4,475

South Londonderry, VT Homes

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  • /12

    $325,000

    • Land
    • 3.42 Acres
    • $95,029 per Acre

    2366 Middletown Rd, Landgrove, VT 05148

    This property is within walking distance to the village of Londonderry and overlooks the town from its location approximately 500 paces up the hill on Middletown Road. The lot encompasses a hill that gives it privacy and security. Spring water flows to the base of the hill at one end of the propertyThe village commercial zoning gives the site options for multiple residential units (condos?),

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    2366 Middletown Rd, Landgrove, VT 05148
  • /44

    $702,000 Sold Oct 24, 2025

    86 Benson Fuller Dr, Bondville, VT 05340

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $344/SF
    • 42 Days On Market

    Current Estimated Value $698,335

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    86 Benson Fuller Dr, Bondville, VT 05340
    • /39

      Est $770,429 Not Listed For Sale

      28 W Branch Rd, Winhall, VT 05340

      • 4 Beds
      • 3.5 Baths
      • 2,300 Sq Ft
      • Built 1989
      28 W Branch Rd, Winhall, VT 05340

      Last Sold Summary

      • 51% Below List Price
      • $678/SF
      • 8 Days On Market
      • Last Sold Price $1,560,000
      • Jun 23, 2023

      Last Listing Agent Jessica Marullo TPW Real Estate

  • /13

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    10 Byington Unit F1, Winhall, VT 05340

    The first showings will be at the open house 3/8/26 from 2-4 pm.Welcome to your Vermont mountain retreat in the sought-after Winhall Acres community. This charming 3-bedroom plus loft, 2-bath condominium chalet offers the perfect blend of comfort, convenience, and year-round adventure.The home features a smart and inviting layout designed for both relaxing and entertaining. Three

    Carrie Mathews Winhall Real Estate

    10 Byington Unit F1, Winhall, VT 05340
  • /25

    $499,000 Sold May 02, 2025

    16 Ober Tal Dr Unit E35, Stratton, VT 05360

    • 2 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • Built 1983

    Last Sold Summary

    • $455/SF
    • 2 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    16 Ober Tal Dr Unit E35, Stratton, VT 05360
    • /38

      Not Listed For Sale

      14 Middle Ridge Rd Unit 19A, Winhall, VT 05155

      • 4 Beds
      • 3.5 Baths
      • 2,160 Sq Ft
      • Built 1986
      14 Middle Ridge Rd Unit 19A, Winhall, VT 05155

      Last Sold Summary

      • $463/SF
      • 9 Days On Market
      • Last Sold Price $1,000,000
      • Jun 22, 2023

      Last Listing Agent MaryKate Grey Stratton Real Estate

  • /27

    $445,000

    • 2 Beds
    • 2 Baths
    • 1,353 Sq Ft

    49 High Point Dr Unit A-14, Stratton, VT 05360

    Embrace the ultimate Stratton lifestyle in this turnkey, one-level 2BR/2BA condo designed for effortless mountain access. Located just moments from the Village and the Stratton training center, this home eliminates the logistics and maximizes the fun with a dedicated gear-ready mudroom and a complimentary shuttle that whisks you straight to the lifts. The interior features a bright, open-concept

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    49 High Point Dr Unit A-14, Stratton, VT 05360
  • /20

    $500,000 Sold Nov 26, 2025

    374 Winhall Hollow Rd, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 1,920 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Above List Price
    • $260/SF
    • 3 Days On Market

    Current Estimated Value $510,861

    Last Listing Agent Annette Gallo Real Broker LLC

    374 Winhall Hollow Rd, Winhall, VT 05340
    • /40

      Est $1,748,027 Not Listed For Sale

      541 Mtn Acres Rd, Jamaica, VT 05343

      • 6 Beds
      • 6.5 Baths
      • 7,426 Sq Ft
      • Built 2018
      541 Mtn Acres Rd, Jamaica, VT 05343

      Last Sold Summary

      • 1% Above List Price
      • $232/SF
      • 346 Days On Market
      • Last Sold Price $1,725,000
      • Oct 10, 2023

      Last Listing Agent Andrew King Stratton Real Estate

  • /26

    $529,000

    • 1 Bed
    • 1 Bath
    • 820 Sq Ft

    12 Ober Tal Dr Unit C-22, Stratton, VT 05360

    Experience Stratton Mountain living in this well-appointed 1-bedroom, 1-bath condo in the desirable Ober Tal community. Set just off the ski trail with convenient access nearby, this unit offers the benefits of trailside living with a touch more privacy. Inside, the condo has been thoughtfully updated with warm wood and stone accents that create a classic mountain feel, centered around a cozy

    Trent Stephens Wohler Realty Group

    12 Ober Tal Dr Unit C-22, Stratton, VT 05360
  • /22

    $445,000 Sold Sep 16, 2025

    163 Vt Route 30, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Below List Price
    • $280/SF
    • 13 Days On Market

    Current Estimated Value $449,583

    Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

    163 Vt Route 30, Winhall, VT 05340
    • /14

      Not Listed For Sale

      47 High Point Dr Unit B-15, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,207 Sq Ft
      • Built 1985
      47 High Point Dr Unit B-15, Stratton, VT 05360

      Last Sold Summary

      • $352/SF
      • 2 Days On Market
      • Last Sold Price $425,000
      • Aug 29, 2023

      Last Listing Agent Sarah Nichols Winhall Real Estate

  • /60

    $8,200,000

    • 6 Beds
    • 10 Baths
    • 10,763 Sq Ft

    557 Trager Rd, Jamaica, VT 05343

    Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in

    Kim Morgan-Wohler Wohler Realty Group

    557 Trager Rd, Jamaica, VT 05343
  • /43

    $547,500 Sold Dec 29, 2025

    66 Hilltop Rd, Londonderry, VT 05155

    • 4 Beds
    • 2.5 Baths
    • 2,149 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Below List Price
    • $255/SF
    • 49 Days On Market

    Last Listing Agent Alison Cummings Cummings & Co

    66 Hilltop Rd, Londonderry, VT 05155
    • /21

      Not Listed For Sale

      38 Quarter Mile Rd, Winhall, VT 05360

      • 4 Beds
      • 4 Baths
      • 1,940 Sq Ft
      • Built 1970
      38 Quarter Mile Rd, Winhall, VT 05360

      Last Sold Summary

      • $389/SF
      • 9 Days On Market
      • Last Sold Price $755,000
      • Oct 27, 2023

      Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

  • /50

    $750,000

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

    57 Pearl Buck Dr Unit 33, Bondville, VT 05340

    WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres.The main level boasts newly refinished oak floors, two bedrooms, a den or living area with

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    57 Pearl Buck Dr Unit 33, Bondville, VT 05340
  • /29

    $526,000 Sold Aug 08, 2025

    176 Pratt Bridge Rd, Jamaica, VT 05343

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Below List Price
    • $325/SF
    • 36 Days On Market

    Current Estimated Value $529,160

    Last Listing Agent Carrie Mathews Winhall Real Estate

    176 Pratt Bridge Rd, Jamaica, VT 05343
    • /40

      Est $1,674,297 Not Listed For Sale

      82 High Meadow Rd, Winhall, VT 05340

      • 6 Beds
      • 5.5 Baths
      • 4,551 Sq Ft
      • Built 2002
      82 High Meadow Rd, Winhall, VT 05340

      Last Sold Summary

      • 4% Above List Price
      • $355/SF
      • 126 Days On Market
      • Last Sold Price $1,615,000
      • Jul 31, 2024

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /15

    $530,000

    • Land
    • 30 Acres
    • $17,667 per Acre

    00 W Hill Rd S, Jamaica, VT 05343

    Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

    Jacki Murano Southern Vermont Realty Group

    00 W Hill Rd S, Jamaica, VT 05343
  • /2

    $205,000 Sold Sep 15, 2025

    24 Stratton Rd W, Winhall, VT 05340

    • 2 Beds
    • 1 Bath
    • 665 Sq Ft
    • Built 1970

    Last Sold Summary

    • $308/SF
    • 0 Days On Market

    Current Estimated Value $209,196

    Last Listing Agent Cheyanne Pugliese

    24 Stratton Rd W, Winhall, VT 05340
    • /24

      Est $469,866 Not Listed For Sale

      13 Lower Taylor Hill Rd, Winhall, VT 05340

      • 3 Beds
      • 2.5 Baths
      • 1,716 Sq Ft
      • Built 1967
      13 Lower Taylor Hill Rd, Winhall, VT 05340

      Last Sold Summary

      • 9% Above List Price
      • $251/SF
      • 26 Days On Market
      • Last Sold Price $430,000
      • Mar 26, 2025

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /35

    $849,000 Under Contract

    • 5 Beds
    • 3 Baths
    • 2,897 Sq Ft

    24 Sugarbush Dr, Jamaica, VT 05343

    Nestled in the highly sought-after Forest Farms neighborhood on Stratton Mountain, this beautifully updated 5-bedroom, 3-bath mountain retreat on Sugarbush Drive offers the perfect blend of comfort, style, and breathtaking natural beauty. The home features an open-concept living space designed to showcase the stunning surroundings, highlighted by a dramatic wall of glass that frames gorgeous

    Carrie Mathews Winhall Real Estate

    24 Sugarbush Dr, Jamaica, VT 05343
  • /53

    $775,000 Sold Aug 13, 2025

    E12 Rock Ridge Rd, Winhall, VT 05155

    • 3 Beds
    • 3 Baths
    • 1,842 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Below List Price
    • $421/SF
    • 7 Days On Market

    Last Listing Agent Cheyanne Pugliese

    E12 Rock Ridge Rd, Winhall, VT 05155
    • /40

      Not Listed For Sale

      13 Old Ridge Rd, Winhall, VT 05155

      • 4 Beds
      • 4.5 Baths
      • 2,327 Sq Ft
      • Built 1996
      13 Old Ridge Rd, Winhall, VT 05155

      Last Sold Summary

      • $367/SF
      • 29 Days On Market
      • Last Sold Price $855,000
      • May 01, 2023

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /38

    $860,000

    • 4 Beds
    • 3.5 Baths
    • 4,104 Sq Ft

    25 Benson Fuller Dr, Jamaica, VT 05343

    Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape. Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for chilly

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Jamaica, VT 05343
  • /2

    $400,000 Sold Mar 09, 2026

    97 N Branch Rd, Winhall, VT 05155

    • Land
    • 1.18 Acres
    • $338,983 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 29 Days On Market

    Last Listing Agent John Sikes Stratton Real Estate

    97 N Branch Rd, Winhall, VT 05155
    • /31

      Not Listed For Sale

      71 Todd Hill Rd, Jamaica, VT 05343

      • 5 Beds
      • 5.5 Baths
      • 3,624 Sq Ft
      • Built 2006
      71 Todd Hill Rd, Jamaica, VT 05343

      Last Sold Summary

      • $635/SF
      • 4 Days On Market
      • Last Sold Price $2,300,000
      • Apr 05, 2024

      Last Listing Agent Kevin Moran Four Seasons Sotheby's Int'l Realty

  • /33

    $880,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft

    3 Stratton Springs Rd Unit 3B, Stratton, VT 05360

    3B Stratton Springs Road. Stratton, VT 05155Located in one of Stratton’s most sought after neighborhoods, this three bedroom townhome combines luxury and convenience with a private location. It has an open floorplan and double height ceilings in the living room. There is a private patio off the back of the home. It has a one car attached garage. Stratton Springs is next door to the Stratton

    Andrew King Stratton Real Estate

    3 Stratton Springs Rd Unit 3B, Stratton, VT 05360
  • /12

    $935,000 Sold Mar 31, 2026

    759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340

    • 3 Beds
    • 3 Baths
    • 1,501 Sq Ft
    • Built 2005

    Last Sold Summary

    • 15% Below List Price
    • $623/SF
    • 313 Days On Market

    Last Listing Agent John Sikes Stratton Real Estate

    759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340
    • /14

      Not Listed For Sale

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

      • 3 Beds
      • 2.5 Baths
      • 1,780 Sq Ft
      • Built 2004
      759 Stratton Mountain Access Rd Unit 331, Stratton, VT 05340

      Last Sold Summary

      • $590/SF
      • 12 Days On Market
      • Last Sold Price $1,050,000
      • Mar 29, 2025

      Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

  • /29

    $699,000 Under Contract

    • 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
  • /22

    $407,000 Sold Oct 08, 2025

    7 Wanderer Rd Unit 7, Stratton, VT 05155

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Above List Price
    • $291/SF
    • 6 Days On Market

    Last Listing Agent Dan McKenna Cummings & Co

    7 Wanderer Rd Unit 7, Stratton, VT 05155
    • /5

      Not Listed For Sale

      0 Karen Dr Unit Lot 12 5021748, Jamaica, VT 05343

      0 Karen Dr Unit Lot 12 5021748, Jamaica, VT 05343

      Last Sold Summary

      • 11 Days On Market
      • Last Sold Price $55,000
      • Dec 17, 2024

      Last Listing Agent Edward Jones Josiah Allen Real Estate, Inc.

  • /17

    $729,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155

    Ski-In/Ski-Out Perfection: Your Premier Stratton Mountain Retreat! Experience the ultimate Vermont lifestyle in this rare 2-bedroom, 2-bathroom condo, perfectly positioned for true ski-in/ski-out convenience. Located just steps from the Villager Chairlift and the bustling heart of Stratton Village, this residence offers a seamless transition from the slopes to your front door.Designed with

    Robin Apps Four Seasons Sotheby's Int'l Realty

    778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155
  • /22

    $265,500 Sold Jul 15, 2025

    18 Stratton Ridge Rd, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1970

    Last Sold Summary

    • 16% Below List Price
    • $199/SF
    • 72 Days On Market

    Last Listing Agent Derek Greene Derek Greene

    18 Stratton Ridge Rd, Winhall, VT 05340
    • /52

      Not Listed For Sale

      E11 Rock Ridge Rd, Winhall, VT 05155

      • 3 Beds
      • 3 Baths
      • 2,300 Sq Ft
      • Built 1986
      E11 Rock Ridge Rd, Winhall, VT 05155

      Last Sold Summary

      • $348/SF
      • 47 Days On Market
      • Last Sold Price $800,000
      • Feb 13, 2025

      Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

  • /33

    $1,350,000 Under Contract

    • 4 Beds
    • 4 Baths
    • 2,377 Sq Ft

    7 Woodfern Run, Stratton, VT 05360

    Enjoy true trailside living in this luxury four-bedroom, four-bathroom townhouse at the highly sought-after Treetop development at Stratton. With mountain views and ski-in/ski-out access, you'll spend more time skiing, less time with logistics!Inside, the open living, dining, and kitchen area reflects classic Adirondack style, creating a warm and inviting space for gathering after a day on

    Christiane Carroccio TPW Real Estate

    7 Woodfern Run, Stratton, VT 05360
  • /35

    $649,000 Sold Dec 04, 2025

    282 Melendy Hill Rd, South Londonderry, VT 05155

    • 3 Beds
    • 3 Baths
    • 2,939 Sq Ft
    • Built 1991

    Last Sold Summary

    • $221/SF
    • 26 Days On Market

    Current Estimated Value $644,377

    Last Listing Agent Kevin Moran Four Seasons Sotheby's Int'l Realty

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

      Not Listed For Sale

      3702 Vermont Route 100, Londonderry, VT 05148

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1970
      3702 Vermont Route 100, Londonderry, VT 05148

      Last Sold Summary

      • $190/SF
      • 13 Days On Market
      • Last Sold Price $379,000
      • Jan 15, 2025

      Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

  • /31

    $699,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

    Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

    Timothy Mich Doddridge Stratton Real Estate

    778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

Showing Results 161 - 200, Page 5 of 18

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