Previous Previous ImageNext Next Image
Slideshow Divider

Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

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.

For more information, any questions you may have & to schedule a show, please feel free to give us a call or contact us online.

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
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3,569

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

{$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: 6.9% last updated on 2024-02-22

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 4960034

  • Land
  • Acreage 591.09
  • Utilities None
  • PricePerSqFt 3214.4
  • Zoning Rural

This 600+/- acre private, unrestricted property is located in the Southern Green Mountains in the town of Jamaica, Vermont near Stratton Mountain, Bromley, and the newly reconstituted Magic Mountain ski areas. The Southern Green Mountains region is a combination of High Peaks, high plateaus, and the property has a steep drop off to the west allowing dramatic view from its two peaks, one of which is a named peak of College Hill with its 2,100' elevation. College Hill is a woodland property that has not been timbered since before the owners purchased the property in 1953. There are 3 small streams that originate on the property and run into Ball Mountain Brook which feeds the West River. A variety of trails run throughout and one terminates at the top of College Hill offering incredible views. Old logging roads on the property can be used for a variety of recreational activities, including mountain biking, snowshoeing, and hiking. A forest management plan describing the various timber stands is available. The property is not in the VT Current Use program. Jamaica is known for its picturesque landscapes and natural beauty. The area is surrounded by the lush Green Mountains, which include pristine forests, and meandering rivers. If you enjoy outdoor activities like hiking, skiing, fishing, or simply appreciating nature, Jamaica offers a stunning backdrop for these pursuits.

Listed by Wade Weathers and Averill Cook of LandVest,Inc-Burlington

{$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: 6.9% last updated on 2024-02-22

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: 6.9% last updated on 2024-02-22

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

1189 Cole Pond Road Jamaica VT 05343

Jamaica, VT1189 Cole Pond Road

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

Est. Mortgage: $/month

MLS Number 4967925

  • Residential Single Family
  • Square Feet 3,363
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5

Experience this waterfront escape in Jamaica, Vermont! This unique property rests on a private .6-acre lot directly on Cole Pond. Only a short drive to Stratton Mountain's base lodge, making it a prime location for all season mountain fun. Bring your kayaks, paddle boards, and canoes, or enjoy the floating dock propelled by an electric motor, allowing you to relax and soak in the incredible views. The house features a spacious 4 bedroom, 3.5 bathroom layout that is perfect for entertaining. Craftsmanship shines through this custom-built home, showcased in its meticulous design and premium finishes. Inside, two distinct living areas provide ample space for leisure and entertainment. Sunlight streams in through large windows, seamlessly merging indoor and outdoor living. The heart of the home is the open kitchen and dining area with glass sliders providing direct access to the deck offering picturesque water views for memorable meals. Rustic charm emanates from a two-story field stone chimney and wood beams, harmonizing with the natural surroundings. An attached 2-car garage includes a studio apartment with private bathroom above, adding extra room for guests or a private workspace. Outside, relish the property's well-tended gardens. Immerse yourself in the ultimate waterfront living at this meticulously designed retreat overlooking Cole Pond. Delayed Showings until 9/6/23. Please no drive-bys

Listed by Jessica Flannery and Andie Fusco of Four Seasons Sotheby's Int'l 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: 6.9% last updated on 2024-02-22

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 4959049

  • Residential Single Family
  • Square Feet 3,840
  • Bedrooms 5
  • Construction Existing
  • Bathroom 5

Welcome to Sweet Berry Farm, a picturesque farmhouse nestled in the charming town of Jamaica, Vermont. This extraordinary property seamlessly blends historical charm with modern updates, offering a truly enchanting living experience. The mature apple trees, blueberry bushes, pear trees, blackberries, and grapes will satisfy any sweet tooth! Originally built in 1850, this farmhouse has stood the test of time and carries with it a rich sense of history. The well-preserved original features showcase the craftsmanship of the era, while a thoughtfully designed new addition provides contemporary comfort and functionality. With five bedrooms, there is ample space for family, friends, or guests to enjoy the serene countryside surroundings. Each room exudes warmth and character, with details such as exposed beams, original hardwood floors, and a cozy woodstove fireplace that invites relaxation. Situated on a generous 5.7 acre plot of land, Sweet Berry Farm boasts three outbuildings that can be utilized for various purposes. Whether you envision a workshop, artist's studio, or additional storage, these versatile spaces offer endless possibilities to cater to your specific needs. One of the remarkable features of this property is its proximity to Stratton Mountain. Imagine waking up to the surrounding mountains, then enjoying a day of skiing or snowboarding, just a short distance away. In the warmer months, explore the area's hiking trails, bike paths, and nearby ponds.

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: 6.9% last updated on 2024-02-22

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: 6.9% last updated on 2024-02-22

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$875,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4975070

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,280

Incredible opportunity to have your very own turn key Stratton Mountain escape! Located on a quiet road, less than 4 miles to the resort, 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 hottub. 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

{$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: 6.9% last updated on 2024-02-22

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

747 Cole Pond Road Jamaica VT 05343

Jamaica, VT747 Cole Pond Road

Price$795,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4981061

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,126

OPEN HOUSE this Friday 1/12/24 2- 4 PM! Welcome to the epitome of comfort and tranquility at this meticulously maintained 3-bedroom, 4-bath home on 15 private acres. When you step into the heart of the home, a cathedral living room adorned with a stone fireplace you immediately feel the inviting ambiance. The kitchen, featuring granite countertops and new appliances, is a culinary haven that seamlessly blends style and functionality. Embrace outdoor living with al fresco dining or enjoy the hot tub while relaxing under the stars. Explore the natural wonders of the property, including a soothing stream, two ponds, and a greenhouse for cultivating your green thumb. Gather around the fire pit for cozy evenings under the open sky. This home is a perfect fusion of modern convenience and serene country living, it includes deeded access to Cole Pond with the option for launching and storing your (non-motorized) boats and a dock to enjoy swimming in the warmer months. The attached garage is perfect for quick access after a day on the nearby ski slopes or golf course. There is ample storage in a dedicated shed. Your dream home awaits, where every detail reflects a commitment to quality and comfort.

Listed by Lavinia Lee Brown and Nancy Jensen of Four Seasons Sotheby's Int'l 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: 6.9% last updated on 2024-02-22

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

000-5 Forresteer Road Jamaica VT 05343

Jamaica, VT000-5 Forresteer Road

Price$649,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 4940189

  • Land
  • Acreage 67
  • Utilities None
  • PricePerSqFt 9700
  • Zoning Residential

This property has 67+/- acres and most of the 11.3+/- acre Forrester Pond and adjoins another parcel of 134.37+/- acres (MLS#4940187). Property can be subdivided for development, investment, multi-family or single family residential dwellings. Permits will be necessary for development of this property. One of the few remaining large parcels of land for development in the town of Jamaica and within minutes to Stratton Mountain Sun Bowl and 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. Both parcels with a total of 201.37+/- acres can be purchased for 1,499,900 (MLS#4940191). Owner is also willing to sell up to 5 lots with the acreage 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: 6.9% last updated on 2024-02-22

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

1308 Turkey Mountain Road Jamaica VT 05343

Jamaica, VT1308 Turkey Mountain Road

Price$339,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4980332

  • Land
  • Acreage 129
  • Utilities None
  • PricePerSqFt 2627.91
  • Zoning unknown

Within 15 miles of Stratton Mountain Resort find this large parcel of land with a small cabin and long frontage on a state stocked trout brook! A substantial bridge crosses Turkey Mountain Brook and gains access to this country parcel. A small cabin was added in 2019 and placed beside the brook for the soothing sounds of nature, the cabin is currently in the flood plain, it is on piers and can be moved to a different site on the property if desired. An older garage remains in what was once a house site, the mobile home was removed many years ago, electric power, phone line remains onsite. The land is in the Current Use Program with approximately 121 acres in Jamaica and about 8 in Townshend. Two separate house sites were engineered and approved by the state in 2007, these are included in the documents but will need to be updated as that area is now in the flood zone. A pond and an old foundation are near these sites. They are on the level section of the land with the topography getting steeper behind these sites. The owners have used the old logging roads for hiking trails with acres and acres of woodlands to enjoy! A neighbor shares the bridge with a written agreement in place, a driveway/road was installed in the past 10 years by the owner that shares the bridge, this allows some access to this property for logging purposes.

Listed by Susan LeCours and Will Cronin of Barrett & Valley Assoc. Inc

{$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: 6.9% last updated on 2024-02-22

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

35 Copeland Lane Jamaica VT 05343

Jamaica, VT35 Copeland Lane

Price$327,500The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4981916

  • Residential Single Family
  • Bathroom 1
  • Construction Existing
  • Bedrooms 2
  • Square Feet 1,152

This meticulously crafted turn key 2-bedroom, 1-bath A-frame home showcases the timeless beauty of cedar construction and diamond paned windows. Situated on one-acre, this property offers tranquility and charm. The exterior, sided in cedar, not only provides durability but also contributes to the home's warm and inviting aesthetic. Recent updates, including a recently installed roof and fresh coat of paint inside and out. The open-concept living space on the main floor features a comfortable living area, perfect for unwinding after a day on the nearby slopes of Mount Snow and Stratton. Large windows allow natural light to flood the space and warmed by the wood stove. The kitchen complements the charm of the A-frame architecture. The first-floor bedroom, provides convenience and accessibility. Venture upstairs to discover the second bedroom, with unique angles and the unmistakable character of an A-frame structure that sleeps four. The one-acre lot provides space for outdoor activities and includes two out buildings for additional storage. Whether you're seeking a weekend getaway or a year-round residence, this A-frame retreat in Vermont is a rare find. Embrace the charm of cedar craftsmanship, revel in the recent updates, and create lasting memories in a home that perfectly blends rustic elegance with modern comfort.

Listed by Betsy Wadsworth of Four Seasons Sotheby's Int'l 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: 6.9% last updated on 2024-02-22

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

3104 West Hill Road Jamaica VT 05343

Jamaica, VT3104 West Hill Road

Price$299,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4975301

  • Land
  • Acreage 14
  • Utilities None
  • PricePerSqFt 21357.14
  • Zoning r2 housesite

Your Vermont dream begins here! This 14+/- acres of land provide space for your vision to unfold, whether it's building your dream home, creating a sustainable homestead, or simply relishing in the beauty of untouched nature. Driveway and house site with views. State Wastewater Permit for 3-bedroom single-family home for up to 6 occupants.

Listed by Andie Fusco of Four Seasons Sotheby's Int'l 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: 6.9% last updated on 2024-02-22

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 February 27, 2024 10:53 PM EST

 

100 Acres in Burke

5 BR, Near Jay Peak, $1,999,000 Details

1852 Classic Farmhouse

6 BR, 204 +/- AC $1,995,000 Details

 

127 Acres, Barn @ Okemo

5BR Renovated Rustic $9,995,595 Details