4,492

South Londonderry, VT Homes

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  • /38

    $495,000

    $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,115 Sq Ft

    367 Stratton Gate Rd, Jamaica, VT 05343

    Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer.Designed for gathering and relaxing, the home features two

    Agent Photo

    Alison Cummings

    Cummings & Co

    367 Stratton Gate Rd, Jamaica, VT 05343
  • /33

    $20,000 Per Month

    • 2 Beds
    • 1 Bath
    • 1,004 Sq Ft
    • Condo for Rent

    16 Old Farm Rd Unit 1, Winhall, VT 05340

    16 OLD FARM ROADThe winter ski season is just around the corner! After a day on the slopes, unwind by the cozy brick wood-burning fireplace or relax in the comfortable living room, where the exposed beams and barn board wainscoting give you the warmth and charm of a classic Vermont ski retreat. The back door opens to a patio and level backyard, perfect for grilling your evening meal and

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    16 Old Farm Rd Unit 1, Winhall, VT 05340
  • /12

    $125,000

    Sold Dec 11, 2025

    0 Dalewood Rd Unit 4955807, Jamaica, VT 05343

    • Land
    • 1.51 Acres
    • $82,781 per Acre

    Last Sold Summary

    • 880 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    0 Dalewood Rd Unit 4955807, Jamaica, VT 05343
    • /39

      Not Listed For Sale

      75 E Birch Rd Unit 39, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,150 Sq Ft
      • Built 1986
      75 E Birch Rd Unit 39, Stratton, VT 05360

      Last Sold Summary

      • 27 Days On Market

  • /55

    $495,000

    $60K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,344 Sq Ft

    935 Old Manchester Rd, Peru, VT 05152

    Cozy Off-Grid Cabin on 10 Private Acres – Peace, Privacy & Ski AccessEscape to your own woodland retreat with this charming 2-bed, 1-bath cabin nestled on 10 serene acres of open meadow and forest. Just 4.5 miles to Bromley Ski & Snowboarding Mountain, this property offers the perfect mix of off-grid living and outdoor adventure.Fully self-sufficient with solar power and propane generator

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    935 Old Manchester Rd, Peru, VT 05152
  • /46

    $5,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,300 Sq Ft
    • House for Rent

    15 Nearing Rd, Winhall, VT 05340

    THE ULTIMATE STRATTON MOUNTAIN RETREAT Experience the perfect Vermont winter getaway in this exceptional home ideally located in the highly desirable Forest Farms neighborhood. Boasting a premier location with effortless mountain access, this property is designed for those who want to maximize their time on the slopes and enjoy a seamless mountain lifestyle. Available for multiple flexible

    David Powers 42 North LP

    15 Nearing Rd, Winhall, VT 05340
  • /26

    $315,000

    Sold Apr 14, 2026

    9047 Vermont 30, Jamaica, VT 05155

    • 2 Beds
    • 2 Baths
    • 976 Sq Ft
    • Built 1940

    Last Sold Summary

    • 3% Below List Price
    • $323/SF
    • 20 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    9047 Vermont 30, Jamaica, VT 05155
    • /22

      Not Listed For Sale

      18 Stratton Ridge Rd, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,332 Sq Ft
      • Built 1970
      18 Stratton Ridge Rd, Winhall, VT 05340

      Last Sold Summary

      • 72 Days On Market

  • /33

    $915,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,529 Sq Ft

    761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360

    A rare opportunity in Long Trail House, this corner residence has been thoughtfully reimagined from two separate units into a spacious, fully renovated retreat designed for flexible living. The expanded layout now includes multiple sleeping areas and a den/office, offering versatility for guests or remote work. Natural light fills the home thanks to its corner position, while open living space

    Edwin Kevil Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360
  • /19

    $70,000 Per Month

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    16 c Winterberry Heights, Stratton, VT 05155

    Best of the Best. Ski on Ski off. Pristine clean unit, very well maintained and original owners. Largest Treetops there is.. 4 bedroom/4 bath, den family room, amazing views, brand new hot tub.. everything you want and need for an amazing winter season. Loads of room for family and guests and entertaining. Enjoy all that Stratton has to offer as well as all the other ski areas close by and

    Wilkie Bushby TPW Real Estate

    16 c Winterberry Heights, Stratton, VT 05155
  • /37

    $340,000

    Sold Aug 14, 2025

    290 Melendy Hill Rd, South Londonderry, VT 05155

    • 3 Beds
    • 3 Baths
    • 2,809 Sq Ft
    • Built 1936

    Last Sold Summary

    • 15% Below List Price
    • $121/SF
    • 159 Days On Market

    Current Estimated Value $351,322

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    290 Melendy Hill Rd, South Londonderry, VT 05155
    • /27

      Not Listed For Sale

      0 W Hill Rd S Unit 5006431, Jamaica, VT 05343

      0 W Hill Rd S Unit 5006431, Jamaica, VT 05343

      Last Sold Summary

      • 136 Days On Market

  • /16

    $1,050,000

    • 4 Beds
    • 3.5 Baths
    • 2,256 Sq Ft

    16 Middle Ridge Rd Unit 22, Winhall, VT 05155

    Unique four bedroom three and one half bath townhome, located directly across the street from the Stratton Village and ski area. Built in 1988, Fox Chapel is the second phase of the Village Chalet neighborhood. Only 27 of these properties exist. Although connected by a breezeway to the property next to it, feels very much like a stand alone home. Walking distance to shops, restaurants and all ski

    John Sikes Stratton Real Estate

    16 Middle Ridge Rd Unit 22, Winhall, VT 05155
  • /13

    $14,000 Per Month

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    41 Cranberry Hill Rd, Winhall, VT 05340

    Le Petite Chalet! -A rare opportunity to rent a beautifully updated 1-bedroom chalet in Strattonwald available this ski season. The house has been fully renovated with many modern updates made to this classic chalet home. There is a delightful open concept kitchen, living and dining on the first floor and a luxurious bedroom, bath and relaxing nook on the lower level. Skip the parking hassle at

    Peggy O'neill Cummings & Co

    41 Cranberry Hill Rd, Winhall, VT 05340
  • /34

    $200,000

    Sold Oct 17, 2025

    533 Pratt Bridge Rd, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 2,613 Sq Ft
    • Built 1970

    Last Sold Summary

    • 27% Below List Price
    • $77/SF
    • 25 Days On Market

    Current Estimated Value $233,328

    Last Listing Agent Mike England Michael England Real Estate

    533 Pratt Bridge Rd, Jamaica, VT 05343
    • /41

      Not Listed For Sale

      35 Old Ridge Rd, Winhall, VT 05155

      • 4 Beds
      • 5.5 Baths
      • 4,826 Sq Ft
      • Built 1997
      35 Old Ridge Rd, Winhall, VT 05155

      Last Sold Summary

      • 369 Days On Market

  • /32

    $1,150,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 1,775 Sq Ft

    43 Middle Ridge Rd Unit RBL 417, Winhall, VT 05155

    Welcome to this beautifully maintained top-floor Rising Bear condominium, where you’ll enjoy stunning views of Stratton Mountain and the Commons Pond from nearly every room. The soaring cathedral ceilings and abundant natural light create a bright, open feel, while the spacious loft overlooking the living area offers a great spot for relaxing, gathering, or extra sleeping space. The living room

    Jamie Wylie Stratton Real Estate

    43 Middle Ridge Rd Unit RBL 417, Winhall, VT 05155
  • /14

    $65,000 Per Month

    • 3 Beds
    • 5 Baths
    • 2,600 Sq Ft
    • Condo for Rent

    790 Stratton Access, Stratton, VT 05155

    Designed for the ultimate winter ski season, this home offers multiple gathering spaces to unwind after a day on the mountain. Gather around the impressive stone wood-burning fireplace in the main living room, challenge each other to a game of pool in the expansive recreation room, or simply savor the warmth of this inviting mountain retreat. Three generously sized bedrooms, including a spacious

    Christine Chovan

    790 Stratton Access, Stratton, VT 05155
  • /48

    $750,000

    Sold Aug 14, 2025

    573 Middletown Rd, Londonderry, VT 05148

    • 4 Beds
    • 3.5 Baths
    • 2,573 Sq Ft
    • Built 1989

    Last Sold Summary

    • 18% Below List Price
    • $291/SF
    • 141 Days On Market

    Current Estimated Value $740,637

    Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    573 Middletown Rd, Londonderry, VT 05148
    • /32

      Est $476,359

      Not Listed For Sale

      476 Edie Ln, Jamaica, VT 05343

      • 3 Beds
      • 3 Baths
      • 1,800 Sq Ft
      • Built 1988
      476 Edie Ln, Jamaica, VT 05343

      Last Sold Summary

      • 40 Days On Market

  • /30

    $1,060,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 1,587 Sq Ft

    778 Stratton Mountain Access Rd Unit 2401, Stratton, VT 05155

    Enjoy elevated mountain living from this top-floor corner residence in Mountain Watch, ideally positioned with expansive valley views and access to the Villager Lift. Bright interiors, abundant natural light, and two private balconies create inviting spaces to take in the surrounding scenery throughout every season. The updated kitchen and bathrooms offer modern finishes while maintaining the

    Jamie Wylie Stratton Real Estate

    778 Stratton Mountain Access Rd Unit 2401, Stratton, VT 05155
  • /23

    $32,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • House for Rent

    65 Cranberry Hill Rd, Bondville, VT 05340

    Never before offered: This Strattonwald contemporary ski house is a well cared-for home base for all who love the mountain lifestyle, in a private woodland setting just 9 minutes to Stratton's Main Base. The expansive living room is the ultimate gathering spot from morning to night, with soaring cathedral ceilings, a super-cozy wood stove, and extraordinary windows looking out at the private

    Jamie Luke TPW Real Estate

    65 Cranberry Hill Rd, Bondville, VT 05340
  • /39

    $735,000

    Sold May 01, 2026

    5 Wall St, Bondville, VT 05340

    • 4 Beds
    • 3 Baths
    • 2,091 Sq Ft
    • Built 1972

    Last Sold Summary

    • $352/SF
    • 20 Days On Market

    Current Estimated Value $741,598

    Last Listing Agent Cheyanne Pugliese

    5 Wall St, Bondville, VT 05340
    • /48

      Est $580,073

      Not Listed For Sale

      418 Diers, Jamaica, VT 05343

      • 3 Beds
      • 2.5 Baths
      • 2,621 Sq Ft
      • Built 1988
      418 Diers, Jamaica, VT 05343

      Last Sold Summary

      • 4 Days On Market

  • /60

    $1,650,000

    • 3 Beds
    • 4 Baths
    • 5,072 Sq Ft

    36 Beaver St, Bondville, VT 05340

    Your Ultimate Vermont Mountain Retreat Awaits! Luxury log home plus a 2,250 sqft guest house! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape - crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage,

    MaryKate Grey Stratton Real Estate

    36 Beaver St, Bondville, VT 05340
  • /23

    $34,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,406 Sq Ft
    • House for Rent

    35 Strattonwald Rd, Winhall, VT 05340

    $28,000 Winter Rental Rate | Spend the winter in Vermont at this inviting 4-bedroom, 3-bath Strattonwald chalet, available mid-November through mid-April. Nestled among the woods yet just minutes from Stratton Mountain, this home offers a welcoming retreat and the perfect base for the ski season. The main living area features soaring vaulted ceilings and a pellet stove, creating a bright and cozy

    Cheyanne Pugliese

    35 Strattonwald Rd, Winhall, VT 05340
  • /32

    $410,000

    Sold Apr 29, 2026

    8 Silver Birch Rd Unit 8, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft
    • Built 1968

    Last Sold Summary

    • 5% Below List Price
    • $337/SF
    • 101 Days On Market

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    8 Silver Birch Rd Unit 8, Winhall, VT 05340
    • /24

      Not Listed For Sale

      30 Styles Branch Rd Unit 307, Stratton, VT 05360

      • 4 Beds
      • 3.5 Baths
      • 1,178 Sq Ft
      • Built 1979
      30 Styles Branch Rd Unit 307, Stratton, VT 05360

      Last Sold Summary

      • 7 Days On Market

  • /18

    $249,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,020 Sq Ft

    19 Winhall Condo Rd Unit 1, Winhall, VT 05340

    Here’s your opportunity to have your own mountain retreat just minutes from Stratton. Set at the end of a quiet road less than a mile from the Stratton Access Road, The Winhall Condos provide a peaceful, convenient setting surrounded by Vermont’s natural beauty. Owners enjoy easy access to both Stratton and Manchester and a true sense of privacy. This three-bedroom, two-bath residence offers

    Cheyanne Pugliese

    19 Winhall Condo Rd Unit 1, Winhall, VT 05340
  • /35

    $7,250 Per Month

    • 4 Beds
    • 3 Baths
    • 2,000 Sq Ft
    • House for Rent

    45 Benson Fuller Dr, Bondville, VT 05340

    THE ULTIMATE STRATTON MOUNTAIN RETREAT Experience the perfect Vermont winter getaway in this exceptional home ideally located directly off the prestigious Stratton Mountain access road. Boasting a premier location with effortless mountain access, this property is designed for those who want to maximize their time on the slopes and enjoy a seamless mountain lifestyle. Available for multiple

    David Powers 42 North LP

    45 Benson Fuller Dr, Bondville, VT 05340
  • /26

    $440,000

    Sold Jun 29, 2026

    36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Below List Price
    • $362/SF
    • 10 Days On Market

    Last Listing Agent Helen Nault

    36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340
    • /19

      Not Listed For Sale

      43 High Point Dr Unit D23, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,130 Sq Ft
      • Built 1983
      43 High Point Dr Unit D23, Stratton, VT 05360

      Last Sold Summary

      • 8 Days On Market

  • /2

    $45,000

    Under Contract
    • Land
    • 1 Acre
    • $45,000 per Acre

    0 Edie Ln, Jamaica, VT 05343

    This is a town sale property. There is a 30 day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residence object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5% of the towns registered voters, the select, Board cannot just sell the property,

    Carrie Mathews Winhall Real Estate

    0 Edie Ln, Jamaica, VT 05343
  • /48

    $45,000 Per Month

    • 4 Beds
    • 4 Baths
    • 5,624 Sq Ft
    • House for Rent

    37 Burnt Hill Rd, Winhall, VT 05340

    Now available for the 26-27 ski season! This spacious, luxurious post-and-beam mountain home has been owner-occupied for past winter weekends, and is now available as the ultimate ski rental just a 7-minute drive to Stratton's base lodge. Beginning with the property's 2-car garage-barn, enviable curb appeal extends throughout. An expansive, well-equipped chef's kitchen offers duel ranges and

    Jamie Luke TPW Real Estate

    37 Burnt Hill Rd, Winhall, VT 05340
  • /33

    $1,650,000

    Sold Jul 17, 2026

    89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360

    • 4 Beds
    • 3.5 Baths
    • 2,698 Sq Ft
    • Built 2002

    Last Sold Summary

    • 6% Below List Price
    • $612/SF
    • 186 Days On Market

    Last Listing Agent Edwin Kevil Stratton Real Estate

    89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
    • /31

      Not Listed For Sale

      6 Black Birch Rd, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1968
      6 Black Birch Rd, Winhall, VT 05340

      Last Sold Summary

      • 8 Days On Market

  • /50

    $565,000

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft

    1886 Winhall Hollow Rd, South Londonderry, VT 05155

    Great Location, New Roof, New Septic, recent exterior painting! This turn key residence is ideally located between three ski areas and near schools and shopping. Gourmet kitchen, wood floors, upscale baths and a huge 3 car garage/ barn with finished office space. Tucked amidst the forest with views of Magic Mountain's ridge line, whether you are looking for a second home in the mountains or

    Kim Morgan-Wohler Wohler Realty Group

    1886 Winhall Hollow Rd, South Londonderry, VT 05155
  • /34

    $45,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,600 Sq Ft
    • House for Rent

    43 Cranberry Hill Rd, Winhall, VT 05340

    This tres chic classic chalet has been fully renovated and decorated with a modern and classy flair. The main living area has an open kitchen, dining and living concept design. With two additional living and gathering areas, there is plenty of room for family and friends to have conversation. Complete with a pool table, a built-in sofa suitable for extra sleeping, a meticulously designed mudroom

    Peggy O'neill Cummings & Co

    43 Cranberry Hill Rd, Winhall, VT 05340
  • /52

    $1,600,000

    Sold Apr 06, 2026

    122 Sunbowl Ridge Rd, Stratton, VT 05360

    • 4 Beds
    • 3.5 Baths
    • 2,698 Sq Ft
    • Built 2001

    Last Sold Summary

    • 7% Below List Price
    • $593/SF
    • 153 Days On Market

    Last Listing Agent John Sikes Stratton Real Estate

    122 Sunbowl Ridge Rd, Stratton, VT 05360
    • /39

      Not Listed For Sale

      6 Cranberry Ct, Stratton, VT 05360

      • 4 Beds
      • 4 Baths
      • 2,625 Sq Ft
      • Built 2003
      6 Cranberry Ct, Stratton, VT 05360

      Last Sold Summary

      • 32 Days On Market

Showing Results 1 - 40, Page 1 of 18

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