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Already operating as a successful short-term rental, 24 Mowrey Road offers the space, setting, and amenities buyers are looking for in a Southern Vermont getaway. Set on 2.3 acres along a town-maintained dead-end road, this spacious 4-bedroom, 4-bath home is positioned between Stratton and Mount Snow, with easy access to year-round recreation. Inside, the open great room creates an inviting gathering space, complete with a wood stove, propane stove, double sliders to the rear deck, and a fun ski-lift chair feature that gives the home unmistakable Vermont ski-house character. The layout works especially well for groups, with a first-floor primary suite with king bed, three additional bedrooms upstairs, 2 with king beds and one with 2 triple bunks, multiple baths, and a mostly finished lower level offering additional family, recreation, and bonus space. A covered front porch and expansive rear deck extend the living outdoors, while the detached garage provides welcome storage for skis, bikes, and Vermont gear. Dual Tesla Powerwall batteries with Tesla backup equipment add valuable energy storage and backup capability during outages.Starlink internet provides reliable high-speed connectivity for streaming, remote work, and guest use, an especially valuable amenity for a Vermont second home or short-term rental. The home is thoughtfully set up for vacation-rental use and is currently professionally managed as an operational STR, giving a new owner the option to continue its established rental use or simply enjoy it as a generously sized second home. Approximately 3,075 finished square feet provide room to spread out without losing the cozy mountain-home feel. Rental history is available for interested buyers. A well-established Vermont retreat with income history, personality, and space for everyone to gather, all within approximately 15 minutes of Mount Snow and 25 to Stratton.

4 Beds ⋅ 4 Baths ⋅ 5111100 MLS

Already operating as a successful short-term rental, 24 Mowrey Road offers the space, setting, and amenities buyers are looking for in a Southern Vermont getaway. Set on 2.3 acres along a town-maintained dead-end road, this spacious 4-bedroom, 4-bath home is positioned between Stratton and Mount Snow, with easy access to year-round recreation. Inside, the open great room creates an inviting gathering space, complete with a wood stove, propane stove, double sliders to the rear deck, and a fun ski-lift chair feature that gives the home unmistakable Vermont ski-house character. The layout works especially well for groups, with a first-floor primary suite with king bed, three additional bedrooms upstairs, 2 with king beds and one with 2 triple bunks, multiple baths, and a mostly finished lower level offering additional family, recreation, and bonus space. A covered front porch and expansive rear deck extend the living outdoors, while the detached garage provides welcome storage for skis, bikes, and Vermont gear. Dual Tesla Powerwall batteries with Tesla backup equipment add valuable energy storage and backup capability during outages.Starlink internet provides reliable high-speed connectivity for streaming, remote work, and guest use, an especially valuable amenity for a Vermont second home or short-term rental. The home is thoughtfully set up for vacation-rental use and is currently professionally managed as an operational STR, giving a new owner the option to continue its established rental use or simply enjoy it as a generously sized second home. Approximately 3,075 finished square feet provide room to spread out without losing the cozy mountain-home feel. Rental history is available for interested buyers. A well-established Vermont retreat with income history, personality, and space for everyone to gather, all within approximately 15 minutes of Mount Snow and 25 to Stratton.

24 Mowrey Rd, Jamaica

$995,000

130 acre tract, this parcel backs up to over 1100 additional acres of Green Mountain National Forest lands. This private setting is less than 3 miles to Stratton Mountain Resort. Being subdivided off a larger 200+ acre parcel. Overhead power currently existing on premise, multiple drilled wells also already on premise and there will be access to this and other lots via existing road/driveway access into this parcel that is currently in use. Residential and recreational opportunities are worth exploring here. See also MLS#5082418 for more information. Taxes are reflective of entire parcel, 130 acre lot will be reflected differently once subdivided and transferred. Multiple parcels being offered for sale, 201 acres at $1.45mil, 67 acres at $799k and a 4 acre parcel at $250k. Owners are willing to discuss owner financing as well. Reclamation of existing pit is well underway and nearing completion. Currently only 15 acres of the 200+ acres is gravel pit and being reclaimed on this property. See the Vermont Land Use Permit 2W1316 online for further information. Views of both Stratton and Mountain Snow can be had from the 1800 foot elevation on the westerly plateau of this lot. Roughed in driveway has been cleared to the location with potential views and future building site(s). 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. Stratton Jamaica Town Line is a partial boundary line of this parcel. Residential and recreational opportunities on this parcel are worthy of exploring. Please, we request in advance, no drive-bys as there is heavy equipment and work being conducted on site daily.

5110773 MLS

130 acre tract, this parcel backs up to over 1100 additional acres of Green Mountain National Forest lands. This private setting is less than 3 miles to Stratton Mountain Resort. Being subdivided off a larger 200+ acre parcel. Overhead power currently existing on premise, multiple drilled wells also already on premise and there will be access to this and other lots via existing road/driveway access into this parcel that is currently in use. Residential and recreational opportunities are worth exploring here. See also MLS#5082418 for more information. Taxes are reflective of entire parcel, 130 acre lot will be reflected differently once subdivided and transferred. Multiple parcels being offered for sale, 201 acres at $1.45mil, 67 acres at $799k and a 4 acre parcel at $250k. Owners are willing to discuss owner financing as well. Reclamation of existing pit is well underway and nearing completion. Currently only 15 acres of the 200+ acres is gravel pit and being reclaimed on this property. See the Vermont Land Use Permit 2W1316 online for further information. Views of both Stratton and Mountain Snow can be had from the 1800 foot elevation on the westerly plateau of this lot. Roughed in driveway has been cleared to the location with potential views and future building site(s). 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. Stratton Jamaica Town Line is a partial boundary line of this parcel. Residential and recreational opportunities on this parcel are worthy of exploring. Please, we request in advance, no drive-bys as there is heavy equipment and work being conducted on site daily.

Forrester Road, Jamaica

$799,000

Own this large 67 acre tract of land just minutes to Stratton Mountain Resort with direct access to Forrester Pond. This parcel backs up to 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. Being subdivided off a larger 200+ acre parcel. Power existing on current right of way and is also access to this lot. Residential and recreational opportunities are worth exploring here. See also MLS#5082418 for more information. Taxes are reflective of entire parcel, 67 acre lot will be reflected differently once subdivided and transferred. Multiple parcels being offered for sale, 201 acres at $1.45mil, 130 acres at $995k and a 4 acre parcel at $250k. Owners are willing to discuss owner financing as well. Reclamation of existing pit is well underway and nearing completion. Currently only 18 acres of the 200+ acres is gravel pit and being reclaimed on this property. See the Vermont Land Use Permit 2W1316 online for further information. There is an old foundation overlooking Forrester Pond with rolling hills that sit at higher elevations! Local mountain views can be had from the 1800 foot elevation on the northeastern 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, we request in advance, no drive-bys as there is heavy equipment and work being conducted on site daily.

5110766 MLS

Own this large 67 acre tract of land just minutes to Stratton Mountain Resort with direct access to Forrester Pond. This parcel backs up to 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. Being subdivided off a larger 200+ acre parcel. Power existing on current right of way and is also access to this lot. Residential and recreational opportunities are worth exploring here. See also MLS#5082418 for more information. Taxes are reflective of entire parcel, 67 acre lot will be reflected differently once subdivided and transferred. Multiple parcels being offered for sale, 201 acres at $1.45mil, 130 acres at $995k and a 4 acre parcel at $250k. Owners are willing to discuss owner financing as well. Reclamation of existing pit is well underway and nearing completion. Currently only 18 acres of the 200+ acres is gravel pit and being reclaimed on this property. See the Vermont Land Use Permit 2W1316 online for further information. There is an old foundation overlooking Forrester Pond with rolling hills that sit at higher elevations! Local mountain views can be had from the 1800 foot elevation on the northeastern 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, we request in advance, no drive-bys as there is heavy equipment and work being conducted on site daily.

Forrester Road, Jamaica

$250,000

Lot 4 IS 4 acres! This private setting is less than 3 miles to Stratton Mountain Resort with easy access in the no zoning town of Jamaica. Five Bedroom Existing State Issued Wastewater Permit WW-2-2200 along with survey already in place for this lot. Being subdivided off a larger 200+ acre parcel. Power existing on current right of way and is also access to this wooded lot. Residential and recreational opportunities are worth exploring here. See also MLS#5082418 for more information. Taxes are reflective of entire parcel, 4 acre lot will be reflected differently once subdivided and transferred. Multiple parcels being offered for sale, 201 acres at $1.45mil, 130 acres at $995k, 67 acres at $799k and this 4 acre parcel at $250k. Owners are willing to discuss owner financing as well. Reclamation of existing pit is well underway and nearing completion.

5110757 MLS

Lot 4 IS 4 acres! This private setting is less than 3 miles to Stratton Mountain Resort with easy access in the no zoning town of Jamaica. Five Bedroom Existing State Issued Wastewater Permit WW-2-2200 along with survey already in place for this lot. Being subdivided off a larger 200+ acre parcel. Power existing on current right of way and is also access to this wooded lot. Residential and recreational opportunities are worth exploring here. See also MLS#5082418 for more information. Taxes are reflective of entire parcel, 4 acre lot will be reflected differently once subdivided and transferred. Multiple parcels being offered for sale, 201 acres at $1.45mil, 130 acres at $995k, 67 acres at $799k and this 4 acre parcel at $250k. Owners are willing to discuss owner financing as well. Reclamation of existing pit is well underway and nearing completion.

Forrester Road, Jamaica

$425,000

Tucked into a quiet, sunny setting just steps from Jamaica State Park and the heart of Jamaica Village, this charming two-bedroom plus loft Cape offers the perfect blend of Vermont character, comfort, and convenience. Filled with natural light and warm wood accents, the home has an inviting feel from the moment you step inside. A spacious mudroom provides a practical entry for every season and opens into the kitchen, where a center island and gas cooktop make it easy to gather, cook, and entertain. The open floor plan flows naturally into the main living area, where a cathedral ceiling adds a wonderful sense of space and a wood-burning stove creates a cozy focal point for winter evenings. The home offers two bedrooms plus a versatile loft, ideal for additional sleeping space, a home office, or a quiet retreat. The primary bedroom features its own ensuite bath, and with two full baths and one half bath, there is plenty of room for family and guests. Adding to the property's future potential, the existing septic permit is approved for three bedrooms, offering flexibility should a future owner wish to expand. Outside, enjoy a peaceful setting with space for gardening and relaxing in the Vermont sunshine. An oversized two-car garage provides exceptional room for vehicles, outdoor gear, bikes, skis, kayaks, and all the equipment that comes with four-season living. The location is hard to beat. Walk to Jamaica State Park for hiking, swimming, and access to the West River, or head into Jamaica Village just moments away. When the snow flies, Stratton Mountain is approximately 15 minutes away and Mount Snow about 25 minutes, while the shops, restaurants, and amenities of Manchester are approximately 30 minutes from your door. Whether you're looking for a full-time Vermont home or a comfortable mountain getaway, this sunny Jamaica Cape puts village life, outdoor recreation, and some of Southern Vermont's best destinations within easy reach—all while offering a quiet place

2 Beds ⋅ 3 Baths ⋅ 5110722 MLS

Tucked into a quiet, sunny setting just steps from Jamaica State Park and the heart of Jamaica Village, this charming two-bedroom plus loft Cape offers the perfect blend of Vermont character, comfort, and convenience. Filled with natural light and warm wood accents, the home has an inviting feel from the moment you step inside. A spacious mudroom provides a practical entry for every season and opens into the kitchen, where a center island and gas cooktop make it easy to gather, cook, and entertain. The open floor plan flows naturally into the main living area, where a cathedral ceiling adds a wonderful sense of space and a wood-burning stove creates a cozy focal point for winter evenings. The home offers two bedrooms plus a versatile loft, ideal for additional sleeping space, a home office, or a quiet retreat. The primary bedroom features its own ensuite bath, and with two full baths and one half bath, there is plenty of room for family and guests. Adding to the property's future potential, the existing septic permit is approved for three bedrooms, offering flexibility should a future owner wish to expand. Outside, enjoy a peaceful setting with space for gardening and relaxing in the Vermont sunshine. An oversized two-car garage provides exceptional room for vehicles, outdoor gear, bikes, skis, kayaks, and all the equipment that comes with four-season living. The location is hard to beat. Walk to Jamaica State Park for hiking, swimming, and access to the West River, or head into Jamaica Village just moments away. When the snow flies, Stratton Mountain is approximately 15 minutes away and Mount Snow about 25 minutes, while the shops, restaurants, and amenities of Manchester are approximately 30 minutes from your door. Whether you're looking for a full-time Vermont home or a comfortable mountain getaway, this sunny Jamaica Cape puts village life, outdoor recreation, and some of Southern Vermont's best destinations within easy reach—all while offering a quiet place

190 Depot St, Jamaica

$500,000

West Hill Road is situated prominently on a mountainside, offering breathtaking views that stretch across the valley to the north, with clearing there will be scenic beauty of the area. This property presents an exceptional opportunity for individuals looking to construct their dream home or a private compound, with an abundance of possibilities limited only by one's imagination. Located just over the town line in Jamaica, Vermont, this parcel of land is accessible via a Class 3 road, ensuring a balance of seclusion and convenience for future residents. The combination of stunning natural surroundings and the potential for development makes this location a truly remarkable investment for those seeking a serene retreat in the mountains

5109880 MLS

West Hill Road is situated prominently on a mountainside, offering breathtaking views that stretch across the valley to the north, with clearing there will be scenic beauty of the area. This property presents an exceptional opportunity for individuals looking to construct their dream home or a private compound, with an abundance of possibilities limited only by one's imagination. Located just over the town line in Jamaica, Vermont, this parcel of land is accessible via a Class 3 road, ensuring a balance of seclusion and convenience for future residents. The combination of stunning natural surroundings and the potential for development makes this location a truly remarkable investment for those seeking a serene retreat in the mountains

W Hill Rd, Jamaica

$995,000

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.

5 Beds ⋅ 5 Baths ⋅ 5108207 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

$975,000

Enjoy Vermont in all the seasons!! This land has a number of options! With 235 acres to call your own! Build somewhere on the property. A stream runs through for your enjoyment! Part of the West River Trail passes through as well. Harvest timber from this lot and make some $$. Pratt Bridge Road is a close drive to Stratton, Magic or Bromley in the winter and enjoy spring, summer and fall exploring your land. Road access and power is close by on the road. Start you Vermont adventure today!!

5107954 MLS

Enjoy Vermont in all the seasons!! This land has a number of options! With 235 acres to call your own! Build somewhere on the property. A stream runs through for your enjoyment! Part of the West River Trail passes through as well. Harvest timber from this lot and make some $$. Pratt Bridge Road is a close drive to Stratton, Magic or Bromley in the winter and enjoy spring, summer and fall exploring your land. Road access and power is close by on the road. Start you Vermont adventure today!!

00 Pratt Bridge Rd, Jamaica

$2,430,000

TWO HOMES | 1BR BARN APARTMENT | RESTORED VINTAGE BARN | 13+ ACRES. A rare Vermont multi-residence estate offering two beautifully renovated homes, a separate 1BR barn apartment, a restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, Winhall River Farm blends authentic character, exceptional craftsmanship, and modern four-season comfort. One residence is a restored 4BR farmhouse once used as the summer home of renowned art historian Meyer Schapiro, with wide-plank floors, antique doors, an expanded kitchen with soapstone counters, updated baths, and custom built-ins. Schapiro’s former art studio now serves as a self-contained 1BR apartment with SMEG appliances, a screened porch, and heated storage below. The second home is a reimagined historic schoolhouse with a timber-frame addition, high ceilings, generous windows, two sunrooms, restored floors, and warm architectural detail throughout. Private hot tubs and inviting outdoor living spaces complement all three residences. Extensive improvements across the property include standing-seam roofs, new Marvin windows, updated electrical and plumbing, modern insulation, mini-split heating and cooling, high-efficiency systems, new appliances, generators, and EV chargers. The 13+ acres include open fields, woods, apple trees, gardens, extensive stonework, patios, decks, and opportunities for trails, recreation, and equestrian use. Set along the Winhall River with direct access to the West River Rail Trail for walking, biking, swimming, and exploring. In the heart of ski country, just minutes from Stratton, Bromley, and Magic Mountain. An exceptional family estate, multi-generational retreat, or investment opportunity. Offered furnished and ready to enjoy, with additional acreage also available. All the hard work has been done--move in and start enjoying Vermont. Properties also offered individually as MLS #5101688 & #5101689. Seller is the listing broker.

9 Beds ⋅ 7 Baths ⋅ 5107418 MLS

TWO HOMES | 1BR BARN APARTMENT | RESTORED VINTAGE BARN | 13+ ACRES. A rare Vermont multi-residence estate offering two beautifully renovated homes, a separate 1BR barn apartment, a restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, Winhall River Farm blends authentic character, exceptional craftsmanship, and modern four-season comfort. One residence is a restored 4BR farmhouse once used as the summer home of renowned art historian Meyer Schapiro, with wide-plank floors, antique doors, an expanded kitchen with soapstone counters, updated baths, and custom built-ins. Schapiro’s former art studio now serves as a self-contained 1BR apartment with SMEG appliances, a screened porch, and heated storage below. The second home is a reimagined historic schoolhouse with a timber-frame addition, high ceilings, generous windows, two sunrooms, restored floors, and warm architectural detail throughout. Private hot tubs and inviting outdoor living spaces complement all three residences. Extensive improvements across the property include standing-seam roofs, new Marvin windows, updated electrical and plumbing, modern insulation, mini-split heating and cooling, high-efficiency systems, new appliances, generators, and EV chargers. The 13+ acres include open fields, woods, apple trees, gardens, extensive stonework, patios, decks, and opportunities for trails, recreation, and equestrian use. Set along the Winhall River with direct access to the West River Rail Trail for walking, biking, swimming, and exploring. In the heart of ski country, just minutes from Stratton, Bromley, and Magic Mountain. An exceptional family estate, multi-generational retreat, or investment opportunity. Offered furnished and ready to enjoy, with additional acreage also available. All the hard work has been done--move in and start enjoying Vermont. Properties also offered individually as MLS #5101688 & #5101689. Seller is the listing broker.

494-564 Goodaleville Rd, Jamaica

$549,000

Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time residence. Conveniently located just 20 minutes from Stratton Mountain and Mount Snow. The south-facing home features bright, open living and dining spaces with large picture windows showcasing beautiful views in every direction. A fieldstone hearth with wood stove creates a warm and inviting atmosphere for entertaining, while the kitchen offers abundant storage. The main level includes three bedrooms, a ¾ bath, and a sun-filled mudroom/sunroom with wall-to-wall windows and its own propane stove. Upstairs, the spacious primary suite or bunk room retreat includes a full bath, cedar walk-in closet, and mountain views. The basement with half bath, and attached 2-car garage provide excellent storage, workshop, recreation, or future living space potential. Outside, enjoy expansive lawns, meadows, a screened gazebo, private trails, mature forest, stone walls from an old homestead, and a year-round creek. Endless hiking, snowmobiling, ATV riding, and outdoor adventure await right from the property. Energy-efficient upgrades include owned REC solar panels, owned Tesla backup batteries, Daikin heat pumps and mini splits, rebuilt chimney, generator-ready setup, multiple heating options, and high-speed Starlink internet with mesh coverage. Tucked at the end of a town-maintained dead-end road, this is a rare opportunity to own a true Vermont escape.

4 Beds ⋅ 3 Baths ⋅ 5106080 MLS

Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time residence. Conveniently located just 20 minutes from Stratton Mountain and Mount Snow. The south-facing home features bright, open living and dining spaces with large picture windows showcasing beautiful views in every direction. A fieldstone hearth with wood stove creates a warm and inviting atmosphere for entertaining, while the kitchen offers abundant storage. The main level includes three bedrooms, a ¾ bath, and a sun-filled mudroom/sunroom with wall-to-wall windows and its own propane stove. Upstairs, the spacious primary suite or bunk room retreat includes a full bath, cedar walk-in closet, and mountain views. The basement with half bath, and attached 2-car garage provide excellent storage, workshop, recreation, or future living space potential. Outside, enjoy expansive lawns, meadows, a screened gazebo, private trails, mature forest, stone walls from an old homestead, and a year-round creek. Endless hiking, snowmobiling, ATV riding, and outdoor adventure await right from the property. Energy-efficient upgrades include owned REC solar panels, owned Tesla backup batteries, Daikin heat pumps and mini splits, rebuilt chimney, generator-ready setup, multiple heating options, and high-speed Starlink internet with mesh coverage. Tucked at the end of a town-maintained dead-end road, this is a rare opportunity to own a true Vermont escape.

116 Teacher Rd, Jamaica

$190,000

Parcel 2 is a forested 30-acre property situated on Schoolhouse Road in Jamaica, Vermont. From the intersection of Schoolhouse and South Hill Roads, the road winds around a sharp bend and climbs a short hill before reaching the majority of the property, which lies along the north side of the road. A weathered stone wall is found along the entire length of the road frontage, hinting at the land's rich agricultural history. The land itself is level, wooded terrain with several natural clearings near the road offering promising building sites for one or two homes, with power already available at the road. Notably, the town of Jamaica has no zoning restrictions, making this an exceptional opportunity to create a private family compound just minutes from some of the region's best outdoor recreation. An old woods road winds along the level contours of the property and continues onto the neighboring parcel, inviting exploration on foot or by ATV. Beyond the road, the land descends to the north into a wetland area a haven for a wide variety of birds and wildlife. Evidence of a resident beaver family can be seen in the twin ponds found just below the wetland, adding to the property's natural charm and biodiversity. The forest itself is impressive, featuring mature trees, some over a century old, lending a sense of peace and quiet while walking the land. While there may have been selective tree harvesting long ago, little trace of that history remains in the forested hillside today. Crisscrossing through the woods, additional stone walls stand as silent reminders of the property's farming past, adding character and a connection to Vermont's rural heritage. Schoolhouse Road eventually transitions into a Legal Town Trail, making it an ideal route for biking enthusiasts leading roughly 3 miles west to scenic Pikes Falls Road.

5105324 MLS

Parcel 2 is a forested 30-acre property situated on Schoolhouse Road in Jamaica, Vermont. From the intersection of Schoolhouse and South Hill Roads, the road winds around a sharp bend and climbs a short hill before reaching the majority of the property, which lies along the north side of the road. A weathered stone wall is found along the entire length of the road frontage, hinting at the land's rich agricultural history. The land itself is level, wooded terrain with several natural clearings near the road offering promising building sites for one or two homes, with power already available at the road. Notably, the town of Jamaica has no zoning restrictions, making this an exceptional opportunity to create a private family compound just minutes from some of the region's best outdoor recreation. An old woods road winds along the level contours of the property and continues onto the neighboring parcel, inviting exploration on foot or by ATV. Beyond the road, the land descends to the north into a wetland area a haven for a wide variety of birds and wildlife. Evidence of a resident beaver family can be seen in the twin ponds found just below the wetland, adding to the property's natural charm and biodiversity. The forest itself is impressive, featuring mature trees, some over a century old, lending a sense of peace and quiet while walking the land. While there may have been selective tree harvesting long ago, little trace of that history remains in the forested hillside today. Crisscrossing through the woods, additional stone walls stand as silent reminders of the property's farming past, adding character and a connection to Vermont's rural heritage. Schoolhouse Road eventually transitions into a Legal Town Trail, making it an ideal route for biking enthusiasts leading roughly 3 miles west to scenic Pikes Falls Road.

Schoolhouse Rd, Jamaica

$120,000

The South Jamaica Parcels consist of two contiguous lots situated along South Hill Road and Schoolhouse Road in South Jamaica, Vermont. Each parcel offers an excellent building opportunity, featuring level, buildable terrain and the convenience of power already available at the street making them ideal, low-hassle sites for a future home. Parcel I is a 10-acre building site located on South Hill Road. A grass-covered access road leads from the street to a flat, area just off the road an ideal spot for a future home. Along the entire road frontage, except for the access driveway, an old stone wall runs the length of the property, lending charm and excellent curb appeal to any home built here. Beyond the potential building site, the woods road continues into the forest, extending past the property boundary. The land slopes down the hill to the south toward a small wetland shared with the neighboring parcel. The surrounding forest offers a rich mix of softwoods and hardwoods, including hemlock, fir, and white pine, alongside maple and yellow birch. South Hill Road is paved near the property, offering easy access to the nearby villages of Wardsboro and Jamaica.

5105314 MLS

The South Jamaica Parcels consist of two contiguous lots situated along South Hill Road and Schoolhouse Road in South Jamaica, Vermont. Each parcel offers an excellent building opportunity, featuring level, buildable terrain and the convenience of power already available at the street making them ideal, low-hassle sites for a future home. Parcel I is a 10-acre building site located on South Hill Road. A grass-covered access road leads from the street to a flat, area just off the road an ideal spot for a future home. Along the entire road frontage, except for the access driveway, an old stone wall runs the length of the property, lending charm and excellent curb appeal to any home built here. Beyond the potential building site, the woods road continues into the forest, extending past the property boundary. The land slopes down the hill to the south toward a small wetland shared with the neighboring parcel. The surrounding forest offers a rich mix of softwoods and hardwoods, including hemlock, fir, and white pine, alongside maple and yellow birch. South Hill Road is paved near the property, offering easy access to the nearby villages of Wardsboro and Jamaica.

S Hill Rd, Jamaica

$299,000

Charming cape style modular home set on a beautiful, level 3.67 acre parcel. The expansive yard is framed by a stunning mountain backdrop that gives the entire property a peaceful, protected feel. Inside, you’ll find a bright and welcoming three bedroom, one and a half bath layout with plenty of natural light and comfortable living spaces. Mudroom entryway offers nice closet space and washer dryer hookups. Kitchen with eat in dining area are open to the living room space. A large back deck extends your living area outdoors, complete with a firepit gathering spot perfect for relaxing evenings. The home has been thoughtfully maintained, including a new furnace installed in 2025. Located near the West River and just a short drive to Stratton, Mount Snow, and Bromley ski resorts, this property offers year round recreation in every direction. Come take a look and experience the setting for yourself.

3 Beds ⋅ 2 Baths ⋅ 5104265 MLS

Charming cape style modular home set on a beautiful, level 3.67 acre parcel. The expansive yard is framed by a stunning mountain backdrop that gives the entire property a peaceful, protected feel. Inside, you’ll find a bright and welcoming three bedroom, one and a half bath layout with plenty of natural light and comfortable living spaces. Mudroom entryway offers nice closet space and washer dryer hookups. Kitchen with eat in dining area are open to the living room space. A large back deck extends your living area outdoors, complete with a firepit gathering spot perfect for relaxing evenings. The home has been thoughtfully maintained, including a new furnace installed in 2025. Located near the West River and just a short drive to Stratton, Mount Snow, and Bromley ski resorts, this property offers year round recreation in every direction. Come take a look and experience the setting for yourself.

170 River Rd, Jamaica

$299,000

Discover the possibilities with this exceptional 57+ acre parcel in the Town of Jamaica, Vermont, where no local zoning provides incredible flexibility for your vision. Ideally located just minutes from Stratton Mountain, Mount Snow, and within easy reach of Bromley, Magic Mountain, Manchester, and Brattleboro, this property offers the perfect balance of privacy, recreation, and convenience. Multiple elevated building sites showcase stunning long-range mountain views, while both a charming private brook and the scenic Wardsboro Brook border portions of the property, creating a truly picturesque setting. A State of Vermont wastewater permit (WW-2-5317) for a three bedroom home is already approved and on file, allowing you to begin building with ease. Looking for more? The expansive acreage offers exciting potential for subdivision, multiple homes, or a private family compound, subject to any applicable state regulations. Whether you're dreaming of a secluded mountain retreat, an investment opportunity, or a legacy property to enjoy for generations, this remarkable parcel offers endless possibilities in one of Southern Vermont's most desirable four-season destinations. Sellers are related to the listing agent.

5103450 MLS

Discover the possibilities with this exceptional 57+ acre parcel in the Town of Jamaica, Vermont, where no local zoning provides incredible flexibility for your vision. Ideally located just minutes from Stratton Mountain, Mount Snow, and within easy reach of Bromley, Magic Mountain, Manchester, and Brattleboro, this property offers the perfect balance of privacy, recreation, and convenience. Multiple elevated building sites showcase stunning long-range mountain views, while both a charming private brook and the scenic Wardsboro Brook border portions of the property, creating a truly picturesque setting. A State of Vermont wastewater permit (WW-2-5317) for a three bedroom home is already approved and on file, allowing you to begin building with ease. Looking for more? The expansive acreage offers exciting potential for subdivision, multiple homes, or a private family compound, subject to any applicable state regulations. Whether you're dreaming of a secluded mountain retreat, an investment opportunity, or a legacy property to enjoy for generations, this remarkable parcel offers endless possibilities in one of Southern Vermont's most desirable four-season destinations. Sellers are related to the listing agent.

Vt Route 100 South, Jamaica

$585,000

A rare opportunity to own over 91 private acres just a short walk from the charming Village of Jamaica. Tucked away off a private right-of-way, this remarkable parcel offers the perfect balance of peaceful seclusion and convenient access to local shops, dining, and community events. The property features a beautiful mix of mature forest, gently rolling terrain, and serene natural surroundings. With selective clearing, there is potential to open up lovely mountain views. Existing trails currently traverse the property as part of a mountain biking trail network, adding immediate recreational appeal, and the land is also enrolled in a forest management plan. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley, Magic, and Mount Snow, the property provides convenient access to year-round recreation, including skiing, hiking, biking, kayaking, fishing, and more. Large parcels offering this level of privacy within walking distance of a quintessential Vermont village are increasingly difficult to find. No engineering or permitting has been completed, and buyers are encouraged to conduct their own due diligence regarding potential development, the forest management plan, and continued trail use. The Seller’s estate is in the process of obtaining the required License to Sell, which is expected to be issued within 30 days.

5102573 MLS

A rare opportunity to own over 91 private acres just a short walk from the charming Village of Jamaica. Tucked away off a private right-of-way, this remarkable parcel offers the perfect balance of peaceful seclusion and convenient access to local shops, dining, and community events. The property features a beautiful mix of mature forest, gently rolling terrain, and serene natural surroundings. With selective clearing, there is potential to open up lovely mountain views. Existing trails currently traverse the property as part of a mountain biking trail network, adding immediate recreational appeal, and the land is also enrolled in a forest management plan. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley, Magic, and Mount Snow, the property provides convenient access to year-round recreation, including skiing, hiking, biking, kayaking, fishing, and more. Large parcels offering this level of privacy within walking distance of a quintessential Vermont village are increasingly difficult to find. No engineering or permitting has been completed, and buyers are encouraged to conduct their own due diligence regarding potential development, the forest management plan, and continued trail use. The Seller’s estate is in the process of obtaining the required License to Sell, which is expected to be issued within 30 days.

Water St, Jamaica

$1,115,000

Set along a quiet back road on the Winhall River, this beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain Resort, the location offers easy access to the mountain, local favorites, and the best of southern Vermont living. High ceilings, generous windows, and two sunrooms fill the interior with natural light, while radiant heat on all three levels adds warmth and comfort throughout. Recent improvements include a standing-seam metal roof, new Marvin windows, mini-split heating and cooling, new appliances, a large new deck, a new drilled well, a whole-house generator, an EV charger, restored floors and fir doors, updated tile, and custom built-ins. The property has a deep connection to the surrounding land. Beautiful landscaping and stonework complement an open field, apple orchard, raised garden beds built with hemlock milled from the property, and a useful storage shed. The large, private deck with hot tub creates an inviting place to relax and take in the serene setting. Situated along the Winhall River with direct access to the West River Rail Trail, the property makes it easy to walk, bike, swim, and enjoy the outdoors right from home. A five-bedroom septic system provides flexibility for future expansion. This is the Vermont home you have been looking for--full of character, warmth, and history, yet updated with the level of care and quality that makes ownership easy from day one. A trusted local builder has already done the hard work. Make this your Vermont address. Seller is the listing broker. Neighboring property also available: 494–498 Goodaleville Road, MLS #5101688.

4 Beds ⋅ 3 Baths ⋅ 5101689 MLS

Set along a quiet back road on the Winhall River, this beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain Resort, the location offers easy access to the mountain, local favorites, and the best of southern Vermont living. High ceilings, generous windows, and two sunrooms fill the interior with natural light, while radiant heat on all three levels adds warmth and comfort throughout. Recent improvements include a standing-seam metal roof, new Marvin windows, mini-split heating and cooling, new appliances, a large new deck, a new drilled well, a whole-house generator, an EV charger, restored floors and fir doors, updated tile, and custom built-ins. The property has a deep connection to the surrounding land. Beautiful landscaping and stonework complement an open field, apple orchard, raised garden beds built with hemlock milled from the property, and a useful storage shed. The large, private deck with hot tub creates an inviting place to relax and take in the serene setting. Situated along the Winhall River with direct access to the West River Rail Trail, the property makes it easy to walk, bike, swim, and enjoy the outdoors right from home. A five-bedroom septic system provides flexibility for future expansion. This is the Vermont home you have been looking for--full of character, warmth, and history, yet updated with the level of care and quality that makes ownership easy from day one. A trusted local builder has already done the hard work. Make this your Vermont address. Seller is the listing broker. Neighboring property also available: 494–498 Goodaleville Road, MLS #5101688.

564 Goodaleville Rd, Jamaica

$1,315,000

4BR MAIN HOUSE, 1BR BARN APARTMENT, AND SEPARATE RESTORED VINTAGE BARN | Tucked along a quiet back road with the gentle sounds of the flowing Winhall River, this beautifully restored Vermont farmhouse feels worlds away, yet is just 10 minutes from Stratton Mountain Resort. Blending authentic character, exceptional craftsmanship, and modern comfort, the property offers a rare sense of privacy and retreat while keeping the mountain and year-round recreation within easy reach. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit that have long defined it. Thoughtfully renovated by Vermont Country Builders, the home preserves its historic soul while providing quality and efficiency suited for each season. The main house spans three levels. An expanded kitchen with soapstone countertops opens to a spacious dining room and cozy sitting area with a gas fireplace. Original wide-plank floors, antique doors, and a classic clawfoot tub celebrate the home’s heritage. Improvements include modern insulation, electrical, plumbing, a new foundation, sheetrock, a high-efficiency propane boiler, HRV ventilation, mini-splits, Marvin windows, and an improved floor plan. Additional upgrades include standing-seam roofs on all buildings, custom gutters and snow guards, updated baths, custom built-ins, new appliances, and AZEK decks. A separate guest house, originally Schapiro’s art studio, offers a 1BR apartment with SMEG appliances, in-unit laundry, and a private hot tub. Below are heated storage and a screened porch. The restored barn offers parking and an EV charger. Extensive stonework, thoughtful landscaping, gardens, decks, a stone patio, and a welcoming front porch complement the peaceful setting along the Winhall River. Direct access to the West River Rail Trail makes it easy to walk, bike, swim, and explore right from home. Listing agent is related to seller. See neighboring property MLS #5101689.

5 Beds ⋅ 4 Baths ⋅ 5101688 MLS

4BR MAIN HOUSE, 1BR BARN APARTMENT, AND SEPARATE RESTORED VINTAGE BARN | Tucked along a quiet back road with the gentle sounds of the flowing Winhall River, this beautifully restored Vermont farmhouse feels worlds away, yet is just 10 minutes from Stratton Mountain Resort. Blending authentic character, exceptional craftsmanship, and modern comfort, the property offers a rare sense of privacy and retreat while keeping the mountain and year-round recreation within easy reach. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit that have long defined it. Thoughtfully renovated by Vermont Country Builders, the home preserves its historic soul while providing quality and efficiency suited for each season. The main house spans three levels. An expanded kitchen with soapstone countertops opens to a spacious dining room and cozy sitting area with a gas fireplace. Original wide-plank floors, antique doors, and a classic clawfoot tub celebrate the home’s heritage. Improvements include modern insulation, electrical, plumbing, a new foundation, sheetrock, a high-efficiency propane boiler, HRV ventilation, mini-splits, Marvin windows, and an improved floor plan. Additional upgrades include standing-seam roofs on all buildings, custom gutters and snow guards, updated baths, custom built-ins, new appliances, and AZEK decks. A separate guest house, originally Schapiro’s art studio, offers a 1BR apartment with SMEG appliances, in-unit laundry, and a private hot tub. Below are heated storage and a screened porch. The restored barn offers parking and an EV charger. Extensive stonework, thoughtful landscaping, gardens, decks, a stone patio, and a welcoming front porch complement the peaceful setting along the Winhall River. Direct access to the West River Rail Trail makes it easy to walk, bike, swim, and explore right from home. Listing agent is related to seller. See neighboring property MLS #5101689.

494-498 Goodaleville Rd, Jamaica

$129,200

Escape to your own private Vermont retreat on this beautiful 14-acre wooded parcel, tucked away along the path less traveled. A thoughtfully established clearing is home to a travel trailer sheltered beneath a well-built pavilion, creating a comfortable, all-weather basecamp for weekends and seasonal getaways. The sale includes the camper complete with generators, tools and more making this a true turnkey opportunity. A storage shed provides convenient space for outdoor gear and supplies, while a seasonal brook meanders through the property, adding to the peaceful setting. Enjoy the sights and sounds of nature with exceptional privacy yet remain less than two miles from Vermont Route 30 for easy access to nearby towns and recreation. Set equally between the bases of Stratton or Mount Snow - be at either lodge in 25 minutes! Currently equipped with water accessed from a new pump and generator-powered electricity. This property is ready to enjoy immediately while offering plenty of potential for future plans. Whether you're seeking a quiet camping retreat, a hunting camp, or a future homesite, this special property offers the peace, privacy, and simple pleasures that define the Vermont lifestyle.

5101508 MLS

Escape to your own private Vermont retreat on this beautiful 14-acre wooded parcel, tucked away along the path less traveled. A thoughtfully established clearing is home to a travel trailer sheltered beneath a well-built pavilion, creating a comfortable, all-weather basecamp for weekends and seasonal getaways. The sale includes the camper complete with generators, tools and more making this a true turnkey opportunity. A storage shed provides convenient space for outdoor gear and supplies, while a seasonal brook meanders through the property, adding to the peaceful setting. Enjoy the sights and sounds of nature with exceptional privacy yet remain less than two miles from Vermont Route 30 for easy access to nearby towns and recreation. Set equally between the bases of Stratton or Mount Snow - be at either lodge in 25 minutes! Currently equipped with water accessed from a new pump and generator-powered electricity. This property is ready to enjoy immediately while offering plenty of potential for future plans. Whether you're seeking a quiet camping retreat, a hunting camp, or a future homesite, this special property offers the peace, privacy, and simple pleasures that define the Vermont lifestyle.

182 Partridge Ln, Jamaica

$219,000

Discover the possibilities on this exceptional 16.9-acre Vermont property, where privacy, natural beauty, and year-round recreation come together. With nearly 300 feet of town-maintained road frontage and accessible utilities, this parcel is ready for your vision. Thoughtfully shaped by nature, the land offers three potential building sites, making it ideal for a family compound, multi-generational retreat, or a custom home with guest accommodations. Mature trees, rambling stone walls, a charming pond, a gentle stream, and patches of wild blueberries create a setting rich in character and Vermont tradition. Follow the land to its highest point to enjoy long-range views that provide a spectacular backdrop in every season. Whether you envision morning walks through the woods, listening to the soothing sounds of the stream, evenings around a fire, or creating a legacy property for generations to enjoy, this property offers the space and flexibility to bring your plans to life. Outdoor enthusiasts will appreciate the convenient access to Bromley Mountain, with Stratton, Magic Mountain, Mount Snow, and Okemo all within an easy drive for outstanding skiing, snowboarding, hiking, mountain biking, golf, and endless four-season adventure. The nearby town of Manchester offers excellent shopping, dining, galleries, and everyday conveniences, while the welcoming community of Jamaica provides a classic Vermont village with a local general store, consignment shop, coffee cafe, community events, farmers markets, and a relaxed pace of life. Conveniently located just 2.5 hours from Boston and approximately 3.5 hours from New York City, this is a rare opportunity to enjoy a private Vermont retreat with easy access to world-class recreation and small-town charm.

5098094 MLS

Discover the possibilities on this exceptional 16.9-acre Vermont property, where privacy, natural beauty, and year-round recreation come together. With nearly 300 feet of town-maintained road frontage and accessible utilities, this parcel is ready for your vision. Thoughtfully shaped by nature, the land offers three potential building sites, making it ideal for a family compound, multi-generational retreat, or a custom home with guest accommodations. Mature trees, rambling stone walls, a charming pond, a gentle stream, and patches of wild blueberries create a setting rich in character and Vermont tradition. Follow the land to its highest point to enjoy long-range views that provide a spectacular backdrop in every season. Whether you envision morning walks through the woods, listening to the soothing sounds of the stream, evenings around a fire, or creating a legacy property for generations to enjoy, this property offers the space and flexibility to bring your plans to life. Outdoor enthusiasts will appreciate the convenient access to Bromley Mountain, with Stratton, Magic Mountain, Mount Snow, and Okemo all within an easy drive for outstanding skiing, snowboarding, hiking, mountain biking, golf, and endless four-season adventure. The nearby town of Manchester offers excellent shopping, dining, galleries, and everyday conveniences, while the welcoming community of Jamaica provides a classic Vermont village with a local general store, consignment shop, coffee cafe, community events, farmers markets, and a relaxed pace of life. Conveniently located just 2.5 hours from Boston and approximately 3.5 hours from New York City, this is a rare opportunity to enjoy a private Vermont retreat with easy access to world-class recreation and small-town charm.

00 Howe Farm Rd, Jamaica

$63,000

Looking for an easy escape to the mountains? This furnished 2-bedroom mobile home sits right on the banks of the West River in West River Park—an ideal spot for seasonal living in Southern Vermont. The park has 23 sites and allows homeowners to stay up to 6 months each year, making it a great option for summer adventures or a winter ski base or, a little bit of both! Stratton is just 20 minutes away, and Mount Snow about 30, so you're never far from the slopes. In warmer months, enjoy fishing, swimming, or hiking nearby. The home has seen several recent updates, including new windows, a new chimney, oil tank, outdoor storage shed, and a propane stove for that cozy cabin feel. Park rent is $435/month and covers water, septic, snow removal, and lawn care—making for simple, low-maintenance living. If you’ve been looking for a quiet spot with river views and easy access to all the region has to offer, this might be the one.

2 Beds ⋅ 1 Baths ⋅ 5097748 MLS

Looking for an easy escape to the mountains? This furnished 2-bedroom mobile home sits right on the banks of the West River in West River Park—an ideal spot for seasonal living in Southern Vermont. The park has 23 sites and allows homeowners to stay up to 6 months each year, making it a great option for summer adventures or a winter ski base or, a little bit of both! Stratton is just 20 minutes away, and Mount Snow about 30, so you're never far from the slopes. In warmer months, enjoy fishing, swimming, or hiking nearby. The home has seen several recent updates, including new windows, a new chimney, oil tank, outdoor storage shed, and a propane stove for that cozy cabin feel. Park rent is $435/month and covers water, septic, snow removal, and lawn care—making for simple, low-maintenance living. If you’ve been looking for a quiet spot with river views and easy access to all the region has to offer, this might be the one.

2022 Rte 30, Jamaica

$480,000

Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and only 3/4 mile to Jamaica State Park, outdoor recreation, dining, and local shops are all close by. Stratton Mountain and Mount Snow are both just 20–25 minutes away, making this an excellent four-season retreat or full-time residence. Inside, the home offers hardwood floors throughout, generous living space, and a wonderful sunroom with a woodstove hookup perfect for cozy evenings year-round. Additional highlights include a paved driveway, easy access to Route 30, an attached garage and workshop space.. For added transparency and peace of mind, the seller has completed a pre-listing property inspection, which is attached in the MLS. Lovingly owned by the same family since it was built, this home is filled with warmth, history, and opportunity for its next chapter. This property has full time tenants and need a minimum of 24 hours notice, longer preferred, on showings. Closing can happen October 1 or after.

5 Beds ⋅ 2 Baths ⋅ 5097573 MLS

Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and only 3/4 mile to Jamaica State Park, outdoor recreation, dining, and local shops are all close by. Stratton Mountain and Mount Snow are both just 20–25 minutes away, making this an excellent four-season retreat or full-time residence. Inside, the home offers hardwood floors throughout, generous living space, and a wonderful sunroom with a woodstove hookup perfect for cozy evenings year-round. Additional highlights include a paved driveway, easy access to Route 30, an attached garage and workshop space.. For added transparency and peace of mind, the seller has completed a pre-listing property inspection, which is attached in the MLS. Lovingly owned by the same family since it was built, this home is filled with warmth, history, and opportunity for its next chapter. This property has full time tenants and need a minimum of 24 hours notice, longer preferred, on showings. Closing can happen October 1 or after.

3327 Rte 30, Jamaica

$1,500,000

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! Listing agent is an owner of this property.

7 Beds ⋅ 8 Baths ⋅ 5097566 MLS

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! Listing agent is an owner of this property.

251 Pratt Bridge Rd, Jamaica

$140,000

Some places stop time. River's Edge is one of them. Step off the front door and onto a 10×12 covered porch shaded by old hemlocks, facing directly over the West River away from the road, away from everything. The sound of moving water. The smell of the trees after rain. This porch is not an afterthought Brand new Lancaster Log Cabins "Sierra" Park Model. This 100% turn-key real log cabin features a rustic aesthetic with modern durability. Includes a 10' covered front porch, a cozy loft for extra space, and cathedral ceilings with exposed log beams. Situated on a newly poured concrete slab in the beautiful French Bridge Chateau community. Perfect for those seeking a high-end, low-maintenance retreat. Park approval is required. This unit can only be occupied 180 days a year per State Permit. The Sierra arrives fully turn-key: kitchen with full appliances including an over-the-range microwave, full bath, living area, two bedrooms, and a sleeping loft that gives you the flex for extra guests. At 320 sq ft of interior space plus 120 sq ft of covered porch, it lives larger than it measures — the layout wastes nothing. Never used and installed in 2026. Will make a great comfortable vacation getaway in any season. The park also maintains the landscaping.

1 Beds ⋅ 1 Baths ⋅ 5097088 MLS

Some places stop time. River's Edge is one of them. Step off the front door and onto a 10×12 covered porch shaded by old hemlocks, facing directly over the West River away from the road, away from everything. The sound of moving water. The smell of the trees after rain. This porch is not an afterthought Brand new Lancaster Log Cabins "Sierra" Park Model. This 100% turn-key real log cabin features a rustic aesthetic with modern durability. Includes a 10' covered front porch, a cozy loft for extra space, and cathedral ceilings with exposed log beams. Situated on a newly poured concrete slab in the beautiful French Bridge Chateau community. Perfect for those seeking a high-end, low-maintenance retreat. Park approval is required. This unit can only be occupied 180 days a year per State Permit. The Sierra arrives fully turn-key: kitchen with full appliances including an over-the-range microwave, full bath, living area, two bedrooms, and a sleeping loft that gives you the flex for extra guests. At 320 sq ft of interior space plus 120 sq ft of covered porch, it lives larger than it measures — the layout wastes nothing. Never used and installed in 2026. Will make a great comfortable vacation getaway in any season. The park also maintains the landscaping.

2074 Vt Rt 30, Jamaica

$495,000

Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer. Designed for gathering and relaxing, the home features two spacious living areas, providing plenty of room for family and guests. A cozy wood stove creates the perfect après-ski atmosphere, while the inviting three-season porch offers a peaceful place to enjoy the natural surroundings from spring through fall. The level, secluded lot provides privacy and outdoor enjoyment, with ample space for entertaining, gardening, or simply unwinding. Conveniently located near Stratton, Bromley, Manchester, and local dining and shopping, this property is equally suited as a full-time residence, vacation retreat, or investment opportunity. Experience the best of Vermont living in a location that puts adventure and relaxation right at your doorstep.

4 Beds ⋅ 3 Baths ⋅ 5097042 MLS

Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer. Designed for gathering and relaxing, the home features two spacious living areas, providing plenty of room for family and guests. A cozy wood stove creates the perfect après-ski atmosphere, while the inviting three-season porch offers a peaceful place to enjoy the natural surroundings from spring through fall. The level, secluded lot provides privacy and outdoor enjoyment, with ample space for entertaining, gardening, or simply unwinding. Conveniently located near Stratton, Bromley, Manchester, and local dining and shopping, this property is equally suited as a full-time residence, vacation retreat, or investment opportunity. Experience the best of Vermont living in a location that puts adventure and relaxation right at your doorstep.

367 Stratton Gate Rd, Jamaica

$3,995,000

Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an 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 Mt Snow ski resorts. 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.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 fireplace sit against a backdrop of vast mountain views. The landscape is adorned with a sea of peony bushes, adding vibrant color to the meticulously designed gardens.

4 Beds ⋅ 6 Baths ⋅ 5096846 MLS

Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an 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 Mt Snow ski resorts. 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.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 fireplace sit against a backdrop of vast mountain views. The landscape is adorned with a sea of peony bushes, adding vibrant color to the meticulously designed gardens.

816 Black Bear Rd, Jamaica

$1,475,000

A long winding driveway through a mountain of foliage leads you to this extraordinary mountain-modern retreat, perched high above nearly 200 acres of protected Vermont wilderness. Thoughtfully crafted by Big Pine Builders LLC, this striking off-grid solar home seamlessly blends contemporary design with Vermont’s rugged natural beauty, allowing you to live on the sun’s rhythm while enjoying refined comfort, complete privacy, and breathtaking surroundings. The cedar and metal exterior complements the landscape, while expansive living room windows provide nearly 180-degree views across your own nature preserve-like setting. Inside, a simple and sleek design creates an airy living space filled with natural light, warm bamboo floors, and clean modern lines. Indoor and outdoor wood-burning fireplaces add warmth and ambiance throughout every season. An additional family room offers flexible living space, perfect for gathering with friends and family, a media room, home office, or quiet retreat. Designed for year-round enjoyment, the property features an extensive town trail system that connects directly to the VAST trail network, making it a dream for outdoor enthusiasts. Entertain or unwind on the large bluestone patio surrounded by complete serenity and nature in every direction. In just 15 minutes, you can be enjoying all that Stratton Mountain has to offer, including skiing, golf, dining, and year-round recreation, while Jamaica Village is just 10 minutes away in the opposite direction. Recent improvements include a new boiler and hot water heater, offering peace of mind for years to come. A propane generator provides added convenience and reliability for off-grid living. Currently enrolled in the Vermont Current Use program, this remarkable property offers a rare opportunity to own nearly 200 acres of protected Vermont wilderness paired with sophisticated, sustainable living.

2 Beds ⋅ 2 Baths ⋅ 5095401 MLS

A long winding driveway through a mountain of foliage leads you to this extraordinary mountain-modern retreat, perched high above nearly 200 acres of protected Vermont wilderness. Thoughtfully crafted by Big Pine Builders LLC, this striking off-grid solar home seamlessly blends contemporary design with Vermont’s rugged natural beauty, allowing you to live on the sun’s rhythm while enjoying refined comfort, complete privacy, and breathtaking surroundings. The cedar and metal exterior complements the landscape, while expansive living room windows provide nearly 180-degree views across your own nature preserve-like setting. Inside, a simple and sleek design creates an airy living space filled with natural light, warm bamboo floors, and clean modern lines. Indoor and outdoor wood-burning fireplaces add warmth and ambiance throughout every season. An additional family room offers flexible living space, perfect for gathering with friends and family, a media room, home office, or quiet retreat. Designed for year-round enjoyment, the property features an extensive town trail system that connects directly to the VAST trail network, making it a dream for outdoor enthusiasts. Entertain or unwind on the large bluestone patio surrounded by complete serenity and nature in every direction. In just 15 minutes, you can be enjoying all that Stratton Mountain has to offer, including skiing, golf, dining, and year-round recreation, while Jamaica Village is just 10 minutes away in the opposite direction. Recent improvements include a new boiler and hot water heater, offering peace of mind for years to come. A propane generator provides added convenience and reliability for off-grid living. Currently enrolled in the Vermont Current Use program, this remarkable property offers a rare opportunity to own nearly 200 acres of protected Vermont wilderness paired with sophisticated, sustainable living.

691 Black Bear Rd, Jamaica

$50,000

This is a land locked parcel. There is no right of way or easement to access it. This is a town sale property. There is a 30 day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residence object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5% of the towns registered voters, the select, Board cannot just sell the property, they must call a special Town meeting, so the voters can decide whether to approve or reject the sale. No engineering has been done on this lot.

5094910 MLS

This is a land locked parcel. There is no right of way or easement to access it. This is a town sale property. There is a 30 day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residence object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5% of the towns registered voters, the select, Board cannot just sell the property, they must call a special Town meeting, so the voters can decide whether to approve or reject the sale. No engineering has been done on this lot.

non Non Pikes Falls Rd, Jamaica

$799,000

Only 8 miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, & multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but contains a new addition from the 21st allowing you & your family to have space. The home has high ceilings, hand-hewn beams, classic woodwork, a wood-burning stove, and walls of windows that bring in warmth & light. The addition includes a grand primary suite with soaring ceilings, views over the land, walk-in closet, large tiled bathroom with a tiled shower, powerful jet tub, and double vanity. With 5 total bedrooms, 4.5 baths, 2 living spaces, and 3 bonus rooms, there is space to host or work from this 3,840SqFt home. The expansive kitchen contains large countertops with space for seating as well as a window covered breakfast nook. The butler’s pantry, complete with a wet bar, makes entertaining easy. Sit by the stove while snow falls across the pasture and enjoy your snow-globe like winter scene, complete with a great sledding hill right outside. On warm days, open the sliders to the brick patio, or to the back deck to grill, pick berries in the garden, walk the orchard trail, or watch the leaves change during the seasons. The home is located near the town of Manchester, ski mountains (Stratton, Bromley, and Mount Snow), excellent golf courses, & local renowned dining at Honeypie, River & Rye and Solo Farm & Table within easy reach. Bradley International Airport is 2 hours away, Boston is 3, and New York City is 4. This is a home you can enjoy now. One whose location, scale, and enchanting views provide the foundation to create your dream oasis. You deserve to enjoy the Vermont life you have been dreaming of, and make this home and timeless setting part of your family’s legacy.

5 Beds ⋅ 5 Baths ⋅ 5093492 MLS

Only 8 miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, & multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but contains a new addition from the 21st allowing you & your family to have space. The home has high ceilings, hand-hewn beams, classic woodwork, a wood-burning stove, and walls of windows that bring in warmth & light. The addition includes a grand primary suite with soaring ceilings, views over the land, walk-in closet, large tiled bathroom with a tiled shower, powerful jet tub, and double vanity. With 5 total bedrooms, 4.5 baths, 2 living spaces, and 3 bonus rooms, there is space to host or work from this 3,840SqFt home. The expansive kitchen contains large countertops with space for seating as well as a window covered breakfast nook. The butler’s pantry, complete with a wet bar, makes entertaining easy. Sit by the stove while snow falls across the pasture and enjoy your snow-globe like winter scene, complete with a great sledding hill right outside. On warm days, open the sliders to the brick patio, or to the back deck to grill, pick berries in the garden, walk the orchard trail, or watch the leaves change during the seasons. The home is located near the town of Manchester, ski mountains (Stratton, Bromley, and Mount Snow), excellent golf courses, & local renowned dining at Honeypie, River & Rye and Solo Farm & Table within easy reach. Bradley International Airport is 2 hours away, Boston is 3, and New York City is 4. This is a home you can enjoy now. One whose location, scale, and enchanting views provide the foundation to create your dream oasis. You deserve to enjoy the Vermont life you have been dreaming of, and make this home and timeless setting part of your family’s legacy.

42 Blackberry Ln, Jamaica

$85,000

Unique! Do you love to camp? swim? fish?.....this may be it for you....Over 2000 feet of West River frontage with electric on site and just off pavement and at the intersection of 2 major access road to skiing and recreation! Much of the frontage is in flood plain and it is subject to flowage rights of the dam, but an amazing site! The current owner has had a Jamaica cottage for camping and the previous owner had a little trailer and shed. Put your feet up and watch the canoes go by in the white water of the spring dam release...or join them and take the challenge. You will love this little piece of Vermont, but do your due diligence for your own intended use so there are no surprises! Seller will consider owner financing to a qualified buyer.

5093083 MLS

Unique! Do you love to camp? swim? fish?.....this may be it for you....Over 2000 feet of West River frontage with electric on site and just off pavement and at the intersection of 2 major access road to skiing and recreation! Much of the frontage is in flood plain and it is subject to flowage rights of the dam, but an amazing site! The current owner has had a Jamaica cottage for camping and the previous owner had a little trailer and shed. Put your feet up and watch the canoes go by in the white water of the spring dam release...or join them and take the challenge. You will love this little piece of Vermont, but do your due diligence for your own intended use so there are no surprises! Seller will consider owner financing to a qualified buyer.

1297 River Rd, Jamaica

$1,295,000

A true Vermont lodge in every sense—warm, welcoming, beautifully appointed, and designed to bring people together. This exceptional mountain retreat combines the character and comfort buyers dream about in a Vermont home with the space, amenities, and proven rental history that make it equally appealing as an investment. The property has enjoyed a strong rental history with repeat guests who return to experience this special home year after year. Inside, the expansive open-concept living areas were made for gathering after a day on the mountain, while thoughtfully designed private spaces allow everyone room to relax and recharge. Curl up beside one of two fireplaces as the snow falls outside, host movie nights in the impressive 11-foot home theater, or gather in the great room around the 90-inch TV for game day. The lodge experience continues outdoors, where four-season entertaining takes center stage. Grill and dine beneath the stars, soak in the six-person hot tub, unwind in the eight-person sauna, then end the evening around the fire pit surrounded by the peaceful Vermont forest. Every detail has been considered to create a property that feels less like simply a house and more like a destination. There is room for extended family, friends, ski weekends, holidays, and generations of memories—all with the comforts and amenities of a private mountain resort. Whether you're searching for a quintessential Vermont escape to enjoy yourself, a gathering place for family and friends, or a property with an established rental history and repeat clientele, this remarkable lodge offers a combination that is increasingly difficult to find. Arrive, settle in, and experience the Vermont lifestyle exactly as it was meant to be.

5 Beds ⋅ 4 Baths ⋅ 5090616 MLS

A true Vermont lodge in every sense—warm, welcoming, beautifully appointed, and designed to bring people together. This exceptional mountain retreat combines the character and comfort buyers dream about in a Vermont home with the space, amenities, and proven rental history that make it equally appealing as an investment. The property has enjoyed a strong rental history with repeat guests who return to experience this special home year after year. Inside, the expansive open-concept living areas were made for gathering after a day on the mountain, while thoughtfully designed private spaces allow everyone room to relax and recharge. Curl up beside one of two fireplaces as the snow falls outside, host movie nights in the impressive 11-foot home theater, or gather in the great room around the 90-inch TV for game day. The lodge experience continues outdoors, where four-season entertaining takes center stage. Grill and dine beneath the stars, soak in the six-person hot tub, unwind in the eight-person sauna, then end the evening around the fire pit surrounded by the peaceful Vermont forest. Every detail has been considered to create a property that feels less like simply a house and more like a destination. There is room for extended family, friends, ski weekends, holidays, and generations of memories—all with the comforts and amenities of a private mountain resort. Whether you're searching for a quintessential Vermont escape to enjoy yourself, a gathering place for family and friends, or a property with an established rental history and repeat clientele, this remarkable lodge offers a combination that is increasingly difficult to find. Arrive, settle in, and experience the Vermont lifestyle exactly as it was meant to be.

4427 W Hill Rd S, Jamaica