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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. ‚ÄčRegister 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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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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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.89% last updated on 2024-07-11

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 William Raveis Winhall

{$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: 6.89% last updated on 2024-07-11

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 William Raveis Winhall

{$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: 6.89% last updated on 2024-07-11

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.

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

{$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: 6.89% last updated on 2024-07-11

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.

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

{$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: 6.89% last updated on 2024-07-11

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

000-5 Forrester Road Jamaica VT 05343

Jamaica, VT000-5 Forrester Road

Price$1,499,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 4940191

  • Land
  • Acreage 204.37
  • Utilities None
  • PricePerSqFt 7339.14
  • Zoning Residential

Property has a total of 201.37+/- acres, however, part of this property has a 134.37+/- acre parcel MLS#4940187 and a 67+/- acre parcel MLS#4940189. The 67 acre parcel has 11.3 acre Forrester Pond almost entirely on that parcel. This property would be perfect for development, investment, multi-family or single family dwellings. Permits will be necessary for development of this property. Current owners had begun the Act 250 process but it was never completed. Any documents the current owners have can be made available to an interested buyer/s. There are at least two drilled wells on the property done as a prerequisite for an Act 250 permit. There is approximately one mile of gravel road into the property and a large gravel pit. One of a kind large parcel properties remaining in Jamaica only minutes to Stratton Mountain Sun Bowl and within a short drive to three other major ski areas including Mount Snow, Magic Mountain and Bromley. Located on a beautiful country road and close to all major recreational activities available in Southern Vermont. Owner is willing to sell up to 5 lots with the sizes of the acreage to be decided by the purchaser/s.

Listed by Ginny Read of Read Realty LTD

{$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: 6.89% last updated on 2024-07-11

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

498 Goodaleville Road Jamaica VT 05155

Jamaica, VT498 Goodaleville Road

Price$1,150,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5003781

  • Residential Single Family
  • Full Bath 6
  • Construction Existing
  • Bedrooms 8
  • Bathroom 6

498 Goodalville Road is made up of three residential spaces, and a barn, on 24 acres. This incredible value is just down the road from the intersection of Route 100 and Route 30 in Rawsonville, minutes to Stratton, Bromley, and Magic Mountains. The 1860 Farmhouse sits overlooking the river. The three bedroom structure was lifted and a new foundation poured, modernizing the old structure while respecting its origins. The garage was once an art studio, and currently has an apartment, which is adjacent to the barn. The Schoolhouse was completed in 2009, and this structure incorporates the original schoolhouse that was on the property. The beams can be seen from the interior of the three bedroom, three bathroom modern style home. The history of this property is special. Former owner Meyer Schapiro has been called “one of the most important art historians of the twentieth century.” The current owners have respected the history by restoring the structures and creating more space to be inspired. Photos to be added of the Farmhoouse upon completing interior paint. Come take a look.

Listed by Christiane Carroccio of TPW 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:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.89% last updated on 2024-07-11

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$999,999The 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 William Raveis Winhall

{$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: 6.89% last updated on 2024-07-11

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

139 Worden Road Jamaica VT 05343

Jamaica, VT139 Worden Road

Price$999,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4996412

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,139

This country retreat is a rare find. Private, yet within walking distance of a village and a state park! Close to hiking, skiing, and kayaking. Surrounded by 25 acres of mown fields and woodlots, the open floor plan and huge windows highlight the mountain views. Watch wildlife from the 700-sf deck. New post-and-beam horse barn and large fenced pastures. Its solar-passive design takes it through the winter on one oil delivery. On-demand generator, covered parking, deep artesian well.

Listed by Carrie Mathews of William Raveis Winhall

{$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: 6.89% last updated on 2024-07-11

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

000-5 Forrester Road Jamaica VT 05343

Jamaica, VT000-5 Forrester Road

Price$949,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4940187

  • Land
  • Acreage 134.37
  • Utilities Other
  • PricePerSqFt 7062.59
  • Zoning Residenteial

This property has 134.37+/- acres but also adjoins another parcel of 67+/- acres (MLS#4940189) which contains most of 11.3+/- acre Forrester Pond. Property can be subdivided for development, investment, multi-family or single family residential dwellings. Permits will be necessary for development of this property. Current owners had begun the Act 250 process but it was never completed. Any documents the current owners have can be made available to an interested buyer/s. There are at least two drilled wells on the property done as a prerequisite for an Act 250 permit. There is approximately one mile of gravel road into the property and a large gravel pit. One of the few remaining large parcels of land for development, minutes to Stratton Sun Bowl and within a short drive to three other major ski areas including Mount Snow, Magic Mountain and Bromley. Located on a beautiful country road and close to all major recreational activities available in Southern Vermont. Also available with a total of 204.37+/- acres MLS#4940189 for $1,499,900.00. The owner is willing to sell up to 5 lots with purchasers deciding the amount of acreage they wish to purchase.

Listed by Ginny Read of Read Realty LTD

{$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: 6.89% last updated on 2024-07-11

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, Unit 16

Price$949,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4996984

  • Residential Single Family
  • Full Bath 4
  • Construction Existing
  • Bedrooms 6
  • Bathroom 5

Minutes to the Stratton Mountain Resort, this residence boasts six bedrooms and four and half bathrooms situated on over 7 private acres in the pristine Green Mountains of Vermont. Enjoy the surrounding woods and trails as well as close proximity to Pikes Falls. The living room and dining area provide ample space for entertaining. The downstairs features four bedrooms and two bathrooms as well as a great den for the kids. This home's cozy wood burning fireplace is great for those cold winter nights and the warmth of the pellet stove keeps the chill out. Great outdoor spaces abound including multiple decks and firepit. The two car garage features great parking and plenty of storage space as well as an unfinished second floor that could be easily converted into a game room. The property has the ability to be subdivided. This is a must see vacation getaway!

Listed by Timothy Mich Doddridge of Stratton 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:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.89% last updated on 2024-07-11

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

366 Stone Hedges Road Jamaica VT 05343

Jamaica, VT366 Stone Hedges Road, Unit 8

Price$875,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5000872

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

Embrace a lifestyle of sustainability and innovation! This remarkable custom-built home seamlessly integrates energy-efficient systems with exquisite design elements. Harnessing Geothermal and Solar Power, the home not only minimizes its environmental footprint but offers the opportunity to embrace a net-zero lifestyle, ensuring eco-friendliness and long-term cost savings. Perched on a knoll and spanning 7.0 acres w/panoramic mountain views & a private pond, perfect for your country living dreams. Step inside and be greeted by a masterful blend of craftsmanship & thoughtful design. An expansive main living area boasts stamped concrete flooring w/radiant heat, providing durability and comfort. The post-and-beam design elements exude rustic charm. The heart of the home, the custom chef's kitchen, is a culinary haven featuring top-of-the-line appliances anchored by an artistically designed staircase highlighting striking metal features. Outdoor living spaces abound, from the covered front porch ideal for morning coffee to the expansive stone patio with raised beds for cultivating your own organic bounty. A screened porch off the main living is a peaceful retreat to enjoy the stunning mountain views. With ample space for family and friends that includes two mudrooms, an oversized two-car garage, a versatile office, lower-level walk-out game room and a charming Vermont-style Sugar Shack nestled on the property. Just a quick drive to all area resorts and amenities. A unique home!

Listed by Helen Nault of Wohler Realty Group

{$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: 6.89% last updated on 2024-07-11

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 July 15, 2024 5:53 PM EDT

 

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