Windham, VT Homes in ZIP Code 05343

• 

  

  

  /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
• 

  

  

  /14

  $17,500 per month

  • 4 Beds
  • 2 Baths
  • 1,550 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
• 

  

  

  /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
• 

  

  

  /38

  Est $750,833 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,081 Sq Ft

  80 Pond View Rd, Winhall, VT 05340

  80 Pond View Rd, Winhall, VT 05340
• 

  

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /35

  Est $613,960 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,577 Sq Ft

  10 Pond View Rd, Winhall, VT 05340

  10 Pond View Rd, Winhall, VT 05340
• 

  

  /45

  $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

  Curtis Trousdale

  184 Schoolhouse Rd, Jamaica, VT 05343
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  /48

  $7,000 per month

  • 5 Beds
  • 3.5 Baths
  • 3,858 Sq Ft
  • House for Rent

  20 Jamie Ln, Winhall, VT 05340

  Escape to the tranquility of Vermont with this stunning long-term rental at "Valley View." Nestled in a desirable neighborhood of Winhall, this spacious contemporary home offers unparalleled panoramic views of the surrounding mountains. Imagine waking up to the beauty of the Green Mountains every day in this expansive retreat!This meticulously maintained 5-bedroom, 3.5 bathroom home

  David Powers 42 North LP

  20 Jamie Ln, Winhall, VT 05340
• 

  

  /27

  $530,000 Sold Aug 08, 2025

  • 1,396 Sq Ft
  • $380/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
• 

  

  /35

  Est $409,069 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
• 

  

  /15

  $775,000

  • Land
  • 52 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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  /46

  $5,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  15 Nearing Rd, Winhall, VT 05340

  Imagine waking up to inspiring vistas every day in this remarkable 3 bedroom, 3.5 bath saltbox home. Perched to capture stunning panoramic views of Stratton Mountain's trails, this classic contemporary ski home offers a truly special living experience. The property is settled upon a 1.63-acre knoll and abuts the Winhall Forest, offering peace and privacy.Embrace sustainable living with a

  David Powers 42 North LP

  15 Nearing Rd, Winhall, VT 05340
• 

  

  /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
• 

  

  /39

  Est $445,520 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
• 

  

  /11

  $595,000

  • Land
  • 69 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
• 

  

  /29

  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft
  • Townhouse for Rent

  90 Turkey Run Rd, Winhall, VT 05340

  Intervale Rental. Available for the winter 25-26 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom

  Christiane Carroccio TPW Real Estate

  90 Turkey Run Rd, Winhall, VT 05340
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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
• 

  

  /32

  Est $311,057 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
• 

  

  /8

  $320,000

  • Land
  • 35 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
• 

  

  /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
• 

  

  /18

  Est $631,212 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
• 

  

  /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
• 

  

  /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
• 

  

  /40

  Est $952,600 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,077 Sq Ft

  1223 Cole Pond Rd, Jamaica, VT 05343

  1223 Cole Pond Rd, Jamaica, VT 05343
• 

  

  /38

  $1,499,999

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

  111 Hughes Ln, Jamaica, VT 05343

  Fully renovated in 2022, 450 ft of lake front footage on picturesque Cole Pond. Nestled on nearly 2 acres in Jamaica, VT, this stunning singlefamily home at 111 Hughes Lane was built in 1989 and offers a peaceful retreat for its next owners. With 3 bedrooms, 3 bathrooms, and 1 half bathroom, and 4 built-in adult size bunks for comfortable sleeping of 10, Air-conditioned master bedroom and

  Derek Greene Derek Greene

  111 Hughes Ln, Jamaica, VT 05343
• 

  

  /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
• 

  

  /33

  Est $467,892 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  1706 Vt Route 30, Jamaica, VT 05343

  1706 Vt Route 30, Jamaica, VT 05343
• 

  

  /37

  $2,400,000

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  115 Benson Fuller Dr, Jamaica, VT 05343

  Perched on 3.5 private acres with commanding views from Stratton’s iconic slopes to Bromley’s trails, this architecturally striking residence blends the serenity of the mountains with sophisticated modern design. A dramatic central staircase anchors the home, leading to a sleek custom kitchen and a vaulted great room where walls of glass frame panoramic vistas. A floor-to-ceiling stone fireplace

  Carrie Mathews Winhall Real Estate

  115 Benson Fuller Dr, Jamaica, VT 05343
• 

  

  /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
• 

  

  /21

  Est $390,720 Not Listed For Sale

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

  60 River Rd, Jamaica, VT 05343

  60 River 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
• 

  

  /37

  $454,000 Sold Apr 28, 2025

  • 1,760 Sq Ft
  • $258/SF
  • 315 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  400 Edie Ln, Jamaica, VT 05343

  Welcome to Hot Toddy Hill. your perfect Vermont Getaway! Nestled minutes away from Stratton, this cozy contemporary home in the charming town of Jamaica, Vermont, is ideal for gatherings and retreats with friends. The living room boasts vaulted ceilings with wood slat detail, its ideal for relaxing in front of the wood-burning fireplace apres ski. The fully equipped eat-in kitchen boasts brand

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  400 Edie Ln, Jamaica, VT 05343
• 

  

  /30

  Est $459,627 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
• 

  

  /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
• 

  

  /24

  $430,000 Sold Mar 26, 2025

  • 1,716 Sq Ft
  • $251/SF
  • 26 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1967

  13 Lower Taylor Hill Rd, Winhall, VT 05340

  This beautifully updated home near Stratton Mountain blends classic charm with modern updates. As you enter, you'll find a mudroom with a convenient storage closet and a half bath. The spacious living and dining area features a striking fieldstone fireplace and sliding doors that open to a large deck, perfect for hosting guests. The custom kitchen offers hardwood floors, a pantry, and a laundry

  Carrie Mathews Winhall Real Estate

  13 Lower Taylor Hill Rd, Winhall, VT 05340
• 

  

  /40

  Est $571,575 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  886 Dalewood Rd, Jamaica, VT 05343

  886 Dalewood Rd, 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
• 

  

  /13

  $150,000 Sold Mar 26, 2025

  • Land
  • 13 Acres
  • $11,811 per Acre

  • 111 Days On Market

  0 Pikes Falls Rd Unit 4993566, Stratton, VT 05360

  Embrace the allure of Vermont living with this exceptional parcel of land located just moments from Stratton Resort. This 12.7-acre parcel boasts a prime location to build your Vermont dream home with the perfect blend of seclusion and accessibility. Located across from the Golf School with frontage on Pikes Falls (Upper Taylor Hill ) and North Rd. and on the border of Winhall and Stratton town

  Cynthia Mitrani Berkshire Hathaway HomeServices Stratton Home

  0 Pikes Falls Rd Unit 4993566, Stratton, VT 05360

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