Jamaica

Browse the latest real estate for sale in Jamaica, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-793-2002 or contact us online.

Create a free account to save your favorite Vermont real estate listings and get notified when similar properties become available.

370 Fischer Lane Jamaica VT 05343

Jamaica, VT370 Fischer Lane

Price$9,950,000

Est. Mortgage: $/month

MLS Number 5015744

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 10

Accessible, but miles from the everyday. Camp Endo's mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark and stone detailing combined with complete comfort, great light and welcoming spaces. The property was featured in the book Rustic Living by Ralph Kylloe as one of the great rustic style homes in the U.S. The 13,393-square-foot home has an open floor plan, massive stone great room fireplace, chef's kitchen and 6 bedrooms en suite, each with magnificent mountain views. Off the kitchen and great room is a screened-in porch and large deck with an outdoor stone fireplace to soak in the panoramic southerly green mountain views. Smaller gathering spaces include a corner office, gym/spa, meditation room and 22-seat home theater. Camp Endo's extensive trail network provides a daily dose of rugged, natural beauty for mountain biking, walking or snow shoeing and playful options include a paintball course and a six-foot square chessboard. The adjacent barn houses a fully appointed 2 bedroom guest suite, 3-bay garage and half-basketball court with surround sound. Next to the apple orchard is a large swimming pond with views of Stratton Mtn. The property has renewable solar and wind energy.

Listed by Dia Jenks and T Story Jenks of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

662 Howe Farm Road Jamaica VT 05343

Jamaica, VT662 Howe Farm Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 4972272

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 5

Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of nature to your daily life. Multiple bedrooms give everyone in your party a private space to relax after a long day exploring the outdoors. Step outside to witness dramatic views of the rolling hills that surround the property. A tranquil pond with gazebo graces the landscape. A well-appointed barn with 5 stalls and a paddock caters to equestrian enthusiasts. Miles of trails crisscross the property, providing endless opportunities for outdoor activities. This property is in Vermont Current Use Program, securing its natural beauty for the future. Whether you are relaxing on the porch or hosting gatherings in the spacious bonus room, this estate balances seclusion and convenience. Situated in bucolic Jamaica, it is 20 minutes from Stratton and 25 minutes from Mount Snow. Let this be your four season retreat, close to the mountains in the winter, swimming holes in the summer, and stunning views all year round!

Listed by Andie Fusco and Tara van de Velde of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

0 West Hill Road South Jamaica VT 05343

Jamaica, VT0 West Hill Road South

Price$1,900,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5006431

  • Land
  • County Windham
  • Square Feet 25,743,960
  • Acreage 591

Welcome to an exceptional opportunity in Jamaica, VT! College Hill, a 591-acre parcel, owned by the same family for 70 years, is a rare find in today's market. Unencumbered by permits or land use restrictions, this property offers limitless possibilities. The current owners have maintained its natural beauty, never logging the land, preserving its pristine condition. At the top of College Hill, enjoy breathtaking views of Stratton Mountain and the surrounding valley. With extensive trails and old logging roads throughout, it's perfect for development, logging, or recreational use. Located just a short distance from Stratton, Bromley, and Magic Mountains, this property offers unparalleled access to premier skiing and outdoor activities. Don't miss the chance to own a piece of Vermont's stunning landscape. This is a once-in-a-lifetime opportunity to acquire a property of this magnitude and beauty.

Listed by Timothy Apps of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

251 Pratt Bridge Road Jamaica VT 05343

Jamaica, VT251 Pratt Bridge Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 5003633

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 8

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!

Listed by Tg Glazer of Winhall Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

251 Pratt Bridge Road Jamaica VT 05343

MLS Number 5003634

  • Commercial
  • County Windham
  • Square Feet 8,364
  • Acreage 16.05

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!

Listed by Tg Glazer of Winhall Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

42 Blackberry Lane Jamaica VT 05343

Jamaica, VT42 Blackberry Lane

Price$899,000

Est. Mortgage: $/month

MLS Number 5004180

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 5

Welcome to Sweet Berry Farm, a picturesque farmhouse in Jamaica, Vermont. This extraordinary property blends historical charm with modern updates, offering an enchanting living experience. Enjoy mature apple trees, blueberry bushes, blackberries, and grapes. There are also many varieties of flowers and bushes that bloom throughout the warmer season. Originally built in 1850, this farmhouse showcases craftsmanship of the era with well-preserved original features. A total farmhouse renovation also provided a new addition with contemporary comfort. The expansive 3 story addition with a large open living room, dining room, 2nd kitchen area on the main floor, a large family room with a separate den and bathroom on the lower walkout level as well as additional bedrooms and bathrooms including a primary suite with vaulted ceilings and spa bathroom with a jetted tub on the upstairs level. There truly is ample space for family and guests, as each room exudes warmth and character, featuring exposed beams, original hardwood floors, and a cozy woodstove fireplace. Situated on a 5.7-acre private plot up a lovely driveway, Sweet Berry Farm includes a large barn and three versatile outbuildings for a workshop, artist's studio, or storage including a garbage shed. Close Proximity to Stratton Mountain is a highlight. Enjoy skiing or snowboarding nearby in Winter, and explore hiking trails, bike paths, and ponds in warmer months. Sweet Berry Farm isn't just a home; it's a lifestyle.

Listed by Carrie Mathews of Winhall Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

West Hill Road Jamaica VT 05343

Jamaica, VTWest Hill Road

Price$850,000

Est. Mortgage: $/month

MLS Number 5021448

  • Land
  • County Windham
  • Square Feet 2,262,071
  • Acreage 51.93

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and rarely do pieces of land like this come onto the market. Lot 5 has a private driveway that begins at Lot 4. The parcel encompasses the entire north side of the subdivision, from the bottom of the hill all the way up the access road. The views from the clearing at the top of the driveway are to the west toward Bromley Mountain, but there are also big views in the other direction looking southeast. There would be several spots to build on this parcel, but the top of the hill seems like the place to be with the ability to have unobstructed views from your new home.

Listed by Thom Milke of Fountains Land Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

544 Dalewood Road Jamaica VT 05343

Jamaica, VT544 Dalewood Road

Price$799,000

Est. Mortgage: $/month

MLS Number 5014833

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 5

Turnkey and fully furnished this home is just a short drive to Stratton Mountain Resort, within walking distance to one of Vermont's most astounding natural swimming holes, and offers tranquility and peacefulness allowing you to embrace the Vermont life. This 5 bedroom, 5 bathroom split level home design and layout is very thoughtful providing a cozy atmosphere, yet spacious for many. The home welcomes you with a foyer and then splits to the top and lower level. The top level of the home opens up to an open-concept kitchen, dining room, and living room area that is booming with natural light, yet can be dialed back to provide a cozy Vermont feel with a wood fireplace. At the bottom of the split level, you will find 1 ensuite bedroom, 3 more bedrooms, a small family room for games and movie nights, and a full bathroom. There are two more en suite bedrooms in the home one located on the same level as the foyer, and the other located on an upper level, each having their private deck. The exterior of the home offers 4 decks with one that is quite expansive, a detached, 2 bay heated garage that is equipped with a generator and hook up for the house, and an upstairs that is partially finished to be used for storage OR has great potential for more living space (bar, gameroom, etc), and lastly, there is a landscaped stone walkway and steps up to a firepit area that provides winter views of the Stratton Sun Bowl. The property is on Lot 16, and sellers are including Lot 17 in the sale.

Listed by Rachel Febbie of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

West Hill Road Jamaica VT 05343

Jamaica, VTWest Hill Road

Price$665,000

Est. Mortgage: $/month

MLS Number 5021418

  • Land
  • County Windham
  • Square Feet 3,000,848
  • Acreage 68.89

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

Listed by Thom Milke of Fountains Land Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

2132 Vermont Route 30 Jamaica VT 05343

MLS Number 5004353

  • Commercial
  • County Windham
  • Acreage 4.43

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

Listed by Carrie Mathews of Winhall Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

64 Gleason Farm Lane Jamaica VT 05343

Jamaica, VT64 Gleason Farm Lane

Price$649,000

Est. Mortgage: $/month

MLS Number 5028607

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

Nestled on nearly 2 flat acres, this beautifully maintained South-facing New England Cape Cod farmhouse is a rare find in the mountains. Located on a private dead-end road, the home offers peaceful seclusion while being just a short drive to Stratton Mountain for skiing and tubing in the winter and Jamaica State Park for hiking and stunning waterfalls in the warmer months. With only one owner, this like-new property has been meticulously cared for and features high ceilings throughout, creating a bright, airy and open feel. The open-concept living space seamlessly blends the kitchen, dining, and living areas, making it perfect for both relaxation and entertaining. An attached garage offers added convenience, and two charming outbuildings, including a unique Jamaica Cottage Shop potting shed, provide additional character and utility. Enjoy the tranquility of the mountains with easy access to outdoor adventures. This home is ideal for those seeking privacy, comfort, and a seamless connection to nature, offering a truly special living experience year-round.

Listed by Carrie Mathews of Winhall Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

5600 Pikes Falls Road Jamaica VT 05343

Jamaica, VT5600 Pikes Falls Road

Price$625,000

Est. Mortgage: $/month

MLS Number 5024801

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

Don't miss this amazing opportunity to own a cozy log cabin nestled in the woods off Pikes Falls road with close proximity to Stratton Mountain Resort. This home has been thoughtfully built, well maintained and loved for many years and is now awaiting its new owners. The property features 15 acres, a wood shed and a 19th century Pikes Falls School House, which can be used for extra storage or let your imagination run wild! The main level of the home offers a nice size mudroom for all your gear, a 3/4 bath, large eat in kitchen and large living area with wood burning fireplace to snuggle up to on cold winter days. Upstairs has three bedrooms with large closets and a full bath. The large covered porch and front yard allows ample space to enjoy the outdoors, entertain or relax. The large full basement has house utilities, laundry and plenty of space for storage. This home offers some unique features which you have to come check out for yourself.

Listed by Jamie Wylie of Stratton Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

418 Diers Road Jamaica VT 05343

Jamaica, VT418 Diers Road

Price$620,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5028314

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

Updated and ready to use immediately! Close to Stratton, located just off Route 30, this solid LOG home is perched on a small hill with 11.19 acres of land. Beautiful field stone woodburning fireplace with cathedral ceilings. The land has a small stream and pond running through the property with two large open lawn areas. Owner currently utilizes it as a three bedroom and two and a half bath peaceful getaway! Kitchen is gorgeous with new appliances all within the past five years! Large open space for gatherings! Sit on your large front porch with your coffee or cocktail in hand and just relax taking in the nice local southern Vermont hillside views. Gas range with downdraft vent, eat in bar area both upstairs and down, solid wood flooring and new deck with outdoor firepit for your summertime outdoor enjoyment. Walk out basement with second kitchen, full bathroom, bedroom with cool bunk and storage areas along with a rec room. This property is located on a town maintained, dead end road, so you will have mostly local traffic to the other couple of homes beyond you. Just minutes to Stratton, Magic & Bromley with the convenience of a gas station, a couple of restaurants, outdoor sporting goods store and let's not forget the amazing Craft Beer Store, all less than a half a mile away!! Come take a peek and get yourself settled in before winter is over!

Listed by Julie Lowe of Lowe's Real Estate,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

201 Pratt Bridge Road Jamaica VT 05343

Jamaica, VT201 Pratt Bridge Road

Price$599,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5013957

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 2

Mountain Oasis in Cole Pond Nestled in the heart of Cole Pond, this fully updated and furnished Swiss Chalet is a nature lover's dream. Situated on 1.72 acres of pristine land, this four-bedroom, two-bathroom home offers ample space and modern amenities. Key Features: Open Floor Plan: Enjoy the spacious living area, featuring a cozy fireplace and a newly renovated kitchen. In-Law Apartment: The lower level offers a separate entrance, living area, kitchenette, bathroom, and wood-burning fireplace, making it ideal for guests or extended family. Outdoor Paradise: Relax on the deck, explore the established perennial gardens, or gather around the fire pit. A brand-new hot tub provides the ultimate in relaxation. Prime Location: Stratton Resort is just 6 miles away, offering world-class skiing and other outdoor activities. Nearby Jamaica State Park, Ball Mountain Dam, Angel Falls, and Hamilton Falls provide endless opportunities for exploration. Don't miss this opportunity to own your own mountain retreat. Contact us today to schedule a viewing.

Listed by Robin Apps and Margaret McMahon of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

69 Chapin Lane Jamaica VT 05343

Jamaica, VT69 Chapin Lane

Price$584,000

Est. Mortgage: $/month

MLS Number 5028853

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 3

Welcome to Sugar Chateau- Nestled in the serene landscape of Vermont, this enchanting 4-bedroom log home offers the perfect blend of rustic charm and contemporary comfort. Embrace the warmth and character with exposed beams and a welcoming atmosphere.Enjoy the convenience of modern amenities in a rustic setting, featuring a recently renovated kitchen and bathrooms. Custom new Anderson Windows throughout the home as well. The finished Lower Level is ideal for entertainment or relaxation and provides additional living space with 3/4 bath, laundry room, den area and walk out access. Wonderful Outdoor Living space-unwind on the spacious deck with stunning views of Vermont's natural beauty. Relax in the hot tub after a day of skiing or hiking. Experience the best of both worlds - tranquility and convenience. Located just 15 minutes from Stratton Mountain Resort and a short drive to Jamaica village, offering local shops, dining, and community events. Your Vermont Retreat awaits, whether you're seeking a weekend getaway or a year-round residence, this charming log home offers a unique opportunity to embrace Vermont's lifestyle. See list of Improvements to this home under Documents.

Listed by Tara van de Velde and Andie Fusco of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

00 West Hill Road South Jamaica VT 05343

Jamaica, VT00 West Hill Road South

Price$530,000

Est. Mortgage: $/month

MLS Number 5011491

  • Land
  • County Windham
  • Square Feet 1,306,800
  • Acreage 30

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

Listed by Jacki Murano of Southern Vermont Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

559 Pratt Bridge Road Jamaica VT 05343

Jamaica, VT559 Pratt Bridge Road

Price$434,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5004896

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 2

Nestled in the serene country setting of Pratt Bridge Road in Jamaica, Vermont, this charming 3-bedroom home, complete with an additional 4th bedroom loft and 2 baths, offers a perfect getaway. One of the bedrooms is on the first floor. The property features a spacious wrap-around deck, ideal for enjoying the picturesque surroundings. Inside, a beautiful brick wood-burning fireplace provides a cozy ambiance, perfect for relaxing after a day on the slopes. Conveniently located close to Stratton, Bromley, and Magic Mountains, this home is a skier's paradise. In addition, there are many year round hiking trails for you to enjoy the seasonal wild flowers and the breathtaking Green Mountain range.Experience the tranquility and beauty of Vermont living in this inviting home.

Listed by Joseph Castelluccio of Winhall Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

6217 Vt Route 30 Jamaica VT 05343

Jamaica, VT6217 Vt Route 30

Price$385,000

Est. Mortgage: $/month

MLS Number 5028573

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 2
  • Bathroom 2

OPEN HOUSE 2/15/25, 10AM-2PM! Perched on a hill above the village of Jamaica, this inviting Cape-style home offers privacy and stunning surroundings just minutes from Stratton Mountain. Sitting on 1.5 acres, the property provides a peaceful retreat with easy access to Winhall, Stratton, and endless outdoor activities. A babbling stream flows nearby, adding to the tranquil setting as you relax on the spacious deck. Inside, vaulted ceilings and a striking wood-burning stove create a warm and welcoming atmosphere. The sunlit kitchen features a cozy breakfast nook, while a versatile bonus room offers space for an office or creative retreat. The primary bedroom includes a private bath, with a second full bath serving the additional bedroom. Delayed showings begin after the Open House. Showings by appointment only. This home is offered furnished for a turnkey experience, with flexibility for those preferring an unfurnished space. A perfect Vermont escape or investment opportunity!

Listed by Trent Stephens of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

West Hill Road Jamaica VT 05343

Jamaica, VTWest Hill Road

Price$355,000

Est. Mortgage: $/month

MLS Number 5021414

  • Land
  • County Windham
  • Square Feet 1,504,127
  • Acreage 34.53

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be built to get into the interior of the forest. There is long frontage along West Hill Road, and it might be possible to build a driveway from that side of the parcel with access directly from West Hill Road. Alternatively, a house could be built closer to the access road where there are some nice views of the mountains to the north and west. The views from the West Hill Road side of this lot would be to the east, and those views could be made better with tree clearing.

Listed by Thom Milke of Fountains Land Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Vt Route 100 South Jamaica VT 05343

Jamaica, VTVt Route 100 South

Price$299,000

Est. Mortgage: $/month

MLS Number 5027632

  • Land
  • County Windham
  • Square Feet 2,516,026
  • Acreage 57.76

Just over 57 ACRES! Large tract of land with stunning views! State wastewater permit already exists and on file for a the construction of a three bedroom home, see WW-2-5317. This lot offers amazing views from several locations, frontage on a private small brook and the larger Wardsboro Brook that flows along Route 100 South in Jamaica. This is a no zoning town and is extremely easy to get your build started this spring! Located just a short drive to Stratton, Mount Snow, Bromley and Magic Mountain Ski Resorts!

Listed by Julie Lowe of Lowe's Real Estate,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

8365 Vermont Route 30 Jamaica VT 05343

Jamaica, VT8365 Vermont Route 30

Price$250,000

Est. Mortgage: $/month

MLS Number 5019736

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 2
  • Bathroom 1

Quintessential Vermont Log Cabin Seeks New Relationship. I'm an adorable 2 bedroom, 1 bath home, located just 2 short miles from Stratton Mountain. I'm open to a variety of possibilities, including a full-time or seasonal resident. I'd also be a great fit for an investor. What I lack in size, I make up for in character. My open kitchen and living room layout is where I shine, and my cathedral ceiling makes me feel open and airy. I've even got a spacious loft for additional space. A full, walk-out basement provides even more potential! I'm a supportive partner, so I've got your back with a Tesla Powerwall, in case the lights go out. Oh, and I've even got a cozy deck, perfect for relaxing with your morning coffee or an evening beverage. I know I'm a catch, so come for a visit and let's see if we're a match!

Listed by Tg Glazer of Winhall Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

30 Water Street Jamaica VT 05343

Jamaica, VT30 Water Street

Price$239,000

Est. Mortgage: $/month

MLS Number 5025783

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 1

Discover the Acorn, a picturesque retreat nestled on the banks of the scenic West River in Jamaica, Vermont. This unique home, a beautifully converted sugar shack, offers an enchanting taste of rustic charm, perfect for those seeking a serene getaway. Ideal for nature lovers and outdoor enthusiasts, the Acorn sits close to the renowned ski resorts of Stratton Mountain and Mount Snow, providing a prime location for both winter sports and summer adventures with walking distance to Jamaica State park.This cozy home features a welcoming open living area with preserved wooden beams and a wood-burning stove that adds to its rustic appeal. The efficient layout includes a fully equipped kitchen, a comfortable bedroom overlooking the river. Whether you're looking for a romantic escape or a solo retreat, the Acorn offers the perfect setting for relaxation and rejuvenation. Step outside to enjoy the tranquil sounds of the West River Right outsde! The Acorn is conveniently located near a variety of local nature trails, the townshend dam; all offering ample opportunities for hiking, biking, and snowshoeing right at your doorstep. If you're in the market for a charming, rustic home that combines accessibility to outdoor recreation with the peace and quiet of a riverfront location.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

West Hill Road Jamaica VT 05343

Jamaica, VTWest Hill Road

Price$235,000

Est. Mortgage: $/month

MLS Number 5021411

  • Land
  • County Windham
  • Square Feet 665,161
  • Acreage 15.27

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot wide road. Lot 2 is slightly sloped to level, and there are two woods roads that lead into the parcel's interior. One of these roads could be made into a driveway and a homesite could be established in the forest. You could also build closer to the access road where there are good views of the mountains to the northwest. From one of the woods roads you can see the back side of Glebe Mountain which is more commonly known as Magic Mountain Ski Area. With some tree thinning you could open up a larger viewshed to the east.

Listed by Thom Milke of Fountains Land Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

8577 Vt Route 30 Jamaica VT 05343

Jamaica, VT8577 Vt Route 30, Unit H

Price$210,000

Est. Mortgage: $/month

MLS Number 5018420

  • Condo
  • County Windham
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 844

Welcome to easy living with this 2 bedroom 1 full bath condo at the well known Willows community. This unit sits back off Route 30 which gives you privacy and peace yet you can easily take a walk to the local hang outs. Willows is also just a three minute drive to the entrance of the Stratton Road so pack your belongings and move in by Thanksgiving for opening day! Wood stove added for additional heat. Offered furnished less personal items. This is a win-win for the buyer who is searching for value and convenience less huge carrying costs. Give us a call before it's gone.

Listed by Terry Hill of Berkshire Hathaway HomeServices Stratton Home

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

0 Dalewood Road Jamaica VT 05343

Jamaica, VT0 Dalewood Road

Price$154,000

Est. Mortgage: $/month

MLS Number 4955807

  • Land
  • County Windham
  • Square Feet 65,776
  • Acreage 1.51

Discover your dream Vermont escape on this enchanting 1.5-acre wooded lot in Jamaica. Perfectly positioned just minutes from the excitement of Stratton Mountain Resort, this prime parcel offers unparalleled access to world-class skiing, golfing, dining, and shopping. Imagine building your mountain retreat amidst nature's splendor. With a coveted State of Vermont 4-bedroom permit (WW-2-7632) in hand, the possibilities are endless. Enjoy refreshing dips in the nearby Pikes Falls during warmer months, then cozy up by the fire as winter paints the landscape in white. Don't miss this opportunity to own your piece of Vermont paradise!

Listed by Michael England of Michael England Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity 

Copyright 2025 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 February 11, 2025 1:37 AM EST