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$850,000
5 Beds 4 Baths 5088809 MLS
Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no matter the weather. Or you can relax in the hot tub after a long day and even enjoy the sounds of a local waterfall located just a short walk from the doorstep. A 1-bedroom apartment with a separate entrance gives this home more flexibility for family and friends to stay for extended visits. The two-car garage provides space for all the outdoor gear you could need to explore the Vermont wilderness year-round. This home has all you need to enjoy all the Vermont has to offer.

4880 Pikes Falls Rd, Jamaica

$1,450,000
5082418 MLS
Own this large tract of land, over 200 acres that abuts over 1100 additional acres of Green Mountain National Forest. This private setting is less than 3 miles to Stratton Mountain Resort with easy owned access on Forrester Pond. Currently only 18 of the 200 acres is gravel pit and being reclaimed and closed out on this property. See the Vermont Land Use Permit 2W1316 online for further information. There are multiple drilled wells located throughout the property, an old foundation, multiple wooded locations with rolling hills that sit at higher elevations with the potential for future development should you want to open them up! Views can be had of Stratton Sun Bowl and Mount Snow from the 1800foot elevation on the Western plateau. Don't miss your opportunity to see this amazing large tract of land that is being offered so close to Stratton yet located in Jamaica, which is a no zoning town. Residential and recreational opportunities on this parcel are worth exploring. Please no drive-bys as there is heavy equipment and work being conducted on site regularly.

Forrester Road, Jamaica

$460,000
3 Beds 2 Baths 5081124 MLS
This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set on 5.65 acres of bright, sunny land, the property includes a greenhouse and is bordered by a picturesque stone wall along a private road. Nestled in the country village of Jamaica, it is surrounded by wooded areas teeming with wildlife, yet conveniently located just 20 minutes from four major ski resorts and close to Jamaica State Park, which offers excellent hiking and camping options. While the home requires some updating, it provides a perfect blend of rural tranquility and accessibility to Vermont's attractions.

57 Oak Ln, Jamaica

$195,000
5080889 MLS
This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this land is ideally positioned to meet that growing demand. The current owner has secured an Act 250 permit for a three-unit, four-season glamping campground, creating an exceptional investment opportunity for a nature-based hospitality concept in the Green Mountains. Future guests—or homeowners—can enjoy evenings under star-filled skies, time spent in the surrounding natural beauty, and easy access to hiking, biking, and outdoor recreation in one of Vermont’s most scenic regions.  The property offers both seclusion and convenience, located just minutes from Stratton Mountain Resort with additional access to Magic Mountain and Bromley. The nearby villages of Jamaica, Londonderry, and Manchester provide year-round dining, shopping, and classic Vermont character.  A state wastewater permit is also in place for a four-bedroom home. Buyers wishing to pursue residential development would need to amend the existing Act 250 permit accordingly. Buyer and buyer’s representatives to verify all permitting and regulatory requirements.  A state wastewater permit is also in place for a four-bedroom home. Buyers wishing to pursue residential development or additional options would need to amend the existing Act 250 permit accordingly, subject to state and local approvals. Buyer and buyer’s representatives to conduct their own due diligence and verify all permitting and regulatory requirements.

4769 Pikes Falls Rd, Jamaica

$500,000
5077252 MLS
Escape to your own private 71-acre Vermont retreat, offering exceptional privacy and possibility plus access to nearby ski mountain villages. Tucked at the end of a town-maintained dead-end road and bordered on two sides by over 1,000 acres of conservation land, this property promises unmatched peace and lasting protection. Only 20 minutes to either Mt. Snow or Stratton, with over 3,300 feet of road frontage and electricity conveniently available at a pad near the beginning, the land provides both accessibility and potential. A ring road winds around the perimeter, complemented by an internal trail through the center, allowing you to explore the entire property by foot or ATV. The diverse topography—a blend of level plateaus, gentle slopes, hills, and steeper elevations—offers multiple potential build sites. Create your dream home with spectacular views of Stratton Mountain or build closer to the road and enjoy private hiking access to scenic overlooks. One of the property’s unique features is a large woodland pond hidden away at the far end—an ideal backdrop for seeing Vermont’s wildlife. The land is not currently enrolled in the Land Use Program, offering flexibility for future development or conservation choices. Located in the town of Jamaica, which has no zoning restrictions, this parcel invites your imagination, with state development laws guiding your vision. Come discover the potential of your personal Vermont sanctuary within reach of the recreational benefits that the state offers.

00 Turkey Mountain Rd, Jamaica

$8,200,000
6 Beds 10 Baths 5076041 MLS
Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in its surroundings while still just a short drive to Stratton Mountain Resort and the Stratton Helipad. Step into an open-concept haven where elegance meets comfort. Framed by soaring timber beam ceilings, the main living area echoes the grandeur of the mountains while preserving the warmth and intimacy of a true retreat. Natural materials, handcrafted details, and thoughtful design choices create a home that feels warm, timeless and deeply personal. The estate preserves uninterrupted views across the landscape—ensuring that natural beauty remains the focal point from every vantage point.The grand stone fireplace anchors the living area, drawing the eye to soaring ceilings and expansive windows that frame breathtaking mountain ridges. Sunlight floods the space, highlighting the harmonious blend of natural textures and refined finishes.The gourmet kitchen blends beauty and function with custom wood cabinetry, hand-carved artistic accents, a welcoming breakfast bar, and an expansive island designed for conversation, connection, and effortless entertaining. Every space in this residence has been intentionally designed with a keen eye to detail. While every room blends effortlessly with the home’s elevated rustic feel, each one remains extremely unique. Offering six en-suite bedroom in the main residence and 2 bedroom2.5 bath guest quarters. Main Residence with extraordinary gathering rooms and multiple suites, 5 bay barn, guest quarters, pond, miles of maintained trails for mountain biking and winter activities,

557 Trager Rd, Jamaica

$210,000
5070790 MLS
Discover the beauty and tranquility of this picturesque wooded parcel—approximately 35 acres—nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a large forested lot can provide. The upper elevations of the land offer the potential for sweeping mountain views, making them ideal locations for a future homesite, cabin, or scenic overlook. Wander through rolling, mature woodland where wildlife thrives, sunlight filters through the canopy, and each season paints the landscape with its own character. Along the river’s edge, relax to the calming sound of the Deerfield River as it winds gracefully past the property—perfect for quiet reflection, picnics, or simply enjoying the natural beauty that surrounds you. With its mix of river frontage, wooded acreage, recreational access, and development possibilities, this versatile property offers a rare opportunity to create your own private Vermont escape.

00 Rte 100, Jamaica

$178,000
5067302 MLS
Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up. A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is underway to establish the final lot lines—essential steps that lay the foundation for a smooth transition into planning and development. The gently rolling terrain, mature trees, and the quiet ambiance of the surrounding landscape create an inviting canvas for a variety of uses. Whether your dream is to build a private country retreat or a primary home surrounded by nature, this property delivers both versatility and potential. With the key groundwork already in motion, the stage is set for you to bring your vision to life.

4441 Rte 30, Jamaica

$475,000
5065110 MLS
Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers significant development potential. Multiple areas throughout the property provide potential home sites with mountain views, and there is frontage available for additional points of access. Located on West Hill Road in Jamaica, VT, this property not only provides a serene and private setting but also offers convenient access to the area's many attractions. Enjoy nearby Jamaica State Park, hike, bike, and explore the West River. Take in the natural beauty of Hamilton Falls, venture to Stratton, Bromley or Magic Mountain Resorts for year-round activities, including skiing, golfing, & hiking. The charming town of Jamaica is just a short drive away, offering local shops, art galleries, and dining options. The surrounding area is rich in history, with local farms, markets, and antique shops that showcase Vermont's agricultural heritage and artisanal craftsmanship. Whether you're looking for a peaceful retreat or a base to explore all that Southern Vermont has to offer, this property presents a rare opportunity to own a piece of paradise with highly desirable features already in place.

00 W Hill Rd S, Jamaica

$1,140,000
4 Beds 3 Baths 5060615 MLS
Discover a truly special Vermont hidden treasure at 70 Hunter Lane, set within the private Highland Forest community in the Cole Pond community . Just five minutes to Stratton Mountain Resort, this exceptional property offers the perfect balance of privacy, convenience, and year-round recreation. This 4,200 square foot home features four bedrooms and three Bathrooms. The generous living spaces highlighted by two fireplaces, creating a warm and inviting atmosphere. A bonus room is an art studio to expand your creative senses. Large windows capture the natural beauty of the surroundings, while a wraparound deck extends the living space outdoors—ideal for entertaining or simply enjoying the peaceful setting. The property is uniquely enhanced by two beautiful private ponds, And an abundance of perennial gardens, offering a serene and picturesque backdrop. Relax in the outdoor hot tub after a day on the slopes. Enjoy Highland Forests private beach access to Cole Pond, This grassy space with a dock is perfect for swimming, kayaking, and quiet enjoyment. Outdoor enthusiasts will appreciate the nearby Hiking and Snowshoe trail access, making this an ideal four-season retreat. Whether you're seeking a full-time residence or a Vermont getaway, this home delivers a rare combination of space, setting, and proximity to one of Southern Vermont’s premier resorts.

70 Hunter Ln, Jamaica

$1,040,000
5 Beds 5 Baths 5060071 MLS
Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless connection with the outdoors. A Pellet stove with the fieldstone fireplace adds warmth and character to the main living space. Just off the living area, a second living room with a sleeping area offers a perfect spot for a home office or guest wing while enjoying lake views. Upstairs, you'll find two bedrooms and a separate office, sharing a full bath. The property also includes a two-car garage with a convenient studio apartment and private bath, ideal for guests. Enjoy direct access to the water with a unique floating dock, perfect for kayaks, paddle-boards, and simply taking in the magnificent scenery. This home is designed to accommodate a life of both leisure and adventure.

1189 Cole Pond Rd, Jamaica

$2,399,000
4 Beds 5 Baths 4972272 MLS
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!

662 Howe Farm Rd, Jamaica

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