1,416

Windham, VT Homes

Section Image
  • /30

    $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
  • /24

    $207,500 Sold Aug 26, 2024

    • 698 Sq Ft
    • $297/SF
    • 15 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1982

    8581 Vt Route 30 Unit A, Jamaica, VT 05343

    Cozy Condo Retreat in the Heart of Vermont's Outdoor Paradise! Escape to this charming 2-bedroom, 1-bathroom condo, perfectly situated just 2 minutes from Stratton Access Road and 10 minutes from Jamaica State Park and the West River. This intimate retreat is designed for those who crave the great outdoors, with endless opportunities for adventure at your doorstep. Enjoy world-class skiing and

    Christina Dryden Berkshire Hathaway HomeServices Stratton Home

    8581 Vt Route 30 Unit A, Jamaica, VT 05343
    • /17

      Est $403,674 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,152 Sq Ft

      35 Copeland Ln, Jamaica, VT 05343

      35 Copeland Ln, 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
  • /32

    $275,000 Sold Aug 23, 2024

    • 956 Sq Ft
    • $288/SF
    • 3 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1963

    192 Howe Farm Rd, Jamaica, VT 05343

    Get away to Jamaica, Vermont! Howe Farm Road is conveniently located off Route 30 in great proximity to all Vermont offers. Local waterfalls, ski areas, farmer's markets, country stores and more, all within an easy distance. Use this cute home as your base of operations for your Vermont adventures, or enjoy the quiet of this privately situated property from your own lean-to. The 12 acres

    Alison Cummings Cummings & Co

    192 Howe Farm Rd, Jamaica, VT 05343
    • /40

      Est $791,426 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,126 Sq Ft

      747 Cole Pond Rd, Jamaica, VT 05343

      747 Cole Pond 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
  • /39

    $657,500 Sold Aug 09, 2024

    • 2,862 Sq Ft
    • $230/SF
    • 33 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1860

    39 Depot St, Jamaica, VT 05343

    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,

    Thomas Dahlin Berkley & Veller Greenwood Country

    39 Depot St, Jamaica, VT 05343
    • /14

      Est $260,896 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,344 Sq Ft

      259 Howe Farm Rd, Jamaica, VT 05343

      259 Howe Farm Rd, 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
    • /19

      Est $604,427 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft

      411 Stratton Gate Rd, Jamaica, VT 05343

      411 Stratton Gate Rd, Jamaica, VT 05343
  • /20

    $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
    • /17

      Est $539,786 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,590 Sq Ft

      201 Pratt Bridge Rd, Jamaica, VT 05343

      201 Pratt Bridge Rd, 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
    • /40

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,554 Sq Ft

      200 Forrester Rd, Jamaica, VT 05360

      200 Forrester Rd, Jamaica, VT 05360
  • /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
    • /23

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 840 Sq Ft

      2014 Vt Route 30, Jamaica, VT 05343

      2014 Vt Route 30, Jamaica, VT 05343
  • /16

    $125,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,331 Sq Ft

    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
    • /27

      Est $499,593 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,988 Sq Ft

      88 Peter's Ln, Wardsboro, VT 05355

      88 Peter's Ln, Wardsboro, VT 05355
  • /34

    $520,000 Under Contract

    • 5 Beds
    • 5 Baths
    • 3,213 Sq Ft

    3708 Vermont 30, Jamaica, VT 05343

    Located in the heart of downtown Jamaica, Vermont, this spacious and beautifully designed Colonial home offers the perfect blend of charm, comfort, and convenience. With 5 bedrooms and 5 bathrooms, there’s plenty of space for a large family or frequent guests. Just minutes from premier ski resorts—Stratton, Bromley, and Magic Mountain—this home is an ideal base for winter and summer adventures.

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    3708 Vermont 30, Jamaica, VT 05343
    • /13

      Not Listed For Sale

      Lot 1 Pikes Falls Rd Unit Lot 1, Jamaica, VT 05343

      Lot 1 Pikes Falls Rd Unit Lot 1, Jamaica, VT 05343
  • /42

    $499,000 Under Contract

    • 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
    • /26

      Est $484,098 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,350 Sq Ft

      195 Stratton Gate Rd, Jamaica, VT 05343

      195 Stratton Gate Rd, Jamaica, VT 05343
  • /37

    $449,000 Under Contract

    • 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
    • /3

      Not Listed For Sale

      00 Blackberry Ln, Jamaica, VT 05343

      00 Blackberry Ln, Jamaica, VT 05343
  • /29

    $549,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    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
    • /33

      Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,767 Sq Ft

      13 Betty Johnson Ln, Jamaica, VT 05343

      13 Betty Johnson Ln, Jamaica, VT 05343
  • /27

    $559,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 2,052 Sq Ft

    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
    • /16

      Not Listed For Sale

      Lot E-2 Stratton Gate Rd, Jamaica, VT 05343

      Lot E-2 Stratton Gate Rd, Jamaica, VT 05343
    • /30

      Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,348 Sq Ft

      180 Vermont Route 100, Jamaica, VT 05343

      180 Vermont Route 100, Jamaica, VT 05343
    • /22

      Est $243,903 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 1,696 Sq Ft

      118 Pineapple Hill Ln, Jamaica, VT 05343

      118 Pineapple Hill Ln, Jamaica, VT 05343
    • /35

      Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 4,729 Sq Ft

      83 Benson Fuller Dr Unit Stocker Acres Lot 14, Jamaica, VT 05343

      83 Benson Fuller Dr Unit Stocker Acres Lot 14, Jamaica, VT 05343
    • /8

      Est $215,018 Not Listed For Sale

      • 3 Beds

      2053 Pikes Falls Rd, Jamaica, VT 05343

      2053 Pikes Falls Rd, Jamaica, VT 05343
    • /22

      Est $81,523 Not Listed For Sale

      • 1 Bed

      1297 River Rd, Jamaica, VT 05343

      1297 River Rd, Jamaica, VT 05343
    • /10

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 356 Sq Ft

      144 Tony's Ln, Jamaica, VT 05343

      144 Tony's Ln, Jamaica, VT 05343
    • /24

      Est $1,070,996 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,300 Sq Ft

      744 Dalewood Rd Unit 30, Jamaica, VT 05343

      744 Dalewood Rd Unit 30, Jamaica, VT 05343
    • /7

      Not Listed For Sale

      Lot 56 Barbara Jane Dr Unit 56, Jamaica, VT 05343

      Lot 56 Barbara Jane Dr Unit 56, Jamaica, VT 05343
    • /38

      Est $644,166 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,800 Sq Ft

      504 Trager Rd, Jamaica, VT 05343

      504 Trager Rd, Jamaica, VT 05343
    • /33

      Est $484,129 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,192 Sq Ft

      6284 Vt Route 30, Jamaica, VT 05343

      6284 Vt Route 30, Jamaica, VT 05343
    • /19

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 920 Sq Ft

      100 Tony's Ln, Jamaica, VT 05343

      100 Tony's Ln, Jamaica, VT 05343

Showing Results 81 - 120, Page 3 of 18

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