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.

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.

Nestled just 5 miles from Stratton's base lodge on the historic grounds of the former White Mop Wringer Co., this remarkable home blends rich history with modern craftsmanship. Built in 2001, the house sits where, in the 1800s, Cassius A. White invented the mop wringer, making Jamaica, Vermont the birthplace of the first mop wringer factory. While the water wheel that powered the factory is no longer standing, the stone wall on the property still bears the outline of where it once stood, a lasting connection to the past. The home’s design reflects a deep appreciation for craftsmanship, with pine floors salvaged from a school gymnasium and a ceiling made from wood reclaimed from a school art center. The result is a warm, inviting space with a nod to the area's heritage. Outdoor enthusiasts will love the direct access to Ball Mountain Brook, an outdoor shower, a fire pit, and a beautiful screened porch—perfect for relaxing and connecting with nature. This home offers a unique opportunity to live in a peaceful sanctuary surrounded by history and modern comforts. In addition there is a 4 x 6 closet in the home that is plumbed for a 1/2 bath. Despite being in a flood zone, the property was untouched by both Hurricane Irene and the significant flooding in July 2023, demonstrating its resilience.

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!

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!

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!

Meticulously maintained and in pristine condition, this exceptional home has been lovingly cared for by the same family for over 50 years. Set back on a level, tree-lined lot on a quiet dead-end road, the home offers serenity and privacy while still being just a short drive to Stratton Mountain. Oversized windows throughout flood the interior with natural light, highlighting the soaring cathedral ceiling and stunning floor-to-ceiling fireplace in the living room. The renovated kitchen and bathrooms blend modern comfort with timeless style. Offered fully furnished with handcrafted Townshend Pioneer furniture, made locally and curated to complement each space. Outdoor enthusiasts will appreciate direct access to neighborhood trails leading to Ball Mountain Dam and Jamaica State Park for walking or mountain biking. This is a rare opportunity to own a turnkey property that balances meticulous upkeep with natural beauty and thoughtful design.

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. Exciting Update! This stunning property has just received a price improvement, making it an even greater opportunity for buyers seeking a quintessential Vermont retreat.

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.

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.

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.

A once-in-a-lifetime opportunity to own a large family home on Vermonts hidden gem! Cole Pond, a spectacular private lake surrounded by mountains and nestled between five ski areas - 5 minutes from Stratton and close to Bromley, Mount Snow, Okemo and Magic. Cole Pond homes rarely come on the market, and this one is one-of-a-kind, with a lake-front lawn, walk-in access to the water (also great for ice skating and hockey), a private dock, four bedrooms, three bathrooms, a great room, living room, music room, eat-in kitchen, screened in dining porch, large deck, over-sized second floor office/gym/playroom, 2-car garage and large shed. All this and sunset views over the mountain, two cherry trees, blueberries and wild blackberries. New roof in 2021.

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.