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Jamaica VT Real Estate

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Below, browse all real estate in Jamaica. You'll find a variety of homes, condos, land, and more. Contact a Wohler Realty Group Agent today to chat about your real estate needs! Search smarter: Register to save your favorite listings and save your search to receive updates when similar listings hit the market.

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The charming town of Jamaica is just 7 miles to the Stratton Mountain Access Road. Many Stratton skiers travel the I-95 corridor to reach the Mountain via picturesque Route 30 which winds its way through valleys that are particularly captivating in the fall as the leaves turn and the colors burst from the trees. 

Jamaica has maintained the character and charm of old Vermont. Located near the confluence of the scenic West River and Ball Mountain Brook, recreational activities include the Ball Mountain Dam release for experienced kayakers and camping and hiking at Jamaica State Park. The small town is surrounded by homes and land that are vintage Vermont, and its simplicity can be appreciated by those who leave the noise and bustle of the city behind.

660 Dalewood Road Jamaica VT 05343

Jamaica, VT660 Dalewood Road

Price$819,900

Est. Mortgage: $/month

MLS Number 4997275

  • 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, 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 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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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544 Dalewood Road Jamaica VT 05343

MLS Number 4996984

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 2,217

Minutes to the Stratton Mountain Resort, this residence boasts six bedrooms and four and half bathrooms situated on over 7 private acres. 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 Vermont 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 Vermont getaway!

Listed by Timothy Mich Doddridge of Stratton Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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1706 Vt Route 30 Jamaica VT 05343

Jamaica, VT1706 Vt Route 30

Price$445,000

Est. Mortgage: $/month

MLS Number 4996808

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,504

This truly charming home offers a unique blend of modern updates, tranquil natural surroundings, and captivating features for the nature enthusiast. The recently remodeled kitchen and adjoining dining area set the stage for comfortable living, flowing into a spacious living area and cozy sitting area. The upper level is complete with a primary bedroom with easy access to the back deck and a full bath nearby. Head downstairs to a generous mudroom that leads to a well-appointed office, two additional bedrooms, and another full bath, providing ample space for living and working. The property also features a pole barn garage with room for 2 cars and additional storage. The expansive deck, lovely screened-in gazebo, and screened-in tree house are perfect for hosting gatherings or simply enjoying the outdoors. Relax among the meticulously maintained landscaping, dynamic displays of ledge rock, and the soothing sounds of a babbling brook in the yard. Explore the extensive walking trails throughout the back half of the property, and don't miss Jamaica's historic "Balancing Rock" at the north end of the property. Strategically located less than 10 minutes to the Stratton access road, and a short drive to Bromley, Magic, Mt. Snow or Okemo. Great hiking abounds at nearby Jamaica State Park, Ball Mountain Dam and the West River Trail. Inspection report will be shared with qualified buyers making an offer. SHOWINGS WILL BEGIN MONDAY 5/27/24!

Listed by Christopher Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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39 Depot Street Jamaica VT 05343

Jamaica, VT39 Depot Street

Price$695,000

Est. Mortgage: $/month

Open House

MLS Number 4996607

  • Residential Single Family
  • Next Open House: Sat 05/25 11:00 am. to 2:00 pm.
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3

If a picture is worth a thousand words, you won't want to miss this incredible property. The pictures tell it all. This hidden Village gem is tucked away in a pastoral setting under a majestic maple with sweeping lawn, perennial plantings, stone walls, picket fence, patio and shaded garden seats. Located right in the in the heart of a Vermont village with its conveniences and sense of community, yet retaining a true sense of nature. Contemplate the scenic setting from the rocking chair under the covered front porch. Amble around the corner to village shops, Jamaica Market, and nearby dining. Meander along the river or hike nearby trails. Enjoy all the close by winter activities and sports. Though the house has been beautifully renovated, the charm and character have been lovingly retained with wood floors, original fixtures and architectural features. With an open floor plan for easy living and entertaining, the 4 distinctive bedrooms, custom kitchen with breakfast bar, library, corner study and vaulted loft invite you to linger, lounge and unwind when you move indoors. An attached storage shed houses all your equipment, gear and garden furniture. Plus a 1,400 sq. ft. two story barn apartment with private entrance, 2 bedrooms, spacious loft, convenient kitchen and wood floors offer extended living opportunities and income potential. A remarkable opportunity to own an outstanding, once in a lifetime property. Delayed showings until May 25th. OPEN HOUSE FROM 11-2.

Listed by Thom Dahlin of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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106 Vt Route 30 Jamaica VT 05343

Jamaica, VT106 Vt Route 30

Price$349,000

Est. Mortgage: $/month

Open House

MLS Number 4996480

  • Land
  • Next Open House: Sat 05/25 11:00 am. to 1:00 pm.
  • Acreage 23
  • Utilities Gas - LP/Bottle
  • PricePerSqFt 15173.91

Discover unparalleled privacy and modern living with this immaculate 3-bedroom manufactured home on a sprawling 23-acre land parcel in Jamaica, VT. Manufactured in 2021, this home features an open-plan living space with a modern kitchen, dining nook, and a comfortable living room, complemented by two full bathrooms. Additional amenities include a charming porch and a hot tub room at the back. Situated at the top of a hill, the property offers stunning scenic views and acres of woodlands, ensuring complete privacy. With septic, water, and electric already in place, this property is not only perfect as-is but also offers an ideal foundation for building your dream home.In addition, this property is conveniently located to Stratton, Bromley and Magic Mountains as well as the outlets in Manchester VT.

Listed by Joseph Castelluccio of William Raveis Winhall

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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139 Worden Road Jamaica VT 05343

Jamaica, VT139 Worden Road

Price$1,200,000

Est. Mortgage: $/month

Open House

MLS Number 4996412

  • Residential Single Family
  • Next Open House: Sun 05/26 11:00 am. to 1:00 pm.
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

Discover the charm of this mountain retreat, now available for the first time in over 80 years. The solar-passive home, boasting an open floor plan and three finished stories, features expansive windows and French doors seamlessly blending indoor and outdoor living. A 700 sq ft deck provides stunning views of pastures and nearby mountains, ideal for summer dining under a retractable awning amidst mature fruit trees and vibrant gardens. Set on 25 tranquil acres, including 12 acres of mown fields bordered by forest, a brook, and a pond, this property offers a Vermont paradise for both humans and animals. Modern comforts include a recently upgraded mudroom, a third-floor bedroom or office, and a media lounge overlooking the living room. The kitchen, with stainless appliances and a large island, combines convenience with style. Advanced systems like a standing-seam solar-ready metal roof, a full house generator, and an oil-burning furnace supplemented by a wood-burning stove ensure comfort and security. Despite its serene setting, proximity to the village, Jamaica State Park, and skiing at Stratton, Bromley, and Magic Mountains adds to its appeal, making it the perfect Vermont retreat for all seasons. Equine enthusiasts will appreciate the brand-new post and beam barn, completed in 2022, featuring stalls for two horses and ample space for them to roam freely. The property also includes a chicken coop, providing fresh eggs daily, enhancing the rural lifestyle this retreat offers.

Listed by Carrie Mathews of William Raveis Winhall

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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276 Bourbon Run Jamaica VT 05343

Jamaica, VT276 Bourbon Run

Price$400,000

Est. Mortgage: $/month

MLS Number 4994923

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,293

Bourbon Run, wonderful 3-bedroom 2-bath home. Located 10 minutes to Stratton Resort, 15 minutes to Bromley and Magic Mountain, and just 30 minutes to Okemo and Mount Snow - all the options within a short drive for winter and summer activities galore. Enjoy the Jamaica State Park, Lowell Lake, and Gail Meadow for paddling and SUP in the summer months as well, maybe even throw a line in, great bass fishing. Enter the home to a dedicated mud room with plenty of gear storage and space. Step into the open concept kitchen, dining, and living area, with a wood burning brick fireplace. The cathedral ceilings pair with the large windows to offer natural light throughout. The master and guest bedrooms are to the rear of the home and upstairs is the spacious 3rd bedroom “loft”. Come see!

Listed by Michael England of Michael England Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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926 Dalewood Road Jamaica VT 05343

Jamaica, VT926 Dalewood Road

Price$500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4994496

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,997

Dalewood Road, be part of the Stratton Resort community. Wonderful 3-bedroom 2-bath home, just minutes to Stratton. This Smart WiFi home has views of the Stratton Trails from the property and abuts the Winhall Forest. Enter the lower level to a mud room with nice slate floors and plenty of room...from there walk through the family room, past the lower bedroom, and up the hardwood stairs to the main living area. Stay warm and cozy with the gas fireplace in the living room and cathedral ceilings in the cooler months…or relax on the generously sized deck in the warmer months. The dining area is just inside from the deck as you walk through to the well-organized kitchen with granite counter tops, an island, and a breakfast bar. Beyond the kitchen is the master suite which has direct access to the hot tub. On the upper level, there is a spacious third bedroom “loft” with a sperate area for an at-home office. Stratton ROFR.

Listed by Michael England of Michael England Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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42 Pine Lane Jamaica VT 05343

Jamaica, VT42 Pine Lane

Price$490,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4991621

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,833

Gorgeous home with many updates! New roof installed 2020, new hot tub placed just off the front deck in 2020, new generator 2022. This home boasts four bedrooms, two baths with a loft and play area. The galley style kitchen connects both wings of the home where you'll find beautiful granite countertops and updated stainless-steel appliances. The large mudroom entryway offers a great place to drop boots, skies, any outdoor gear with the convenience of laundry right on the first floor. Nice wood floors cover the entire living and dining room space with cathedral ceilings and the focal point being the amazing wood burning fireplace! Floor to ceiling tinted windows with sliders leading out to a great deck space with enclosed split rail and wire fenced front yard. Three separate outbuildings, a shed for storing personal items, a woodshed to store firewood just off the side front deck for easy winter access and a large two car garage with storage above. Trails to play on and open area with expansive backyard to explore. Short drive to Stratton, Mount Snow, Bromley or Magic, just take your pick! Property being sold furnished.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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162 Upper Bear Lane Jamaica VT 05343
Active With Contract

MLS Number 4991543

  • Condo
  • Square Feet 1,425
  • Bedrooms 3
  • New Contruction Existing
  • Complex Bear Creek

This beautifully renovated home nestled in the tranquil setting of Bear Creek presents a rare opportunity for those seeking comfort and adventure in Vermont. Boasting three bedrooms and three baths, including two en-suite baths upstairs and a bedroom and bath on the main level, it offers ample space for relaxation and privacy. The focal point of the living/dining area is the magnificent stone fireplace, ensuring cozy gatherings, with unlimited firewood conveniently delivered to you and stacked in the wood closet right outside the front door. Located just minutes from the slopes of Stratton Mountain, outdoor enthusiasts will delight in the proximity to all-season enjoyment. During the winter months, take advantage of the convenient shuttle service to Stratton. But the allure of this home extends beyond winter sports. Spring, summer, and fall beckon with tennis matches on the courts and children exploring the playground. Cool off in the inviting swimming pool during the warmer months, or gather around the fire pit for cozy evenings throughout the year. Moreover, the present of a full-time caretaker ensures that every detail is taken care of, allowing you to fully immerse yourself in the Bear Creek lifestyle.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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1297 River Road Jamaica VT 05343

Jamaica, VT1297 River Road

Price$97,700

Est. Mortgage: $/month

MLS Number 4990586

  • Land
  • Acreage 6.2
  • Area Rural
  • Utilities Telephone Available
  • PricePerSqFt 15758.06

Unique! Do you love to camp? swim? fish?.....this may be it for you....Over 2000 feet of West River frontage with electric on site and just off pavement and at the intersection of 2 major access road to skiing and recreation! Much of the frontage is in flood plain and it is subject to flowage rights of the dam, but an amazing site! The current owner has had a Jamaica cottage for camping and the previous owner had a little trailer and shed. Put your feet up and watch the canoes go by in the white water of the spring dam release...or join them and take the challenge. You will love this little piece of Vermont, but do your due diligence for your own intended use so there are no surprises!

Listed by Christine Lewis of Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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8581 Vermont Route 30 Jamaica VT 05343
Active With Contract

MLS Number 4990181

  • Condo
  • Square Feet 691
  • Bedrooms 2
  • New Contruction Existing
  • Complex The Willows

Embrace Vermont in all season's, just 2 minutes away from Stratton Access Road, and 10 minutes from Jamaica State Park and the West River, you'll find skiing/boarding, paddling, swimming, hiking and biking, just to name a few! This charming 2 bedroom, 1 bathroom condo is the perfect cozy retreat and ensures you're always close to the action but still able to stay tucked away for some relaxation! We invite you to come and tour this intimate getaway for yourself!

Listed by Christina Dryden of Berkshire Hathaway HomeServices Stratton Home

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on May 23, 2024
* 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.

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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 May 25, 2024 7:23 AM EDT