in the peaceful surroundings. Inside, this 4-bedroom, 4-bath home offers more than 3,000 square feet of living space across three finished levels, providing plenty of room to gather while still giving everyone space of their own. The home features a bright open floor plan with 10-foot ceilings on every level and wood flooring throughout. The main living area flows effortlessly from the kitchen to the dining space and into a warm, inviting sitting area anchored by a wood stove. A first-floor bedroom with Jack-and-Jill ensuite bath provides flexible space for guests or first floor living. Upstairs are three additional large bedrooms, including a spacious primary suite with ensuite bath and two walk-in closets, plus a second full bath, home office, and laundry closet. The finished lower level adds substantial living space with tile floors, a wood-burning fireplace, and sliding doors leading directly to the backyard. Additional features include attached garage, surround sound throughout the first floor and basement, central vacuum, infrastructure for a heated garage, a new hot water tank in 2022, and a new pressure tank in 2023. Nearby VAST trail access, along with an indoor heated pool, tennis, and pickleball at the Snow Mountain Farms clubhouse, provides plenty of ways to enjoy the area year-round.

This spacious 5 bedroom home is located on a private lot in the popular Snow Mountain Farms community. The Property has a brand new roof!!! The three levels offer privacy and quiet with an outdoor fire pit, garden shed, and access to the VAST snowmobile trails across the street. Its open floor plan with vaulted ceilings and stone hearth gas fireplace is perfect for aprés ski gatherings, and the large open kitchen is ready to accommodate cooking for a large group. Just off the kitchen is a dining room with views over the wooded lot with convenient access to the screened porch for summer entertaining.The property includes all furnishings, A Tesla Battery Back up system as well as an electric car charger.The property has a new roof installed 4/12/26 The Snow Mountain Farms clubhouse features an indoor pool, plus outdoor tennis and pickle ball courts. Make an appointment today to tour this special property located 15 minutes to Mount Snow and 20 minutes to Stratton Mountain.

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.

Already operating as a successful short-term rental, 24 Mowrey Road offers the space, setting, and amenities buyers are looking for in a Southern Vermont getaway. Set on 2.3 acres along a town-maintained dead-end road, this spacious 4-bedroom, 4-bath home is positioned between Stratton and Mount Snow, with easy access to year-round recreation. Inside, the open great room creates an inviting gathering space, complete with a wood stove, propane stove, double sliders to the rear deck, and a fun ski-lift chair feature that gives the home unmistakable Vermont ski-house character. The layout works especially well for groups, with a first-floor primary suite with king bed, three additional bedrooms upstairs, 2 with king beds and one with 2 triple bunks, multiple baths, and a mostly finished lower level offering additional family, recreation, and bonus space. A covered front porch and expansive rear deck extend the living outdoors, while the detached garage provides welcome storage for skis, bikes, and Vermont gear. Dual Tesla Powerwall batteries with Tesla backup equipment add valuable energy storage and backup capability during outages.Starlink internet provides reliable high-speed connectivity for streaming, remote work, and guest use, an especially valuable amenity for a Vermont second home or short-term rental. The home is thoughtfully set up for vacation-rental use and is currently professionally managed as an operational STR, giving a new owner the option to continue its established rental use or simply enjoy it as a generously sized second home. Approximately 3,075 finished square feet provide room to spread out without losing the cozy mountain-home feel. Rental history is available for interested buyers. A well-established Vermont retreat with income history, personality, and space for everyone to gather, all within approximately 15 minutes of Mount Snow and 25 to Stratton.

Nestled among the trees in the sought-after Snow Mountain Farms community, this beautifully maintained four-bedroom home is just 7.6 miles to Mount Snow and 13 miles to Stratton Mountain Resort. The welcoming front porch leads to a spacious wrap around deck, creating an ideal setting for entertaining or simply enjoying the peaceful natural surroundings. The main living area features pine floors and a cozy wood-burning fireplace, delivering that classic Vermont feel. The primary suite with its own bath, along with two additional bedrooms, are located on the main level for easy living. The lower level expands the living space with a workshop, a recreation room complete with an indoor hot tub, and direct walkout access to the backyard. A fourth bedroom and a versatile bonus room provide additional flexibility for guests, a home office, or hobbies. The community offers an indoor pool for year-round enjoyment and a outdoor tennis court. Whether you're seeking a full-time residence or vacation getaway, this home is ready to deliver a mountain lifestyle at its best.

Village living with room for possibilities! Just steps from Jamaica State Park and downtown Jamaica, this versatile home offers a wonderful opportunity to enjoy Vermont living with the added benefit of separate living spaces and potential rental income. Abutting the river, the property is currently configured as three spacious two-bedroom apartments—two with one bath and a third with two baths. Make one apartment your full-time residence or Vermont getaway while renting the others, or explore options for bringing extended family together while maintaining privacy and independence. Two apartments are currently vacant and ready for immediate occupancy. The third is home to long-term tenants who hope to stay, offering potential ongoing income. Recent improvements include a new furnace, new well pump, freshly painted exterior, and replacement windows where needed. The hot water heaters are approximately five years old. One apartment features a new refrigerator and stove, while another includes a three-year-old washer and dryer along with a new dishwasher. Enjoy a location that puts outdoor adventure and village charm right outside your door. Walk to Jamaica State Park for hiking, biking, swimming, and exploring, or stroll downtown to enjoy this welcoming Vermont community. Stratton Mountain and other Southern Vermont attractions are within easy reach, making this an appealing home base in every season. Whether you envision a primary home with supplemental income, a vacation retreat with space for guests, or a future reconfiguration to suit your needs, this property offers exceptional flexibility. Any conversion or changes in use would be subject to applicable approvals. A special opportunity to make yourself at home in the heart of Jamaica!

Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and only 3/4 mile to Jamaica State Park, outdoor recreation, dining, and local shops are all close by. Stratton Mountain and Mount Snow are both just 20–25 minutes away, making this an excellent four-season retreat or full-time residence. Inside, the home offers hardwood floors throughout, generous living space, and a wonderful sunroom with a woodstove hookup perfect for cozy evenings year-round. Additional highlights include a paved driveway, easy access to Route 30, an attached garage and workshop space.. For added transparency and peace of mind, the seller has completed a pre-listing property inspection, which is attached in the MLS. Lovingly owned by the same family since it was built, this home is filled with warmth, history, and opportunity for its next chapter. This property has full time tenants and need a minimum of 24 hours notice, longer preferred, on showings. Closing can happen October 1 or after.

Sweet! So easy... nothing to do but move right in and start to enjoy. This second-generation owner has updated the living area to an open concept featuring a huge kitchen island, dining area with built-ins, and a focal point fireplace/hearth to anchor the room. Add a picture window overlooking the meticulously landscaped lawn and pond the ducks call home, and you have a perfect recipe for home. Enter on the walk out level and find a mud room, sauna, 3/4 bath and family room, plus plenty of storage for equipment or lock away area if you are renting. Just off RT 100 and merely 11 minutes to Mount Snow, Skiing is an easy get, as well as boating, hiking and a ton of other recreation. Tuck in as a primary, easy care paved drive, garage parking and a sun porch off 2 of the bedrooms are all bonuses to ease of year round living. Possession after 11/1/26 please. Come, feed the ducks...play a little...

This four-bedroom, three-bathroom home with additional office or bonus room space can be yours! Offering a spacious family room with fireplace, a cozy den off the garage entry. A formal dining room in addition to kitchen that allows for another sitting area with plenty of wall space to decorate. The location is set back off Route 100, so very minimal road noise yet the highway is always maintained well by the state. Private pond with a sprawling yard. The two-car attached garage with access to both the basement and storage space above is very convenient for the colder months! Cedar exterior siding with a Brazilian rosewood oil finish, lovely hardwood flooring throughout most of the home with a walnut finish. Only two smaller rooms have carpeting. Wonderful mudroom entryway to hang your coats and boots. A surround sound system both inside and out for your enjoyment during our warmer months here in southern Vermont. This home has been lovingly cared for and enjoyed for many years! Nice concrete patio at the front of the home with custom Coolaroo shades and an additional rear deck off the back of the home with easy access through the French doors located just off the kitchen overlooking the pond. This home is a solid, well-built home with a nice layout. Very short driving distances to both Stratton and Mount Snow. Truly a hidden gem!

Attention Buyers looking for a Turn Key property and or business location: Proven Short Term Rental Income, 142k gross over the past 8 years with 2 of those years virtually closed due to COVID. 135k net. Being on Route 100 gives you easy access to everything including Commercial and Mixed Use prime location. Welcome to Your Vermont Retreat on scenic Route 100 in Wardsboro. Beautifully maintained and thoughtfully designed, this turnkey 3-bedroom, 2-bath home is ready to enjoy from day one whether as your full time residence, vacation getaway, or a highly successful short-term rental that guests absolutely love. Walking in through the covered entry you’ll find soaring cathedral ceilings in the living room, abundant natural light, a cozy brick hearth with wood stove, and an inviting open kitchen and dining area perfect for gathering with family and friends. This main floor also has a full bathroom. The 3 bedrooms and another full bath are upstairs. Step back outside to a spacious deck featuring a hot tub, sauna, outdoor seating, and peaceful views and sounds of the beautiful Wardsboro Brook. The oversized two car garage includes a finished bonus room above, ideal for a studio apartment, office, or guest space. Bring ALL of your Big Wheels and Small Wheels! Complete with paved driveway and walkways including paved go cart and biking paths around the house and garage and directly onto the paved state road. Just for you, these sellers built a charming and expansive fieldstone fire pit, room for an RV, plenty of lawn space for play and entertaining and some beautiful flowering plantings. Located on desirable Route 100 and just 6 miles from Mount Snow, 12 from Stratton Mtn this property offers year-round adventure and exceptional investment potential. A true Vermont gem fully furnished with memories waiting to be made and income opportunities ready to continue.