Jamaica Vermont Real Estate

Discover the Acorn, a picturesque retreat nestled on the banks of the scenic West River in Jamaica, Vermont. This unique home, a beautifully converted sugar shack, offers an enchanting taste of rustic charm, perfect for those seeking a serene getaway. Ideal for nature lovers and outdoor enthusiasts, the Acorn sits close to the renowned ski resorts of Stratton Mountain and Mount Snow, providing a prime location for both winter sports and summer adventures with walking distance to Jamaica State park.This cozy home features a welcoming open living area with preserved wooden beams and a wood-burning stove that adds to its rustic appeal. The efficient layout includes a fully equipped kitchen, a comfortable bedroom overlooking the river. Whether you're looking for a romantic escape or a solo retreat, the Acorn offers the perfect setting for relaxation and rejuvenation. Step outside to enjoy the tranquil sounds of the West River Right outsde! The Acorn is conveniently located near a variety of local nature trails, the townshend dam; all offering ample opportunities for hiking, biking, and snowshoeing right at your doorstep. If you're in the market for a charming, rustic home that combines accessibility to outdoor recreation with the peace and quiet of a riverfront location.

Perched on a hill above the village of Jamaica, this inviting Cape-style home offers privacy and stunning surroundings just minutes from Stratton Mountain. Sitting on 1.5 acres, the property provides a peaceful retreat with easy access to Winhall, Stratton, and endless outdoor activities. A babbling stream flows nearby, adding to the tranquil setting as you relax on the spacious deck. Despite its proximity to the stream, this property is not in a FEMA-designated flood zone and has never required flood insurance. The sellers have documentation from insurance providers confirming no flood risk, though some third-party online sources, like Zillow’s First Street maps, do not reflect FEMA’s official data. Inside, vaulted ceilings and a striking wood-burning stove create a warm and welcoming atmosphere. The sunlit kitchen features a cozy breakfast nook, while a versatile bonus room offers space for an office or creative retreat. The primary bedroom includes a private bath, with a second full bath serving the additional bedroom. Showings by appointment only. Offered furnished for a turnkey experience, with flexibility for those preferring an unfurnished space. A perfect Vermont escape or investment opportunity!

This charming ranch-style home, lovingly maintained for years, is ready for its next chapter. Ideally located at the entrance of the sought-after Mountain Acres neighborhood, it offers easy access to local activities while maintaining a peaceful retreat-like feel. Inside, five comfortable bedrooms and two baths provide ample space for family and guests. The open-concept living area, highlighted by a vaulted ceiling and large windows, is bathed in natural light—creating an inviting setting for gatherings year-round. In 2024, the owners made significant upgrades, including basement mitigation with an enhanced support and drainage system, along with two new water tanks—ensuring lasting peace of mind for the next owner. Whether you're an outdoor enthusiast or simply seeking a serene escape, this home blends location and comfort seamlessly. Don't miss this opportunity—schedule a viewing today!

Welcome to Hot Toddy Hill. your perfect Vermont Getaway! Nestled minutes away from Stratton, this cozy contemporary home in the charming town of Jamaica, Vermont, is ideal for gatherings and retreats with friends. The living room boasts vaulted ceilings with wood slat detail, its ideal for relaxing in front of the wood-burning fireplace apres ski. The fully equipped eat-in kitchen boasts brand new appliances including refrigerator, stove, microwave, and dishwasher. Gather around the large dining room table when hosting meals with friends. Main level has a full bathroom and bedroom with a king bed. Second floor has a bunk room and a room with a king bed, they share another full bathroom. All bedrooms feature new plush carpeting with antimicrobial memory foam padding and ample closet and dresser space. The finished lower level offers entertainment in the form of a game room with a flat-screen TV and bean bag chairs. The outdoor space is a double lot that showcases the serene Vermont landscape. Included in the sale is a 1 acre parcel that offers additional privacy and/or future possibility to develop a second home (buyer to do due diligence). Hot Toddy Hill provides the perfect backdrop for your Vermont dreams! Being offered less a few personal items, ask us about our list of improvements!

Nestled in the serene woods of Jamaica, VT, this charming 4-bedroom, 3-bathroom home is a perfect blend of comfort and custom craftsmanship. The beautifully updated interior features a granite kitchen with stainless steel appliances, seamlessly flowing into inviting living spaces warmed by a cozy wood stove. The finished lower level offers a true retreat with an indoor hot tub and sauna, ideal for relaxation after a day of outdoor adventures. Step outside to a peaceful wooded setting where a delightful treehouse adds a touch of whimsy. Whether you're seeking a full-time residence or a mountain getaway, this home offers the perfect balance of modern amenities and rustic charm. Closing must occur after May 1.

Don't miss this amazing opportunity to own a cozy log cabin nestled in the woods off Pikes Falls road with close proximity to Stratton Mountain Resort. This home has been thoughtfully built, well maintained and loved for many years and is now awaiting its new owners. The property features 15 acres, a wood shed and a 19th century Pikes Falls School House, which can be used for extra storage or let your imagination run wild! The main level of the home offers a nice size mudroom for all your gear, a 3/4 bath, large eat in kitchen and large living area with wood burning fireplace to snuggle up to on cold winter days. Upstairs has three bedrooms with large closets and a full bath. The large covered porch and front yard allows ample space to enjoy the outdoors, entertain or relax. The large full basement has house utilities, laundry and plenty of space for storage. This home offers some unique features which you have to come check out for yourself.

Welcome to Sugar Chateau- Nestled in the serene landscape of Southern Vermont, this enchanting 4-bedroom log home offers the perfect blend of rustic charm and contemporary comfort. Embrace the warmth and character with exposed beams and a welcoming atmosphere. Enjoy the convenience of modern amenities in a rustic setting, featuring a recently renovated kitchen and bathrooms. Custom new Anderson Windows throughout the home as well. The finished lower level is ideal for entertainment or relaxation and provides additional living space with 3/4 bath, laundry room, den area and walk out access. Wonderful outdoor, living space- unwind on the spacious deck with stunning views of Vermont's natural beauty. Relax in the hot tub after a day of skiing or hiking. Experience the best of both worlds - tranquility and convenience. Located just 15 minutes from Stratton Mountain Resort and a short drive to Jamaica village, offering local shops, dining, and community events. Your Vermont retreat awaits, whether you're seeking a weekend getaway or a year-round residence, this charming log home offers a unique opportunity to embrace Vermont's lifestyle.

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!

Nestled on nearly 2 flat acres, this beautifully maintained South-facing New England Cape Cod farmhouse is a rare find in the mountains. Located on a private dead-end road, the home offers peaceful seclusion while being just a short drive to Stratton Mountain for skiing and tubing in the winter and Jamaica State Park for hiking and stunning waterfalls in the warmer months. With only one owner, this like-new property has been meticulously cared for and features high ceilings throughout, creating a bright, airy and open feel. The open-concept living space seamlessly blends the kitchen, dining, and living areas, making it perfect for both relaxation and entertaining. An attached garage offers added convenience, and two charming outbuildings, including a unique Jamaica Cottage Shop potting shed, provide additional character and utility. Enjoy the tranquility of the mountains with easy access to outdoor adventures. This home is ideal for those seeking privacy, comfort, and a seamless connection to nature, offering a truly special living experience year-round.

Turnkey and fully furnished (SEE VIDEO) this home is just a short drive to Stratton Mountain Resort, within walking distance to one of Vermont's most astounding natural swimming holes, and offers tranquility and peacefulness allowing you to embrace the Vermont life. This 5 bedroom, 5 bathroom split level home design and layout is very thoughtful providing a cozy atmosphere, yet spacious for many. The home welcomes you with a foyer and then splits to the top and lower level. The top level of the home opens up to an open-concept kitchen, dining room, and living room area that is booming with natural light, yet can be dialed back to provide a cozy Vermont feel with a wood fireplace. At the bottom of the split level, you will find 1 ensuite bedroom, 3 more bedrooms, a small family room for games and movie nights, and a full bathroom. There are two more en suite bedrooms in the home one located on the same level as the foyer, and the other located on an upper level, each having their private deck. The exterior of the home offers 4 decks with one that is quite expansive, a detached, 2 bay heated garage that is equipped with a generator and hook up for the house, and an upstairs that is partially finished to be used for storage OR has great potential for more living space (bar, gameroom, etc), and lastly, there is a landscaped stone walkway and steps up to a firepit area that provides winter views of the Stratton Sun Bowl. The home is on Lot 16, and Lot 17 is included in the sale.

Welcome to Sweet Berry Farm, a picturesque farmhouse in Jamaica, Vermont. This extraordinary property blends historical charm with modern updates, offering an enchanting living experience. Enjoy mature apple trees, blueberry bushes, blackberries, and grapes. There are also many varieties of flowers and bushes that bloom throughout the warmer season. Originally built in 1850, this farmhouse showcases craftsmanship of the era with well-preserved original features. A total farmhouse renovation also provided a new addition with contemporary comfort. The expansive 3 story addition with a large open living room, dining room, 2nd kitchen area on the main floor, a large family room with a separate den and bathroom on the lower walkout level as well as additional bedrooms and bathrooms including a primary suite with vaulted ceilings and spa bathroom with a jetted tub on the upstairs level. There truly is ample space for family and guests, as each room exudes warmth and character, featuring exposed beams, original hardwood floors, and a cozy woodstove fireplace. Situated on a 5.7-acre private plot up a lovely driveway, Sweet Berry Farm includes a large barn and three versatile outbuildings for a workshop, artist's studio, or storage including a garbage shed. Close Proximity to Stratton Mountain is a highlight. Enjoy skiing or snowboarding nearby in Winter, and explore hiking trails, bike paths, and ponds in warmer months. Sweet Berry Farm isn't just a home; it's a lifestyle.

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!

Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of nature to your daily life. Multiple bedrooms give everyone in your party a private space to relax after a long day exploring the outdoors. Step outside to witness dramatic views of the rolling hills that surround the property. A tranquil pond with gazebo graces the landscape. A well-appointed barn with 5 stalls and a paddock caters to equestrian enthusiasts. Miles of trails crisscross the property, providing endless opportunities for outdoor activities. This property is subject to an Act 250 permit and enrolled in Vermont Current Use Program, securing its natural beauty for the future. Whether you are relaxing on the porch or hosting gatherings in the spacious bonus room, this estate balances seclusion and convenience. Situated in bucolic Jamaica, it is 20 minutes from Stratton and 25 minutes from Mount Snow. Let this be your four season retreat, close to the mountains in the winter, swimming holes in the summer, and stunning views all year round!

Set atop a scenic Vermont hillside, this five bedroom custom-built home by The Wadsworth Design Build/Vermont Barns is a stunning 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 Mount Snow ski resorts, it is the ultimate retreat. 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. Exposed 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 fire place sit against a backdrop of vast mountain views.The surrounding landscape is adorned with a sea of peony bushes, adding vibrant color to the meticulously designed gardens.

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.