Jamaica, VT Homes

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  /10

  $185,000

  • Land
  • 8 Acres
  • $23,125 per Acre

  4441 Vt Route 30, Jamaica, VT 05343

  Discover the potential of this serene and wooded 8.0± acre parcel, offering a peaceful setting and natural beauty just minutes from the heart of Jamaica Village. Currently being subdivided from a larger tract, the lot features a 5 Bedroom Wastewater Permit pending state approval and a survey in progress to finalize boundaries—laying the foundation for your future plans. An existing electric

  

  Trent Stephens

  Wohler Realty Group

  (802) 808-6056

  4441 Vt Route 30, Jamaica, VT 05343
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  /17

  $20,000 per month

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • House for Rent

  72 Depot St, Jamaica, VT 05343

  Seasonal Rental Available! Charming and cozy 1900 Cape available for winter rental from November through April. Located in a peaceful village setting, walk to the charming village of Jamaica. Only 15 minutes to Stratton Mountain. This 3-bedroom, 2-bath home offers the perfect ski-season escape with classic New England charm.

  Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  72 Depot St, Jamaica, VT 05343
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  /42

  $499,000 Sold Aug 29, 2025

  • 1,986 Sq Ft
  • $251/SF
  • 21 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1970

  168 Howard Rd, Jamaica, VT 05343

  This loving home has seen many years of enjoyment from its current owners. Four bedrooms, two and a half baths, large open kitchen dining area with a beautiful granite island to gather around. Separate living room space with beautiful stone fireplace and half bath all on the main floor. The four bedrooms with a lovely large primary suite with private bath, cathedral ceilings will be the perfect

  Julie Lowe Lowe's Real Estate, LLC

  168 Howard Rd, Jamaica, VT 05343
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  /35

  Est $410,908 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 3,169 Sq Ft

  3796 Vt Route 30, Jamaica, VT 05343

  3796 Vt Route 30, Jamaica, VT 05343
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  /41

  $8,950,000

  • 6 Beds
  • 10 Baths
  • 13,393 Sq Ft

  370 Fischer Ln, Jamaica, VT 05343

  Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

  Dia Jenks LandVest, Inc/Woodstock

  370 Fischer Ln, Jamaica, VT 05343
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  /14

  $17,500 per month

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • House for Rent

  4591 Vermont 30, Jamaica, VT 05343

  This is a delightful Winter retreat...After a long fun day of skiing come home to this warm and cozy, meticulously maintained 4 bedroom home that is in great shape. Just 8 minutes from Stratton access Rd.Upstairs there are 2.5 bedrooms , kitchen, and living room with wood burning fireplace. Downstairs is another full bedroom and a 2nd kitchen, full bath, laundry and family room with TV,

  Wilkie Bushby TPW Real Estate

  4591 Vermont 30, Jamaica, VT 05343
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  /16

  $130,000 Sold Aug 13, 2025

  • 1,331 Sq Ft
  • $98/SF
  • 12 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  272 Landman Ln, Jamaica, VT 05343

  Jamaica Landman Lane off Cole Pond Rd. This 2.7 acres has a 3 bedroom septic, electricity and spring. Nice location... 15 minutes to 3 major Ski Resorts and golf, 30 minutes to Manchester shopping and dining. Close to Jamaica State Park great hiking. Seller has asked that all buyer be pre qualified, as this most likely will need to be a cash sale. SOLD AS IS. Home is compromised. No entry.

  Mike England Michael England Real Estate

  272 Landman Ln, Jamaica, VT 05343
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  /39

  Est $388,267 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,081 Sq Ft

  3996 Vt Route 30, Jamaica, VT 05343

  3996 Vt Route 30, Jamaica, VT 05343
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  /15

  $775,000

  • Land
  • 51.93 Acres
  • $14,924 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /26

  $30,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,800 Sq Ft
  • House for Rent

  197 Monadnock View Ln, Jamaica, VT 05343

  Perfect private location only minutes to Ski resorts.Home could accommodate two families comfortably. Hot Tub, fireplace, towels and linens. Sleeping space for up to 10. Close to shopping and to Interstate 91. Beautiful home to spend the winter season at!

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  197 Monadnock View Ln, Jamaica, VT 05343
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  /54

  $759,000 Sold Aug 08, 2025

  • 2,600 Sq Ft
  • $292/SF
  • 24 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1985

  544 Dalewood Rd, Jamaica, VT 05343

  Exceptional Vermont Retreat – Turnkey & Fully Furnished! Welcome to this beautifully maintained 5-bedroom, 5-bathroom contemporary home, offering a perfect mix of spacious comfort and cozy charm. Nestled in a peaceful neighborhood, and just 4 miles from SunBowl and minutes from the base lodge, this home features three en-suite bedrooms,two additional bedrooms, and a flexible extra room ideal for

  Rachel Febbie EXP Realty

  544 Dalewood Rd, Jamaica, VT 05343
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  /32

  Est $309,534 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 576 Sq Ft

  3790 S Hill Rd, Jamaica, VT 05343

  3790 S Hill Rd, Jamaica, VT 05343
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  /11

  $595,000

  • Land
  • 68.89 Acres
  • $8,637 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /29

  $526,000 Sold Aug 08, 2025

  • 1,620 Sq Ft
  • $325/SF
  • 36 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1965

  176 Pratt Bridge Rd, Jamaica, VT 05343

  Meticulously maintained and in pristine condition, this exceptional home has been lovingly cared for by the same family for over 50 years. Set back on a level, tree-lined lot on a quiet dead-end road, the home offers serenity and privacy while still being just a short drive to Stratton Mountain. Oversized windows throughout flood the interior with natural light, highlighting the soaring cathedral

  Carrie Mathews Winhall Real Estate

  176 Pratt Bridge Rd, Jamaica, VT 05343
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  /18

  Est $593,220 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  155 Pratt Bridge Rd, Jamaica, VT 05343

  155 Pratt Bridge Rd, Jamaica, VT 05343
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  /8

  $320,000

  • Land
  • 34.53 Acres
  • $9,267 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /27

  $530,000 Sold Aug 08, 2025

  • 2,052 Sq Ft
  • $258/SF
  • 135 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1986

  69 Chapin Ln, Jamaica, VT 05343

  Welcome to Sugar Chateau- Nestled in the serene landscape of Southern Vermont, this enchanting 4-bedroom log home offers the perfect blend of rustic charm and contemporary comfort. Embrace the warmth and character with exposed beams and a welcoming atmosphere. Enjoy the convenience of modern amenities in a rustic setting, featuring a recently renovated kitchen and bathrooms. Custom new Anderson

  Tara van de Velde Four Seasons Sotheby's Int'l Realty

  69 Chapin Ln, Jamaica, VT 05343
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  /40

  Est $906,954 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,197 Sq Ft

  1223 Cole Pond Rd, Jamaica, VT 05343

  1223 Cole Pond Rd, Jamaica, VT 05343
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  /7

  $235,000

  • Land
  • 15.27 Acres
  • $15,390 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /27

  $1,300,000 Sold Jul 31, 2025

  • Land
  • 591 Acres
  • $2,200 per Acre

  • 136 Days On Market

  0 W Hill Rd S Unit 5006431, Jamaica, VT 05343

  Welcome to an exceptional opportunity in Jamaica, VT! College Hill, a 591-acre parcel, owned by the same family for 70 years, is a rare find in today's market. Unencumbered by permits or land use restrictions, this property offers limitless possibilities. The current owners have maintained its natural beauty, never logging the land, preserving its pristine condition. At the top of College Hill,

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  0 W Hill Rd S Unit 5006431, Jamaica, VT 05343
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  /33

  Est $481,198 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 848 Sq Ft

  1706 Vt Route 30, Jamaica, VT 05343

  1706 Vt Route 30, Jamaica, VT 05343
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  /44

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 4,193 Sq Ft

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly special Vermont retreat at 70 Hunter Lane, nestled in the private Cole Pond community of Jamaica. This exceptional residence offers over 4,200 square feet of living space, thoughtfully designed to blend comfort, luxury, and the natural beauty of its surroundings. Newer Stainless Steel appliances in kitchen!Featuring four spacious bedrooms, this home provides plenty of

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, Jamaica, VT 05343
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  /50

  $469,000 Sold Jul 25, 2025

  • 1,346 Sq Ft
  • $348/SF
  • 47 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 2003

  2194 Mowrey Rd, Jamaica, VT 05343

  Diamond in the rough! Don't miss this opportunity to own a property in Jamaica, Vermont that has so much to offer! This property has been absolutely stunning in the past! Perched on a hill overlooking a private pond, fields that used to be pastures where your animals can roam and you can take in the local ridgeline view of the beautiful Green Mountains of Vermont! This is a true log home with

  Julie Lowe Lowe's Real Estate, LLC

  2194 Mowrey Rd, Jamaica, VT 05343
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  /32

  Est $296,000 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 956 Sq Ft

  192 Howe Farm Rd, Jamaica, VT 05343

  192 Howe Farm Rd, Jamaica, VT 05343
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  /30

  $1,040,000

  • 5 Beds
  • 4.5 Baths
  • 3,363 Sq Ft

  1189 Cole Pond Rd, Jamaica, VT 05343

  Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts.The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1189 Cole Pond Rd, Jamaica, VT 05343
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  /22

  $360,000 Sold Jun 20, 2025

  • 1,430 Sq Ft
  • $252/SF
  • 112 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1960

  9 Mountain Acres Rd, Jamaica, VT 05343

  This charming ranch-style home, lovingly maintained for years, is ready for its next chapter. Ideally located at the entrance of the sought-after Mountain Acres neighborhood, it offers easy access to local activities while maintaining a peaceful retreat-like feel.Inside, five comfortable bedrooms and two baths provide ample space for family and guests. The open-concept living area, highlighted by

  Helen Nault

  9 Mountain Acres Rd, Jamaica, VT 05343
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  /21

  Est $348,324 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  60 River Rd, Jamaica, VT 05343

  60 River Rd, Jamaica, VT 05343
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  /35

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 2,370 Sq Ft

  5 Linscott Rd Unit 56, Jamaica, VT 05343

  This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 and a half baths has an inviting ambiance as well as appealing floor plan flow. Past the foyer with half bath is the open living concept with white oak hardwood floors. The glow and warmth of the raised hearth stone fireplace in the living area is shared from windowed dining area to bright kitchen with all new appliances,

  Diana Stugger Four Seasons Sotheby's Int'l Realty

  5 Linscott Rd Unit 56, Jamaica, VT 05343
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  /30

  $510,000 Sold Jun 05, 2025

  • 1,459 Sq Ft
  • $350/SF
  • 170 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  5600 Pikes Falls Rd, Jamaica, VT 05343

  Don't miss this amazing opportunity to own a cozy log cabin nestled in the woods off Pikes Falls road with close proximity to Stratton Mountain Resort. This home has been thoughtfully built, well maintained and loved for many years and is now awaiting its new owners. The property features 15 acres, a wood shed and a 19th century Pikes Falls School House, which can be used for extra storage or

  Jamie Wylie Stratton Real Estate

  5600 Pikes Falls Rd, Jamaica, VT 05343
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  /30

  Est $501,277 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft

  1973 Pikes Falls Rd, Jamaica, VT 05343

  1973 Pikes Falls Rd, Jamaica, VT 05343
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  /60

  $899,000

  • 5 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  Idyllic, Picturesque, Expansive, Vast Family Farm with outbuildings and Large Farmhouse! Known to some as Sweet Berry Farm the blueberries and blackberries are plentiful along with many other productive fruits trees, a grove of 20 mature apple trees with many over 30 years old, , flowers and veggies in the gardens. This location just off of Route 30 is perfect for ALL of your Vermont dreams and

  Steve Goldfarb Deerfield Valley Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
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  /34

  $338,000 Sold May 16, 2025

  • 1,296 Sq Ft
  • $261/SF
  • 100 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  6217 Vt Route 30, Jamaica, VT 05343

  Perched on a hill above the village of Jamaica, this inviting Cape-style home offers privacy and stunning surroundings just minutes from Stratton Mountain. Sitting on 1.5 acres, the property provides a peaceful retreat with easy access to Winhall, Stratton, and endless outdoor activities. A babbling stream flows nearby, adding to the tranquil setting as you relax on the spacious deck.Despite its

  Trent Stephens Wohler Realty Group

  6217 Vt Route 30, Jamaica, VT 05343
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  /40

  Est $653,860 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 768 Sq Ft

  886 Dalewood Rd, Jamaica, VT 05343

  886 Dalewood Rd, Jamaica, VT 05343
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  /38

  $980,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Jamaica, VT 05343

  Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Jamaica, VT 05343
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  /15

  $159,500 Sold May 14, 2025

  • Land
  • 11.08 Acres
  • $14,395 per Acre

  • 440 Days On Market

  000 Rose Ln, Londonderry, VT 05148

  MOTIVATED SELLERS!!!! This 11 acre parcel is located just off Cole Pond, and is just a few miles to Stratton Mountain Access Road. One lot sits high in the sky with breathtaking views and all the serenity of nature. A well constructed driveway runs approximately halfway up the property where you will find a partial building site with an incredible view of Bromley Mountain, from there if you

  Rachel Febbie EXP Realty

  000 Rose Ln, Londonderry, VT 05148
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  /26

  Est $289,651 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,122 Sq Ft

  80 Henderson Rd, Jamaica, VT 05343

  80 Henderson Rd, Jamaica, VT 05343
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  /42

  $899,000

  • 4 Beds
  • 3 Baths
  • 3,551 Sq Ft

  1247 Cole Pond Rd, Jamaica, VT 05343

  A once-in-a-lifetime opportunity to own a large family home on Vermonts hidden gem! Cole Pond, a spectacular private lake surrounded by mountains and nestled between five ski areas - 5 minutes from Stratton and close to Bromley, Mount Snow, Okemo and Magic. Cole Pond homes rarely come on the market, and this one is one-of-a-kind, with a lake-front lawn, walk-in access to the water (also great

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1247 Cole Pond Rd, Jamaica, VT 05343
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  /29

  $750,000 Sold May 12, 2025

  • 3,084 Sq Ft
  • $243/SF
  • 82 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2003

  12 Jamie Ln, Jamaica, VT 05343

  Showings begin Saturday, February 22, 2025. Set in the heart of Vermont’s stunning landscape, this handcrafted Lincoln Log home offers the perfect blend of privacy and convenience. Surrounded by towering Maples and classic stone walls, it’s just minutes from Stratton’s ski slopes and a short drive to Bromley, Magic Mountain, and Manchester. Inside, a bright, open floor plan features soaring

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  12 Jamie Ln, Jamaica, VT 05343
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  /40

  Est $545,707 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,506 Sq Ft

  482 Pratt Bridge Rd, Jamaica, VT 05343

  482 Pratt Bridge Rd, Jamaica, VT 05343
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  /41

  $795,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  202 Pratt Bridge Rd, Jamaica, VT 05343

  Your slice of heaven awaits! Leave your worries behind and step into a beautiful Southern Vermont home that's truly turnkey. This well-designed, fully furnished, 3 bedroom, 2.5 bath home on 1.8+/- professionally landscaped acres offers privacy and convenience to the area's premier slopes, trails and natural beauty. The heart of the home is an expansive chef’s kitchen where country cabinetry and

  Geralyn Donohue Engel & Völkers Okemo

  202 Pratt Bridge Rd, Jamaica, VT 05343

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