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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.

201 Pratt Bridge Road Jamaica VT 05343

Jamaica, VT201 Pratt Bridge Road

Price$375,000

Est. Mortgage: $/month

Pending

MLS Number 4978031

  • Residential Single Family
  • Bedrooms 4
  • Construction Existing
  • Bathroom 2
  • Square Feet 1,590

Tucked away on a secluded country road, this delightful 4-bedroom, 2-bathroom chalet provides a sanctuary for those in search of peace and natural splendor. A mere 4 miles from the Stratton access road, this residence achieves an ideal fusion of seclusion and accessibility. The exterior exudes rustic charm, showcasing the timeless allure of the classic chalet design that warmly welcomes you. Upon entering, the embrace of two wood-burning fireplaces radiates warmth, creating a cozy atmosphere perfect for chilly mountain evenings. Designed with comfort in mind, this home features two living rooms, offering ample space for family gatherings or entertaining friends. Step outside, and the property provides expansive outdoor areas for activities or simply basking in the rejuvenating mountain air. Boasting an idyllic location on a private country road and close proximity to the Stratton access road, this chalet stands as the quintessential retreat for those desiring a harmonious blend of comfort, convenience, and the inherent beauty of Vermont's mountain landscape. Embrace the mountain lifestyle and make this chalet your new home.

Listed by Kevin Moran of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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200 Forrester Road Jamaica VT 05343

Jamaica, VT200 Forrester Road

Price$369,000

Est. Mortgage: $/month

Pending

MLS Number 4977395

  • Residential Single Family
  • Square Feet 1,554
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3

What a sweet log cabin to come home to nestled on 11.5 private acres off of Forrester Road within ten minutes to Stratton's Sun Bowl. Three bedrooms, two baths plus loft. Enter a very quaint interior with fireplace and wood stove. Lower floor offers an extra room, a utility room, second bath, laundry as well as sauna. Please note, the spa room off living room is in need of a new hot tub or remove and use as additional living space. If you are searching for that Vermont cabin in the woods super close to skiing and boarding yet away enough to enjoy privacy look know further. This is a win win purchase and you can be in before the holidays.

Listed by Terry Hill of Berkshire Hathaway HomeServices Stratton Home

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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3104 West Hill Road Jamaica VT 05343

Jamaica, VT3104 West Hill Road

Price$299,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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660 Dalewood Road Jamaica VT 05343

Jamaica, VT660 Dalewood Road

Price$875,000

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! Open House Saturday, 10/28, 10am - 1:00pm!

Listed by Christopher Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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662 Howe Farm Road Jamaica VT 05343

Jamaica, VT662 Howe Farm Road

Price$2,499,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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482 Pratt Bridge Road Jamaica VT 05343

Jamaica, VT482 Pratt Bridge Road

Price$595,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4972214

  • Residential Single Family
  • Square Feet 2,364
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing

Discover the perfect Vermont retreat! This 3-bedroom home, just 10 minutes from Stratton Mountain, near Bromley & Magic Mountain, and a quick half-hour drive to Mount Snow, is your gateway to the Green Mountains. Situated on a generous 1.4-acre lot, this residence offers a spacious mudroom with slate flooring and built-in cubbies for convenience. Upon entering the living room, your eyes will be drawn to the majestic fieldstone fireplace that stretches from floor to ceiling and the vaulted wood ceiling, infusing a rustic charm that's hard to resist. The tastefully renovated kitchen features granite countertops, stainless appliances, ceramic tile and a breakfast bar. The light and bright dining area is open to the kitchen and living room and accesses the private back deck with hot tub. The main level has a primary bedroom for easy living, while the upper level houses two generously sized bedrooms and a full bath. Both bathrooms have been upgraded with elegant granite tops and ceramic tile. The lower level is a haven for family enjoyment, with a den area equipped with built-ins, a perfect spot for kids to hang out, and a versatile office/bonus room and a laundry/utility room. Outside, the house was just painted and the property is professionally landscaped, creating an oasis of natural beauty and enhancing the curb appeal. Stay connected with high-speed internet and explore the nearby Jamaica State Park for hiking and camping adventures. Get it before it's gone.

Listed by Chad Lackey of Deerfield Valley Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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4769 Pike Falls Road Jamaica VT 05143

Jamaica, VT4769 Pike Falls Road

Price$169,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4970303

  • Land
  • Acreage 1.2
  • PricePerSqFt 140833.33
  • Zoning residential

A RARE find, this parcel could be considered Vermont's equivalent to an oceanfront property with it abutting one of the most beautiful, natural river falls and swimming holes in Southern Vermont. This special lot offers it's own path from the parcel down to the swimming hole and falls, which are part of the Conservation Society of Southern Vermont' s Land. Current owner has the 1.2 acre lot ready to roll with a state wastewater permit in place for a 3 bedroom home AS WELL as 1 bedroom detached dwelling, house plans for both, site plan, a roughed in driveway, and areas of the lot are already cleared. Besides the location being a spring, summer, and fall nature haven it is also only 5 minutes to your winter sports at Stratton Mountain Ski Resort! This property is truly special!

Listed by Rachel Febbie of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Pratt Bridge Road Jamaica VT 05143

Jamaica, VTPratt Bridge Road

Price$239,000

Est. Mortgage: $/month

MLS Number 4968630

  • Land
  • Acreage 12.97
  • Utilities Cable - Available
  • PricePerSqFt 18427.14
  • Zoning None

This wonderful 4 lot subdivision is close to Stratton and located on a well maintained road is ideal to build your dream home. Options are to develop all four sites and sell them or keep this as is for recreation and fun on 12.97+/- acres. Great investment opportunity as new homes are fast becoming a demand in the area. Waster water permit and a great driveway are already in place and power is right at the road. Don't pass this fabulous opportunity.

Listed by Daire Gibney and Susan LeCours of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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1189 Cole Pond Road Jamaica VT 05343

Jamaica, VT1189 Cole Pond Road

Price$1,000,000

Est. Mortgage: $/month

MLS Number 4967925

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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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00 Blackberry Lane Jamaica VT 05343-0173

Jamaica, VT00 Blackberry Lane

Price$92,500

Est. Mortgage: $/month

MLS Number 4967296

  • Land
  • Acreage 5.63
  • Utilities None
  • PricePerSqFt 16429.84
  • Zoning Residential

THIS LAND IS PERMITTED FOR A WASTE WATER SYSTEM for a single family residence with maximum Three (3) bedrooms and maximum of six (6) person occupancy on the approved lot. Also, the lot has a rough cut driveway onto the property off of Karen Drive. These feature making it easier to bring your Vermont home vision to life. Discover the beauty of Vermont with this incredible opportunity to build on this 5.63 acres of pristine land in the charming town of Jamaica. Just a short 15-minute drive away from the renowned Stratton Mountain Resort, this parcel offers the perfect blend of tranquility and convenience. Don't miss this opportunity to build your dream home in Vermont.

Listed by Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

80 Henderson Road Jamaica VT 05343

Jamaica, VT80 Henderson Road

Price$299,000

Est. Mortgage: $/month

MLS Number 4966090

  • Residential Single Family
  • Bedrooms 2
  • Construction Existing
  • Bathroom 2
  • Square Feet 1,122

The Dunbar Schoolhouse was built for school district number 6 about 1865, and was converted in 1959 to what it is today, which is a very cozy cottage with an abundance of old school character from the wide plank coffee bar to the exposed rafters. The main floor offers an open space concept with a country kitchen, the coffee bar, dining, plenty of living space to gather around the woodstove, 2 bathrooms, and washer/dryer. The second level has a loft area currently used for sleeping, and two charming bedrooms. New roof, new septic tank, new bathroom, new woodstove, and some new electrical since seller's ownership. The outside offers a hot tub deck and hook up! The schoolhouse- now ski house- is conveniently located between Stratton and Mount Snow Ski Resorts!

Listed by Rachel Febbie of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Lot E-2 Stratton Gate Road Jamaica VT 05343

MLS Number 4963718

  • Land
  • Acreage 10.09
  • Utilities None
  • PricePerSqFt 9811.69
  • Zoning none

Beautiful parcel nestled in the woods with over 10 acres of unimproved land only minutes to Stratton Mountain. Right of Way access is not currently driveable but can be accessed by walking to the property which is nicely sited off of a quiet dirt road ending in a cul de sac. Please note that buyer will need to do due diligence on electric, utilities, septic, etc. as the sellers have not done any permitting or testing. Wonderful opportunity to own a lovely piece of Vermont close to the West River and all of the recreational activities that Southern Vermont offers.

Listed by Penny Larson and Betsy Wadsworth of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.29% last updated on Nov 22, 2023
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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Copyright 2023 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 November 30, 2023 9:25 AM EST