Jamaica Real Estate

Welcome to Jamaica, Vermont – a hidden gem nestled in the picturesque Windham County. This charming town is a perfect blend of serene landscapes, vibrant community spirit, and rich history, making it an ideal place for those seeking a tranquil lifestyle away from the hustle and bustle of city life.

Jamaica boasts stunning natural beauty, with the stunning Green Mountain National Forest as its backdrop. Outdoor enthusiasts will find endless opportunities for adventure, from hiking and biking in the summer to skiing and snowshoeing in the winter. The nearby Jamaica State Park offers breathtaking views, pristine rivers, and well-maintained trails, perfect for family outings or a peaceful escape into nature.

The town itself is steeped in history, with quaint architecture and a warm, welcoming atmosphere. Explore the local shops and eateries that line Main Street, where you can find everything from artisanal goods to delicious homemade treats. The community hosts various events throughout the year, including farmers' markets, craft fairs, and seasonal festivals, fostering a strong sense of camaraderie among residents.

For families, Jamaica offers excellent educational opportunities and a safe, nurturing environment. The tight-knit community ensures that everyone feels at home, making it a wonderful place to raise children or enjoy retirement.

With its unique blend of natural beauty, rich history, and friendly atmosphere, Jamaica, Vermont, is not just a place to live but a place to thrive. Come discover the charm of this enchanting town and find your perfect home in the heart of Windham County!

Newest Listings in Jamaica

$489,000

6 Beds ⋅ 4 Baths ⋅ 5113514 MLS

Village living with room for possibilities! Just steps from Jamaica State Park and downtown Jamaica, this versatile home offers a wonderful opportunity to enjoy Vermont living with the added benefit of separate living spaces and potential rental income. Abutting the river, the property is currently configured as three spacious two-bedroom apartments—two with one bath and a third with two baths. Make one apartment your full-time residence or Vermont getaway while renting the others, or explore options for bringing extended family together while maintaining privacy and independence. Two apartments are currently vacant and ready for immediate occupancy. The third is home to long-term tenants who hope to stay, offering potential ongoing income. Recent improvements include a new furnace, new well pump, freshly painted exterior, and replacement windows where needed. The hot water heaters are approximately five years old. One apartment features a new refrigerator and stove, while another includes a three-year-old washer and dryer along with a new dishwasher. Enjoy a location that puts outdoor adventure and village charm right outside your door. Walk to Jamaica State Park for hiking, biking, swimming, and exploring, or stroll downtown to enjoy this welcoming Vermont community. Stratton Mountain and other Southern Vermont attractions are within easy reach, making this an appealing home base in every season. Whether you envision a primary home with supplemental income, a vacation retreat with space for guests, or a future reconfiguration to suit your needs, this property offers exceptional flexibility. Any conversion or changes in use would be subject to applicable approvals. A special opportunity to make yourself at home in the heart of Jamaica!

154 Depot St, Jamaica

$489,000

5113501 MLS

An exceptional investment opportunity in the heart of Jamaica! Just steps from Jamaica State Park and the charm of downtown Jamaica, this three-unit multifamily property offers an ideal combination of location, flexibility, and income potential. Whether you’re looking to live in one unit while generating income from the others, create a Vermont getaway with rental income, or add a versatile property to your investment portfolio, the possibilities are plentiful. The property abuts the river and features three spacious two-bedroom units: two with one bath and a third with two baths. Two units are currently vacant and ready for immediate occupancy, while the third is occupied by long term tenants—offering the potential for income from day one. Consider long-term rentals, seasonal leases, or short-term rentals such as Airbnb, subject to applicable local and state requirements. Recent improvements make this an especially attractive opportunity. Updates include a new furnace, new well pump, freshly painted exterior, and replacement windows where needed. The hot water heaters are approximately five years old. One apartment features a new refrigerator and stove, while another offers a three-year-old washer and dryer along with a new dishwasher. And then there’s the location! Walk to Jamaica State Park for hiking, biking, swimming, and outdoor recreation, or stroll into the village to enjoy everything this quintessential Vermont community has to offer. With Stratton Mountain and other Southern Vermont attractions within easy reach, the property is well positioned to appeal to year-round, seasonal, and vacation renters alike. Three units, multiple income possibilities, recent improvements, and an outstanding village location make this a rare opportunity to invest in one of Southern Vermont’s most desirable four-season communities.

154 Depot St, Jamaica

$549,000

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

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

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

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

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

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

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

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

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

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

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