4,475

South Londonderry, VT Homes

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  • /31

    $359,000

    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    410 Tallwood Cir, Londonderry, VT 05148

    This cute Sherwood Forest house is ready for the next owners! Nicely renovated over the past several years, this 3 bedroom, 1 and a half bath chalet is located in the heart of Vermont ski country. In between Londonderry and Bromley, minutes from Manchester or Stratton and Magic ,this central location allows for access to all that makes Vermont special! Enjoy the open living area after a day of

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 392-0721

    410 Tallwood Cir, Londonderry, VT 05148
  • /16

    $4,000 per month

    • 4 Beds
    • 3 Baths
    • 2,500 Sq Ft
    • 13 Deer

    13 Deer St, Winhall, VT 05340

    The Burrow is a generously appointed four-bedroom, three-bathroom sanctuary that serves as the ultimate year-round base camp for Vermont living. This home offers a rare balance of privacy and convenience, situated just 10 to 15 minutes from the slopes of Stratton and Bromley, the Manchester outlets, and local schools. The interior provides ample space for everyone while the exterior is designed

    13 Deer St, 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
    • /6

      Est $124,847 Not Listed For Sale

      10 Little Brook Rd, Winhall, VT 05340

      10 Little Brook Rd, Winhall, VT 05340

      Last Sold Summary

      • 2% Above List Price
      • 53 Days On Market
      • Last Sold Price $122,500
      • Apr 18, 2025

      Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

  • /32

    $420,000 Under Contract

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

    8 Silver Birch Rd Unit 8, Winhall, VT 05340

    Remarkable 3BR Birch Hill Value!Exceptional three-bedroom, two-bath end unit at Birch Hill! This well-thought-out floor plan is a true standout, providing two distinct living areas ideal for entertaining guests or relaxing after a day on the slopes. Features include an updated kitchen and dining space, two modernized baths, and a practical, renovated mudroom—essential for storing all your

    Agent Photo

    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    (802) 300-3975

    8 Silver Birch Rd Unit 8, Winhall, VT 05340
  • /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
  • /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
    • /32

      Est $471,323 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

      • 5% Above List Price
      • $249/SF
      • 40 Days On Market
      • Last Sold Price $449,000
      • Oct 25, 2024

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /55

    $495,000

    • 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

    (802) 481-3493

    935 Old Manchester Rd, Peru, VT 05152
  • /36

    $40,000 per month

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft
    • House for Rent

    33 Strattonwald Rd, Winhall, VT 05340

    Lock in your rental for ski season '26-'27! This cheerful, modern-yet-classic Strattonwald chalet is nestled in a private community just 7 minutes to Stratton's Main Base, with shuttle access. There is so much room for everyone, with two primary bedroom suites plus two more bedrooms; a gourmet open-concept kitchen/dining/living room with wood stove; second living/TV room. Downstairs living room

    Jamie Luke TPW Real Estate

    33 Strattonwald Rd, Winhall, VT 05340
  • /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 $355,271

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    290 Melendy Hill Rd, South Londonderry, VT 05155
    • /48

      Est $638,068 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

      • 1% Below List Price
      • $246/SF
      • 4 Days On Market
      • Last Sold Price $645,000
      • Mar 13, 2025

      Last Listing Agent Julie Lowe Lowe's Real Estate, LLC

  • /41

    $1,775,000 Under Contract

    • 4 Beds
    • 4 Baths
    • 2,401 Sq Ft

    43 Middle Ridge Rd Unit 416, Winhall, VT 05155

    Experience the pinnacle of alpine sophistication in this completely renovated turn-key residence. Located in Rising Bear, this 4-bedroom, 4-bath condo blends modern design with an unbeatable location that defines luxury mountain lifestyle. Park your car in one of two designated spots in the heated underground garage and leave it, there's no need drive anywhere during your stay! Whether you prefer

    Agent Photo

    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    (802) 802-9370

    43 Middle Ridge Rd Unit 416, Winhall, VT 05155
  • /7

    $2,100 per month

    • 2 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • House for Rent

    3292 Vt Route 100 N, Londonderry, VT 05148

    Beautifully maintained 2 bedroom home in South Londonderry, VT. Back patio to enjoy the immaculate gardens and the VT outdoors. 1st floor hosts a large eat in kitchen, livingroom, laundry room and full bath. 2nd floor has 2 oversized bedrooms with built-ins and a 3/4 bath. Tenant is responsible for all utilities and services. Credit Check and References required for move in.

    Team BVA Rentals Barrett and Valley Associates Inc.

    3292 Vt Route 100 N, Londonderry, VT 05148
  • /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 $225,463

    Last Listing Agent Mike England Michael England Real Estate

    533 Pratt Bridge Rd, Jamaica, VT 05343
    • /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

      • $581/SF
      • 7 Days On Market
      • Last Sold Price $685,000
      • Sep 25, 2024

      Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  • /60

    $849,000

    • 5 Beds
    • 4.5 Baths
    • 3,840 Sq Ft

    42 Blackberry Ln, Jamaica, VT 05343

    Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

    MaryKate Grey Stratton Real Estate

    42 Blackberry Ln, Jamaica, VT 05343
  • /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
  • /2

    $700,000 Sold Jul 21, 2025

    40 Founders Hill Rd, Stratton, VT 05360

    • 4 Beds
    • 2 Baths
    • 1,084 Sq Ft
    • Built 1960

    Last Sold Summary

    • $646/SF
    • 0 Days On Market

    Current Estimated Value $706,145

    Last Listing Agent Margretta Fischer Wohler Realty Group

    40 Founders Hill Rd, Stratton, VT 05360
    • /30

      Not Listed For Sale

      30 Styles Branch Rd Unit 309, Stratton, VT 05360

      • 5 Beds
      • 4 Baths
      • 2,088 Sq Ft
      • Built 1979
      30 Styles Branch Rd Unit 309, Stratton, VT 05360

      Last Sold Summary

      • $244/SF
      • 9 Days On Market
      • Last Sold Price $510,000
      • May 05, 2023

      Last Listing Agent Stephen Coombs Stratton Real Estate

  • /33

    $1,760,000

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

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

    Trailside!!! Ski in, ski out!! The very best Ski Direct Access at Stratton!! Most popular of luxury townhomes---offering an enlarged patio with Hot Tub, Open and Sunny, Four Bedrooms plus a Den Floorplan, Single Car Garage! Fully Furnished. Hardwood Flooring, floor to ceiling stone, wood burning fireplace! Enjoy this outstanding trailside location. And as an added benefit, the Stratton Training

    Edwin Kevil Stratton Real Estate

    89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
  • /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
  • /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 $769,107

    Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    573 Middletown Rd, Londonderry, VT 05148
    • /31

      Not Listed For Sale

      12 Stratton Rd W Unit 12, Winhall, VT 05340

      • 5 Beds
      • 2 Baths
      • 1,888 Sq Ft
      • Built 1968
      12 Stratton Rd W Unit 12, Winhall, VT 05340

      Last Sold Summary

      • $201/SF
      • 5 Days On Market
      • Last Sold Price $380,000
      • Apr 21, 2023

      Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  • /28

    $1,495,000

    • 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
  • /29

    $30,000 per month

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft
    • Townhouse for Rent

    90 Turkey Run Rd, Winhall, VT 05340

    Intervale Rental. Available for the 26-27 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom serves the

    Christiane Carroccio TPW Real Estate

    90 Turkey Run Rd, Winhall, VT 05340
  • /44

    $640,000 Sold Apr 25, 2025

    13 Winhall Station Rd, Londonderry, VT 05155

    • 7 Beds
    • 4 Baths
    • 3,988 Sq Ft
    • Built 1942

    Last Sold Summary

    • 1% Below List Price
    • $160/SF
    • 52 Days On Market

    Current Estimated Value $673,784

    Last Listing Agent Julie Lowe Lowe's Real Estate, LLC

    13 Winhall Station Rd, Londonderry, VT 05155
    • /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

      • $336/SF
      • 8 Days On Market
      • Last Sold Price $380,000
      • Oct 06, 2023

      Last Listing Agent Julie Lowe Lowe's Real Estate, LLC

  • /8

    $275,000 Under Contract

    • Land
    • 34.53 Acres
    • $7,964 per Acre

    0 W Hill Rd, 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 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /21

    $375,000 Sold May 05, 2025

    61 Birch Hill Rd Unit 6, Winhall, VT 05340

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

    Last Sold Summary

    • $309/SF
    • 42 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    61 Birch Hill Rd Unit 6, Winhall, VT 05340
    • /28

      Not Listed For Sale

      27 Mountain View Rd, Winhall, VT 05360

      • 6 Beds
      • 6.5 Baths
      • 5,896 Sq Ft
      • Built 2000
      27 Mountain View Rd, Winhall, VT 05360

      Last Sold Summary

      • $195/SF
      • 22 Days On Market
      • Last Sold Price $1,150,000
      • Jun 01, 2024

      Last Listing Agent Andrew King Stratton Real Estate

  • /11

    $495,000 Under Contract

    • Land
    • 68.89 Acres
    • $7,185 per Acre

    0 W Hill Rd, 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 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /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
    • /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

      • $278/SF
      • 8 Days On Market
      • Last Sold Price $338,000
      • Nov 10, 2023

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /7

    $195,000 Under Contract

    • Land
    • 15.27 Acres
    • $12,770 per Acre

    0 W Hill Rd, 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 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /2

    $692,000 Sold Oct 03, 2025

    19 Village Lodge Rd Unit 207, Stratton, VT 05155

    • 2 Beds
    • 2 Baths
    • 1,663 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $416/SF
    • 0 Days On Market

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    19 Village Lodge Rd Unit 207, Stratton, VT 05155
    • /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

      • $476/SF
      • 32 Days On Market
      • Last Sold Price $1,250,000
      • Apr 02, 2025

      Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  • /15

    $650,000 Under Contract

    • Land
    • 51.93 Acres
    • $12,517 per Acre

    0 W Hill Rd, 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 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /31

    $895,000 Sold Dec 12, 2025

    73 Cranberry Hill Rd, Winhall, VT 05340

    • 4 Beds
    • 4.5 Baths
    • 2,658 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $337/SF
    • 222 Days On Market

    Current Estimated Value $907,480

    Last Listing Agent Carrie Mathews Winhall Real Estate

    73 Cranberry Hill Rd, Winhall, VT 05340
    • /31

      Est $656,593 Not Listed For Sale

      78 Middle Ridge Rd Unit 106, Stratton, VT 05155

      • 2 Beds
      • 3 Baths
      • 1,375 Sq Ft
      • Built 2006
      78 Middle Ridge Rd Unit 106, Stratton, VT 05155

      Last Sold Summary

      • 3% Above List Price
      • $465/SF
      • 175 Days On Market
      • Last Sold Price $640,000
      • Apr 25, 2024

      Last Listing Agent Andrew King Stratton Real Estate

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