Windham, VT Homes

• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /14

  Not Listed For Sale

  0 S Hill Rd, Jamaica, VT 05343

  0 S 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
• 

  

  /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
• 

  

  /11

  Est $101,316 Not Listed For Sale

  12 Sugar Lot Ln, Jamaica, VT 05343

  12 Sugar Lot Ln, Jamaica, VT 05343
• 

  

  /34

  $275,000

  • 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
• 

  

  /23

  $249,000 Sold Jan 10, 2025

  • 1,286 Sq Ft
  • $194/SF
  • 187 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2021

  106 Vermont 30 Unit Property 3, Jamaica, VT 05359

  Discover unparalleled privacy and modern living with this immaculate 3-bedroom manufactured home, set on a peaceful 23-acre lot in Jamaica, VT. Built in 2021, this home boasts a bright and open-plan living space, featuring a modern kitchen, dining nook, and a comfortable living room and two full bath rooms. Enjoy the added luxury of a porch and a hot tub room at the back. Positioned 1/2 mile

  Joe Castaluccio Winhall Real Estate

  106 Vermont 30 Unit Property 3, Jamaica, VT 05359
• 

  

  /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
• 

  

  /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
• 

  

  /5

  $55,000 Sold Dec 17, 2024

  • Land
  • 1.00 Acre
  • $55,000 per Acre

  • 11 Days On Market

  0 Karen Dr Unit Lot 12 5021748, Jamaica, VT 05343

  Wooded building lot located at the end of a cul-de-sac near Stratton Mountain and other recreational areas. Perfect site for that primary or second home. The septic Design has been done and approved for a 4 bedroom home.

  Edward Jones Josiah Allen Real Estate, Manchester Branch Office

  0 Karen Dr Unit Lot 12 5021748, Jamaica, VT 05343
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  /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
• 

  

  /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
• 

  

  /35

  $640,000 Sold Nov 13, 2024

  • 3,280 Sq Ft
  • $195/SF
  • 146 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1996

  660 Dalewood Rd, Jamaica, VT 05343

  Incredible opportunity to have your very own turnkey Stratton Mountain escape! Located on a quiet road, 3.5 miles from the Village, this lovely home has generated a treasure trove of memories for the owner's family for the last several years. Enter from the comfort of the attached garage into a generous mudroom, and head up to the main level where you'll find a well appointed chef's kitchen and

  Christopher Cummings Cummings & Co

  660 Dalewood Rd, 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
• 

  

  /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
• 

  

  /32

  $281,000 Sold Nov 08, 2024

  • 808 Sq Ft
  • $348/SF
  • 8 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  232 Worden Rd, Jamaica, VT 05343

  Welcome to off-grid living in Vermont! This well maintained cabin sits high in the trees with beautiful mountaintop views. The new owner can cut access to the 750 feet of frontage on the West River and enjoy summer water fun including swimming, tubing and fishing. A generator brings fresh spring water to the home, propane serves the lights, cooking stove and heating. A wood stove in the living

  Jessica Citera Cummings & Co

  232 Worden Rd, 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
• 

  

  /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
• 

  /2

  $50,000 Sold Nov 08, 2024

  • Land
  • 23 Acres
  • $2,174 per Acre

  • 13 Days On Market

  0 Stratton Gate Rd, Jamaica, VT 05343

  Welcome to an opportunity to own a piece of natural paradise! This expansive piece of land is situated at the end of a town-maintained road, ensuring privacy while remaining easily accessible. One of the highlights of this property is its cascading year-round trout stream that gracefully winds its way, culminating at the breathtaking Angel Falls and Ball Mountain Lake. This property offers an

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  0 Stratton Gate Rd, Jamaica, VT 05343
• 

  

  /40

  Est $1,650,211 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 7,426 Sq Ft

  541 Mtn Acres Rd, Jamaica, VT 05343

  541 Mtn Acres 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
• 

  

  /38

  $275,000 Sold Nov 07, 2024

  • 1,760 Sq Ft
  • $156/SF
  • 85 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1930

  3883 Vermont 30, Townshend, VT 05353

  Looking for a great location with one of the larger lots in the Village of Jamaica? This might be the perfect fit. Live in this great old farmhouse while you operate your business from home or out of the large, detached barn. One of the nicest in town, open level lots with great space in the back yard! House and barn in need of a little love but has potential! Three bedrooms, two baths, open

  Julie Lowe Lowe's Real Estate, LLC

  3883 Vermont 30, Townshend, VT 05353
• 

  

  /31

  Not Listed For Sale

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

  71 Todd Hill Rd, Jamaica, VT 05343

  71 Todd Hill 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
• 

  

  /33

  $580,000 Sold Oct 26, 2024

  • 1,484 Sq Ft
  • $391/SF
  • 91 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  39 Todd Hill Rd, Jamaica, VT 05343

  Set amidst the picturesque landscape of Vermont, located off the Stratton Mountain Access Road only 3.5 miles to Stratton Resort, this well-maintained home is your gateway to Green Mountain adventures. Whether it is an exhilarating day on the slopes, a round at Stratton’s spectacular 27-whole course, a hike in the woods, or sun-filled afternoon at the Snowmaking pond, this location offers easy

  Cheyanne Pugliese

  39 Todd Hill Rd, Jamaica, VT 05343
• 

  

  /22

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 691 Sq Ft

  8581 Vt Route 30 Unit B, Jamaica, VT 05343

  8581 Vt Route 30 Unit B, 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
• 

  

  /32

  $449,000 Sold Oct 25, 2024

  • 2,500 Sq Ft
  • $180/SF
  • 40 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1988

  476 Edie Ln, Jamaica, VT 05343

  Nestled in the serene Mountain Acres community of Jamaica, VT, this charming 3-bedroom home offers the perfect blend of convenience and privacy. The spacious layout includes a versatile loft space, three full baths, and a cozy wood-burning fireplace. Just four miles from the Stratton Mountain Access Road, this home is an ideal retreat for outdoor enthusiasts. The updated kitchen features granite

  Carrie Mathews Winhall Real Estate

  476 Edie Ln, Jamaica, VT 05343
• 

  

  /33

  Est $766,787 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,936 Sq Ft

  366 Stone Hedge Rd Unit 8, Jamaica, VT 05343

  366 Stone Hedge Rd Unit 8, Jamaica, VT 05343
• 

  

  /30

  $275,000

  • Land
  • 58 Acres
  • $4,761 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
• 

  

  /29

  $830,000 Sold Oct 24, 2024

  • 2,139 Sq Ft
  • $388/SF
  • 130 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1984

  139 Worden Rd, Jamaica, VT 05343

  This country retreat is a rare find, though modest in size, this gem makes a big impact. Private, yet within walking distance of a village and a state park! Close to hiking, skiing, and kayaking. Surrounded by 25 acres of mown fields and woodlots, the open floor plan and huge windows highlight the mountain views. Watch wildlife from the 700-sf deck. New post-and-beam horse barn and large fenced

  Carrie Mathews Winhall Real Estate

  139 Worden Rd, Jamaica, VT 05343

Showing Results 41 - 80, Page 2 of 18