Jamaica Homes for Sale

Welcome to Jamaica, Vermont – a hidden gem nestled in the picturesque Windham County. Known for its stunning natural beauty and serene atmosphere, Jamaica is the perfect retreat for those seeking a tranquil lifestyle away from the hustle and bustle of city life. With its lush green landscapes, charming local shops, and friendly community, Jamaica offers a unique blend of rustic charm and modern convenience.

The town is surrounded by the breathtaking Green Mountains, making it an ideal location for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking in the scenic views, Jamaica provides countless opportunities to immerse yourself in nature. The nearby Jamaica State Park features pristine trails and the enchanting Ball Mountain Dam, perfect for a family picnic or a peaceful day of fishing.

As for homes for sale, Jamaica boasts a delightful array of properties that cater to various tastes and budgets. From cozy cabins tucked away in the woods to elegant country homes with sweeping views, there’s something for everyone. Many of these homes showcase classic New England architecture, complete with charming details and modern amenities. Imagine waking up to the sound of birds chirping and the sight of vibrant foliage right outside your window.

Living in Jamaica means embracing a close-knit community where neighbors become friends and local events bring everyone together. With its rich history, stunning scenery, and welcoming atmosphere, Jamaica, Vermont is not just a place to live; it’s a place to call home. Explore the homes for sale today, and discover the enchanting lifestyle that awaits you in this idyllic town.

Newest Jamaica Homes for Sale

$549,000

4 Beds ⋅ 4 Baths ⋅ 5111100 MLS

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.

24 Mowrey Rd, Jamaica

$425,000

2 Beds ⋅ 3 Baths ⋅ 5110722 MLS

Tucked into a quiet, sunny setting just steps from Jamaica State Park and the heart of Jamaica Village, this charming two-bedroom plus loft Cape offers the perfect blend of Vermont character, comfort, and convenience. Filled with natural light and warm wood accents, the home has an inviting feel from the moment you step inside. A spacious mudroom provides a practical entry for every season and opens into the kitchen, where a center island and gas cooktop make it easy to gather, cook, and entertain. The open floor plan flows naturally into the main living area, where a cathedral ceiling adds a wonderful sense of space and a wood-burning stove creates a cozy focal point for winter evenings. The home offers two bedrooms plus a versatile loft, ideal for additional sleeping space, a home office, or a quiet retreat. The primary bedroom features its own ensuite bath, and with two full baths and one half bath, there is plenty of room for family and guests. Adding to the property's future potential, the existing septic permit is approved for three bedrooms, offering flexibility should a future owner wish to expand. Outside, enjoy a peaceful setting with space for gardening and relaxing in the Vermont sunshine. An oversized two-car garage provides exceptional room for vehicles, outdoor gear, bikes, skis, kayaks, and all the equipment that comes with four-season living. The location is hard to beat. Walk to Jamaica State Park for hiking, swimming, and access to the West River, or head into Jamaica Village just moments away. When the snow flies, Stratton Mountain is approximately 15 minutes away and Mount Snow about 25 minutes, while the shops, restaurants, and amenities of Manchester are approximately 30 minutes from your door. Whether you're looking for a full-time Vermont home or a comfortable mountain getaway, this sunny Jamaica Cape puts village life, outdoor recreation, and some of Southern Vermont's best destinations within easy reach—all while offering a quiet place

190 Depot St, Jamaica

$995,000

5 Beds ⋅ 5 Baths ⋅ 5108207 MLS

Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless connection with the outdoors. A Pellet stove with the fieldstone fireplace adds warmth and character to the main living space. Just off the living area, a second living room with a sleeping area offers a perfect spot for a home office or guest wing while enjoying lake views. Upstairs, you'll find two bedrooms and a separate office, sharing a full bath. The property also includes a two-car garage with a convenient studio apartment and private bath, ideal for guests. Enjoy direct access to the water with a unique floating dock, perfect for kayaks, paddle-boards, and simply taking in the magnificent scenery. This home is designed to accommodate a life of both leisure and adventure.

1189 Cole Pond Rd, Jamaica

$2,430,000

9 Beds ⋅ 7 Baths ⋅ 5107418 MLS

TWO HOMES | 1BR BARN APARTMENT | RESTORED VINTAGE BARN | 13+ ACRES. A rare Vermont multi-residence estate offering two beautifully renovated homes, a separate 1BR barn apartment, a restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, Winhall River Farm blends authentic character, exceptional craftsmanship, and modern four-season comfort. One residence is a restored 4BR farmhouse once used as the summer home of renowned art historian Meyer Schapiro, with wide-plank floors, antique doors, an expanded kitchen with soapstone counters, updated baths, and custom built-ins. Schapiro’s former art studio now serves as a self-contained 1BR apartment with SMEG appliances, a screened porch, and heated storage below. The second home is a reimagined historic schoolhouse with a timber-frame addition, high ceilings, generous windows, two sunrooms, restored floors, and warm architectural detail throughout. Private hot tubs and inviting outdoor living spaces complement all three residences. Extensive improvements across the property include standing-seam roofs, new Marvin windows, updated electrical and plumbing, modern insulation, mini-split heating and cooling, high-efficiency systems, new appliances, generators, and EV chargers. The 13+ acres include open fields, woods, apple trees, gardens, extensive stonework, patios, decks, and opportunities for trails, recreation, and equestrian use. Set along the Winhall River with direct access to the West River Rail Trail for walking, biking, swimming, and exploring. In the heart of ski country, just minutes from Stratton, Bromley, and Magic Mountain. An exceptional family estate, multi-generational retreat, or investment opportunity. Offered furnished and ready to enjoy, with additional acreage also available. All the hard work has been done--move in and start enjoying Vermont. Properties also offered individually as MLS #5101688 & #5101689. Seller is the listing broker.

494-564 Goodaleville Rd, Jamaica

$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

$1,115,000

4 Beds ⋅ 3 Baths ⋅ 5101689 MLS

Set along a quiet back road on the Winhall River, 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, the location offers easy access to the mountain, local favorites, and the best of southern Vermont living. High ceilings, generous windows, and two sunrooms fill the interior with natural light, while radiant heat on all three levels adds warmth and comfort 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, private 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 also available: 494–498 Goodaleville Road, MLS #5101688.

564 Goodaleville Rd, Jamaica

$1,315,000

5 Beds ⋅ 4 Baths ⋅ 5101688 MLS

4BR MAIN HOUSE, 1BR BARN APARTMENT, AND SEPARATE RESTORED VINTAGE BARN | Tucked along a quiet back road with the gentle sounds of the flowing Winhall River, this beautifully restored Vermont farmhouse feels worlds away, yet is just 10 minutes from Stratton Mountain Resort. Blending authentic character, exceptional craftsmanship, and modern comfort, the property offers a rare sense of privacy and retreat while keeping the mountain and year-round recreation within easy reach. 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 levels. An expanded kitchen with soapstone countertops opens to a spacious dining room and cozy sitting area with a gas fireplace. Original wide-plank floors, antique doors, and a classic clawfoot tub celebrate the home’s heritage. Improvements include modern insulation, electrical, plumbing, a new foundation, sheetrock, a high-efficiency propane boiler, HRV ventilation, mini-splits, Marvin windows, and an improved floor plan. Additional upgrades include standing-seam roofs on all 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 1BR apartment with SMEG appliances, in-unit laundry, and a private hot tub. Below are heated storage and a screened porch. The restored barn offers parking and an EV charger. Extensive stonework, thoughtful landscaping, gardens, decks, a stone patio, and a welcoming front porch complement the peaceful 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. 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

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