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Jamaica, VT Homes for Sale

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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
  • /46

    $210,000

    • Land
    • 30 Acres
    • $6,977 per Acre

    184 Schoolhouse Rd, Jamaica, VT 05343

    Jamaica, Vermont’s hidden gem! Experience this wonderful 30.1+/- acre forested parcel with views of the local mountains. The land gently slopes to the southeast, perfect for solar, but better yet, utility lines are located along much of the frontage! Bounded on two sides by classic stone walls, there is a woods road that travels through the property making exploration easy. Jamaica has NO local

    Curtis Trousdale Preferred Properties

    184 Schoolhouse Rd, Jamaica, VT 05343
  • /37

    $119,000

    • Land
    • 10 Acres
    • $11,667 per Acre

    1105 S Hill Rd, Jamaica, VT 05343

    Explore this exciting wooded 10.2+/- acre lot in the desirable town of Jamaica, VT. Jamaica has NO local zoning, making for simplified development, multiple cabins, camping and more. Plenty of road frontage on a year-round town plowed and maintained road. Best of all it is paved all the way to Wardsboro eliminating the difficulties of Vermont Mud Season. Utilities are located across from the

    Curtis Trousdale Preferred Properties

    1105 S Hill Rd, Jamaica, VT 05343
  • /15

    $850,000

    • Land
    • 52 Acres
    • $16,368 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 unique,

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /11

    $665,000

    • Land
    • 69 Acres
    • $9,653 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 solid

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /8

    $355,000

    • Land
    • 35 Acres
    • $10,281 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 to be

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /7

    $235,000

    • Land
    • 15 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
  • /40

    $1,695,000

    • 7 Beds
    • 7.5 Baths
    • 8,364 Sq Ft

    251 Pratt Bridge Rd, Jamaica, VT 05343

    Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

    TG Glazer Winhall Real Estate

    251 Pratt Bridge Rd, Jamaica, VT 05343
  • /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
  • /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
  • /42

    $949,000

    • 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
  • /35

    $629,000

    • 3 Beds
    • 2.5 Baths
    • 2,033 Sq Ft

    64 Gleason Farm Ln, Jamaica, VT 05343

    Nestled on nearly 2 flat acres, this beautifully maintained South-facing New England Cape Cod farmhouse is a rare find in the mountains. Located on a private dead-end road, the home offers peaceful seclusion while being just a short drive to Stratton Mountain for skiing and tubing in the winter and Jamaica State Park for hiking and stunning waterfalls in the warmer months. With only one owner,

    Carrie Mathews Winhall Real Estate

    64 Gleason Farm Ln, Jamaica, VT 05343
  • /4

    $59,900

    • Land
    • 2.40 Acres
    • $24,958 per Acre

    0 Route 30 Unit 5048856, Jamaica, VT 05343

    Tucked along a quiet, town-maintained road in Jamaica, Vermont, this beautifully wooded parcel places you right in the heart of southern Vermont’s legendary ski country. Stratton, Magic, and Bromley Mountains are each only minutes away, giving you three distinct downhill experiences—plus miles of lift-served mountain-bike trails—at your fingertips. Yet winter fun is just the beginning: the West

    Joe Castaluccio Winhall Real Estate

    0 Route 30 Unit 5048856, Jamaica, VT 05343
  • /13

    $165,000

    • Land
    • 1.20 Acres
    • $137,500 per Acre

    4769 Pikes Falls Rd, Jamaica, VT 05143

    A Rare Vermont Gem:This 1.2-acre parcel offers what few can—a front-row seat to one of Southern Vermont’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this property is the equivalent of what would be Vermont’s oceanfront real estate.A wooded path leads directly from the land to the pristine falls, which are preserved by the

    Rachel Febbie EXP Realty

    4769 Pikes Falls Rd, Jamaica, VT 05143
  • /42

    $499,000

    • 4 Beds
    • 2.5 Baths
    • 1,986 Sq Ft

    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
  • /45

    $295,000

    • 3 Beds
    • 1 Bath
    • 1,586 Sq Ft

    2277 Vermont 30, Jamaica, VT 05343

    Meander down the winding private drive and “LO AND BEHOLD” an enchanting country cottage nestled on a serene 4.8 acres awaits you! This quaint 3-bedroom, 1-bath home is brimming with potential. Inside, you'll find wideboard pine flooring in the dining and living rooms, 2 woodstoves, and an additional den area. In 2024, SEVCA conducted an energy service, enhancing the home with spray foam

    Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    2277 Vermont 30, Jamaica, VT 05343
  • /37

    $449,000

    • 6 Beds
    • 2.5 Baths
    • 3,032 Sq Ft

    3458 Vt Route 30, Jamaica, VT 05343

    This lovely, updated 1790 Cape blends timeless New England charm with modern functionality and post-and-beam construction. Ideally located just outside the quaint village of Jamaica, the home offers easy access to four major ski resorts—Stratton, Bromley, Magic Mountain, and Mount Snow. Step into the welcoming kitchen, where a cozy fireplace creates a perfect winter haven. A soaring cathedral

    Thomas Dahlin Berkley & Veller Greenwood Country

    3458 Vt Route 30, Jamaica, VT 05343
  • /30

    $299,000

    • Land
    • 58 Acres
    • $5,177 per Acre

    0 Vermont Route 100, Jamaica, VT 05343

    Over 57 IMPRESSIVE ACRES located in a NO ZONING town close to Stratton and Mount Snow! Large tract of land with stunning views from multiple locations throughout the property! State wastewater permit already in place and on file with the State of Vermont for construction of a three bedroom home, see permit number WW-2-5317 attached. So many other options available should you want to subdivide or

    Julie Lowe Lowe's Real Estate, LLC

    0 Vermont Route 100, Jamaica, VT 05343
  • /28

    $205,000

    • 2 Beds
    • 1 Bath
    • 844 Sq Ft

    8577 Vermont 30 Unit H, Jamaica, VT 05343

    Welcome to The Willows. Where convenience, comfort, and value come together in this well-appointed 2 bedroom, 1 bathroom condominium. Set privately back from Route 30, this thoughtfully maintained unit offers peaceful surroundings just two minutes from Strattons Access Road and within easy reach of Jamaica State Park and the West River.Ideal for first-time homebuyers or those looking to

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

    8577 Vermont 30 Unit H, Jamaica, VT 05343
  • /30

    $415,000

    • 3 Beds
    • 1 Bath
    • 1,338 Sq Ft

    2779 Pikes Falls Rd, Jamaica, VT 05343

    Nestled just 5 miles from Stratton's base lodge on the historic grounds of the former White Mop Wringer Co., this remarkable home blends rich history with modern craftsmanship. Built in 2001, the house sits where, in the 1800s, Cassius A. White invented the mop wringer, making Jamaica, Vermont the birthplace of the first mop wringer factory. While the water wheel that powered the factory is no

    Carrie Mathews Winhall Real Estate

    2779 Pikes Falls Rd, Jamaica, VT 05343
  • /23

    $1,250,000

    • Land
    • 108 Acres
    • $11,574 per Acre

    585 Pleasant Valley Rd, Jamaica, VT 05343

    108 Acres of Pristine Land For Sale – 2 Miles to Stratton Sun Bowl with Panoramic ViewsA rare opportunity to own ~108 acres of stunning land with sweeping views of Stratton’s Sun Bowl and Mount Snow. Just 2 miles to the Sun Bowl base and 15 minutes to Mount Snow, this Jamaica, VT property (on the Stratton line) offers unmatched privacy, no zoning restrictions, and incredible

    Britt Wohler Wohler Realty Group

    585 Pleasant Valley Rd, Jamaica, VT 05343
  • /60

    $4,495,500

    • 4 Beds
    • 5.5 Baths
    • 5,500 Sq Ft

    816 Black Bear Rd, Jamaica, VT 05343

    Set atop a scenic Vermont hillside, this five-bedroom custom-built home by The Wadsworth Design Build/Vermont Barns is a stunning example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mount Snow ski resorts, it is the ultimate

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    816 Black Bear Rd, Jamaica, VT 05343
  • /13

    $150,000

    • Land
    • 4.68 Acres
    • $32,051 per Acre

    8559 Vt Route 30 Unit Lots 2 & 3, Jamaica, VT 05343

    Waaaaait a minute! There’s buildable land just minutes from Stratton Mountain, and it’s already got septic not only approved, but basically installed?!?! I can just build my house on these 4.68 acres and enjoy all of the beauty and convenience of the area? And it's approved for 2 three bedroom houses!!! 2 miles to Stratton and 20 minutes to Manchester. I almost can’t believe this is

    TG Glazer Winhall Real Estate

    8559 Vt Route 30 Unit Lots 2 & 3, Jamaica, VT 05343
  • /6

    $109,000

    • Land
    • 1.78 Acres
    • $61,236 per Acre

    0000 Wonder Ln Unit Lot 18, Jamaica, VT 05343

    Prime 1.78-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled in a serene and private subdivision, this magnificent 1.78-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

    Rachel Febbie EXP Realty

    0000 Wonder Ln Unit Lot 18, Jamaica, VT 05343
  • /7

    $99,000

    • Land
    • 2.06 Acres
    • $48,058 per Acre

    000 Wonder Ln Unit LOT 15, Jamaica, VT 05343

    Prime 2.06-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled in a serene and private subdivision, this magnificent 2.08-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

    Rachel Febbie EXP Realty

    000 Wonder Ln Unit LOT 15, Jamaica, VT 05343
  • /19

    $215,000

    • 3 Beds
    • 1 Bath
    • 636 Sq Ft

    30 Water St, Jamaica, VT 05343

    Discover the Acorn, a picturesque retreat nestled on the banks of the scenic West River in Jamaica, Vermont. This unique home, a beautifully converted sugar shack, offers an enchanting taste of rustic charm, perfect for those seeking a serene getaway. Ideal for nature lovers and outdoor enthusiasts, the Acorn sits close to the renowned ski resorts of Stratton Mountain and Mount Snow, providing a

    Daire Gibney Barrett and Valley Associates Inc.

    30 Water St, Jamaica, VT 05343
  • /15

    $530,000

    • Land
    • 30 Acres
    • $17,667 per Acre

    00 W Hill Rd S, Jamaica, VT 05343

    Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

    Jacki Murano Southern Vermont Realty Group

    00 W Hill Rd S, Jamaica, VT 05343
  • /12

    $135,000

    • Land
    • 1.51 Acres
    • $89,404 per Acre

    0 Dalewood Rd Unit 4955807, Jamaica, VT 05343

    Discover your dream Vermont escape on this enchanting 1.5-acre wooded lot in Jamaica. Perfectly positioned just minutes from the excitement of Stratton Mountain Resort, this prime parcel offers unparalleled access to world-class skiing, golfing, dining, and shopping.Imagine building your mountain retreat amidst nature's splendor. With a coveted State of Vermont 4-bedroom permit (WW-2-7632) in

    Mike England Michael England Real Estate

    0 Dalewood Rd Unit 4955807, Jamaica, VT 05343
  • /6

    $495,000

    • Land
    • 7 Acres
    • $71,429 per Acre

    lot#2 Margeaux Ln, Stratton, VT 05155

    This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    lot#2 Margeaux Ln, Stratton, VT 05155
  • /5

    $465,000

    • Land
    • 6 Acres
    • $83,935 per Acre

    Lot #4 Margeaux Ln, Stratton, VT 05155

    Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    Lot #4 Margeaux Ln, Stratton, VT 05155
  • /4

    $225,000

    • Land
    • 1.99 Acres
    • $113,065 per Acre

    00 Margeaux Ln, Stratton, VT 05155

    This beautiful 1.99-acre parcel, nestled in the woods, offers the perfect setting to build the home of your dreams. With a 5-bedroom septic permit already in place, you’ll be ready to start construction right away. Access is easy via a right-of-way from Margeaux Lane, providing both privacy and convenience. Located just minutes from the Sun Bowl at Stratton. It is close to everything Stratton

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    00 Margeaux Ln, Stratton, VT 05155

Why Live in Jamaica

Jamaica is a mountainous town in Vermont known for its natural beauty and outdoor activities. The West River winds through Jamaica State Park, offering nearly 800 acres of forested recreation areas for anglers, swimmers, and boaters. Cyclists can enjoy the rail trail leading to Ball Mountain Dam, while hikers frequent Hamilton Falls, one of Vermont's tallest waterfalls. The Green Mountains to the west feature major winter sports destinations like Stratton Mountain Resort and Bromley Mountain Ski Resort, popular for skiing, mountain biking, and golfing. Housing in Jamaica ranges from early 1800s farmhouses to modern A-frame chalets and cabins, with median single-family home prices around $500,000. The village of Jamaica hosts community events such as Old Home Day, featuring historical reenactments, craft vendors, and live music. Jamaica Village School and Townshend Village School are highly rated, serving prekindergarten through fifth grade. Residents often travel about 20 miles to Manchester for shopping and dining, with the nearest large grocery store, Shaw’s, located there. While Jamaica is safer than the national average, low-lying areas along the West River are prone to flooding after heavy rain. The nearest major airport is Albany International Airport, approximately 80 miles away.

Frequently Asked Questions

What is the average home price in Jamaica, VT?
Homes for sale in Jamaica, VT have an average home price of $977,587.
Are home prices dropping in Jamaica?
Yes, home prices in Jamaica are down 15% in the last 12 months.
How many homes have sold over the last 12 months in Jamaica, VT?
21 homes have sold in Jamaica, VT over the last 12 months.
What are the most popular zip codes in Jamaica, VT?
The most popular zip codes in Jamaica, VT include 05356, 05301, 05363, 05156 and 05143.
How much do you need to make to afford a house in Jamaica?
The median home price in Jamaica is $499,000. If you put a 20% down payment of $99,800 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $2,590 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $111K a year to afford the median home price in Jamaica.
How are the schools in Jamaica, VT?
Jamaica, VT has highly rated public and private schools. Some of the best schools in Jamaica based on Niche Grades are Jamaica Village School, Townshend Village School and Flood Brook School. Browse all the schools in Jamaica, VT to learn more.

Home Trends in Jamaica, VT

Housing Trends

Median Sale Price
$449,000
Median Single Family Sale Price
$499,500
Median Townhouse Sale Price
$207,500
Median 2 Bedroom Sale Price
$206,250
Average Price Per Sq Ft
$316
Number of Homes for Sale
12
Last 12 months Home Sales
21
Months of Supply
6.90
Median List Price
$499,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-8%
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