Jamaica Real Estate

Jamaica Real Estate

Welcome to Jamaica, Vermont—a hidden gem nestled in the heart of Windham County! This charming town, enveloped by the breathtaking Green Mountains, offers a perfect blend of natural beauty and small-town charm. With a population of just over 1,000 residents, Jamaica exudes a warm, welcoming atmosphere that makes it an ideal place to call home.

Jamaica is renowned for its stunning landscapes, featuring lush forests, rolling hills, and picturesque rivers. Outdoor enthusiasts will find themselves in paradise here, with a plethora of recreational activities at their fingertips. From hiking and mountain biking in the summer to skiing and snowboarding in the winter at nearby resorts, adventure awaits in every season.

The town’s rich history is evident in its well-preserved architecture and community events. Stroll through the quaint streets and discover local shops, artisan galleries, and cozy cafes that reflect the town's unique character. Jamaica is also home to the vibrant Jamaica State Park, where visitors can enjoy camping, fishing, and scenic picnics along the West River.

Families will appreciate the strong sense of community and the excellent educational opportunities available in the area. With a focus on nurturing young minds, the local schools foster a supportive environment for students to thrive.

Whether you’re seeking a peaceful retreat or a vibrant community filled with activities, Jamaica, Vermont, offers the perfect backdrop for your next chapter. Experience the charm and beauty of this delightful town—where nature, history, and community come together in perfect harmony. Welcome home!

Newest Listings in Jamaica

$99,000
5101763 MLS
Discover the perfect blend of privacy, natural beauty, and convenience with this exceptional 6.4-acre parcel featuring river frontage in the heart of Southern Vermont. Tucked away in a peaceful setting, this unique property offers a rare opportunity to enjoy the serenity of nature while being just a short walk to both Jamaica State Park and the charming Village of Jamaica. Spend your days hiking, biking, kayaking, fishing, or simply relaxing by the river. Jamaica State Park is just steps away, while the village offers a restaurant, local market, and year-round community events. The property also enjoys easy access to Stratton, Bromley, Magic, and Mount Snow, making it an ideal base for four-season recreation. Surrounded by mature trees and abundant wildlife, this parcel offers the privacy and tranquility that make Vermont so special. Whether you're looking for a peaceful retreat, recreational property, or a long-term investment, opportunities like this are increasingly hard to find. Riverfront acreage within walking distance of both a quintessential Vermont village and one of the state's most beloved parks is truly a rare offering. No engineering or permitting has been completed on the property. Buyers are encouraged to perform their own due diligence regarding potential development and suitability for their intended use. If you've been dreaming of owning a piece of Vermont where privacy, recreation, and small-town charm come together, this remarkable property is ready to inspire your next adventure. The Seller's estate is in the process of obtaining the required License to Sell, which is expected to be issued within 30 days.

Worden Road, 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. Showings begin 7/24.

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. Showings begin 7/26.

494-498 Goodaleville Rd, Jamaica
$136,000
5101508 MLS
Escape to your own private Vermont retreat on this beautiful 14-acre wooded parcel, tucked away along the path less traveled. A thoughtfully established clearing is home to a travel trailer sheltered beneath a well-built pavilion, creating a comfortable, all-weather basecamp for weekends and seasonal getaways. The sale includes the camper complete with generators, tools and more making this a true turnkey opportunity. A storage shed provides convenient space for outdoor gear and supplies, while a seasonal brook meanders through the property, adding to the peaceful setting. Enjoy the sights and sounds of nature with exceptional privacy yet remain less than two miles from Vermont Route 30 for easy access to nearby towns and recreation. Set equally between the bases of Stratton or Mount Snow - be at either lodge in 25 minutes! Currently equipped with water accessed from a new pump and generator-powered electricity. This property is ready to enjoy immediately while offering plenty of potential for future plans. Whether you're seeking a quiet camping retreat, a hunting camp, or a future homesite, this special property offers the peace, privacy, and simple pleasures that define the Vermont lifestyle.

182 Partridge Ln, Jamaica
$290,000
5101033 MLS
Windham Woods Forest offers 289.12 acres of productive, predominantly hardwood timberland in the scenic southern Green Mountains of Jamaica, VT, an area prized for sparse development, strong wildlife habitat, and proximity to the Green Mountain National Forest and Stratton Mountain Resort. The property boasts significant Legal Trail frontage on both Black Bear and Melis Roads and sits directly on VAST Trail 710, offering outstanding snowmobile access. A recent F&W Forestry timber inventory (April 2026) documented 1,409 MBF of sawlog volume and 5,449 cords of pulpwood, for a Capital Timber Value of $290,100 ($1,031/commercial acre), a well-stocked, diverse forest managed for decades with excellent regrowth potential. Terrain rises to 2,040' at the property's high point, with a former log landing offering a ready building site. The land will be conveyed subject to a conservation easement held by the Vermont Land Trust, permitting sustainable forestry, agricultural use, and recreation, including rights to build an 800 sq ft off-grid camp, use ATVs, and post against trespassing. Nearby amenities include Jamaica village (5.5 mi), Stratton (6.6 mi), Mount Snow (14 min), and Manchester (24 mi), plus renowned fishing on the West River and Battenkill, swimming at Pikes Falls, and hiking to Hamilton Falls and the Long Trail. Boston is 3 hours away; Albany is 1.75 hours away. A rare blend of recreation, timber investment, and conserved Vermont character.

Black Bear Rd, Jamaica
$219,000
5098094 MLS
Discover the possibilities on this exceptional 16.9-acre Vermont property, where privacy, natural beauty, and year-round recreation come together. With nearly 300 feet of town-maintained road frontage and accessible utilities, this parcel is ready for your vision. Thoughtfully shaped by nature, the land offers three potential building sites, making it ideal for a family compound, multi-generational retreat, or a custom home with guest accommodations. Mature trees, rambling stone walls, a charming pond, a gentle stream, and patches of wild blueberries create a setting rich in character and Vermont tradition. Follow the land to its highest point to enjoy long-range views that provide a spectacular backdrop in every season. Whether you envision morning walks through the woods, listening to the soothing sounds of the stream, evenings around a fire, or creating a legacy property for generations to enjoy, this property offers the space and flexibility to bring your plans to life. Outdoor enthusiasts will appreciate the convenient access to Bromley Mountain, with Stratton, Magic Mountain, Mount Snow, and Okemo all within an easy drive for outstanding skiing, snowboarding, hiking, mountain biking, golf, and endless four-season adventure. The nearby town of Manchester offers excellent shopping, dining, galleries, and everyday conveniences, while the welcoming community of Jamaica provides a classic Vermont village with a local general store, consignment shop, coffee cafe, community events, farmers markets, and a relaxed pace of life. Conveniently located just 2.5 hours from Boston and approximately 3.5 hours from New York City, this is a rare opportunity to enjoy a private Vermont retreat with easy access to world-class recreation and small-town charm.

00 Howe Farm Rd, Jamaica
$63,000
2 Beds ⋅ 1 Baths ⋅ 5097748 MLS
Looking for an easy escape to the mountains? This furnished 2-bedroom mobile home sits right on the banks of the West River in West River Park—an ideal spot for seasonal living in Southern Vermont. The park has 23 sites and allows homeowners to stay up to 6 months each year, making it a great option for summer adventures or a winter ski base or, a little bit of both! Stratton is just 20 minutes away, and Mount Snow about 30, so you're never far from the slopes. In warmer months, enjoy fishing, swimming, or hiking nearby. The home has seen several recent updates, including new windows, a new chimney, oil tank, outdoor storage shed, and a propane stove for that cozy cabin feel. Park rent is $435/month and covers water, septic, snow removal, and lawn care—making for simple, low-maintenance living. If you’ve been looking for a quiet spot with river views and easy access to all the region has to offer, this might be the one.

2022 Rte 30, 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
$140,000
1 Beds ⋅ 1 Baths ⋅ 5097088 MLS
Some places stop time. River's Edge is one of them. Step off the front door and onto a 10×12 covered porch shaded by old hemlocks, facing directly over the West River — away from the road, away from everything. The sound of moving water. The smell of the trees after rain. This porch is not an afterthought Brand new Lancaster Log Cabins "Sierra" Park Model. This 100% turn-key real log cabin features a rustic aesthetic with modern durability. Includes a 10' covered front porch, a cozy loft for extra space, and cathedral ceilings with exposed log beams. Situated on a newly poured concrete slab in the beautiful French Bridge Chateau community. Perfect for those seeking a high-end, low-maintenance retreat. Park approval is required. This unit can only be occupied 180 days a year per State Permit. The Sierra arrives fully turn-key: kitchen with full appliances including an over-the-range microwave, full bath, living area, two bedrooms, and a sleeping loft that gives you the flex for extra guests. At 320 sq ft of interior space plus 120 sq ft of covered porch, it lives larger than it measures — the layout wastes nothing. Never used and installed in 2026. Will make a great comfortable vacation getaway in any season. The park also maintains the landscaping.

2074 Vt Rt 30, 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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