Windham, VT Homes in ZIP Code 05155

• 

  

  

  /25

  $499,000 Sold May 02, 2025

  • 1,096 Sq Ft
  • $455/SF
  • 2 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  16 Ober Tal Dr Unit E35, Stratton, VT 05360

  This top-floor, 2-bedroom, 2-bath condo in the sought-after E section of Ober Tal offers the ultimate in mountain access. Located just steps from the lifts, it's a true ski-in/ski-out property, and in the warmer months, enjoy hiking and mountain biking directly from your door. Whether you're hitting the slopes, exploring the trails, or biking the mountain, this condo offers the perfect location

  Carrie Mathews Winhall Real Estate

  16 Ober Tal Dr Unit E35, Stratton, VT 05360
• 

  

  

  /29

  Est $703,263 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,156 Sq Ft

  109 Fieldstone Way, South Londonderry, VT 05155

  109 Fieldstone Way, South Londonderry, VT 05155
• 

  

  

  /53

  $795,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 1,842 Sq Ft

  E12 Rock Ridge Rd, Winhall, VT 05155

  Move right in and start enjoying the Vermont lifestyle at Piper Ridge E12 —an impeccably updated, fully furnished 3-bedroom plus den, 3-bath townhome just minutes from Stratton Mountain. Inside this turnkey home, you'll find bright and welcoming spaces designed for comfort and functionality. Every detail has been thoughtfully considered —a brand-new kitchen, stylishly renovated baths, new

  Cheyanne Pugliese

  E12 Rock Ridge Rd, Winhall, VT 05155
• 

  

  

  /35

  $227,000 Sold May 02, 2025

  • 2,072 Sq Ft
  • $110/SF
  • 146 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1830

  347 Main St, South Londonderry, VT 05155

  Nestled in a peaceful location just 10 minutes from Bromley, Stratton, and Magic Mountains, this 3-bedroom, 2-bathroom home offers the perfect mix of comfort, charm, and functionality. With stunning views in every direction, it’s an ideal spot for both relaxation and entertaining. The spacious living room, featuring a beautiful fireplace, serves as the heart of the home. Large windows frame

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  347 Main St, South Londonderry, VT 05155
• 

  

  

  /13

  Est $147,875 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,146 Sq Ft

  1797 Thompsonburg Rd, South Londonderry, VT 05155

  1797 Thompsonburg Rd, South Londonderry, VT 05155
• 

  

  /56

  $1,330,500 Under Contract

  • 4 Beds
  • 4.5 Baths
  • 3,692 Sq Ft

  225 W Jamaica Rd, Stratton, VT 05360

  Perfectly situated between Mount Snow and Stratton Resort, and just a short drive to scenic Grout Pond and the National Forest, this Stratton, Vermont retreat offers the ideal balance of privacy, recreation, and comfort. Set on landscaped grounds with a tranquil pond, the main residence features four spacious bedrooms, two of which are en suite and four bathrooms. The open concept great room

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  225 W Jamaica Rd, Stratton, VT 05360
• 

  

  /53

  $825,000 Sold Apr 29, 2025

  • Land
  • 36 Acres
  • $23,109 per Acre

  • 102 Days On Market

  324 Pikes Falls Rd, South Londonderry, VT 05155

  Extraordinary Stratton Mountain Acreage Opportunity:Discover a rare gem in Stratton Mountain, a 35.7-acre parcel offering breathtaking, commanding views of the resort. Just 5 minutes away from the the Main Base Lodge and less to Sun Bowl. This exceptional property features two building sites, each supported by wastewater systems for a 6-bedroom and a 4-bedroom home.The established driveway leads

  Britt Wohler Wohler Realty Group

  324 Pikes Falls Rd, South Londonderry, VT 05155
• 

  

  /3

  Est $128,429 Not Listed For Sale

  • 3 Beds

  28 Melendy Hill Rd, South Londonderry, VT 05155

  28 Melendy Hill Rd, South Londonderry, VT 05155
• 

  

  /53

  $1,525,000 Under Contract

  • 3 Beds
  • 3.5 Baths
  • 5,105 Sq Ft

  3333 Under the Mountain Rd, Londonderry, VT 05148

  Perched gracefully along one of Vermont’s most storied and picturesque country roads, 3333 Under the Mountain Road is a rare and refined offering in the heart of South Londonderry. Encompassing 40 serene acres with sweeping panoramic views across sunlit valleys and distant resort ridgelines, this remarkable estate captures the very essence of elevated mountain living.The residence itself

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  3333 Under the Mountain Rd, Londonderry, VT 05148
• 

  

  /44

  $640,000 Sold Apr 25, 2025

  • 3,988 Sq Ft
  • $160/SF
  • 52 Days On Market

  • 7 Beds
  • 4 Baths
  • Built 1942

  13 Winhall Station Rd, Londonderry, VT 05155

  Solid six-bedroom home with detached one bedroom apartment being offered fully furnished on 3.4 acres of land! Surrounded by mature maples and beautiful local views of Stratton Mountain. This property sits on the corner of Winhall Station Road and Route 100 in Londonderry Vermont. Winhall Station Road will lead out a dead-end road to the Winhall Campground and the West River area with wonderful

  Julie Lowe Lowe's Real Estate, LLC

  13 Winhall Station Rd, Londonderry, VT 05155
• 

  

  /7

  Est $538,398 Not Listed For Sale

  • 9 Beds
  • 4.5 Baths
  • 4,292 Sq Ft

  270 Vt Route 121, Londonderry, VT 05148

  270 Vt Route 121, Londonderry, VT 05148
• 

  

  /26

  $529,000

  • 4 Beds
  • 2.5 Baths
  • 1,864 Sq Ft

  1966 Thompsonburg Rd, South Londonderry, VT 05155

  A quiet, private sanctuary in a prime location—just minutes from all three local ski areas, Lowell Lake, and the shopping and dining of Londonderry and Manchester. This 4-bedroom retreat is ready to be loved by a new family. Enjoy newly updated bathrooms, appliances, countertops, a new chimney liner, a wood-burning fireplace, and a wood stove insert that makes the family room especially cozy on

  Wilkie Bushby TPW Real Estate

  1966 Thompsonburg Rd, South Londonderry, VT 05155
• 

  

  /31

  $355,000 Sold Apr 18, 2025

  • 1,350 Sq Ft
  • $263/SF
  • 2 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1968

  5 Snow Drift Ln, Londonderry, VT 05155

  You must see this charming 4 bedroom, 2 bath condo with an open kitchen/ living area, inviting entry, spacious lower level mudroom and sleeping loft. Everything has been updated- bathrooms, kitchen, flooring, decks. Walk out of the lower level mudroom and be on the lift at Magic in 2 minutes. Views of Bromley Mtn from your new deck! Okemo, Bromley and Stratton all within 25 minutes. Come unpack

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  5 Snow Drift Ln, Londonderry, VT 05155
• 

  

  /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
• 

  

  /37

  $730,000

  • 5 Beds
  • 3 Baths
  • 2,275 Sq Ft

  341 Under the Mountain Rd, Londonderry, VT 05148

  Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

  Andy Reed Four Seasons Sotheby's Int'l Realty

  341 Under the Mountain Rd, Londonderry, VT 05148
• 

  

  /41

  $2,100,000 Sold Apr 04, 2025

  • 5,300 Sq Ft
  • $396/SF
  • 248 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1974

  20 W Ridge Rd, Stratton, VT 05360

  OPEN HOUSE. Friday July 5th, 2-4pm. All Welcome.The exquisite craftsmanship of this stunning Austrian-style chalet evokes the lure of Stratton's early days. A location that was selected for incredible views, and close ski trail access. This true mountain haus has been thoughtfully updated to preserve its charm and authenticity. Imagine waking up to incredible mountain views every morning and

  Christiane Carroccio TPW Real Estate

  20 W Ridge Rd, Stratton, VT 05360
• 

  

  /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
• 

  

  /28

  $1,700,000

  • 4 Beds
  • 3.5 Baths
  • 2,363 Sq Ft

  43 Middle Ridge Rd Unit 415, Winhall, VT 05155

  Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the

  Edwin Kevil Stratton Real Estate

  43 Middle Ridge Rd Unit 415, Winhall, VT 05155
• 

  

  /39

  $1,250,000 Sold Apr 02, 2025

  • 2,625 Sq Ft
  • $476/SF
  • 32 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2003

  6 Cranberry Ct, Stratton, VT 05360

  Designed for mountain living, this expansive 4-bedroom, 4-bathroom townhome is the largest floor plan in Tree Top, offering unparalleledsquare footage and luxurious features. The property includes a total of 4 bedrooms, 3 are spacious primary suites with private baths, a cozy lower-level family room, and an open-concept great room adorned with a stone fireplace, soaring cathedral ceilings, and

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  6 Cranberry Ct, 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
• 

  

  /33

  $820,000

  • 4 Beds
  • 3 Baths
  • 2,317 Sq Ft

  0 Maple Ridge Rd Unit B-2, Winhall, VT 05340

  Beautifully updated Piper Ridge townhouse just steps from the private sports center and offering weekend/holiday shuttle service to Stratton’s lifts in winter. This light-filled home features an updated kitchen and baths, gleaming hardwood floors, and elegant tilework throughout. The one-car garage has been thoughtfully converted into a spacious ski room plus a large storage or owner’s

  Carrie Mathews Winhall Real Estate

  0 Maple Ridge Rd Unit B-2, Winhall, VT 05340
• 

  

  /35

  $1,900,000 Sold Apr 01, 2025

  • 2,581 Sq Ft
  • $736/SF
  • 14 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1986

  16 Mountain Reach Mews Rd, Stratton, VT 05155

  Located just steps from Stratton Village and the lifts, this luxurious slopeside townhouse offers a seamless blend of upscale contemporary design and unbeatable convenience. With gated access and no public roads to cross, this end-unit residence provides a true retreat in the heart of Stratton’s trailside community.Step into the bright, open floor plan where modern elegance meets extraordinary

  Trent Stephens Wohler Realty Group

  16 Mountain Reach Mews Rd, Stratton, VT 05155
• 

  

  /13

  Not Listed For Sale

  234 Mountain Rd, Stratton, VT 05155

  234 Mountain Rd, Stratton, VT 05155
• 

  

  /31

  $799,000

  • 3 Beds
  • 3 Baths
  • 2,317 Sq Ft

  9 F Cobble Ridge Rd, Winhall, VT 05340

  Step into a lifestyle of luxury and convenience at Piper Ridge D9! This stunning community offers the perfect blend of comfort and excitement, with fantastic amenities like a sparkling swimming pool, tennis courts, a clubhouse for social gatherings, and even a weekend shuttle service in the winter—ideal for enjoying the nearby slopes! Inside the impeccably maintained townhouse, you'll find a cozy

  Carrie Mathews Winhall Real Estate

  9 F Cobble Ridge Rd, Winhall, VT 05340
• 

  

  /19

  $585,000 Sold Apr 01, 2025

  • 1,811 Sq Ft
  • $323/SF
  • 180 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  47 High Point Dr Unit B21, Stratton, VT 05360

  This top-floor, end-unit 3-bedroom, 3-bath Crown Point condominium offers the ideal balance of comfort and convenience. Located just a short walk from the Stratton Sports Center and Stratton Village, it's perfectly situated for both relaxation and adventure. The shuttle provides easy access to the slopes and all that Stratton has to offer. Inside, the open floor plan features cathedral ceilings

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  47 High Point Dr Unit B21, Stratton, VT 05360
• 

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,872 Sq Ft

  244 Derry Ln, Londonderry, VT 05155

  244 Derry Ln, Londonderry, VT 05155
• 

  

  /49

  $795,000

  • 4 Beds
  • 3.5 Baths
  • 1,993 Sq Ft

  65 Styles Branch Rd Unit 819, Stratton, VT 05360

  Welcome to Styles Brook 819, an impeccably maintained end unit townhome nestled in the heart of Stratton Mountain Resort. This spacious and light filled 4 bedroom, 3.5 bath residence offers everything you need for four season mountain living, whether you're hitting the slopes in winter or enjoying the cool summer breeze from your private deck. Soak, unwind and recharge after a day on the mtn in

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  65 Styles Branch Rd Unit 819, Stratton, VT 05360
• 

  

  /14

  $1,050,000 Sold Mar 29, 2025

  • 1,780 Sq Ft
  • $590/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  759 Stratton Mountain Access Rd Unit 331, Stratton, VT 05340

  Incredible opportunity to own in one of Stratton Mountain Resort's most desirable communities! One of the largest three bedroom floor plans in all of Hearthstone Lodge. This home boasts three bedroom and two and half bathrooms, corner location directly off the elevator, open floor plan with mountain views, cozy gas fireplace, air conditioning for Summer use and two assigned underground parking

  Timothy Mich Doddridge Stratton Real Estate

  759 Stratton Mountain Access Rd Unit 331, Stratton, VT 05340
• 

  

  /21

  Est $308,840 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
• 

  

  /28

  $525,000

  • 2 Beds
  • 2 Baths
  • 1,096 Sq Ft

  8 Ober Tal Unit A-32, Stratton, VT 05155

  Located trailside at the Tamarack Lift, this two-bedroom, two-bathroom Ober Tal condo offers prime proximity to the slopes—no need to spend time driving or finding parking. Simply gear up from the comfort of your home and head straight to the lift. In the summer, you'll also have direct access to hiking, mountain biking, and seasonal events and concerts in Stratton Village. Inside, the condo

  Cheyanne Pugliese

  8 Ober Tal Unit A-32, Stratton, VT 05155
• 

  

  /29

  $550,000 Sold Mar 28, 2025

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

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  43 Styles Branch Rd Unit 1008, Stratton, VT 05360

  Nestled in the desirable Styles Brook community, this inviting 3-bedroom, 2.5-bath townhome offers the perfect blend of privacy and convenience. With a sought-after location just steps away from the pool and paddle tennis court, this property provides the ideal setting for relaxation and recreation. Enjoy a private and serene atmosphere while being part of a vibrant neighborhood, with easy access

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  43 Styles Branch Rd Unit 1008, Stratton, VT 05360
• 

  

  /32

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  43 Middle Ridge Rd Unit 120, Winhall, VT 05155

  43 Middle Ridge Rd Unit 120, Winhall, VT 05155
• 

  

  /30

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft

  340 Melendy Hill Rd, Londonderry, VT 05155

  340 Melendy Hill Road, South Londonderry, VT40 Acres | 3 Beds | 2 Baths | Expansive Barn | Mountain ViewsTucked away in the hills of South Londonderry, this charming three-bedroom, two-bath cabin offers the perfect balance of privacy, natural beauty, and quintessential Vermont living. Sited on 40 peaceful acres with sweeping mountain views, the property feels like a private

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  340 Melendy Hill Rd, Londonderry, VT 05155
• 

  

  /29

  $689,000 Sold Mar 14, 2025

  • 1,207 Sq Ft
  • $571/SF
  • 17 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2004

  19 Village Lodge Rd Unit 302, Stratton, VT 05155

  Getting to and from the ski slopes and village doesn't get much easier! Landmark is located within Stratton Mountain Resorts iconic clock tower, nestled within the heart of the walking village. Step out the front door for a few laps, pop down to the market for a quick lunch, or a stroll through the village shops. This 2 bedroom, 2 bath home is conveniently located in the village, with tons of

  Jamie Wylie Stratton Real Estate

  19 Village Lodge Rd Unit 302, Stratton, VT 05155
• 

  

  /37

  Est $299,374 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,000 Sq Ft

  176 Melendy Hill Rd, South Londonderry, VT 05155

  176 Melendy Hill Rd, South Londonderry, VT 05155
• 

  

  /26

  $795,000

  • 3 Beds
  • 3 Baths
  • 2,044 Sq Ft

  6 Quarter Mile Rd, Winhall, VT 05340

  AMAZING LOCATION! Walking distance to Stratton Mountain! This home is located on the shuttle route and being offered fully furnished! Walk to the slopes or just take a nice walk around the local trails. Spacious home with ample room for everyone. The open concept kitchen, dining, living room offers cathedral ceilings and woodburning fireplace. French doors leading out to the firepit area for

  Julie Lowe Lowe's Real Estate, LLC

  6 Quarter Mile Rd, Winhall, VT 05340
• 

  

  /25

  $825,000 Sold Mar 14, 2025

  • 2,317 Sq Ft
  • $356/SF
  • 135 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  0 Cobble Ridge Rd Unit D2, Winhall, VT 05340

  This nicely appointed and updated townhome nestled in the Piper Ridge community is a must see. Close proximity to Stratton Mountain Resort, this nice Highgate unit offers three bedrooms with an additional family room on the lower level that has been converted into another bedroom. The bright and inviting living room with wood burning fireplace creates the perfect space for enjoying cold wintery

  Jamie Wylie Stratton Real Estate

  0 Cobble Ridge Rd Unit D2, Winhall, VT 05340
• 

  

  /28

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,014 Sq Ft

  43 Middle Ridge Rd Unit 312, Winhall, VT 05155

  43 Middle Ridge Rd Unit 312, Winhall, VT 05155
• 

  

  /28

  $825,000

  • 4 Beds
  • 2 Baths
  • 1,068 Sq Ft

  6 Roundtree Rd, Winhall, VT 05340

  Prime Stratton location! This charming 4-bedroom, 2-bathroom retreat offers vaulted ceilings, an open-concept living area with a wood burning fireplace, and a private deck and backyard for relaxing after a day on the slopes. With weekend and holiday shuttle service during ski season, plus easy access to Stratton Village’s shops, dining, and year-round activities, it’s the ideal spot to recharge

  Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  6 Roundtree Rd, Winhall, VT 05340
• 

  

  /59

  $5,150,000 Sold Mar 12, 2025

  • 7,498 Sq Ft
  • $687/SF
  • 93 Days On Market

  • 9 Beds
  • 10.5 Baths
  • Built 2014

  64 Tamarack Rd, Stratton, VT 05360

  Discover this Extraordinary Stratton Mountain Resort Tamarack Heights premier trailside residence. Situated on a sprawling 1.4-acre trailside lot, this property exudes unassuming grandeur from the moment you enter its magnificent great room with a soaring two-story fireplace and floor-to-ceiling windows that frame breathtaking panoramic views of Stratton Village and the surrounding mountains.

  Kim Morgan-Wohler Wohler Realty Group

  64 Tamarack Rd, Stratton, VT 05360

Showing Results 41 - 80, Page 2 of 18