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585 Pleasant Valley Rd, Jamaica
$1,000,000
5033269 MLS
108 Acres of Pristine Land For Sale – 2 Miles to Stratton Sun Bowl with Panoramic Views A rare opportunity to own ~108 acres of stunning land with sweeping views of Stratton’s Sun Bowl and Mount Snow. Just 2 miles to the Sun Bowl base and 15 minutes to Mount Snow, this Jamaica, VT property (on the Stratton line) offers unmatched privacy, no zoning restrictions, and incredible potential. Permits are in place for a 6-bedroom home, plus a 4-bedroom home on a 5-acre development lot. Underground power is already run to the highest point—ideal for building and capturing panoramic views. The land features rolling hills, private ponds, and direct access to nature. Bordering 1,173 acres of Green Mountain National Forest on the eastern side, you’ll enjoy forever-protected views and privacy. Much of the land is enrolled in Vermont’s Current Use program for reduced taxes. Snowmobile, ATV, or simply enjoy the quiet serenity and wide-open skies. In addition to purchase of the land, architectural plans for a timber frame home, custom windows, and a full timber frame package available for sale. Whether you’re building a retreat, estate, or exploring development, this is a one-of-a-kind Vermont opportunity.

585 Pleasant Valley Rd, Jamaica
460 Stratton Gate Rd, Jamaica
$887,000
4 Beds ⋅ 3 Baths ⋅ 5057731 MLS
This exceptional property blends classic post-and-beam farmhouse design with modern craftsmanship. The stunning barn addition is an architectural masterpiece, admired from every angle and flooded with natural light through expansive windows that frame the serene surroundings. Soaring ceilings, rich hardwood floors, and custom finishes create an atmosphere of timeless elegance. An expansive loft offers limitless possibilities—office, art studio, fitness haven, or guest retreat—while a thoughtfully designed utility kitchen and cozy propane stove make everyday living and entertaining a delight. The open-concept main living area features a custom kitchen flowing effortlessly into a great room anchored by a dramatic floor-to-ceiling stone fireplace, cathedral ceilings, and a wall of windows. Four bedrooms across two levels provide comfort and privacy, complemented by abundant storage throughout. Practical luxuries include an impressive mudroom designed for post-adventure convenience, an oversized two-car garage with Tesla charger, energy-efficient solar panels, and a pristine basement for safe storage. Set on two peaceful acres at the end of a quiet cul-de-sac, offers a private landscaped retreat. Meticulously maintained by its current owners, it is ideally located just minutes from local amenities, attractions, and the region’s premier ski resorts.

460 Stratton Gate Rd, Jamaica
202 Pratt Bridge Rd, Jamaica
$785,000
3 Beds ⋅ 3 Baths ⋅ 5051393 MLS
Your slice of heaven awaits! Leave your worries behind and step into a beautiful Southern Vermont home that's truly turnkey. This well-designed, fully furnished, 3 bedroom, 2.5 bath home on 1.8+/- professionally landscaped acres offers privacy and convenience to the area's premier slopes, trails and natural beauty. The heart of the home is an expansive chef’s kitchen where country cabinetry and stone countertops create a refined haven of sophistication. A three-season screened porch is perfect for curling up with a favorite novel while admiring your tranquil and lush domain. The cottage style dining room features a lovely terrace that overlooks the vibrant perennial gardens. With a high, vaulted natural wood ceiling and woodburning fireplace, the living room creates a sense of spaciousness and warmth for entertaining. The inspired primary ensuite is a true sanctuary replete with a study/nook, powder room, and private, luxurious bath with a deep soaking tub. The lower level, a near-self-sufficient retreat, features two bedrooms, a welcoming mudroom/entry with woodstove, a large living area with 75” TV, stylish bath with tiled shower and a fully-equipped laundry room. Recent improvements include a brand new mini-split system (A/C and heat), full home battery back-up and comprehensive security system. Just 3 miles from Stratton Access Road, 15 minutes to Bromley and Magic Mountains and a scenic hike to Jamaica State Park, this exceptional home is truly a four-season paradise!

202 Pratt Bridge Rd, Jamaica
1247 Cole Pond Rd, Jamaica
$775,000
4 Beds ⋅ 3 Baths ⋅ 5043153 MLS
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.

1247 Cole Pond Rd, Jamaica
177 Alwin Ln, Jamaica
$615,000
3 Beds ⋅ 4 Baths ⋅ 5094046 MLS
Nestled in a peaceful and private mountain setting, this beautifully maintained home offers a seamless blend of comfort, functionality, and timeless Vermont charm. Thoughtfully updated and designed for easy living. The main level features a spacious primary suite with custom built-in cabinetry, a convenient mudroom, and an updated kitchen highlighted by Vermont Verde marble countertops and warm hardwood floors. At the heart of the home, the inviting living room is anchored by a wood-burning fireplace and a dramatic wall of glass that fills the space with natural light while framing the surrounding landscape. Upstairs, two additional bedrooms and an open loft provide flexible space for family & guests, a home office, or a cozy reading nook. The finished lower level expands the living area with a full bathroom and a versatile bonus room ideal for movie nights, a fitness studio, playroom, or workspace. Storage is exceptional, with an oversized detached garage, loft space above, along with an expansive attached storage area perfect for outdoor equipment, seasonal gear, and recreational toys. Numerous recent upgrades, including a whole-house generator, further reflect the care and attention invested in the property. Located less than two miles from Stratton Mountain Access Road, this home offers easy access to skiing, hiking, golf, and the area's many amenities, while maintaining a peaceful sense of privacy and seclusion. Whether as a full-time residence or a seasonal mountain retreat, this inviting property is perfectly suited for year-round enjoyment.

177 Alwin Ln, Jamaica
2132 Vt Route 30, Jamaica
$610,000
5004353 MLS
Welcome to The West River Park, an exceptional investment opportunity in Jamaica, VT, featuring a mobile home community with 1300 +/- feet of picturesque West River frontage! This unique property includes 22 mobile home pads, with 20 currently occupied, providing a steady income stream. 19 seasonal pads and 3 year round. Nestled right on the banks of the serene West River, residents enjoy unparalleled access to the natural beauty and recreational opportunities it offers. The park is conveniently located near both Stratton and Mount Snow ski areas, making it an ideal location for those who love outdoor adventures year-round. Many tenants use their homes as a base for skiing in the winter and fishing in the river during the summer months. Each residence can enjoy the park for 6 months out of the year used however they wish, spring, summer, fall, or winter. Don't miss out on this rare opportunity to own a piece of Vermont's natural beauty while benefiting from a thriving mobile home community. The West River Park offers a compelling blend of location, convenience, and recreational appeal.

2132 Vt Route 30, Jamaica
98 Gleason Farm Ln, Jamaica
$586,750
3 Beds ⋅ 3 Baths ⋅ 5078425 MLS
Nestled within a peaceful pine grove on 11.5 private acres between Stratton Mountain Resort and Mount Snow, this renovated 3-bedroom, 3-bathroom residence offers the perfect blend of secluded Vermont beauty and modern design. The heart of the home is a dramatic great room featuring 20+ foot soaring ceilings, skylights, and expansive windows that flood the space with natural light. On chilly winter days, enjoy the warmth and ambiance of the gas fireplace with its floor-to-ceiling brick chimney. The home was thoughtfully updated in 2024 with new sliding glass doors and new flooring throughout the kitchen, dining area, and great room. The kitchen was tastefully renovated in 2024, boasting sleek shaker cabinetry, a farmhouse apron sink, premium quartz countertops, and stainless appliances. All three bathrooms were updated in 2019. The home features three spacious bedrooms, including two ensuite retreats. The primary suite serves as a true sanctuary, anchored by a gas fireplace for ultimate relaxation. In addition to the open-concept living, the home includes a flexible bonus room and a lower-level walk-out family room—perfect for guests, entertaining, or a home office. Step outside to the large wrap-around deck, which features a modern wire railing system (updated in 2024) and covered portions for year-round enjoyment. With an attached garage, a covered side entrance for easy grocery unloading, a garden shed, and direct backyard access for hiking through your own private woods, this serene property delivers on every level. Credit for new heating system available.

98 Gleason Farm Ln, Jamaica
9 Beaver Pond Ln, Jamaica
$560,000
4 Beds ⋅ 4 Baths ⋅ 5094302 MLS
Rare Multi-Dwelling Retreat with Endless Possibilities A truly exceptional and meticulously maintained property featuring three separate residences on one beautifully landscaped lot, a setup buyers often dream about but rarely find. The main residence is a stylish 2-bedroom, 2-bath contemporary home thoughtfully designed for comfortable living. Built with sustainability in mind, the home features an environmentally friendly geothermal system that provides efficient heating and cooling year-round. Complementing the main home are two charming tiny houses, each with its own unique character and appeal. Whether used for guests, rental income, extended family, or creative workspace opportunities, these versatile structures offer tremendous flexibility. The grounds are nothing short of spectacular. A beautiful pond with a sandy beach and cascading waterfall creates a private oasis right outside your door. Mature landscaping throughout the property provides beauty, tranquility, and a clear sense of pride of ownership. Adding to the property's appeal is a septic system permitted for three two-bedroom residences. This substantial infrastructure provides valuable flexibility for future use. Subject to applicable permits and approvals, the existing tiny houses could potentially be replaced with larger two-bedroom cabins, or bedroom capacity could potentially be reallocated to an expanded main residence. Properties offering multiple residences, income potential, privacy, natural beauty, and convenient access to Stratton are exceptionally rare. Here, much of the groundwork has already been completed: the infrastructure is installed, the homes are in place, and significant future potential remains. Don't miss this unique opportunity to own a one-of-a-kind Vermont retreat offering flexibility for today and possibilities for tomorrow.

9 Beaver Pond Ln, Jamaica
64 Gleason Farm Ln, Jamaica
$555,000
3 Beds ⋅ 3 Baths ⋅ 5049166 MLS
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.

64 Gleason Farm Ln, Jamaica
155 Pratt Bridge Rd, Jamaica
$550,000
4 Beds ⋅ 3 Baths ⋅ 5094845 MLS
You may wake up to the singing of Cole Pond resident loons at your next VT home awaiting you just minutes from the Stratton Access road. Tucked away on a quiet country road this inviting 4 bedroom, 2.5 bath home offers the perfect balance of comfort, convenience and charm. Designed for gathering with friends and family, entry level offers a family room with woodstove , open concept on main level with attractive fieldstone wood burning fireplace, appealing kitchen with Jenn air stove. Updated baths and pretty wood floors complete this move in residence, set on a nice level lot, the property provides plenty of space for outdoor enjoyment year round. No HOA fees to worry about, just lock and leave at the end of your stay. Don't miss the opportunity to own a well-maintained and appointed escape in a highly desirable area. Schedule your showing today.

155 Pratt Bridge Rd, Jamaica
4138 W Hill Rd S, Jamaica
$530,000
3 Beds ⋅ 3 Baths ⋅ 5077783 MLS
Nestled on 2.37 private acres in a serene mountain setting just minutes from skiing, this custom-built three-bedroom, three-bath log home offers the perfect blend of rustic charm and comfort. Constructed with double tongue-and-groove logs, the home showcases the rich wood interior and craftsmanship you would expect in a classic mountain retreat. The open-concept main level centers around a stunning fieldstone hearth and cozy wood stove, complemented by beautiful oak flooring throughout. A covered front porch overlooks the peaceful wooded landscape, while the back deck enjoys long hours of sunshine—ideal for relaxing or entertaining. The main level includes a spacious primary bedroom with an ensuite bath, a bunk room, an additional full bathroom, and a versatile bonus room perfect for a den, home office, or extra sleeping space. Downstairs, the walkout lower level features a generous mudroom designed for all your outdoor gear, a large bedroom, a full bathroom, and another flexible bonus room ideal for recreation or entertaining. Set well back from a quiet country road yet conveniently located near the quaint village of Jamaica, the property is accented by classic stone walls and gladed woods, enhancing its Vermont charm. A two-car garage, storage shed for recreational equipment, and a timber shed complete this exceptional offering. Whether you're seeking a full-time residence or a mountain getaway, this inviting log home delivers privacy, character, and convenience in one beautiful package.

4138 W Hill Rd S, Jamaica
3996 Rte 30, Jamaica
$510,000
4 Beds ⋅ 3 Baths ⋅ 5076624 MLS
Village charm meets mountain lifestyle in this beautifully updated home in the heart of Jamaica. Set above the road for added privacy, the property captures lovely winter views of the surrounding mountains and river while remaining just a short stroll to local shops and village conveniences. Inside, you’ll find generous living space with warm wood floors and a flowing, open layout designed for gathering. The inviting great room features a wood-burning stove and sliders that lead to a private deck and sunny yard—perfect for summer barbecues or peaceful mornings with coffee. The renovated kitchen offers an island, large pantry, and easy access to a bright dining area lined with windows. Minimum of 24 hours notice for showings during the month of March. Upstairs are four comfortable bedrooms, including a spacious primary suite with its own bath. With three bathrooms, a dedicated laundry area, office, mudroom, and abundant storage throughout, this home blends classic character with everyday functionality. Adventure is always within reach—just minutes to Stratton Mountain Resort, Jamaica State Park, and Pikes Falls—with hiking, biking, skiing, and kayaking right at your fingertips. A sunny lot with garden potential and storage for bikes and kayaks complete the picture. Extensive updates over the past three years—including new windows, siding, flooring, a new furnace, and much more—offer peace of mind and modern efficiency while preserving the home’s timeless appeal. A true four-season retreat at an exceptional value—come experience the best of Vermont living.

3996 Rte 30, Jamaica
1905 Turkey Mountain Rd, Jamaica
$500,000
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
1905 Turkey Mountain Rd, Jamaica
$484,000
3 Beds ⋅ 3 Baths ⋅ 5090336 MLS
BEST AND FINAL OFFERS DUE BY WEDNESDAY, MAY 27TH AT 5PM 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 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
West Hill Road, Jamaica
$482,972
5021448 MLS
The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and rarely do pieces of land like this come onto the market. Lot 5 has a private driveway that begins at Lot 4. The parcel encompasses the entire north side of the subdivision, from the bottom of the hill all the way up the access road. The views from the clearing at the top of the driveway are to the west toward Bromley Mountain, but there are also big views in the other direction looking southeast. There would be several spots to build on this parcel, but the top of the hill seems like the place to be with the ability to have unobstructed views from your new home.

West Hill Road, Jamaica
199 Turkey Mountain Rd, Jamaica
$480,000
3 Beds ⋅ 3 Baths ⋅ 5079024 MLS
Welcome to country living with room to breathe. This expanded and renovated 1985 ranch sits on nearly 8 rolling acres offering the perfect blend of privacy, open space and modern comfort. Step outside and enjoy country side living suited for gardening, recreation, snowmobiling or simply relaxing. Inside, thoughtful updates and expanded layout create bright, inviting living areas for everyday living or entertaining. Primary suite and additional two bedrooms with sleek bath on main level. Bumped out addition of den for your office/reading area with access to outdoors. Well equipped kitchen with pantry open to dining area and mornings you can enjoy all the sun beaming through. Owner created a wonderful family room on the lower level walk out with half bath and a bonus room. Two car attached garage. The well maintained John Deer tractor is available for purchase to keep your meadow preserved. Enlarged deck for all your bbques and entertaining. Plus, outdoor storage shed/lean -to for your ATVS , snowmobiles etc . We invite you to take a tour. This home will not last on the market.

199 Turkey Mountain Rd, Jamaica
163 Howe Farm Rd, Jamaica
$450,000
3 Beds ⋅ 3 Baths ⋅ 5094647 MLS
***BEST AND HIGHEST DUE BY 6/23/2026 AT 5PM*** Let the sunshine in! This beautifully maintained 3-bedroom, 3-bath home features an open-concept kitchen, living, and dining area centered around a stunning floor-to-ceiling brick fireplace. Cathedral ceilings and abundant windows fill the space with natural light, creating a warm and inviting atmosphere. The spacious primary suite offers a private full bath, while two additional bedrooms and another full bath are conveniently located on the main level. A charming loft overlooks the entryway, providing flexible space for a home office, reading nook, or additional sleeping area. The finished lower level is perfect for entertaining and accommodating guests, featuring a second fireplace, movie projector with surround sound, heated radiant entryway, bonus bunk room, full bath, laundry room, and ample storage space. The kitchen is equipped with stainless steel appliances, and numerous upgrades that were completed to home in 2019. Outside, enjoy every season from the expansive deck, complete with grill, fire pit area and hot tub at ground level. Additional highlights include a durable standing-seam roof, circular driveway, and a private setting tucked back from a town-maintained road. A beautiful stone retaining wall provides excellent curb appeal and a welcoming first impression. Located in a town with no zoning restrictions and just minutes from Stratton Mountain, this property offers the perfect combination of comfort, convenience, and year-round recreation.

163 Howe Farm Rd, Jamaica
994 W Jamaica Rd, Jamaica
$450,000
3 Beds ⋅ 3 Baths ⋅ 5093205 MLS
A Rare Riverfront Investment & Lifestyle Opportunity Nestled along the banks of a picturesque river, this magical 8.5-acre property offers a unique blend of natural beauty, privacy, and income-producing potential. Surrounded by mature trees, and the soothing sounds of the water, this is a truly special retreat in Southern Vermont. The main residence was thoughtfully updated in 2015 and features 3 bedrooms, 2.5 bathrooms, and a highly efficient split heating and cooling system installed in 2023. Comfortable and well-appointed, the home serves as an ideal primary residence, vacation getaway, or investment property. Adding to the property's appeal are two exceptional off-grid guest cabins designed for the growing glamping market. The first cabin, constructed in 2019 and situated near the river, features a one-bedroom design, kitchen, loft sleeping area, and wood/pellet stove hookup, creating a memorable guest experience. A second off-grid cabin, completed in 2024, offers a one-bedroom layout with loft sleeping space, wood/pellet stove hookup, and a peaceful connection to nature. The property's income potential is substantial, with the guest cabins projected to generate approximately $60,000 annually in gross rental income, while the main home has demonstrated gross rental income of approximately $48,634 annually. Whether you're seeking a Vermont retreat, a hospitality venture, or a combination of both, this property presents a compelling opportunity with multiple revenue streams. Only 10 Min. to Stratton Mountain Resort and 20 Min. to Mount Snow Resort. Bromley and Magic Mountain within 30 min. drive. Rarely does a property combine riverfront beauty, modern improvements, off-grid luxury accommodations, and strong investment potential in such a remarkable setting.

994 W Jamaica Rd, Jamaica
132 Pratt Bridge Rd, Jamaica
$405,000
3 Beds ⋅ 2 Baths ⋅ 5060417 MLS
Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water. Inside, the home offers 3 bedrooms and 2 full baths, along with a versatile second floor bonus room that can serve as additional sleeping space, a cozy den, or a private office. The eat-in kitchen provides a welcoming gathering space, complemented by a separate dining area for larger meals or entertaining. The living room features a vaulted ceiling and a cozy fireplace, creating a warm and inviting atmosphere. Expansive windows along the back of the home bathe the interior in natural light and bring the outdoors in. Outdoors, a level yard invites recreation and gatherings, while the spacious deck with built-in seating is perfect for entertaining or soaking in the Vermont scenery after a day on the slopes or lakes. Whether you're seeking a ski house, summer getaway, or welcoming full-time residence, this property offers the perfect balance of comfort, convenience, and four-season enjoyment. *Showings to start Thursday 9/11*

132 Pratt Bridge Rd, Jamaica
2779 Pikes Falls Rd, Jamaica
$380,000
3 Beds ⋅ 1 Baths ⋅ 5035904 MLS
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.

2779 Pikes Falls Rd, Jamaica
Black Bear Rd, Jamaica
$377,500
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
West Hill Road, Jamaica
$367,802
5021418 MLS
The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods road leading from the main access road into the property’s interior. Immediately next to the road is the first clearing where a house could be built. This is a level spot, and by removing some of the trees near the road, views of the mountains would be seen. Continuing up the road there is another large clearing. This site would have great views, possibly in two directions once some tree clearing has been done. As with the rest of the parcels, this land is not in Current Use, so there are no restrictions on where you can build.

West Hill Road, Jamaica
29 Pikes Falls Rd, Jamaica
$315,000
4 Beds ⋅ 2 Baths ⋅ 5078084 MLS
MOTIVATED SELLERS! Bring your offers! Experience the timeless appeal of this beautifully preserved 1800s Greek Revival residence in the center of Jamaica Village. Offering more than 2,500 square feet of living space, the home pairs classic architectural detail with thoughtful modern updates for effortless year-round living. Ideally situated just 15 minutes from Stratton Mountain and 25 minutes to Mount Snow, the location balances village convenience with premier access to Southern Vermont’s ski resorts and outdoor recreation. From the covered porch to the deck and veranda, the property invites relaxed outdoor living amid established gardens and peaceful surroundings. Jamaica State Park, River & Rye, the West River, the village library, and the local general store are all within easy walking distance. Inside, generous proportions define the layout. The expansive primary suite is complemented by three additional well-sized bedrooms, providing flexibility for guests or remote work. A well-appointed kitchen with a center island opens seamlessly to a formal dining room designed for memorable gatherings. The spacious living room offers a warm and welcoming setting, while the back porch and veranda create additional spaces to unwind. Blending historic character, modern comfort, and an exceptional village location, this property represents a rare opportunity to own a quintessential Vermont home—equally suited as a primary residence, seasonal retreat, or investment opportunity.

29 Pikes Falls Rd, Jamaica
9047 Vt Route 30, Jamaica
$315,000
2 Beds ⋅ 2 Baths ⋅ 5075664 MLS
“The Yellow Sweetie” offers a rare blend of charm, convenience, and proven income potential. This stylish country-meets-shabby-chic retreat has been a high-income producing rental for many years, making it an excellent opportunity for investment, year-round living, or a Vermont vacation retreat. Ideally located near the base of Stratton Mountain, the property sits just one minute from the Stratton Access road and only eight minutes to the slopes. Enjoy easy access to beloved local destinations including Gale Meadows Pond for kayaking and hiking, Honey Pie and Family Kitchen for lunch or dinner, and the Stratton Village shops. The home features two bedrooms and two baths, including one with a classic clawfoot tub. Thoughtfully updated while preserving its inviting character, the home features comfortable living spaces and a large cook stove, creating a warm and welcoming atmosphere. Filled with warmth and personality, this turnkey property presents an outstanding opportunity for personal use, rental income, or a combination of both in a highly desirable Stratton location.

9047 Vt Route 30, Jamaica
1829 W Jamaica Rd, Jamaica
$308,500
3 Beds ⋅ 2 Baths ⋅ 5082108 MLS
Vermont Charming! Tucked away along a peaceful river in Jamaica, Vermont this charming cape offers the perfect blend of privacy, character and convenience just 4 miles from Stratton Mountain Resort. With three bedrooms and one and three quarters baths, the home has been thoughtfully maintained and updated while preserving its classic New England charm. Recent upgrades to the kitchen and bathrooms provide modern comfort, new windows throughout make it energy efficient. A cozy wood stove creates the perfect atmosphere after a day on the slopes while the deck overlooking the river offers a relaxing spot to unwind and enjoy the natural setting. Outside, a fire pit area adds to the appeal, creating a wonderful gathering space for evenings under the stars. Private and secluded, yet minutes from skiing, dining, golf and year round recreation, this property is an ideal retreat or full time residence. Great price and location- sold furnished and move in ready - make an appointment to see it today!

1829 W Jamaica Rd, Jamaica
270 Castle Hill Rd, Jamaica
$302,500
3 Beds ⋅ 2 Baths ⋅ 5103863 MLS
OFFER DEADLINE, MONDAY AUGUST 9TH 2026 5PM. Escape to this charming turnkey cabin nestled in the hills of Southern Vermont, just a short drive from Stratton Mountain. Being sold fully furnished and as is, what you see is what you get, simply bring your personal belongings and start enjoying your mountain retreat! Privately situated on 9.7 wooded acres, this cozy getaway offers the perfect blend of seclusion and convenience. A paved driveway leads you to your own peaceful slice of Vermont paradise. The open-concept interior features a warm post-and-beam design with locally harvested wood countertops that add rustic character to the kitchen and living space. The main level offers two bedrooms, one with its own three-quarter bathroom, providing privacy and convenience for family or guests. Upstairs, a spacious open area offers endless possibilities, use it as additional sleeping space, a game room, home office, or cozy lounge area. The cabin is comfortably heated year-round by a Rinnai direct vent propane heater, with electric baseboard heat available for backup. Annual propane usage was 365 gallons total heating the cabin year-round, and the average annual electric bill was $670 total for the current owner. Whether you're looking for a four-season getaway, or a peaceful place to unwind, this inviting cabin is ready for its next owners to enjoy.

270 Castle Hill Rd, Jamaica
756 Turkey Mountain Rd, Jamaica
$300,000
3 Beds ⋅ 2 Baths ⋅ 5074237 MLS
Tucked away on 2.5± mostly level acres with stonewalls and a brook at the edge of the property, this Jamaica, Vermont, Cape offers a rare combination of usable land, privacy, and natural beauty. Inside, the 3-bedroom, 2-bath home offers a sensible, functional floor plan with solid bones and the opportunity to update and personalize over time. First-floor bedroom with a newly refreshed full bath, spacious kitchen, formal dining room, and living room. The 2nd story has 2 more bedrooms, including a primary bedroom with a walk-in closet. A ¾ bath with a skylight is also on this level. Full concrete basement with a workshop area, laundry, and plenty of storage with bulkhead access to the back yard for easy access as well as interior stairs from the kitchen. In addition to baseboard hot water heat, mini splits are on the main level and in the primary bedroom for AC! The setting feels peaceful, with a large open yard that gradually leads to a more hidden, intimate area along the brook—an ideal place to unwind, cool off, explore, or simply enjoy the sounds of nature. A front covered farmer’s porch and side deck off the kitchen provide comfortable outdoor spaces, while the property also includes garden beds, a chicken coop, and a shed for tools or hobbies—supporting a relaxed, outdoor-focused lifestyle. Located just minutes from Jamaica Village and close to Stratton Mountain Resort, Mount Snow, Bromley Mountain and Magic Mountain ski resorts, the area offers four-season recreation, including hiking and exploring in Jamaica State Forest and kayaking or swimming on the West River. Whether envisioned as a primary home or Vermont getaway, this property invites you to enjoy the setting and location now while adding value and updates at your own pace over time. **home is not in flood zone. FEMA LOMA -Letter of ( flood) Map Amendment on file.

756 Turkey Mountain Rd, Jamaica
4410 Pikes Falls Rd, Jamaica
$299,000
3 Beds ⋅ 2 Baths ⋅ 5070982 MLS
This charming cabin in the woods is the perfect retreat for those seeking adventure and tranquility alike. Surrounded by 10.7 acres of forest, it offers a cozy haven just a short walk from the breathtaking Pikes Falls and is 5 minutes to Stratton Mountain, ideal for skiing enthusiasts during the winter months. In warmer weather, the nearby trails beckon hikers and mountain bikers to explore the stunning landscapes and vibrant wildlife. With three spacious bedrooms and two baths this home comfortably accommodates multiple friends and guests. The rich history of the area, formerly enjoyed by many who moved from the Cities in the 40's to come to Vermont and live off the land, adds an intriguing layer making it not just a getaway but a connection to the past. Whether you're passionate about outdoor activities like maple sugaring or simply wish to unwind with a book by the woodstove or roaring firepit out back, this special offering is a delightful escape into nature's embrace. Deed, tax map and lister card are for 48.4 acres. This 10.7 acres is being subdivided off of the larger piece. Road frontage is approximate. Original Aframe was built in 1962 by earlier family and addition in 1976 with some upgrades C.2020 . Furnished and sold "AS IS". Some protective covenants and restrictions will be added soon.

4410 Pikes Falls Rd, Jamaica
00 Pratt Bridge Rd, Jamaica
$285,000
5080983 MLS
Thinking of building!! Enjoy Vermont in all the seasons!! This land has a number of options! A sectioned parcel of 30 acres of land has been already approved for a 4 lot subdivision with state approved septic designs. OR develop one site to sell and keep one for yourself with more land to share. OR keep it all to yourself and build your dream home. Pratt Bridge Road is a close drive to Stratton, Magic or Bromley in the winter and enjoy summers exploring some of the 55 state parks that Vermont has to offer! Take a hike at Ball Mountain Dam, Jamaica State Park or Lowell Lake - all just minutes away. A driveway is in place and power is close by on the road. Start you Vermont adventure today!!

00 Pratt Bridge Rd, Jamaica
1018 S Hill Rd, Jamaica
$275,000
2 Beds ⋅ 1 Baths ⋅ 5102407 MLS
OPEN HOUSE - Sunday 8/2, 1-3 ** BEST AND FINAL DEADLINE - Monday, August 3rd, 5pm. This charming A-frame offers a woodsy Vermont retreat on 2.8 acres on quiet and scenic South Hill Road. Set at the end of a long driveway and perched on a hill, surrounded by mature woods, this 2 bedroom, 1 bath home blends rustic character with a warm, inviting atmosphere. Natural wood flooring and wood features throughout complement the distinctive A-frame design, while a wall of windows fills the home with natural light and brings in the surrounding woodland setting. The main level offers an open living, kitchen and dining space that walks out to a deck in the trees. Also on this main level is a bedroom and bath and access to an additional deck on the front side of the home. Stairs off the living room take you up to the loft bedroom overlooking the living space on one side and large windows to the outside on the other. The lower level offers an opportunity to finish additional space for expanded living, recreation, or guest accommodations. Enjoy the peace and privacy of your own wooded retreat while remaining just a short drive to both Mount Snow and Stratton ski areas. Adding to the country setting is a local general store only four minutes away. Whether you’re looking for a weekend escape, vacation home, or year-round residence, this property offers a wonderful opportunity to create your own Vermont getaway. Property is being sold as is.

1018 S Hill Rd, Jamaica

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