Jamaica, Vermont listings for sale

​
$8,950,000 - Jamaica, VT
370 Fischer Lane Jamaica, VT - Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark and stone detailing combined with complete comfort, great light and welcoming spaces. The property was featured in the book Rustic Living by Ralph Kylloe as one of the great rustic style homes in the U.S. The 13,393-square-foot home has an open floor plan, massive stone great room fireplace, chef’s kitchen and 6 bedrooms en suite, each with magnificent mountain views. Off the kitchen and great room is a screened-in porch and large deck with an outdoor stone fireplace to soak in the panoramic southerly green mountain views. Smaller gathering spaces include a corner office, gym/spa, meditation room and 22-seat home theater. Camp Endo’s extensive trail network provides a daily dose of rugged, natural beauty for mountain biking, walking or snow shoeing and playful options include a paintball course and a six-foot square chessboard. The adjacent barn houses a fully appointed 2 bedroom guest suite, 3-bay garage and half-basketball court with surround sound. Next to the apple orchard is a large swimming pond with views of Stratton Mtn. The property has renewable solar and wind energy.
2005 | 6 | 8 | 13,393 sqft.
​
$899,000 - Jamaica, VT
42 Blackberry Lane Jamaica, VT - Idyllic, Picturesque, Expansive, Vast Family Farm with outbuildings and Large Farmhouse!  Known to some as Sweet Berry Farm the blueberries and blackberries are plentiful along with many other productive fruits trees, a grove of 20 mature apple trees with many over 30 years old, , flowers and veggies in the gardens. This location just off of Route 30 is perfect for ALL of your Vermont dreams and desires.  Close to world renowned downhill skiing at Stratton, Mount Snow, Magic, Okemo & Cross Country Skiing at Viking, Grafton Outdoor Center, Wild Wings.  PLUS hiking, canoeing, outdoor life along with arts, festivals & great culinary options. Beautiful Manchester Vermont is 20 minutes away. Fabulous back yard sliding hill and plenty of land to play on, close to everything AND an expansive interior with a large addition. Walk through the WIDE entry door into the big mud room with loads of storage then into the kitchen with large peninsula, living room and kitchen / dining room.  Over to the butler’s kitchen and huge (full of windows) living/dining/playing rooms complete with beautiful hearth and chimney.  MORE space downstairs with a bedroom/bath/2nd family room and then upstairs to a sweepingly large primary with bath and 4 other bedrooms with 2 other bathrooms, still yet another play area.  This homestead is a generational gem awaiting its next Stewart.
1850 | 5 | 2 | 5,000 sqft.
​
$769,000 - Jamaica, VT
544 Dalewood Road Jamaica, VT - Exceptional Vermont Retreat – Turnkey & Fully Furnished! Welcome to this beautifully maintained 5-bedroom, 5-bathroom contemporary home, offering a perfect mix of spacious comfort and cozy charm. Nestled in a peaceful neighborhood, and just 4 miles from SunBowl and minutes from the base lodge, this home features three en-suite bedrooms,two additional bedrooms, and a flexible extra room ideal for an office or additional sleeping space,which ensures ample space for family and guests. Thoughtfully designed with hardwood kitchen cabinetry, a wood-burning fireplace, and an efficient pellet stove, warmth and elegance fill every corner. Abundant natural lighting enhances the inviting atmosphere, complemented by a grand living room, a large dining room, and a family room ideal for relaxation and entertainment. Step outside to enjoy multiple expansive decks,offering a serene setting to take in Vermont’s picturesque surroundings. A stone walkway leads to a fire pit, perfect for gathering on crisp evenings. The heated two-bay garage includes an unfinished upstairs—a space bursting with potential for customization. Plus,with a generator hookup capable of powering nearly the entire house, you’ll have peace of mind year-round. Located within walking distance to the stunning Pikes Falls, this cherished home is a rare gem in an unbeatable location. The home sits on Lot 16, and Lot 17 is included in this sale. Abutting Lots(MLS # 5028445/5028450) can be purchased as well with a big discount.
1985 | 5 | 2 | 2,600 sqft.
​
$590,000 - Jamaica, VT
4138 West Hill Road S Jamaica, VT - This three-bedroom, three-bath custom-built log home is situated on 2.37 acres in a tranquil mountain setting just minutes from skiing. Built with double tongue-and-groove log construction, the cozy home provides the warm wood interior one would expect. The open-concept main level focuses on the fieldstone hearth, wood stove, and beautiful oak floors. A covered porch in the front of the home overlooks the lovely wooded property and a back deck that enjoys long hours of sun. The main level features the primary bedroom ensuite, a bunk room, an additional bathroom, and a bonus room that can serve as a den, office, or overflow sleeping. The lower level includes a large mudroom for all your gear, a spacious bedroom, a bathroom, and another bonus room for entertaining. The house is set well off a quiet country road yet convenient to the quaint village of Jamaica, with stone walls and gladed woods. A two-car garage, storage shed for all your toys, and a timber shed complete this charming property!
2002 | 3 | 3 | 2,704 sqft.
​
$574,000 - Jamaica, VT
4138 West Hill Road S Jamaica, VT - This three-bedroom, three-bath custom-built log home is situated on 2.37 acres in a tranquil mountain setting just minutes from skiing. Built with double tongue-and-groove log construction, the cozy home provides the warm wood interior one would expect. The open-concept main level focuses on the fieldstone hearth, wood stove, and beautiful oak floors. A covered porch in the front of the home overlooks the lovely wooded property and a back deck that enjoys long hours of sun. The main level features the primary bedroom ensuite, a bunk room, an additional bathroom, and a bonus room that can serve as a den, office, or overflow sleeping. The lower level includes a large mudroom for all your gear, a spacious bedroom, a bathroom, and another bonus room for entertaining. The house is set well off a quiet country road yet convenient to the quaint village of Jamaica, with stone walls and gladed woods. A two-car garage, storage shed for all your toys, and a timber shed complete this charming property!
2002 | 3 | 3 | 2,704 sqft.
​
$520,000 - Jamaica, VT
3708 Vt Rt 30 Jamaica, VT - Located in the heart of downtown Jamaica, Vermont, this spacious and beautifully designed Colonial home offers the perfect blend of charm, comfort, and convenience. With 5 bedrooms and 5 bathrooms, there’s plenty of space for a large family or frequent guests. Just minutes from premier ski resorts—Stratton, Bromley, and Magic Mountain—this home is an ideal base for winter and summer adventures. Step into the welcoming new mudroom, complete with cubbies and large window with bucholic views, then gather around one of the home’s inviting gas fireplaces for après-ski dining or relaxing winter nights. In the summer, enjoy cool comfort with central air and stroll to the local market, library, or take a scenic walk to Jamaica State Park. The renovated kitchen, along with updated furnaces and hot water tanks (2021), offer modern ease in a classic setting. The versatile third floor includes a full bathroom and endless potential for work, storage or play. A small barn is ready for your imagination—studio, office, garage or recreation room—plus a handy storage shed completes this must-see Vermont retreat! Come explore the best of Vermont living—come home to Jamaica! This property has its own septic tank with a shared leach field. Road frontage and acreage are estimated.
1818 | 5 | 4 | 3,213 sqft.
​
$499,000 - Jamaica, VT
168 Howard Road Jamaica, VT - This loving home has seen many years of enjoyment from its current owners. Four bedrooms, two and a half baths, large open kitchen dining area with a beautiful granite island to gather around. Separate living room space with beautiful stone fireplace and half bath all on the main floor. The four bedrooms with a lovely large primary suite with private bath, cathedral ceilings will be the perfect place to lay your head at night! The outdoor entertaining space is great for any time of the year! Large deck and attached covered porch with firepit to hang out with your family after the day is done! Outdoor garden shed to keep all your equipment for the many beautiful existing flower beds and perennial gardens. Raised garden beds and an older established garden space on the side lawn will allow you to garden as much or as little as you want during the summer months. Hardwood and tile throughout the home, with lots of natural wood accents. If you're looking for a nice spread with a large, detached shop with over 1100sqft of space to work on projects, don't miss this opportunity. Located just 3 miles from the center of town and 10 miles to Stratton Access Road. Walk out basement with more storage space. The owners are excited for their next chapter and hope you are too!
1970 | 4 | 0 | 1,986 sqft.
​
$469,000 - Jamaica, VT
2194 Mowrey Road Jamaica, VT - Diamond in the rough! Don't miss this opportunity to own a property in Jamaica, Vermont that has so much to offer! This property has been absolutely stunning in the past! Perched on a hill overlooking a private pond, fields that used to be pastures where your animals can roam and you can take in the local ridgeline view of the beautiful Green Mountains of Vermont! This is a true log home with large front deck and second story porch off the primary bedroom. The eat in kitchen offers nice soapstone countertops, appliances that may or may not work. This home has not been lived in for a couple of years, but the heat, hot water and electric have been on. The power to the property is underground, there is a drilled well that is 200ft deep and yielding 30 gallons per minute per the state records and a conventional private septic. All measurements are approximate. The property will be transferring AS IS condition. If you have the ability to see the potential, this place has all the characteristics of a true Vermont homestead!
2003 | 2 | 0 | 1,346 sqft.
​
$449,000 - Jamaica, VT
3458 Vt Route 30 Jamaica, VT - This lovely, updated 1790 Cape blends timeless New England charm with modern functionality and post-and-beam construction. Ideally located just outside the quaint village of Jamaica, the home offers easy access to four major ski resorts—Stratton, Bromley, Magic Mountain, and Mount Snow. Step into the welcoming kitchen, where a cozy fireplace creates a perfect winter haven. A soaring cathedral ceiling adds an airy feel, while the adjacent breakfast nook, framed by expansive backyard views, is ideal for year-round dining. The spacious living room is bathed in natural light and anchored by a working fireplace, offering a warm and inviting atmosphere. A convenient first-floor bedroom and nearby handicap-accessible bathroom make single-level living an option. At the same time, the laundry room at the end of the hall adds to the home's functionality. Upstairs, you'll find two additional bedrooms and a cozy office. A charming two-bedroom apartment with a soaring ceiling, wood stove, and skylights sits above the oversized garage, easily fitting three vehicles. Whether used as guest quarters, an in-law suite, or a rental unit, it offers exceptional flexibility and added value. The property includes two lots: the main house rests on nearly an acre, with an adjacent lot of almost the same size directly to the north. If looking for a full-time residence, a seasonal getaway, or a rental investment, this property delivers!
1790 | 6 | 2 | 3,032 sqft.
​
$295,000 - Jamaica, VT
2277 Vt Rt 30 Jamaica, VT - Meander down the winding private drive and “LO AND BEHOLD” an enchanting country cottage nestled on a serene 4.8 acres awaits you! This quaint 3-bedroom, 1-bath home is brimming with potential. Inside, you'll find wideboard pine flooring in the dining and living rooms, 2 woodstoves, and an additional den area. In 2024, SEVCA conducted an energy service, enhancing the home with spray foam insulation in key basement areas, a new water heater and more. The property features several outbuildings, including a carpenter's workshop with power, a woodshed and a gardening shed. This will be a dream home for someone who cherishes both privacy and accessibility in the beautiful setting of Jamaica, Vermont. Outdoor enthusiasts will appreciate the proximity to a variety of activities, skiing, mtn biking, hiking with an easy drive to cultural and recreational spots: just 20 min. to Stratton Mountain, 23 min. to Mount Snow and 30 minutes to Manchester. New York City is 4.5 hours away, Boston is 2.75 hours, from your doorstep. While this home does require some work, including the installation of a new kitchen, we have consulted a local mortgage broker who has a financing option that allows you to borrow up to 10% of the purchase price to complete the kitchen renovation. This then can be incorporated into a single loan upon completion. For further details, it is recommended to reach out to a home loan specialist to explore your options. Measurements are approximate.
1960 | 3 | 1 | 1,586 sqft.