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Jamaica VT Real Estate - Residential Property

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Below, browse residential homes for sale in Jamaica, VT. To save your favorite listings and receive status notifications, be sure to register today. For an alternative way to explore homes, you can build a custom search. Feel free to contact Wohler Realty Group with any questions or to set up a property showing!

Tour Homes for Sale in Jamaica VT

Jamaica, Vermont is a hidden gem located in Southern Vermont's Green Mountains, offering a unique blend of natural beauty and small-town charm. The town features numerous hiking trails, including the famous Hamilton Falls, which boasts a 125-foot cascading waterfall. Jamaica's idyllic Main Street boasts several quaint general stores and charming country inns. Foodies will also find their spot in Jamaica with several dining establishments featuring farm-to-table cuisine and delicious handcrafted brews. Jamaica's annual Wildflower Festival, which celebrates the spring blooms in the region, is another must-attend event.

Browse Jamaica, VT Real Estate By Property Type:
Commercial | Multi-Family | Condos | Land | Rentals

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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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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

3796 Vt Route 30 Jamaica VT 05343

Jamaica, VT3796 Vt Route 30

Sale Price$371,195

Sold

MLS Number 4988549

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 3,169

3-4 bedroom Jamaica Village home features 2 additional home office spaces, plus den! Flexible floor plan spans three full finished stories, ample room for customization to suit your lifestyle needs. The open kitchen/living/dining w/ high ceilings & exposed beams and lots of light leads to both a new deck and covered side porch. New wood stove in the living area and wood floors throughout the home as well as charming finish details create a feel of timeless comfort and warmth. With a history as rich and eclectic as the Village itself, this property has been transformed from a home for early settlers to the town post office, phone office, to an artists studio and retail space, catering business with commercial kitchen, rental income use and now back to an updated single family home. Newer roof and windows, 3 bedroom septic with maintenance history, drilled well, updated kitchen and appliances- all of the modern systems while retaining that old home charm. Additionally, there is a back yard ( property is surveyed! ) w/ underground dog fence and ample driveway & street parking. Whether you're seeking a permanent residence, a lucrative investment, or a creative haven, this historic property offers a timeless opportunity to become part of Jamaica's vibrant community. With its storied past and versatile layout, this home is ready to transform into the next owner's unique vision or remain the perfect Vermont oasis, just as it is.

Listed by Jacki Murano of Southern Vermont Realty Group

Listing Sold by 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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5807 Pikes Falls Road Jamaica VT 05343
Sold

MLS Number 4986880

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 476

Just a 4 minute drive from Stratton's Sun Bowl, this will be your cozy weekend getaway! Boasting lovely winter views, this 1 bedroom camp/cabin style home comes with a large indoor and a huge outdoor fireplace, as well as a separate, large outbuilding/shed with a woodburning stove. This home will need some TLC, but has so much potential for such an amazing location!

Listed by Tg Glazer of William Raveis Winhall

Listing Sold by Wohler Realty Group

$
$
%
$/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.

Ask A QuestionMore Details

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 May 25, 2024 6:23 AM EDT