Windham, VT Homes in ZIP Code 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
• 

  

  

  /40

  Est $571,575 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 768 Sq Ft

  886 Dalewood Rd, Jamaica, VT 05343

  886 Dalewood Rd, Jamaica, VT 05343
• 

  

  

  /43

  $899,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 3,155 Sq Ft

  460 Stratton Gate Rd, Jamaica, VT 05343

  This exceptional property blends classic post-and-beam farmhouse design with modern craftsmanship. The stunning barn addition is an architectural masterpiece, admired from every angle and flooded with natural light through expansive windows that frame the serene surroundings. Soaring ceilings, rich hardwood floors, and custom finishes create an atmosphere of timeless elegance. An expansive loft

  Helen Nault

  460 Stratton Gate Rd, 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
• 

  

  

  /26

  Est $280,221 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
• 

  

  /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
• 

  

  /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
• 

  

  /40

  Est $505,484 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
• 

  

  /24

  $69,900

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  2080 Vermont 30, Jamaica, VT 05343

  Riverside Retreat in West River Park!Looking for a Vermont getaway that’s equal parts cozy charm and riverside relaxation? Welcome to this 2-bedroom, 1-bath home with a bonus addition in the highly desired West River Park. Whether you’re dreaming of summer dips in the river, autumn hikes, or apres-ski evenings, this spot has you covered.Step inside to find a bright and inviting living

  TG Glazer Winhall Real Estate

  2080 Vermont 30, 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
• 

  

  /31

  Est $605,517 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,593 Sq Ft

  81 Edie Ln, Jamaica, VT 05343

  81 Edie Ln, Jamaica, VT 05343
• 

  

  /6

  $84,900

  • Land
  • 1.78 Acres
  • $47,697 per Acre

  0000 Wonder Ln, Jamaica, VT 05343

  Prime 1.78-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled down a serene and private dirt road, 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, 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
• 

  

  /25

  Est $770,949 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,550 Sq Ft

  110 Upper Taylor Hill Rd, Jamaica, VT 05343

  110 Upper Taylor Hill Rd, Jamaica, VT 05343
• 

  

  /7

  $74,900

  • Land
  • 2.06 Acres
  • $36,359 per Acre

  000 Wonder Ln, Jamaica, VT 05343

  Prime 2.06-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled down a serene and private dirt road, 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, Jamaica, VT 05343
• 

  

  /11

  $160,000 Sold Mar 19, 2025

  • Land
  • 2.18 Acres
  • $73,394 per Acre

  • 212 Days On Market

  E3 Nearing Rd, Winhall, VT 05340

  Welcome to Stratton Mountain Forest Farms Neighborhood! One of the few remaining lots with 2.18 acres in a most desirable and convenient location just minutes to the Base Lodge, SMS and SunBowl! Providing easy access for a driveway off of Nearing Road the lot widens to offer privacy and south easterly orientation and abuts the Winhall Town Forest, protected lands from further development. State

  Britt Wohler Wohler Realty Group

  E3 Nearing Rd, Winhall, VT 05340
• 

  

  /39

  Est $632,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,862 Sq Ft

  39 Depot St, Jamaica, VT 05343

  39 Depot St, Jamaica, VT 05343
• 

  

  /34

  $225,000

  • 3 Beds
  • 2 Baths
  • 2,613 Sq Ft

  533 Pratt Bridge Rd, Jamaica, VT 05343

  Nestled in the peaceful and desirable Cole Pond neighborhood, while being merely minutes away from: Stratton Mountain Resort, renowned for its skiing and year-round recreational activities The picturesque landscapes of Southern Vermont – offering hiking, fishing, and various outdoor pursuits Seclusion and serenity on your own 1.6-acre sanctuary. This contemporary 3 bedroom with loft 2 bath,

  Mike England Michael England Real Estate

  533 Pratt Bridge Rd, Jamaica, VT 05343
• 

  

  /31

  $637,000 Sold Mar 14, 2025

  • 2,470 Sq Ft
  • $258/SF
  • 11 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1989

  69 Fox Hollow Rd, Winhall, VT 05340

  Uncover your ideal retreat! This highly desirable townhome in the Intervale community is situated along the Stratton Mountain Resort access road. Featuring 3 bedrooms and 3 bathrooms, this stunning residence is tucked away in the serene woods of the private Intervale community. Experience the charm of this beautifully designed home, complete with a cathedral ceiling, a cozy wood-burning

  Jamie Wylie Stratton Real Estate

  69 Fox Hollow Rd, Winhall, VT 05340
• 

  

  /14

  Not Listed For Sale

  0 S Hill Rd, Jamaica, VT 05343

  0 S Hill Rd, Jamaica, VT 05343
• 

  

  /38

  $789,000

  • 4 Beds
  • 4 Baths
  • 2,997 Sq Ft

  44 Hilltop Rd, Winhall, VT 05340

  Four bedroom, four bathroom Intervale townhouse has all the space you need in a Stratton home. This is the largest Intervale floor plan, with a second living room and wet bar on the lower, walk out floor. The main floor has a mud room entry, living room with wood burning fireplace, and dining room open to kitchen. The primary suite is on the main floor, secondary suite is upstairs, and an

  Christiane Carroccio TPW Real Estate

  44 Hilltop Rd, Winhall, VT 05340
• 

  

  /48

  $645,000 Sold Mar 13, 2025

  • 2,621 Sq Ft
  • $246/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  418 Diers, Jamaica, VT 05343

  Updated and ready to use immediately! Close to Stratton, located just off Route 30, this solid LOG home is perched on a small hill with 11.19 acres of land. Beautiful field stone woodburning fireplace with cathedral ceilings. The land has a small stream and pond running through the property with two large open lawn areas. Owner currently utilizes it as a three bedroom and two and a half bath

  Julie Lowe Lowe's Real Estate, LLC

  418 Diers, Jamaica, VT 05343
• 

  

  /11

  Est $101,316 Not Listed For Sale

  12 Sugar Lot Ln, Jamaica, VT 05343

  12 Sugar Lot Ln, 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
• 

  

  /39

  $615,000 Sold Mar 12, 2025

  • 1,650 Sq Ft
  • $373/SF
  • 32 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1998

  81 Pond View Rd Unit 81, Winhall, VT 05340

  THE BEST LOCATION AT INTERVALE! Bask in the sun on your expansive deck and private pond front area! Experience breathtaking views of Intervale’s serene, picturesque pond from all rooms of your home! Discover this spacious 3 BR, 3 bath Townhome with a loft just a quick 5 minute shuttle ride to Stratton’s slopes! Being one of the last Intervales built (1998), this condo is newer and more

  Lauren Behm Berkshire Hathaway HomeServices Stratton Home

  81 Pond View Rd Unit 81, Winhall, VT 05340
• 

  

  /21

  Est $291,000 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 320 Sq Ft

  1406 Cole Pond Rd, Jamaica, VT 05343

  1406 Cole Pond Rd, Jamaica, VT 05343
• 

  

  /9

  $169,000

  • Land
  • 6 Acres
  • $26,000 per Acre

  530 Mowrey Rd, Jamaica, VT 05343

  This 6.5 acre lot is a beautiful combination of open sloping field and wooded land with road frontage on both Mowrey Road and Brooks Road. The land currently has a state approved wastewater permit in place for two separate 5 bedroom homes. So, take your pick, you can build in the woods or out in the open field or BOTH, the choice is yours! This parcel will require an act250 permit prior to

  Julie Lowe Lowe's Real Estate, LLC

  530 Mowrey Rd, Jamaica, VT 05343
• 

  /2

  $1,850,000 Sold Mar 10, 2025

  • 7,954 Sq Ft
  • $233/SF
  • 135 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2003

  92 County Rd, Stratton, VT 05155

  This exquisitely-built mountain estate is ready to enjoy and to rent! A mere 3 mins' drive to Stratton's Sun Bowl, 5 mins to the Village and 8 mins to the Golf course. Currently one of the few luxury rental properties near Stratton, this home could be your escape for all seasons. All necessary permits are in place, several rentals are confirmed for 24/25 winter should the buyer want to continue

  Lauren Niles Coldwell Banker LIFESTYLES - Quechee

  92 County Rd, Stratton, VT 05155
• 

  

  /34

  Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 2,400 Sq Ft

  291 Pikes Falls Rd, Stratton, VT 05360

  291 Pikes Falls Rd, Stratton, VT 05360
• 

  

  /22

  $130,000

  • Land
  • 10 Acres
  • $12,500 per Acre

  oos-65-13 Partridge Ln, Jamaica, VT 05343

  Wooded 10 acre lot #17 end of road, past camp. Part of the Gleason Farm Deed of Conservation Easement for Wildlife and Forest Land Protection, granted by Patten Corp. Property being offer with Travel Trailer. Enjoy your Vermont get away.

  Mike England Michael England Real Estate

  oos-65-13 Partridge Ln, Jamaica, VT 05343
• 

  

  /39

  $410,000 Sold Feb 21, 2025

  • 1,232 Sq Ft
  • $333/SF
  • 181 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1978

  559 Pratt Bridge Rd, Jamaica, VT 05343

  Nestled in the serene country setting of Pratt Bridge Road in Jamaica, Vermont, this charming 3-bedroom home, complete with an additional 4th bedroom loft and 2 baths, offers a perfect getaway. One of the bedrooms is on the first floor. The property features a spacious wrap-around deck, ideal for enjoying the picturesque surroundings. Inside, a beautiful brick wood-burning fireplace provides a

  Joe Castaluccio Winhall Real Estate

  559 Pratt Bridge Rd, Jamaica, VT 05343
• 

  

  /26

  Est $692,123 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,359 Sq Ft

  116 Teacher Rd, Jamaica, VT 05343

  116 Teacher Rd, Jamaica, VT 05343
• 

  

  /41

  $574,000

  • 3 Beds
  • 3 Baths
  • 2,704 Sq Ft

  4138 W Hill Rd S, Jamaica, VT 05343

  This three-bedroom, three-bath custom-built log home is situated on 2.37 acres in a tranquil mountain setting just minutes from skiing. Built with double tongue-and-groove log construction, the cozy home provides the warm wood interior one would expect. The open-concept main level focuses on the fieldstone hearth, wood stove, and beautiful oak floors. A covered porch in the front of the home

  Patricia Fitzpatrick Skihome Realty

  4138 W Hill Rd S, Jamaica, VT 05343
• 

  

  /7

  $115,000 Sold Feb 20, 2025

  • Land
  • 10 Acres
  • $11,220 per Acre

  • 64 Days On Market

  0 W Hill Rd S Unit 5021406, 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 1 is 10.25 acres and is accessed directly from West Hill Road where a driveway could be

  Thom Milke Fountains Land Inc.

  0 W Hill Rd S Unit 5021406, Jamaica, VT 05343
• 

  

  /26

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,833 Sq Ft

  42 Pine Ln, Jamaica, VT 05359

  42 Pine Ln, Jamaica, VT 05359
• 

  

  /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
• 

  

  /21

  $327,000 Sold Jan 22, 2025

  • 1,100 Sq Ft
  • $297/SF
  • 35 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1988

  63 Reynolds Ln, Jamaica, VT 05343

  Wonderful secluded hideaway on 5 acres near Stratton Mountain and Mount Snow. This cozy property is minutes away from two major resorts and an abundance of hiking, biking, hunting and more surround this home. Three bedrooms and a loft that can sleep eight. Wood stove to keep you warm during Winter. Also a shed for your tools and barbecue. Come and see this property and enjoy the country drive.

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  63 Reynolds Ln, Jamaica, VT 05343
• 

  

  /26

  Est $515,000 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,763 Sq Ft

  121 Stratton Gate Rd, Jamaica, VT 05343

  121 Stratton Gate Rd, Jamaica, VT 05343
• 

  

  /6

  $54,900

  • Land
  • 2.40 Acres
  • $22,875 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
• 

  

  /55

  $899,000 Sold Jan 13, 2025

  • 2,900 Sq Ft
  • $310/SF
  • 7 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1996

  45 Hilltop Rd, Winhall, VT 05340

  Our Sellers have certainly raised the bar with this stunning 5 bedroom, 4 bath residence. Taken down to the studs in 2018/19 and lovingly renovated with beautiful custom features in every corner. This mountain modern decor boasts gorgeous wall to wall engineered hardwood white oak floors throughout the entire property softened by inviting area rugs. The attractive kitchen was designed for

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  45 Hilltop Rd, Winhall, VT 05340

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