Windham, VT Homes

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  /14

  $120,000

  • Land
  • 2.07 Acres
  • $57,971 per Acre

  191 Pingree Park Ln, Londonderry, VT 05148

  Discover this hidden gem in Londonderry. River frontage on pristine Utley Brook with headwaters flowing from the Green Mountain National Forest create a serene setting minutes from downtown. Full time residence or vacation home, you choose! Ready to build. Completely engineered- State and Town permits for a 4 bedroom home in place including septic permits, well and house placement, updated

  

  Alison Cummings

  Cummings & Co

  (802) 848-6904

  191 Pingree Park Ln, Londonderry, VT 05148
• 

  

  

  /18

  $25,000 per month

  • 3 Beds
  • 2 Baths
  • 1,423 Sq Ft
  • House for Rent

  378 Tuttle Hill Rd, Londonderry, VT 05155

  Welcome to your turn-key home for the '25-'26 ski season! Fully renovated with attention to detail, this cheerful, sunny Scandinavian Modern space welcomes and inspires. 15 minutes to Stratton Base, 14 minutes to Bromley Village, and 10 minutes to Magic Mountain, you are in the middle of it all, with your choice to either explore or stick to your home mountain. The main floor includes a

  Jamie Luke TPW Real Estate

  378 Tuttle Hill Rd, Londonderry, VT 05155
• 

  

  

  /8

  $30,000 Sold Jul 31, 2025

  • Land
  • 2.67 Acres
  • $11,236 per Acre

  • 3 Days On Market

  0 Loon Circle Private, Londonderry, VT 05148

  Nestled in the Powder Mill neighborhood of Londonderry, VT, this expansive 2.67-acre parcel offers a prime opportunity to build your dream home in a serene, wooded setting. With a 4-bedroom wastewater permit already in place and electricity at the street, much of the groundwork has been laid for seamless development. Powder Mill boasts its own network of private hiking trails and is located

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  0 Loon Circle Private, Londonderry, VT 05148
• 

  

  

  /40

  Est $951,472 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  1751 Under the Mountain Rd, South Londonderry, VT 05155

  1751 Under the Mountain Rd, South Londonderry, VT 05155
• 

  

  

  /18

  $130,000

  • Land
  • 2.19 Acres
  • $59,361 per Acre

  192 Pingree Park Ln, Londonderry, VT 05148

  Discover this hidden gem in Londonderry. River frontage on pristine Utley Brook with headwaters flowing from the Green Mountain National Forest create a serene setting minutes from downtown. Full time residence or vacation home, you choose! Ready to build. Completely engineered- State and Town permits for a 4 bedroom home in place including septic permits, well and house placement, updated

  

  Alison Cummings

  Cummings & Co

  (802) 444-8158

  192 Pingree Park Ln, Londonderry, VT 05148
• 

  

  /39

  $13,000 per month

  • 7 Beds
  • 7 Baths
  • 6,600 Sq Ft
  • House for Rent

  89 Jaquith Rd, Londonderry, VT 05148

  It's time to start planning a Vermont winter retreat like no other. This stunning, architect designed property is located centrally to Okemo, Stratton, Bromley and Magic Mountains. The property is perfect for snowshoeing, cross country skiing ice skating and apres ski warming around the rustic fire pit area. Inside, you will have breathtaking views, top of the line amenities and features abound.

  Peggy O'neill Cummings & Co

  89 Jaquith Rd, Londonderry, VT 05148
• 

  

  /17

  $195,000 Sold Jul 25, 2025

  • 1,414 Sq Ft
  • $138/SF
  • 26 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1880

  2147 N Main St, Londonderry, VT 05148

  Terrific in-town location! Improvements include new roof and trim last year, 24kw Generator, serviced annually, new flooring on first level and new washer and dryer. Easy to maintain yard space, walk to the plaza for shopping and restaurants, minutes to 3 ski resorts!

  Lisa Kelley Cummings & Co

  2147 N Main St, Londonderry, VT 05148
• 

  

  /32

  Est $453,849 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,838 Sq Ft

  4232 Vt Route 11, Londonderry, VT 05148

  4232 Vt Route 11, Londonderry, VT 05148
• 

  

  /56

  $350,000

  • 6 Beds
  • 4.5 Baths
  • 3,042 Sq Ft

  2072 N Main St, Londonderry, VT 05148

  Rare Mixed-Use Opportunity in Downtown Londonderry, VT – Live, Work, or Invest! Unlock the full potential of this versatile and beautifully situated property in the heart of Londonderry’s vibrant downtown district. With major West River frontage, expansive lawn space, and prime visibility on North Main Street, this unique listing offers endless possibilities — perfect for residential, commercial,

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 441-6058

  2072 N Main St, Londonderry, VT 05148
• 

  

  /22

  $30,000 per month

  • 4 Beds
  • 2.5 Baths
  • 3,154 Sq Ft
  • House for Rent

  157 Old Sawmill Rd, Londonderry, VT 05148

  Wonderful Norwegian style chalet available for seasonal rental in southern VT ski country. Watch the snow cats on Magic Mountain from the home. Magic Mountain is 1.5 miles/4 minutes from the home. Stratton and Bromley Mountains are 20 minutes away. Okemo is 25 minutes away, and Killington is 55 minutes away. The VAST system for snowmobiling is accessible from the house, no need to trailer

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  157 Old Sawmill Rd, Londonderry, VT 05148
• 

  

  /40

  $840,000 Sold Jun 27, 2025

  • 6,570 Sq Ft
  • $128/SF
  • 27 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1990

  359 Chaves Rd, Londonderry, VT 05148

  Experience the best of Vermont in this private mountain retreat, perfectly located near Magic, Bromley, Okemo, and Stratton Mountains for skiing, as well as cross-country trails and Lowell Lake. Situated on 36 picturesque acres, the driveway winds past a neighboring pond to reveal a home with a level grassy yard, perfect for lawn games and evenings around the fire pit.This 5-bedroom

  Julie Citron RE/MAX Four Seasons

  359 Chaves Rd, Londonderry, VT 05148
• 

  

  /18

  Est $379,694 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,440 Sq Ft

  107 Pond St, Londonderry, VT 05148

  107 Pond St, Londonderry, VT 05148
• 

  

  /42

  $829,000

  • 5 Beds
  • 2.5 Baths
  • 3,102 Sq Ft

  1410 Haven Hill Rd, South Londonderry, VT 05155

  This beautiful Timber frame home on an 8.1 acre lot is located a few miles from the base of Stratton, Bromley, and Magic Mountain making it a versatile investment. Whether a seasonal prospect or primary home, being next door to Gale Meadow Pond provides a wonderful destination to walk, hike, fish, or just paddle. This home has a private, beautiful yard with its own pond, stream, and firepit just

  Amy Carson Lowe's Real Estate, LLC

  1410 Haven Hill Rd, South Londonderry, VT 05155
• 

  

  /19

  $3,000 per month

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft
  • Condo for Rent

  47 Crown Point Dr Unit B-13, Stratton, VT 05155

  Need a place to get away this Summer or Fall? Look no further. This well-equipped condo has three bedrooms and three full baths. The main living area is the much-desired open concept style which is wonderful for entertaining. There is a second living room on the lower level which is fantastic for company. This condo has several mini splits which will conquer those humid nights that we get

  Peggy O'neill Cummings & Co

  47 Crown Point Dr Unit B-13, Stratton, VT 05155
• 

  

  /26

  $593,500 Sold Jun 17, 2025

  • 1,607 Sq Ft
  • $369/SF
  • 75 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  2513 Thompsonburg Rd Unit 3A, South Londonderry, VT 05155

  Welcome to this well-cared-for, one-owner home in the charming town of Londonderry, VT. Nestled on a private, beautifully landscaped lot, this property offers both tranquility and convenience, with easy access to three major ski areas—perfect for outdoor enthusiasts.This bright and inviting home features an open layout that maximizes natural light throughout. The spacious main floor boasts a cozy

  Carrie Mathews Winhall Real Estate

  2513 Thompsonburg Rd Unit 3A, South Londonderry, VT 05155
• 

  

  /40

  Est $636,697 Not Listed For Sale

  • 8 Beds
  • 4 Baths
  • 4,473 Sq Ft

  55 Pond St, Londonderry, VT 05148

  55 Pond St, Londonderry, VT 05148
• 

  

  /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
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  /43

  $490,000 Sold Jun 16, 2025

  • 1,204 Sq Ft
  • $407/SF
  • 239 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  132 Pingree Park Ln, Londonderry, VT 05148

  The interior footprint of this home is over 3900 sq feet! The original 1200 finished sq feet is enhanced by an addition needing interior finishing only. The large main floor of the addition (595 sq ft) has top quality construction, lots of natural light and an open floor plan. The 595 sq ft space above will make a stunning primary suite. Situated on a lovely parcel of land you will find

  Alison Cummings Cummings & Co

  132 Pingree Park Ln, Londonderry, VT 05148
• 

  

  /28

  Est $329,940 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,782 Sq Ft

  2197 N Main St, Londonderry, VT 05148

  2197 N Main St, Londonderry, VT 05148
• 

  

  /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
• 

  

  /30

  $275,000 Sold Jun 11, 2025

  • 1,350 Sq Ft
  • $204/SF
  • 48 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1962

  5 Snow Drift Ln Unit 6, Londonderry, VT 05155

  Are you looking to add a little Magic to your life? Then, this is the place for you! Located just off the base area of Vermont’s beloved Magic Mountain in Londonderry, this small, welcoming condo development has just 6 units and embodies the spirit of its nearby mountain with a closeknit and friendly community. Walk to the lifts and ski home in the winter months, wander over to the base area for

  Claudia Harris Mary Mitchell Miller Real Estate

  5 Snow Drift Ln Unit 6, Londonderry, VT 05155
• 

  

  /27

  Est $206,401 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,356 Sq Ft

  765 Thompsonburg Rd, South Londonderry, VT 05155

  765 Thompsonburg Rd, South Londonderry, VT 05155
• 

  

  /37

  $759,000

  • 3 Beds
  • 4 Baths
  • 3,352 Sq Ft

  183 Vacation Lodge Rd, Londonderry, VT 05148

  Welcome to your mountain oasis tucked away in the scenic hills of Londonderry, Vermont. This contemporary 3-bedroom, 4-bathroom home is designed for comfort, entertaining, and enjoying every season. Whether you're looking for a relaxing retreat, a rental income opportunity, or a full-time family compound, this property offers something special for everyone.Step into a space that blends

  Brian Hill Remax Summit

  183 Vacation Lodge Rd, Londonderry, VT 05148
• 

  

  /39

  $405,000 Sold May 16, 2025

  • 1,215 Sq Ft
  • $333/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  5 Red Hickory Rd, Winhall, VT 05340

  The season is not over! Red Hickory 5 at Birch Hill is one of the best values today offered at Stratton. This ready to move into attractively appointed Co-Op townhome is located at the quiet end of popular Birch Hill street with views of the mountain. Three bedrooms, two baths, family room. Winter shuttle service to the base lodge. Brand new in ground pool for your summer enjoyment. This

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  5 Red Hickory Rd, Winhall, VT 05340
• 

  

  /4

  Est $335,082 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  283 Main St, South Londonderry, VT 05155

  283 Main St, South Londonderry, VT 05155
• 

  

  /58

  $825,000

  • 4 Beds
  • 3.5 Baths
  • 3,588 Sq Ft

  524 Reilly Rd, Londonderry, VT 05148

  Are you looking for a home with spectacular winter views of Stratton Mountain and seated on a private lot? Look no further. This home has it all. Spectacular views, soaring spacious rooms and more in this stunning Vermont facade log home. Vaulted ceilings and a dramatic stone fireplace framed by multiple windows looking out at your full wrap around deck and the slopes of Stratton across the open

  Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  524 Reilly Rd, Londonderry, VT 05148
• 

  

  /15

  $159,500 Sold May 14, 2025

  • Land
  • 11 Acres
  • $14,395 per Acre

  • 440 Days On Market

  000 Rose Ln, Londonderry, VT 05148

  MOTIVATED SELLERS!!!! This 11 acre parcel is located just off Cole Pond, and is just a few miles to Stratton Mountain Access Road. One lot sits high in the sky with breathtaking views and all the serenity of nature. A well constructed driveway runs approximately halfway up the property where you will find a partial building site with an incredible view of Bromley Mountain, from there if you

  Rachel Febbie EXP Realty

  000 Rose Ln, Londonderry, VT 05148
• 

  

  /38

  Est $522,412 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,856 Sq Ft

  116 Deerwood Hill, South Londonderry, VT 05155

  116 Deerwood Hill, South Londonderry, VT 05155
• 

  

  /51

  $970,000

  • 6 Beds
  • 8 Baths
  • 5,764 Sq Ft

  24 Vt Route 11, Londonderry, VT 05148

  Step into a world of potential with this beautiful country retreat, set on the edge of pristine Green Mountain National Forest. Adventure truly begins here, with nearby access to the Catamount Trail and four renowned ski areas just minutes away. Once home to the beloved Nordic Inn, this versatile property carries a rich legacy of hospitality, having once hosted a restaurant and cross-country ski

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  24 Vt Route 11, Londonderry, VT 05148
• 

  

  /16

  $195,000 Sold May 09, 2025

  • Land
  • 22 Acres
  • $8,667 per Acre

  • 152 Days On Market

  5734 Vermont 11, Landgrove, VT 05148

  MAKE YOUR MEMORIES HERE!! The possibilities are endless for turning this diversified property into your heart's desire. Loved, ownedby, gathered upon, and maintained by the same family for generations, and now it's your turn to make it your own haven. This 23.5 acre parcel is just fullof natural beauty, with an abundance of birds and wildlife. Some of the features include a stream-fed pond, 2

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  5734 Vermont 11, Landgrove, VT 05148
• 

  

  /36

  Est $362,971 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,940 Sq Ft

  74 Evergreen Ln, Londonderry, VT 05148

  74 Evergreen Ln, Londonderry, VT 05148
• 

  

  /60

  $899,000

  • 7,902 Sq Ft

  3806 Vermont 11, Londonderry, VT 05148

  This property features a 18-unit motel, that includes two apartment suites, alongside a spacious 3-bedroom, 2-bathroom home, making it a unique investment opportunity. Situated in the charming town of Londonderry, this property is perfectly positioned to attract visitors year-round with its proximity to two of Vermont's most popular ski destinations—Okemo Mountain Resort and Stratton Mountain

  Flex Realty Group Flex Realty

  3806 Vermont 11, Londonderry, VT 05148
• 

  

  /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
• 

  

  /23

  Est $225,379 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  534 Sherwood Forest, Londonderry, VT 05148

  534 Sherwood Forest, Londonderry, VT 05148
• 

  

  /33

  $799,000 Pending

  • 5 Beds
  • 5 Baths
  • 3,431 Sq Ft

  389 Howard Hill Rd, Londonderry, VT 05148

  Showing to start July 7th. The Octagon at Powder Mill: An Exceptional Mountain GetawayThis extraordinary modern home is a true gem, offering a perfect blend of natural light, expansive space, and architectural elegance. With panoramic windows framing awe-inspiring mountain vistas from every corner, this property showcases a unique design that masterfully balances aesthetics with practicality.

  Carrie Mathews Winhall Real Estate

  389 Howard Hill 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
• 

  

  /34

  Est $453,742 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  26 Sherwood Forest, Londonderry, VT 05148

  26 Sherwood Forest, Londonderry, VT 05148
• 

  

  /48

  $895,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,573 Sq Ft

  573 Middletown Rd, Londonderry, VT 05148

  Wonderful four bedroom home in the desirable town of Londonderry, Vermont. Once part of the Janeway Farm and Middletown Dairy this property has served as a primary home for many years. Spacious home has four bedrooms with three en-suite bedrooms. Land is suitable for gardens and room for play. There is a garden shed and a work shop just behind the house for any hobbies or projects. Living room

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  573 Middletown Rd, Londonderry, VT 05148
• 

  

  /32

  $267,500 Sold Apr 21, 2025

  • 864 Sq Ft
  • $310/SF
  • 117 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1966

  38 Pine Tree Hill, Londonderry, VT 05148

  Two homes for the price of one on 4+ acres, w/frontage on the West River! Main home is a charming Mid-Century Modern Ranch featuring 2 beds, 1 full bath, wood floors, large sliders open from th living areas to the covered porch. Two-car garage w/sink & mechanics pit an excellent workshop, hobby, or storage spot. Across the property, a spacious ‘90s manufactured home w/3 beds, 2 full baths,

  Jacki Murano Southern Vermont Realty Group

  38 Pine Tree Hill, Londonderry, VT 05148
• 

  

  /20

  Est $403,383 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,528 Sq Ft

  23 Hemlock Dr, Londonderry, VT 05148

  23 Hemlock Dr, Londonderry, VT 05148

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