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Jamaica VT Real Estate

Named after the Natick word for “beaver”, the town of Jamaica is located in the southern Vermont region of Windham County. Included in the town are the villages of East Jamaica and Rawsonville. The town is also home to Jamaica State Park, noted for its exceptional beauty, camping sites, and hiking; the park includes Hamilton Falls, one of Vermont’s tallest waterfalls. 

Search the latest real estate in Jamaica, Vermont with Maple Sweet Real Estate. Find the right property for you from a variety of listings. ​Register to save your favorite listings and you can get email notifications when similar properties are posted. Have an account? Log in here.

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370 Fischer Lane Jamaica VT 05343

Jamaica, VT370 Fischer Lane

Price$9,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5015744

  • Residential Single Family
  • Full Bath 7
  • Construction Existing
  • 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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

662 Howe Farm Road Jamaica VT 05343

Jamaica, VT662 Howe Farm Road

Price$2,399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4972272

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • 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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

251 Pratt Bridge Road Jamaica VT 05343

Jamaica, VT251 Pratt Bridge Road

Price$2,000,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5003633

  • Residential Single Family
  • Full Bath 7
  • Construction Existing
  • 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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

251 Pratt Bridge Road Jamaica VT 05343

Jamaica, VT251 Pratt Bridge Road

Price$2,000,000The price has recently decreased

MLS Number 5003634

  • Commercial
  • Year Built 2002
  • Square Feet 8,364
  • Acreage 16.05
  • PricePerSqFt 239.12

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

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

West Hill Road South Jamaica VT 05343

Jamaica, VTWest Hill Road South

Price$1,900,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5006431

  • Land
  • Acreage 591
  • Utilities None
  • PricePerSqFt 3214.89
  • Zoning none

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3732 Vt Route 30 Jamaica VT 05343

Jamaica, VT3732 Vt Route 30

Price$1,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5002491

  • Residential Single Family
  • Full Bath 11
  • Construction Existing
  • Bedrooms 15
  • Bathroom 14

Nestled in the quaint Vermont village of Jamaica this charming Estate Compound features two beautiful antique dwellings each with five bedrooms exuding timeless character and New England charm. Around every corner your eye catches a fireplace. Enter the third dwelling to an updated kitchen, living space and additional bedrooms. The warm inviting cottage awaits that special guest. In addition the property boasts a luxurious in-ground swimming pool, perfect for summer relaxation and gatherings. A large storage building finishes out the estate. Located in prime ski country, this is an ideal retreat for winter sports enthusiasts, offering both historic elegance and modern amenities in a picturesque setting. Walk to Jamaica State Park, West River Provisions, Library and Post Office! The Stratton ski resort and many other southern Vermont attractions are just a short drive away. Come see what possibilities await you! This unique Estate Compound provides a rare opportunity to own a piece of Vermont's rich heritage while enjoying all-season recreational activities. An added feature-automatic generator for peace of mind. Video available on request. This property is two separate parcels and can be subdivided.

Listed by Sandy Laserte and Elyn Bischof of Berkshire Hathaway HomeServices Stratton Home

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3732 Vt Route 30 Jamaica VT 05343

Jamaica, VT3732 Vt Route 30

Price$1,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5002492

  • Multifamily
  • Units 4
  • Bathroom 11
  • Acreage 1.26
  • Square Feet 11,923

Nestled in the quaint Vermont village of Jamaica this charming Estate Compound features two beautiful antique dwellings each with five bedrooms exuding timeless character and New England charm. Around every corner your eye catches a fireplace. Enter the third dwelling to an updated kitchen, living space and additional bedrooms. The warm inviting cottage awaits that special guest. In addition the property boasts a luxurious in-ground swimming pool, perfect for summer relaxation and gatherings. A large storage building finishes out the estate. Located in prime ski country, this is an ideal retreat for winter sports enthusiasts, offering both historic elegance and modern amenities in a picturesque setting. Walk to Jamaica State Park, West River Provisions, Library and Post Office! The Stratton ski resort and many other southern Vermont attractions are just a short drive. Come see what possibilities await you! This unique Estate Compound provides a rare opportunity to own a piece of Vermont's rich heritage while enjoying all-season recreational activities. An added feature-automatic generator for peace of mind. Video available on request. This property is two separate parcels and can be subdivided.

Listed by Sandy Laserte and Elyn Bischof of Berkshire Hathaway HomeServices Stratton Home

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

42 Blackberry Lane Jamaica VT 05343

Jamaica, VT42 Blackberry Lane

Price$965,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5004180

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • 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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

544 Dalewood Road Jamaica VT 05343

Jamaica, VT544 Dalewood Road

Price$799,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5014833

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 6
  • Bathroom 5

A short drive to Stratton Mountain Resort, walking distance to one of Vermont's most astounding natural swimming holes, and simply tranquil and peaceful this property allows you to embrace the Vermont life. This 6 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 gorgeous 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 sale. OPEN HOUSE, OCTOBER 13, SUNDAY 10AM-12PM!

Listed by Rachel Febbie of EXP Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2132 Vermont Route 30 Jamaica VT 05343

Jamaica, VT2132 Vermont Route 30

Price$699,000The price has recently decreased

MLS Number 5004353

  • Commercial
  • 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

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

660 Dalewood Road Jamaica VT 05343

Jamaica, VT660 Dalewood Road

Price$696,911The price has recently decreased

Est. Mortgage: $/month

MLS Number 4997275

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Incredible opportunity to have your very own turnkey Stratton Mountain escape! Located on a quiet road, 3.5 miles from the Village, this lovely home has generated a treasure trove of memories for the owner's family for the last several years. Enter from the comfort of the attached garage into a generous mudroom, and head up to the main level where you'll find a well appointed chef's kitchen and large adjacent dining area. Kick back and relax in the ambiance of your spacious living room with soaring cathedral ceilings, huge windows and efficient fireplace insert. Ensuite primary on the main level, a second ensuite primary and two more bedrooms on the finished lower level provide plenty of room to spread out. Bonus room located above the garage. Large wraparound deck for dining al fresco, or enjoy the Stratton mountaintop view with a favorite beverage in the warm embrace of your hot tub. There is also a whole house generator to ensure your continued comfort during the rare power outages. Detached second garage. Offered fully furnished.

Listed by Christopher Cummings of Cummings & Co

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

64 Gleason Farm Lane Jamaica VT 05343

Jamaica, VT64 Gleason Farm Lane

Price$675,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5000962

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

Welcome to this stunning home 20 minutes from Stratton Mountain! Also Mount Snow, Bromley Mountain, and Magic Mountain are all within 20 miles. The home has had one owner and been well maintained in this private setting. The yard offers a spacious feel with covered porches to access along with a storage shed and plant potting shed. Enjoy the outdoor firepit and ease of the 2 1/2 attached car garage. The home has 9 1/2 foot ceilings, beautiful natural light throughout, mountain views, a spacious first floor bedroom with ensuite full bath. Hardwood floors, new custom thermal shades throughout first floor, solid wood doors as well. On the first floor you will also enjoy the open flow of the kitchen, dining room and living room. First floor laundry and 1/2 bath await you. The landing to the second floor has an abundant amount of lighting for a sitting area reading nook. On the second floor has two large bedrooms with two oversized storage rooms along with a full bath with double sink vanity. Full basement with interior access and basement walk-up to the gorgeous yard. This could be a great space to finish as well if desired! So much to offer in this home!

Listed by Amy Gerrity-Parent of Amy Gerrity-Parent Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.32% last updated on 2024-10-10

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity 

Copyright 2024 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 October 14, 2024 2:53 PM EDT

 

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