Jamaica VT Real Estate & Homes for Sale

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Beds:
2
Baths:
1.00
Sq.Ft.:
698
Status:
NEW LISTING
MLS#:
5117132
Type:
Condo
Year built:
1982
Courtesy: Winhall Real Estate
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ADDITIONAL INFORMATION

This two bedroom one bath townhouse is just minutes from Stratton, Bromley, and Magic Mountain, with Jamaica State Park and the West River nearby! Steps from Honey Pie, Equipe Sport, Family Kitchen, Rawsonville Marketplace, Meulemans' Craft Draughts, and Ungrounded Coffee Roasters…what more could you want!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,504
Status:
NEW LISTING
MLS#:
5116624
Type:
Single Family
Subdivision:
Mountain Acres
Lot size:
1.03 Acres
Year built:
1988
Courtesy: Winhall Real Estate
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ADDITIONAL INFORMATION

Less scrolling. More Vermont. Pick a mountain. Pack the snacks. Forget what day it is. Here in Jamaica's Mountain Acres neighborhood, your Vermont routine comes with considerably better scenery. Set on a skosh (It's a word! Look it up!) over 1 acre, this three-bedroom home offers a skosh (It's growing on you, isn't it?) over 1,500 square feet, two baths (one of which has been beautifully updated), and room to gather without spending your weekend cleaning it. Vaulted ceilings, skylights, and woodland views bring the outside in...the brick fireplace makes a strong case for staying put. The kitchen serves up wood cabinetry, granite counters, stainless appliances, and a hammered-metal apron-front sink with a little extra personality. A generous peninsula keeps the cook in the conversation...and the snacks within reach. Slide outside for dinner on the deck, stash your gear in the shed, and put the large, unfinished basement to work for laundry and storage. Or let your imagination run wild and create even more space for fun or relaxing! Stratton, Bromley, Magic Mountain, and Mount Snow give you four reasons to check the snow report. When the skis take a break, Jamaica State Park offers hiking, swimming, and time along the West River. This is a home base for more than winter. Your biggest project here? Perfecting the art of **unwinding**.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,943
Status:
Active
MLS#:
5116285
Type:
Single Family
Lot size:
10.3 Acres
Year built:
1982
Courtesy: Michael England Real Estate
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ADDITIONAL INFORMATION

Nestled in the picturesque countryside of Jamaica, Vermont, this charming residence offers an idyllic retreat just a stone's throw away from renowned ski areas such as Stratton Mountain, Bromley, Magic Mountain, and Mount Snow. The property is situated on a private road, ensuring tranquility and seclusion, while boasting four bedrooms, bonus room on the 3rd floor and two and a half baths, complemented by a cozy fireplace that enhances the home's inviting atmosphere. The mountain view across the valley serve as a stunning backdrop, making it an ideal setting for nature enthusiasts. The proximity to Jamaica State Park provides ample opportunities for hiking and camping, while the West River Trail and the river's celebrated whitewater release weekends cater to adventure seekers. During the winter months, the nearby ski resorts offer exhilarating skiing and snowboarding experiences, while the surrounding area features Townshend State Park, Townshend Lake, and various outdoor activities such as hiking, swimming, fly fishing, and leaf-peeping, allowing residents to fully embrace the beauty of each season in classic Vermont style.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,062
Status:
Active
MLS#:
5114286
Type:
Single Family
Lot size:
0.14 Acres
Year built:
1860
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

Step into a piece of Jamaica Village history. Once home to the F.E. Smith Dry Goods, Ready-Made Clothing, and Grocery Store, this distinctive red-and-white building blends Greek Revival presence with Vermont farmhouse character and now serves as a year-round residence filled with history and personality. The classic façade features full-width double-decker porches, white picket railing, and bold corner pilasters. Inside, this C. 1860 building's commercial past lives on in a dramatic great room with original built-in storefront shelving and drawer banks once used to display dry goods. Now a unique library, studio and sitting area, the space features wide-plank wood floors, exposed beams, and natural light from the original storefront windows and door. A vintage interior sash window adds another unexpected architectural detail. The kitchen features sage cabinetry, granite tile counters, a pot rack, sunny breakfast area, and walk-in pantry. A cozy living and dining room offers a comfortable gathering space, while upstairs bedrooms retain original wide pine floors and vintage details. Both bathrooms have been updated, and the oil tank, on-demand hot water heater, pressure tank, and well pump have all been recently replaced. Garden beds and a painted harlequin porch floor add personality outside, while the covered porch invite you to enjoy morning coffee and the rhythm of village life. A rare opportunity to own a property with a story to tell and the potential to make it your own. Buyers who appreciate historic homes and are comfortable with a project will find opportunities to build on its existing character.

Beds:
6
Baths:
5.00
Sq.Ft.:
2,426
Status:
Active
MLS#:
5113514
Type:
Single Family
Lot size:
0.53 Acres
Year built:
1835
Courtesy: Winhall Real Estate
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ADDITIONAL INFORMATION

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!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,075
Status:
Active
MLS#:
5111100
Type:
Single Family
Lot size:
2.3 Acres
Year built:
1950
Courtesy: Southern Vermont Realty Group
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ADDITIONAL INFORMATION

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 22 to Stratton.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,257
Status:
Active
MLS#:
5110722
Type:
Single Family
Lot size:
0.33 Acres
Year built:
2000
Courtesy: Winhall Real Estate
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ADDITIONAL INFORMATION

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

Beds:
5
Baths:
5.00
Sq.Ft.:
3,363
Status:
Active
MLS#:
5108207
Type:
Single Family
Lot size:
0.6 Acres
Year built:
1990
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

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.

Beds:
9
Baths:
7.00
Sq.Ft.:
4,996
Status:
Active
MLS#:
5107418
Type:
Single Family
Lot size:
13.66 Acres
Year built:
1860
Courtesy: The Haven Group
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,359
Status:
Active
MLS#:
5106080
Type:
Single Family
Lot size:
14.4 Acres
Year built:
1971
Courtesy: Winhall Real Estate
View additional info

ADDITIONAL INFORMATION

Avoid the high cost of heating oil with this this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat. Recent energy-efficient upgrades include owned REC solar panels, owned Tesla backup batteries, and Daikin heat pumps and mini splits. Located just 20 minutes from Stratton Mountain and Mount Snow, this home sits on 14.4 acres bordering the beautiful Green Mountain National Forest and offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property can be used as a fully-equipped, turn-key vacation rental or exceptional full-time residence. 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 the VAST trail can be accessed from the property. Also included, an oil forced-air heating system, rebuilt chimney, generator-ready setup, and high-speed Starlink internet with mesh coverage. Tucked at the end of a town-maintained dead-end road, yet only half a mile from Rt. 100, this is a rare opportunity to own a true Vermont escape.

Beds:
5
Baths:
4.00
Sq.Ft.:
2,974
Status:
Active
MLS#:
5101688
Type:
Single Family
Lot size:
2.96 Acres
Year built:
1860
Courtesy: The Haven Group
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,022
Status:
Active
MLS#:
5101689
Type:
Single Family
Lot size:
2.31 Acres
Year built:
2009
Courtesy: The Haven Group
View additional info

ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
2.00
Sq.Ft.:
2,194
Status:
Active
MLS#:
5097573
Type:
Single Family
Lot size:
1.25 Acres
Year built:
1955
Courtesy: Winhall Real Estate
View additional info

ADDITIONAL INFORMATION

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.

Beds:
7
Baths:
8.00
Sq.Ft.:
8,364
Status:
Active
MLS#:
5097566
Type:
Single Family
Lot size:
16.05 Acres
Year built:
2002
Courtesy: Winhall Real Estate
View additional info

ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
1.00
Sq.Ft.:
672
Status:
Active
MLS#:
5097748
Type:
Mobile Home
Year built:
1970
Courtesy: Winhall Real Estate
View additional info

ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
1.00
Sq.Ft.:
320
Status:
Active
MLS#:
5097088
Type:
Mobile Home
Year built:
2026
Courtesy: Michael England Real Estate
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ADDITIONAL INFORMATION

Brand-New Log Cabin on the West River Near Stratton Turn-Key Ski Getaway ... Wake up to the sound of the West River and be on the Stratton lifts while the corduroy is still fresh. Stratton Mountain Resort is expected to open Thanksgiving week, and this brand-new Lancaster Log Cabins “Sierra” park model puts you close enough to chase first tracks all winter. Mount Snow, Bromley and Magic are all within reach for day trips. This is a real log cabin. It was installed in 2026 on a newly poured concrete slab and has never been lived in. It sits at French Bridge Chateau, a small riverfront community in Jamaica, Vermont. Cathedral ceilings and exposed log beams open up 320 square feet of finished interior with: • two bedrooms • a sleeping loft for extra guests • a full bath • a full kitchen with all appliances, including an over-the-range microwave A heat pump with mini split keeps the cabin warm on January nights and cool in July. The metal roof sheds snow, so you don't have to. Step out onto the 10x12 covered porch, shaded by old hemlocks and facing the river, away from the road. After a day on the mountain, this is where the après happens. Arrive with your skis and a bag of groceries. The cabin comes fully turn-key. For $306 per month, the park handles plowing, water, sewer and landscaping, so your weekends go to the mountain, not maintenance. When the snow melts, you have the West River, Jamaica State Park and Southern Vermont's hiking and paddling. The State permit allows seasonal use up to 180 days per year, which covers an entire ski season with room to spare. It is not for use as a primary residence, and park approval is required. Ski season is weeks away, so schedule your showing now and spend this winter skiing from your own cabin.

Beds:
4
Baths:
6.00
Sq.Ft.:
5,500
Status:
Active
MLS#:
5096846
Type:
Single Family
Lot size:
44.47 Acres
Year built:
2010
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,115
Status:
Active
MLS#:
5097042
Type:
Single Family
Lot size:
2.4 Acres
Year built:
1972
Courtesy: Cummings & Co
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ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,601
Status:
Active
MLS#:
5095401
Type:
Single Family
Lot size:
199.73 Acres
Year built:
2009
Courtesy: Winhall Real Estate
View additional info

ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,840
Status:
Active
MLS#:
5093492
Type:
Single Family
Lot size:
5.7 Acres
Year built:
1850
Courtesy: The Haven Group
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ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,040
Status:
Active
MLS#:
5090616
Type:
Single Family
Lot size:
11.12 Acres
Year built:
2006
Courtesy: Winhall Real Estate
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,430
Status:
Active
MLS#:
5089830
Type:
Single Family
Lot size:
0.7 Acres
Year built:
1960
Courtesy: Winhall Real Estate
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ADDITIONAL INFORMATION

Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system provides efficient heating and air conditioning year-round. In 2024, the basement underwent major upgrades, including mitigation with an improved support and drainage system, along with the installation of two new water tanks—providing long-term confidence and reassurance for the next owner. Ideally located near Stratton Mountain, Ball Mountain Dam, and Jamaica State Park, this home is a perfect base for four-season recreation—from skiing and snowboarding to hiking, swimming, and exploring nature. A true turnkey retreat in an unbeatable location!

Beds:
5
Baths:
4.00
Sq.Ft.:
3,218
Status:
Active
MLS#:
5088809
Type:
Single Family
Lot size:
2 Acres
Year built:
1995
Courtesy: Michael England Real Estate
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ADDITIONAL INFORMATION

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

Beds:
4
Baths:
2.00
Sq.Ft.:
1,902
Status:
Active
MLS#:
5082980
Type:
Single Family
Lot size:
1 Acres
Year built:
1970
Courtesy: Brattleboro Area Realty
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ADDITIONAL INFORMATION

Looking for a project? Featuring a drilled well, existing septic, electric, and driveway, you have a good start for a new build, renovation or a combination of the two. The cabin has been added onto many times, making room for a growing family. The land is mostly level, with some nice plantings and the house sits back a little distance from the neighbors. The well is being shared, electric is run from this property to the neighbor. There is some clean up on this property, but more around the neighborhood. Fix it up for a great ski crash pad, or do more and enjoy an affordable primary. This is an estate so no SPIR is available. The rooms beyond the staircase should not be walked on for safety. But, includes 2 bedrooms and a partially finished 3/4 bath. Power is not on, plumbing is not working.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,888
Status:
Active
MLS#:
5081124
Type:
Single Family
Lot size:
5.65 Acres
Year built:
1980
Courtesy: Michael England Real Estate
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ADDITIONAL INFORMATION

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

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Andrea D. Conner, License 71221, Xome Inc., License 68390, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067


Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated {{last updated}}.




Jamaica Real Estate

Jamaica is located in Vermont. Jamaica, Vermont has a population of 881. Jamaica is less family-centric than the surrounding county with 8.81% of the households containing married families with children. The county average for households married with children is 20.95%.

The median household income in Jamaica, Vermont is $57,800. The median household income for the surrounding county is $59,195 compared to the national median of $69,021. The median age of people living in Jamaica is 51.3 years.

Jamaica Weather

The average high temperature in July is 79 degrees, with an average low temperature in January of 8.7 degrees. The average rainfall is approximately 51.7 inches per year, with 105.9 inches of snow per year.

Jamaica Map

Jamaica Real Estate Market Conditions

  • Median sales price

    $376,250
    19.1%
    change since last quarter
  • # Active listings

    52
    30-day change

Jamaica Schools and Demographics

Education near Jamaica, VT

City County
High School Graduates 96.76 93.68
College Degree - 2 year 5.74 6.48
College Degree - 4 year 22.98 40.85
Graduate Degree 4.71 13.17
Expenditures per Student 23,709 23,709
Students per Teacher 11.5 11.5

Elementary Schools near Jamaica, VT

Grades Students P/T Ratio ZIP
Dover Elementary School PK - 06 109 14.7 05341
Jamaica Village School PK - 06 65 10.5 05343
Townshend Village School PK - 06 80 11.2 05353
Wardsboro Central School PK - 06 58 8.3 05355
Windham Elementary School PK - 05 20 5.7 05359

High Schools near Jamaica, VT

Grades Students P/T Ratio ZIP
Leland & Gray UHSD #34 07 - 12 349 11.3 05353

Demographics near Jamaica, VT

City County
Neighborhood Type Small Town
Population 881 45,811
Population Density 18 58
Median Age 51.3 47
People per Household 2.1 2.3
Median Household Income 57,800 59,195
Average Income per Capita 38,549 35,856

Real estate near Jamaica