Windham, VT Homes

• 

  

  

  /39

  $1,455,000 Sold Feb 10, 2025

  • 1,960 Sq Ft
  • $742/SF
  • 180 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2005

  759 Stratton Mountain Access Rd Unit 433, Stratton, VT 05340

  Luxury abounds in this premier Summit Level Hearthstone, boasting direct views of Stratton Mountain from a coveted resort location. Previously leased long-term, this exclusive two-story unit is now on the market, featuring a dramatic cathedral ceiling, majestic beams, and a magnificent stone fireplace. Floor-to-ceiling windows frame year-round sunset vistas over Stratton’s sprawling ski trails,

  Kim Morgan-Wohler Wohler Realty Group

  759 Stratton Mountain Access Rd Unit 433, Stratton, VT 05340
• 

  

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,671 Sq Ft

  13 Old Ridge Rd, Winhall, VT 05155

  13 Old Ridge Rd, Winhall, VT 05155
• 

  

  

  /22

  $665,000

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft

  43 Middle Ridge Rd Unit 311, Winhall, VT 05155

  Exceptional 2 bedroom /2 bath Rising Bear Unit with Viking Kitchen, propane fireplace and private covered deck. Amenities abound with underground heated parking, year round private outdoor heated pool, sauna and spas. Enjoy private shuttle from the elevator to the Base Lodge during the winter, yet just a short stroll across the Commons into the Village for dining and shopping! Granite

  Kim Morgan-Wohler Wohler Realty Group

  43 Middle Ridge Rd Unit 311, Winhall, VT 05155
• 

  

  

  /41

  $1,225,000 Sold Feb 10, 2025

  • 4,200 Sq Ft
  • $292/SF
  • 182 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1985

  22 Old Ridge Rd, Winhall, VT 05340

  This is a private setting in the High Meadow neighborhood with a spectacular, dead-on view of the Stratton slopes. The snow cat lights twinkle in your windows as they groom your runs for tomorrow’s turns. There is plenty of room for the entire family and friends in the gourmet kitchen, dining room, living room with fire place, family room with wood stove, den, five bedrooms, 3 1/2 baths with

  Dan McKenna Cummings & Co

  22 Old Ridge Rd, Winhall, VT 05340
• 

  

  

  /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
• 

  

  /54

  $749,000

  • 3 Beds
  • 3 Baths
  • 2,118 Sq Ft

  A6 Ridge Unit A6, Winhall, VT 05340

  It’s the Premier Location and commanding views that set this Piper Ridge townhome apart. The stunning unobstructed views are central to thetownhomes design, while the southern exposure provides all day sunshine and a light and airy atmosphere. You’ll experience the evening’s magic watching stunning sunsets with the resort lights on full display and will have the premier “front row seats” to

  Karin Hardy Berkshire Hathaway HomeServices Stratton Home

  A6 Ridge Unit A6, Winhall, VT 05340
• 

  

  /22

  $450,000 Sold Jan 31, 2025

  • 850 Sq Ft
  • $529/SF
  • 155 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 1983

  8 Ober Tal Dr Unit A24, Stratton, VT 05360

  Luxury trailside condominium in Stratton Mountain Resort. Completely renovated in 2020 down to the studs! From an all new layout including two new bathrooms featuring heated floors and showers, open gourmet kitchen with oversized granite island, custom cabinets, new high end appliances, new insulation and sound proofing throughout as well as a new modern stone wood burning fireplace. Too many

  Timothy Mich Doddridge Stratton Real Estate

  8 Ober Tal Dr Unit A24, Stratton, VT 05360
• 

  

  /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
• 

  

  /31

  $949,000

  • 4 Beds
  • 4.5 Baths
  • 2,658 Sq Ft

  73 Cranberry Hill Rd, Winhall, VT 05340

  Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort.

  Carrie Mathews Winhall Real Estate

  73 Cranberry Hill Rd, Winhall, VT 05340
• 

  

  /22

  $208,000 Sold Jan 30, 2025

  • 880 Sq Ft
  • $236/SF
  • 8 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1979

  3389 Vt Route 100 N, Londonderry, VT 05148

  The River House is an iconic gem in South Londonderry that has served as a full time home for several residents since 1979! Beautiful deck in the rear of the property provides privacy. Home has a beautiful dining room with great views towards the West River. There are hiking and snowshoe trails out back that run along the river. Home also has a small studio that has been a great work space for

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  3389 Vt Route 100 N, Londonderry, VT 05148
• 

  

  /38

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,673 Sq Ft

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340
• 

  

  /44

  $2,500,000

  • 5 Beds
  • 7 Baths
  • 6,625 Sq Ft

  19 Old Town Rd, Bondville, VT 05340

  Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain.The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking

  Christiane Carroccio TPW Real Estate

  19 Old Town Rd, Bondville, VT 05340
• 

  

  /31

  $765,000 Sold Jan 23, 2025

  • 1,311 Sq Ft
  • $584/SF
  • 210 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1983

  790 Stratton Mountain Access Rd Unit 3415, Stratton, VT 05155

  True Ski-in/Ski-out Bliss Awaits! This rare corner, end-unit condo offers the ultimate convenience of slope-side living. Stairs to two chairlifts (Tamarack and Villager) are right outside the door. This 3-bedroom, 2-bathroom condo is truly turnkey. The recently renovated kitchen and bathrooms feature granite countertops and stainless steel appliances. Unwind by the wood-burning fireplace in the

  Robin Apps Four Seasons Sotheby's Int'l Realty

  790 Stratton Mountain Access Rd Unit 3415, Stratton, VT 05155
• 

  

  /39

  Est $607,322 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  22 Cranberry Hill Rd, Winhall, VT 05340

  22 Cranberry Hill Rd, Winhall, VT 05340
• 

  

  /35

  $649,000

  • 8 Beds
  • 3.5 Baths
  • 2,520 Sq Ft

  405 Vermont 30, Winhall, VT 05340

  Ski Resort Investment Gem! 2-Family Home Near Stratton & BromleyRare investment opportunity in the heart of Vermont's premier ski region. Located on scenic Vermont Route 30, this property offers unparalleled access to both Stratton Mountain Resort and Bromley Mountain Ski Resort. Whether you're looking to live in one unit and rent the other, or convert it to a single-family home, this

  Robin Apps Four Seasons Sotheby's Int'l Realty

  405 Vermont 30, Winhall, VT 05340
• 

  

  /48

  $379,000 Sold Jan 15, 2025

  • 2,000 Sq Ft
  • $190/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  3702 Vermont Route 100, Londonderry, VT 05148

  If you are looking for a property in a nice location for a good price, look no further. This single level residence sits off Route 100 in a super convenient neighborhood. Walk into an inviting floor plan beginning with a sunroom/mudroom and second entrance to basement. The eat in country kitchen is well planned for the ambitious cook, including a second sink. The kitchen/dining opens up into

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  3702 Vermont Route 100, Londonderry, VT 05148
• 

  

  /19

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,215 Sq Ft

  0 Birch Hill Rd Unit Sugar Maple 5003081, Winhall, VT 05340

  0 Birch Hill Rd Unit Sugar Maple 5003081, Winhall, VT 05340
• 

  

  /16

  $635,000

  • 2 Beds
  • 2 Baths
  • 916 Sq Ft

  761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360

  Beautifully renovated two bedroom two bathroom condominium in the ever popular Long Trail House community at Stratton Mountain Resort. Recently updates include new flooring throughout, paint, granite counter tops in kitchen and bathrooms, stainless steel appliances, window treatments, furniture and decor. Not many details have been left out. This particular floorplan boasts a large primary

  Timothy Mich Doddridge Stratton Real Estate

  761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360
• 

  

  /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
• 

  

  /26

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  147 Quarter Mile Rd Unit 1, Stratton, VT 05360

  147 Quarter Mile Rd Unit 1, Stratton, VT 05360
• 

  

  /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
• 

  

  /24

  $249,000 Sold Jan 10, 2025

  • Land
  • 23 Acres
  • $10,826 per Acre

  • 187 Days On Market

  106 Vt Route 30 Unit Property 3, Jamaica, VT 05343

  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 Vt Route 30 Unit Property 3, 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
• 

  

  /48

  $2,999,000

  • 6 Beds
  • 6.5 Baths
  • 6,500 Sq Ft

  25 Mountain Haunts Rd, Winhall, VT 05340

  Attend the PUBLIC OPEN HOUSE Monday February 17 from 10:00-2:00. Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4

  Kim Morgan-Wohler Wohler Realty Group

  25 Mountain Haunts Rd, Winhall, VT 05340
• 

  

  /36

  $725,000 Sold Jan 03, 2025

  • 1,800 Sq Ft
  • $403/SF
  • 30 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  11 Todd Hill Rd, Winhall, VT 05340

  Move into this pristine 3-bedroom, 2-bath home, just a short drive from Stratton Mountain. The ground floor features a custom-built mudroom with individual lockers and built-in boot warmers—perfect for mountain living. Fully updated with high-end finishes, the home boasts a chef’s kitchen with marble countertops and a spacious center island, seamlessly flowing into the dining area and a large

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  11 Todd Hill Rd, Winhall, VT 05340
• 

  

  /40

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,997 Sq Ft

  926 Dalewood Rd, Jamaica, VT 05343

  926 Dalewood Rd, Jamaica, VT 05343
• 

  

  /45

  $619,000

  • 3 Beds
  • 3 Baths
  • 2,341 Sq Ft

  49 High Point Dr Unit A122, Stratton, VT 05360

  Crown Point, Stratton Vermont. Enjoy this two-level, three bedroom, three bath condo. This home has an upper and lower entry, both with plenty of storage for outdoor gear. The upper level opens into the kitchen, dining area, and living room with wood burning fireplace and a small deck. The primary ensuite bedroom, with a jacuzzi tub, is also on the upper level. The lower level has a second living

  Mike England Michael England Real Estate

  49 High Point Dr Unit A122, Stratton, VT 05360
• 

  

  /14

  $370,000 Sold Dec 30, 2024

  • 820 Sq Ft
  • $451/SF
  • 75 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1983

  8 Ober Tal, Stratton, VT 05155

  Nice opportunity to make Stratton Mountain Resort your home away from home. This spacious 1 bedroom, 1 bath is located in close proximity to the Tamarack lift. It features a wood burning fireplace, large living area and dining area. This lower level unit has direct access to the ground floor. Being offered furnished.

  Jamie Wylie Stratton Real Estate

  8 Ober Tal, Stratton, VT 05155
• 

  

  /34

  Est $446,403 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,425 Sq Ft

  162 Upper Bear Ln Unit C-19, Jamaica, VT 05343

  162 Upper Bear Ln Unit C-19, Jamaica, VT 05343
• 

  

  /41

  $649,000

  • 3 Beds
  • 3 Baths
  • 1,886 Sq Ft

  4A Ridge, Winhall, VT 05340

  This immaculate 3-bedroom, 3-bath condominium sleeping eight comfortably is located in the desirable Piper Ridge Community. The first floor includes a spacious mudroom with built-in storage, a full-sized laundry area, and a guest bedroom suite. The living/dining room boasts a brick fireplace, knotty pine walls, and a cathedral ceiling. The kitchen, which is ideal for family gatherings, includes

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  4A Ridge, Winhall, VT 05340
• 

  

  /28

  $550,000 Sold Dec 20, 2024

  • 1,778 Sq Ft
  • $309/SF
  • 72 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  49 Styles Branch Rd Unit 904, Stratton, VT 05360

  Located just 1 mile from the Stratton Base Lodge, this Styles Brook townhome offers three levels of living and a prime location with winter weekend/holiday shuttle service. New owners will delight in the convenience and cozy modern-mountain style of this turn key gem, which is offered fully furnished. On the main level, you’ll find the kitchen, dining and living areas complete with a wood-burning

  Cheyanne Pugliese

  49 Styles Branch Rd Unit 904, Stratton, VT 05360
• 

  

  /27

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,215 Sq Ft

  5 Oak Rd Unit 5, Winhall, VT 05340

  5 Oak Rd Unit 5, Winhall, VT 05340
• 

  

  /21

  $609,000

  • 2 Beds
  • 2 Baths
  • 916 Sq Ft

  771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360

  771 Stratton Mountain Access Rd, Stratton, VT 05155Long Trail House is Stratton’s #1 location for owners who wish to combine personal use with an optional rental offset when not in residence. Walk to Village shops, restaurants and ski lifts. The floor plan for Long Trail House #261 is one of the largest of the 2 bedroom layouts. Master bedrooms has nice views of the Village Common.

  Andrew King Stratton Real Estate

  771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360
• 

  

  /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
• 

  

  /32

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,268 Sq Ft

  79 Shattarack Rd Unit E7B, Stratton, VT 05360

  79 Shattarack Rd Unit E7B, Stratton, VT 05360
• 

  

  /36

  $998,500

  • 4 Beds
  • 3.5 Baths
  • 2,070 Sq Ft

  32 Shattarack Rd Unit B5, Stratton, VT 05360

  They say beauty is only skin deep, but not in the case of this meticulously renovated Slopeside residence, which offers a rare combination of quality, comfort, and location. With more than $500,000 invested, this home delivers far more than surface-level appeal — the kind of work that is not always seen but is most certainly felt. Every system and surface has been thoughtfully addressed. Unlike

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  32 Shattarack Rd Unit B5, Stratton, VT 05360
• 

  

  /60

  $817,500 Sold Dec 13, 2024

  • 3,772 Sq Ft
  • $217/SF
  • 30 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1989

  53 Stratton View Rd, Bondville, VT 05340

  This is the mountain house you have been waiting! Just 5 minutes to the Stratton Mountain access road, this spacious residence boasts cathedral ceilings, 2 fireplaces, granite/stainless kitchen and wonderful views of Stratton Mountain trails. Situated on an oversized 2.95 acre parcel with pond, this home has what you are looking for in a Vermont getaway: 4 bedrooms /3.5 baths plus studio, office,

  Kim Morgan-Wohler Wohler Realty Group

  53 Stratton View Rd, Bondville, VT 05340
• 

  

  /37

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,751 Sq Ft

  2418 Vermont Route 100, Londonderry, VT 05148

  2418 Vermont Route 100, Londonderry, VT 05148
• 

  

  /40

  $1,450,000

  • 5 Beds
  • 3.5 Baths
  • 4,017 Sq Ft

  11 Founders Hill Rd, Winhall, VT 05360

  Stratton Mountain location for full time or vacation style living! Spacious home that you can walk to Village, gondola, golf and Sports center. Corner lot justdown the street from the Stratton Mountain Club and the Base Lodge. Home has five bedrooms with a chefs kitchen that has Viking Stove, ice-maker and three dishwashers for entertaining guests. Living room and dining room are graced with

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  11 Founders Hill Rd, Winhall, VT 05360
• 

  

  /32

  $950,000 Sold Dec 06, 2024

  • 3,658 Sq Ft
  • $260/SF
  • 58 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1991

  154 High Meadow Rd Unit C-17, Winhall, VT 05155

  Experience the charm of this updated mountain retreat, nestled in the coveted High Meadow area on Stratton Mountain. This home perfectly blends modern comfort with rustic elegance, featuring a large heated mudroom designed to store all your ski and snowboard gear after a day on the slopes. Inside, unwind in a beautifully maintained contemporary space, complete with two cozy fireplaces and

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  154 High Meadow Rd Unit C-17, Winhall, VT 05155

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