Jamaica Homes for Sale

Welcome to Jamaica, Vermont – a hidden gem nestled in the heart of Windham County! This charming town boasts a rich tapestry of natural beauty, outdoor adventures, and a tight-knit community that welcomes newcomers with open arms. Surrounded by the picturesque Green Mountains, Jamaica is perfect for those who crave a serene lifestyle while still being close to vibrant local culture.

The town is renowned for its stunning landscapes, from the rolling hills to the lush forests, making it an ideal spot for hiking, biking, and exploring nature. In the winter, nearby ski resorts provide exhilarating slopes for winter sports enthusiasts. Jamaica also features charming local shops, cozy eateries, and a vibrant arts scene, ensuring there’s always something to enjoy.

For those looking to settle down in this idyllic setting, there are a variety of homes for sale that cater to different tastes and budgets. Whether you’re in search of a quaint cottage, a spacious family home, or a rustic retreat, Jamaica offers an array of options that blend seamlessly with the natural surroundings. Many of these homes feature stunning views, ample outdoor space, and modern amenities, allowing you to enjoy the best of both worlds – comfort and nature.

Discover the warmth and charm of Jamaica, Vermont. With its friendly community, breathtaking scenery, and diverse real estate options, it’s the perfect place to call home. Explore our listings today and take the first step toward your dream lifestyle in this enchanting town!

Newest Jamaica Homes for Sale

$549,000

4 Beds ⋅ 3 Baths ⋅ 5106080 MLS

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.

116 Teacher Rd, Jamaica

$299,000

3 Beds ⋅ 2 Baths ⋅ 5104265 MLS

Charming cape style modular home set on a beautiful, level 3.67 acre parcel. The expansive yard is framed by a stunning mountain backdrop that gives the entire property a peaceful, protected feel. Inside, you’ll find a bright and welcoming three bedroom, one and a half bath layout with plenty of natural light and comfortable living spaces. Mudroom entryway offers nice closet space and washer dryer hookups. Kitchen with eat in dining area are open to the living room space. A large back deck extends your living area outdoors, complete with a firepit gathering spot perfect for relaxing evenings. The home has been thoughtfully maintained, including a new furnace installed in 2025. Located near the West River and just a short drive to Stratton, Mount Snow, and Bromley ski resorts, this property offers year round recreation in every direction. Come take a look and experience the setting for yourself.

170 River Rd, Jamaica

$499,000

3 Beds ⋅ 3 Baths ⋅ 5103908 MLS

Welcome to Cloister Falls, a truly special offering in the Green Mountains! Tucked among extensive grounds with mature gardens, a pond, and thoughtfully landscaped outdoor spaces, this 3+ bed plus den and office, 3 bath log home offers a setting that feels connected to the surrounding Vermont landscape. The property's signature feature is its swimming hole and waterfall , a natural gathering place for relaxing, entertaining, or enjoying the sound of moving water right outside your door. Inside, the home has both comfortable and impressive gathering spaces and a flexible floor plan. The formal living room is centered around a stone wood-burning fireplace and framed by natural wood details and rich textures throughout. The country kitchen features cherry cabinetry, granite countertops, and a vintage-inspired Glenwood propane and wood cookstove with plenty of workspace, counter and storage. The main level also includes a library or office space, spacious den, and solarium, creating multiple options for work, hobbies, or quiet retreat spaces.The second floor offers two inviting guest bedrooms one with a view of the pond and gardens and the either with its own balcony. A generously sized guest bath is also on this level along with a primary suite featuring a private bath and dual walk-in closets. An attached two-car garage with 2nd floor adds convenience while the surrounding grounds provide room to garden, explore, and enjoy the outdoors through every season. The walk to the screen house past the pond gives a secret garden feel. From there, take the foot bridge into your 25 acres for exploration. This is a property where the landscape and home come together to create a special experience and offering that doesn’t come along often.

1905 Turkey Mountain Rd, Jamaica

$1,250,000

4 Beds ⋅ 3 Baths ⋅ 5101689 MLS

10 MINUTES TO STRATTON RESORT | This beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition, and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain Resort and less than a mile from Honeypie Restaurant and Rawsonville Market, the location offers easy access to the mountain, local favorites, and everything the area has to offer. High ceilings, generous windows, and two sunrooms fill the interior with natural light, while quality construction and thoughtful details are evident throughout. Recent improvements include a standing-seam metal roof, new Marvin windows, mini-split heating and cooling, new appliances, a large new deck, a new drilled well, a whole-house generator, an EV charger, restored floors and fir doors, updated tile, and custom built-ins. The property has a deep connection to the surrounding land. Beautiful landscaping and stonework complement an open field, apple orchard, raised garden beds built with hemlock milled from the property, and a useful storage shed. The large deck with hot tub creates an inviting place to relax and take in the serene setting. Situated along the Winhall River with direct access to the West River Rail Trail, the property makes it easy to walk, bike, swim, and enjoy the outdoors right from home. A five-bedroom septic system provides flexibility for future expansion. This is the Vermont home you have been looking for-full of character, warmth, and history, yet updated with the level of care and quality that makes ownership easy from day one. A trusted local builder has already done the hard work. Make this your Vermont address. Seller is the listing broker. Neighboring property available 494-498 Goodaleville Road - MLS#5101688.

564 Goodaleville Rd, Jamaica

$1,450,000

5 Beds ⋅ 4 Baths ⋅ 5101688 MLS

10 MINUTES TO STRATTON RESORT | 4BR main house, 1BR barn apartment, and separate restored vintage barn | Just minutes from Stratton Mountain Resort, this beautifully restored Vermont farmhouse blends authentic character, exceptional craftsmanship, and modern comfort. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit that have long defined it. Thoughtfully renovated by Vermont Country Builders, the home preserves its historic soul while providing quality and efficiency suited for each season. The main house spans three finished levels. An expanded kitchen with soapstone countertops opens to a spacious dining room and cozy sitting area with gas fireplace. Original wide-plank floors, antique doors, and a classic clawfoot tub celebrate the home’s heritage. Extensive improvements include modern insulation, electrical, plumbing, a new foundation, sheetrock, high-efficiency propane boiler, HRV ventilation, mini-splits, Marvin windows, and an improved floor plan. Additional upgrades include standing-seam roofs on all three buildings, custom gutters and snow guards, updated baths, custom built-ins, new appliances, and AZEK decks. A separate guest house, originally Schapiro’s art studio, offers a self-contained one-bedroom apartment with SMEG appliances, in-unit laundry and private hot tub. Below is a large heated storage area and screened porch. The vintage barn has been stabilized and restored with parking and EV charger. Extensive stonework, thoughtful landscaping, gardens, decks, a stone patio, and welcoming front porch complement the setting along the Winhall River. Direct access to the West River Rail Trail makes it easy to walk, bike, swim, and explore right from home. Less than a mile from Honeypie and Rawsonville Market and only minutes from Stratton Mountain Resort. Listing agent is related to seller. See neighboring property MLS # 5101689.

494-498 Goodaleville Rd, Jamaica

$480,000

5 Beds ⋅ 2 Baths ⋅ 5097573 MLS

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.

3327 Rte 30, Jamaica

$1,500,000

7 Beds ⋅ 8 Baths ⋅ 5097566 MLS

Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An open floor plan unfolds into a breathtaking two-story great room, showcasing panoramic mountain views. Prepare feasts fit for royalty in the commercial-grade kitchen, then unwind in one of 6 spacious bedrooms, each with a private en-suite bath. Rise with the sun on the first-floor primary suite: Cozy up by the fireplace, or step out to the deck & savor the scenery with a steaming cup of coffee. Unwind in the lower-level living room, a haven for gatherings. An exercise room, office, & billiard room cater to every mood, while a walk-out door beckons you farm-side. A two-level barn currently houses a menagerie of friendly goats, sheep, chickens, & ducks! A heated garage provides convenient access, while a workshop & storage area keep things organized. The milking room & stalls below are ready for those who dream of a farm-to-table lifestyle. Plus, a charming 1-bedroom, 1-bath guesthouse offers the perfect space for visiting family, friends or potential rental income. Just 4 mi. from Stratton & close to Bromley, Magic & Snow, Cold Moon Farm puts you at the heart of all that Vermont offers! Listing agent is an owner of this property.

251 Pratt Bridge Rd, Jamaica

$495,000

4 Beds ⋅ 3 Baths ⋅ 5097042 MLS

Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer. Designed for gathering and relaxing, the home features two spacious living areas, providing plenty of room for family and guests. A cozy wood stove creates the perfect après-ski atmosphere, while the inviting three-season porch offers a peaceful place to enjoy the natural surroundings from spring through fall. The level, secluded lot provides privacy and outdoor enjoyment, with ample space for entertaining, gardening, or simply unwinding. Conveniently located near Stratton, Bromley, Manchester, and local dining and shopping, this property is equally suited as a full-time residence, vacation retreat, or investment opportunity. Experience the best of Vermont living in a location that puts adventure and relaxation right at your doorstep.

367 Stratton Gate Rd, Jamaica

$3,995,000

4 Beds ⋅ 6 Baths ⋅ 5096846 MLS

Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mt Snow ski resorts. The moment you arrive; the home’s striking presence is undeniable. A porte-cochère welcomes you, setting the tone for the beauty that lies within. The heart of the home is the gourmet chef’s kitchen, anchored by a La Cornue stove, rich custom cabinetry, and an expansive island.Douglas fir beams and wide oak floors lend warmth and character, while a masonry fireplace in the great room offers the perfect setting to unwind after a day on the slopes. One of the home’s most captivating features is its silo with a winding staircase illuminated by gas lanterns. A bonus playroom above the three-car garage provides additional space for recreation, while a custom wine room and private movie theater elevate the home’s entertainment offerings. The seamless connection between indoor and outdoor living is one of the home’s greatest attributes. Heated pool, hot tub and fireplace sit against a backdrop of vast mountain views. The landscape is adorned with a sea of peony bushes, adding vibrant color to the meticulously designed gardens.

816 Black Bear Rd, Jamaica

$1,475,000

2 Beds ⋅ 2 Baths ⋅ 5095401 MLS

A long winding driveway through a mountain of foliage leads you to this extraordinary mountain-modern retreat, perched high above nearly 200 acres of protected Vermont wilderness. Thoughtfully crafted by Big Pine Builders LLC, this striking off-grid solar home seamlessly blends contemporary design with Vermont’s rugged natural beauty, allowing you to live on the sun’s rhythm while enjoying refined comfort, complete privacy, and breathtaking surroundings. The cedar and metal exterior complements the landscape, while expansive living room windows provide nearly 180-degree views across your own nature preserve-like setting. Inside, a simple and sleek design creates an airy living space filled with natural light, warm bamboo floors, and clean modern lines. Indoor and outdoor wood-burning fireplaces add warmth and ambiance throughout every season. An additional family room offers flexible living space, perfect for gathering with friends and family, a media room, home office, or quiet retreat. Designed for year-round enjoyment, the property features an extensive town trail system that connects directly to the VAST trail network, making it a dream for outdoor enthusiasts. Entertain or unwind on the large bluestone patio surrounded by complete serenity and nature in every direction. In just 15 minutes, you can be enjoying all that Stratton Mountain has to offer, including skiing, golf, dining, and year-round recreation, while Jamaica Village is just 10 minutes away in the opposite direction. Recent improvements include a new boiler and hot water heater, offering peace of mind for years to come. A propane generator provides added convenience and reliability for off-grid living. Currently enrolled in the Vermont Current Use program, this remarkable property offers a rare opportunity to own nearly 200 acres of protected Vermont wilderness paired with sophisticated, sustainable living.

691 Black Bear Rd, Jamaica

$650,000

3 Beds ⋅ 4 Baths ⋅ 5094046 MLS

Nestled in a peaceful and private mountain setting, this beautifully maintained home offers a seamless blend of comfort, functionality, and timeless Vermont charm. Thoughtfully updated and designed for easy living. The main level features a spacious primary suite with custom built-in cabinetry, a convenient mudroom, and an updated kitchen highlighted by Vermont Verde marble countertops and warm hardwood floors. At the heart of the home, the inviting living room is anchored by a wood-burning fireplace and a dramatic wall of glass that fills the space with natural light while framing the surrounding landscape. Upstairs, two additional bedrooms and an open loft provide flexible space for family & guests, a home office, or a cozy reading nook. The finished lower level expands the living area with a full bathroom and a versatile bonus room ideal for movie nights, a fitness studio, playroom, or workspace. Storage is exceptional, with an oversized detached garage, loft space above, along with an expansive attached storage area perfect for outdoor equipment, seasonal gear, and recreational toys. Numerous recent upgrades, including a whole-house generator, further reflect the care and attention invested in the property. Located less than two miles from Stratton Mountain Access Road, this home offers easy access to skiing, hiking, golf, and the area's many amenities, while maintaining a peaceful sense of privacy and seclusion. Whether as a full-time residence or a seasonal mountain retreat, this inviting property is perfectly suited for year-round enjoyment.

177 Alwin Ln, Jamaica

$839,000

5 Beds ⋅ 5 Baths ⋅ 5093492 MLS

Only 8 miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, & multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but contains a new addition from the 21st allowing you & your family to have space. The home has high ceilings, hand-hewn beams, classic woodwork, a wood-burning stove, and walls of windows that bring in warmth & light. The addition includes a grand primary suite with soaring ceilings, views over the land, walk-in closet, large tiled bathroom with a tiled shower, powerful jet tub, and double vanity. With 5 total bedrooms, 4.5 baths, 2 living spaces, and 3 bonus rooms, there is space to host or work from this 3,840SqFt home. The expansive kitchen contains large countertops with space for seating as well as a window covered breakfast nook. The butler’s pantry, complete with a wet bar, makes entertaining easy. Sit by the stove while snow falls across the pasture and enjoy your snow-globe like winter scene, complete with a great sledding hill right outside. On warm days, open the sliders to the brick patio, or to the back deck to grill, pick berries in the garden, walk the orchard trail, or watch the leaves change during the seasons. The home is located near the town of Manchester, ski mountains (Stratton, Bromley, and Mount Snow), excellent golf courses, & local renowned dining at Honeypie, River & Rye and Solo Farm & Table within easy reach. Bradley International Airport is 2 hours away, Boston is 3, and New York City is 4. This is a home you can enjoy now. One whose location, scale, and enchanting views provide the foundation to create your dream oasis. You deserve to enjoy the Vermont life you have been dreaming of, and make this home and timeless setting part of your family’s legacy.

42 Blackberry Ln, Jamaica

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