Jamaica Real Estate

Jamaica Real Estate

Welcome to Jamaica, Vermont – a hidden gem nestled in the picturesque Windham County. This charming town is a perfect blend of serene landscapes, vibrant community spirit, and rich history, making it an ideal place for those seeking a tranquil lifestyle away from the hustle and bustle of city life.

Jamaica boasts stunning natural beauty, with the stunning Green Mountain National Forest as its backdrop. Outdoor enthusiasts will find endless opportunities for adventure, from hiking and biking in the summer to skiing and snowshoeing in the winter. The nearby Jamaica State Park offers breathtaking views, pristine rivers, and well-maintained trails, perfect for family outings or a peaceful escape into nature.

The town itself is steeped in history, with quaint architecture and a warm, welcoming atmosphere. Explore the local shops and eateries that line Main Street, where you can find everything from artisanal goods to delicious homemade treats. The community hosts various events throughout the year, including farmers' markets, craft fairs, and seasonal festivals, fostering a strong sense of camaraderie among residents.

For families, Jamaica offers excellent educational opportunities and a safe, nurturing environment. The tight-knit community ensures that everyone feels at home, making it a wonderful place to raise children or enjoy retirement.

With its unique blend of natural beauty, rich history, and friendly atmosphere, Jamaica, Vermont, is not just a place to live but a place to thrive. Come discover the charm of this enchanting town and find your perfect home in the heart of Windham County!

Newest Listings in 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
$190,000
5105324 MLS
Parcel 2 is a forested 30-acre property situated on Schoolhouse Road in Jamaica, Vermont. From the intersection of Schoolhouse and South Hill Roads, the road winds around a sharp bend and climbs a short hill before reaching the majority of the property, which lies along the north side of the road. A weathered stone wall is found along the entire length of the road frontage, hinting at the land's rich agricultural history. The land itself is level, wooded terrain with several natural clearings near the road offering promising building sites for one or two homes, with power already available at the road. Notably, the town of Jamaica has no zoning restrictions, making this an exceptional opportunity to create a private family compound just minutes from some of the region's best outdoor recreation. An old woods road winds along the level contours of the property and continues onto the neighboring parcel, inviting exploration on foot or by ATV. Beyond the road, the land descends to the north into a wetland area a haven for a wide variety of birds and wildlife. Evidence of a resident beaver family can be seen in the twin ponds found just below the wetland, adding to the property's natural charm and biodiversity. The forest itself is impressive, featuring mature trees, some over a century old, lending a sense of peace and quiet while walking the land. While there may have been selective tree harvesting long ago, little trace of that history remains in the forested hillside today. Crisscrossing through the woods, additional stone walls stand as silent reminders of the property's farming past, adding character and a connection to Vermont's rural heritage. Schoolhouse Road eventually transitions into a Legal Town Trail, making it an ideal route for biking enthusiasts leading roughly 3 miles west to scenic Pikes Falls Road.

Schoolhouse Rd, Jamaica
$120,000
5105314 MLS
The South Jamaica Parcels consist of two contiguous lots situated along South Hill Road and Schoolhouse Road in South Jamaica, Vermont. Each parcel offers an excellent building opportunity, featuring level, buildable terrain and the convenience of power already available at the street making them ideal, low-hassle sites for a future home. Parcel I is a 10-acre building site located on South Hill Road. A grass-covered access road leads from the street to a flat, area just off the road an ideal spot for a future home. Along the entire road frontage, except for the access driveway, an old stone wall runs the length of the property, lending charm and excellent curb appeal to any home built here. Beyond the potential building site, the woods road continues into the forest, extending past the property boundary. The land slopes down the hill to the south toward a small wetland shared with the neighboring parcel. The surrounding forest offers a rich mix of softwoods and hardwoods, including hemlock, fir, and white pine, alongside maple and yellow birch. South Hill Road is paved near the property, offering easy access to the nearby villages of Wardsboro and Jamaica.

S Hill 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
$299,000
5103450 MLS
Discover the possibilities with this exceptional 57+ acre parcel in the Town of Jamaica, Vermont, where no local zoning provides incredible flexibility for your vision. Ideally located just minutes from Stratton Mountain, Mount Snow, and within easy reach of Bromley, Magic Mountain, Manchester, and Brattleboro, this property offers the perfect balance of privacy, recreation, and convenience. Multiple elevated building sites showcase stunning long-range mountain views, while both a charming private brook and the scenic Wardsboro Brook border portions of the property, creating a truly picturesque setting. A State of Vermont wastewater permit (WW-2-5317) for a three bedroom home is already approved and on file, allowing you to begin building with ease. Looking for more? The expansive acreage offers exciting potential for subdivision, multiple homes, or a private family compound, subject to any applicable state regulations. Whether you're dreaming of a secluded mountain retreat, an investment opportunity, or a legacy property to enjoy for generations, this remarkable parcel offers endless possibilities in one of Southern Vermont's most desirable four-season destinations. Sellers are related to the listing agent.

Vt Route 100 South, Jamaica
$585,000
5102573 MLS
A rare opportunity to own over 91 private acres just a short walk from the charming Village of Jamaica. Tucked away off a private right-of-way, this remarkable parcel offers the perfect balance of peaceful seclusion and convenient access to local shops, dining, and community events. The property features a beautiful mix of mature forest, gently rolling terrain, and serene natural surroundings. With selective clearing, there is potential to open up lovely mountain views. Existing trails currently traverse the property as part of a mountain biking trail network, adding immediate recreational appeal, and the land is also enrolled in a forest management plan. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley, Magic, and Mount Snow, the property provides convenient access to year-round recreation, including skiing, hiking, biking, kayaking, fishing, and more. Large parcels offering this level of privacy within walking distance of a quintessential Vermont village are increasingly difficult to find. No engineering or permitting has been completed, and buyers are encouraged to conduct their own due diligence regarding potential development, the forest management plan, and continued trail use. The Seller’s estate is in the process of obtaining the required License to Sell, which is expected to be issued within 30 days.

Water St, 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.

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
$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
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