36,490

Windsor County, VT Homes

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  • /52

    $260,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    50 Bates Rd, Cavendish, VT 05142

    Welcome to 50 Bates Rd, a charming 1920s Vermont farmhouse perched above the village of Cavendish, offering a country setting with the convenience of being in town. The standout feature is the large covered porch — the kind of welcoming outdoor space that feels from another era and invites you to slow down and take in the setting. This home is ready for updating, but the character is already

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    50 Bates Rd, Cavendish, VT 05142
  • /60

    $850,000

    Sold Aug 13, 2025

    82 Button Hook Ln, Barnard, VT 05031

    • 4 Beds
    • 2 Baths
    • 2,915 Sq Ft
    • Built 1989

    Last Sold Summary

    • 5% Below List Price
    • $292/SF
    • 98 Days On Market

    Last Listing Agent Eric Johnston Four Seasons Sotheby's Int'l Realty

    82 Button Hook Ln, Barnard, VT 05031
    • /34

      Est $297,914

      Not Listed For Sale

      82 Wellwood Orchard Rd, Springfield, VT 05156

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1970
      82 Wellwood Orchard Rd, Springfield, VT 05156

      Last Sold Summary

      • 4 Days On Market

  • /40

    $450,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,268 Sq Ft

    20 Edwins Pond Rd, Rochester, VT 05767

    Set on a quiet, rural corner lot just off Middle Hollow Road, this contemporary Vermont home offers a compelling blend of efficiency, flexibility, and long-term upside. Built in 1989 with a durable standing seam metal roof and solid wood-frame construction, the home provides 3+ bedrooms and 2.5 baths across a thoughtfully scaled footprint, with additional finished space in the walkout lower

    William Brokhof Vermont Backcountry Real Estate

    20 Edwins Pond Rd, Rochester, VT 05767
  • /58

    $475,000

    Sold Oct 10, 2025

    1923 N Hill Rd, Chester, VT 05143

    • 5 Beds
    • 3 Baths
    • 2,316 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $205/SF
    • 6 Days On Market

    Last Listing Agent Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    1923 N Hill Rd, Chester, VT 05143
    • /40

      Est $328,335

      Not Listed For Sale

      305 Summer St, Springfield, VT 05156

      • 4 Beds
      • 2 Baths
      • 2,264 Sq Ft
      • Built 1918
      305 Summer St, Springfield, VT 05156

      Last Sold Summary

      • 34 Days On Market

  • /60

    $625,000

    • 4 Beds
    • 3.5 Baths
    • 2,656 Sq Ft

    758 Weston-Andover Rd, Chester, VT 05143

    A rare opportunity to own two well-maintained homes on one beautiful country property! The main residence offers 3 bedrooms and 3 baths with a warm, inviting interior featuring hardwood floors, abundant built-ins, and thoughtfully designed living spaces that blend character with everyday comfort. Step outside to the back deck overlooking beautifully landscaped gardens and a spacious lawn—an ideal

    Kevin Barnes William Raveis Real Estate Vermont Properties

    758 Weston-Andover Rd, Chester, VT 05143
  • /30

    $418,000

    Sold Dec 19, 2025

    1191 Baker Turn Unit 3B, Quechee, VT 05059

    • 3 Beds
    • 2.5 Baths
    • 1,564 Sq Ft
    • Built 1972

    Last Sold Summary

    • $267/SF
    • 8 Days On Market

    Last Listing Agent Mary Paino Coldwell Banker LIFESTYLES - Quechee

    1191 Baker Turn Unit 3B, Quechee, VT 05059
    • /32

      Est $679,052

      Not Listed For Sale

      13 Golf Ave, Woodstock, VT 05091

      • 2 Beds
      • 2 Baths
      • 1,520 Sq Ft
      • Built 1880
      13 Golf Ave, Woodstock, VT 05091

      Last Sold Summary

      • 0 Days On Market

  • /21

    $110,000

    • Land
    • 1.13 Acres
    • $97,345 per Acre

    00 Evergreen Acres, Ludlow, VT 05149

    Located just 3.5 miles from Okemo Mountain, this prime parcel offers endless potential for your dream home. With selective clearing, enjoy breathtaking views of Okemo Mountain. The property comes with an existing Vermont Wastewater permit for a 3-bedroom residence, making it ready for your plans. Whether you're looking to build your perfect retreat or a year-round residence, this location is

    Kevin Barnes William Raveis Real Estate Vermont Properties

    00 Evergreen Acres, Ludlow, VT 05149
  • /35

    $650,000

    Sold Sep 02, 2025

    28 Webster Rd, Hartland, VT 05048

    • 3 Beds
    • 2.5 Baths
    • 2,230 Sq Ft
    • Built 2008

    Last Sold Summary

    • 4% Below List Price
    • $291/SF
    • 6 Days On Market

    Current Estimated Value $652,649

    Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

    28 Webster Rd, Hartland, VT 05048
    • /27

      Est $980,171

      Not Listed For Sale

      7 Golf Ave, Woodstock, VT 05091

      • 5 Beds
      • 3 Baths
      • 3,579 Sq Ft
      • Built 1832
      7 Golf Ave, Woodstock, VT 05091

      Last Sold Summary

      • 47 Days On Market

  • /40

    $2,950,000

    $550K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 5,433 Sq Ft

    61 Academy Cir, Woodstock, VT 05071

    Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

    Carol Wood Williamson Group Sothebys Intl. Realty

    61 Academy Cir, Woodstock, VT 05071
  • /10

    $95,000

    Sold Dec 18, 2025

    459 Sugar Hill Rd, Bethel, VT 05032

    • Land
    • 11.4 Acres
    • $8,333 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 41 Days On Market

    Last Listing Agent Stan Butler Four Seasons Sotheby's Int'l Realty

    459 Sugar Hill Rd, Bethel, VT 05032
    • /36

      Est $686,038

      Not Listed For Sale

      24 High St, Woodstock, VT 05091

      • 5 Beds
      • 2 Baths
      • 2,996 Sq Ft
      • Built 1840
      24 High St, Woodstock, VT 05091

      Last Sold Summary

      • 325 Days On Market

  • /37

    $435,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,125 Sq Ft

    143 Okemo Acres, Ludlow, VT 05149

    Charming Fixer-Upper in a Dream Location – Your Canvas Awaits! Step into a world of endless possibilities with this house, nestled in the heart of a picturesque neighborhood just a mere 0.8 miles from the magnificent Okemo Mountain. This property is not just a house; it’s a golden opportunity for those with a vision, a passion for design, and a desire to create a home that reflects their unique

    Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

    143 Okemo Acres, Ludlow, VT 05149
  • /56

    $3,300,000

    Sold Apr 15, 2026

    2769 Cloudland Rd, Pomfret, VT 05067

    • 4 Beds
    • 3.5 Baths
    • 3,485 Sq Ft
    • Built 1927

    Last Sold Summary

    • 3% Below List Price
    • $947/SF
    • 24 Days On Market

    Last Listing Agent Dan Noble Snyder Donegan Real Estate Group

    2769 Cloudland Rd, Pomfret, VT 05067
    • /39

      Est $850,673

      Not Listed For Sale

      6 Highland Ave, Woodstock, VT 05091

      • 1 Bed
      • 1 Bath
      • 1,052 Sq Ft
      • Built 1930
      6 Highland Ave, Woodstock, VT 05091

      Last Sold Summary

      • 97 Days On Market

  • /50

    $625,000

    $25K PRICE DROP Under Contract
    • 4 Beds
    • 4 Baths
    • 2,904 Sq Ft

    5 Malagash Rd, South Reading, VT 05153

    Tucked within the peaceful hamlet of South Reading, this inviting property offers a lifestyle where the pace slows, and everyday living feels a bit more enjoyable. Set on over three acres, this spacious four-bedroom, four-bath home combines comfort, functionality, and natural beauty. The true highlight is the backyard oasis—featuring a tranquil pond, a generous deck ideal for entertaining, a

    Kevin Barnes William Raveis Real Estate Vermont Properties

    5 Malagash Rd, South Reading, VT 05153
  • /27

    $305,000

    Sold Aug 11, 2025

    942 Christian St, White River Junction, VT 05001

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 1945

    Last Sold Summary

    • $339/SF
    • 2 Days On Market

    Current Estimated Value $308,701

    Last Listing Agent Susanne Pacilio Martha E. Diebold/Hanover

    942 Christian St, White River Junction, VT 05001
    • /37

      Est $900,499

      Not Listed For Sale

      13 High St, Woodstock, VT 05091

      • 3 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1900
      13 High St, Woodstock, VT 05091

      Last Sold Summary

      • 14 Days On Market

  • /30

    $770,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 1,820 Sq Ft

    2762 Route 12, Barnard, VT 05031

    Conveniently situated on a secluded knoll central to Woodstock Village and beautiful Silver Lake, this impeccably maintained 13.4 AC property offers privacy and convenience. The Classic Cape Home is spotless, and turn-key. The rooms are bright, and airy, with a great flow for everyday living and entertaining. The living room features a wood burning stove. The kitchen has quality appliances,

    Danny Kogut Williamson Group Sothebys Intl. Realty

    2762 Route 12, Barnard, VT 05031
  • /34

    $240,000

    Sold Sep 19, 2025

    58 Valley View Rd Unit 1, Bridgewater Corners, VT 05035

    • 2 Beds
    • 2 Baths
    • 1,373 Sq Ft
    • Built 1990

    Last Sold Summary

    • 24% Below List Price
    • $175/SF
    • 162 Days On Market

    Last Listing Agent Terry Davis Williamson Group Sothebys Intl. Realty

    58 Valley View Rd Unit 1, Bridgewater Corners, VT 05035
    • /38

      Est $617,936

      Not Listed For Sale

      39 South St, Woodstock, VT 05091

      • 2 Beds
      • 1.5 Baths
      • 1,020 Sq Ft
      • Built 1869
      39 South St, Woodstock, VT 05091

      Last Sold Summary

      • 83 Days On Market

  • /59

    $2,395,000

    • 3 Beds
    • 5 Baths
    • 4,329 Sq Ft

    719 Walker Hill Rd, Barnard, VT 05068

    An exquisite, private retreat for artists, writers, nature-lovers, composers or simply as a quiet, serene getaway gathering house on 66 stunningly beautiful acres with stone walls, gardens, patios, open lawns, a beautiful swimming pond, in-ground heated saltwater pool with stone patio, and a breathtakingly beautiful outdoor screened pergola. The residence was constructed using reclaimed frames

    John Snyder Snyder Donegan Real Estate Group

    719 Walker Hill Rd, Barnard, VT 05068
  • /44

    $1,700,000

    Sold Aug 15, 2025

    2090 Randall Rd, Woodstock, VT 05091

    • 3 Beds
    • 2.5 Baths
    • 2,423 Sq Ft
    • Built 2007

    Last Sold Summary

    • 6% Below List Price
    • $702/SF
    • 177 Days On Market

    Current Estimated Value $1,758,766

    Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

    2090 Randall Rd, Woodstock, VT 05091
    • /39

      Est $3,500,469

      Not Listed For Sale

      3 Church St, Woodstock, VT 05091

      • 10 Beds
      • 15 Baths
      • 10,206 Sq Ft
      • Built 1831
      3 Church St, Woodstock, VT 05091

      Last Sold Summary

      • 345 Days On Market

  • /31

    $149,900

    • Land
    • 10,018 Sq Ft
    • $651,739 per Acre

    0 Prospect St Unit 5091432, Ludlow, VT 05149

    Discover a rare opportunity to own the last village building lot on desirable Prospect Street in Ludlow. Tucked away at the end of a newly created cul-de-sac, Lot 3 offers a level setting with outstanding potential for your future home or getaway retreat. Enjoy partial seasonal views of Okemo Mountain Resort, along with beautiful sunset views that make this location truly special. Convenience is

    Kevin Barnes William Raveis Real Estate Vermont Properties

    0 Prospect St Unit 5091432, Ludlow, VT 05149
  • /34

    $55,000

    Sold Aug 29, 2025

    420 Qtr III Jackson Gore Inn, Ludlow, VT 05149

    • 1 Bath
    • 496 Sq Ft
    • Built 2003

    Last Sold Summary

    • 15% Below List Price
    • $111/SF
    • 413 Days On Market

    Last Listing Agent Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

    420 Qtr III Jackson Gore Inn, Ludlow, VT 05149
    • /40

      Est $1,497,313

      Not Listed For Sale

      26 River St, Woodstock, VT 05091

      • 6 Beds
      • 4 Baths
      • 3,719 Sq Ft
      • Built 1845
      26 River St, Woodstock, VT 05091

      Last Sold Summary

      • 102 Days On Market

  • /39

    $725,000

    • 2 Beds
    • 2 Baths
    • 1,193 Sq Ft

    58 Harrison Ln Unit K301, Ludlow, VT 05149

    Top-floor, two-bedroom condo in the desirable Winterplace community with direct slope access and trail views. The open living area features hardwood floors, gas fireplace, a wall of windows overlooking the slopes and a cathedral ceiling that adds light and space. Functional layout with two bedrooms, two baths, and a tiled mudroom entry, AND the ability to add loft space above the bedrooms.

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    58 Harrison Ln Unit K301, Ludlow, VT 05149
  • /60

    $700,000

    Sold Nov 14, 2025

    104 Spruce Ln, Ludlow, VT 05149

    • 2 Beds
    • 2 Baths
    • 1,644 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Below List Price
    • $426/SF

    Current Estimated Value $740,782

    Last Listing Agent Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

    104 Spruce Ln, Ludlow, VT 05149
    • /29

      Est $780,060

      Not Listed For Sale

      42 River St, Woodstock, VT 05091

      • 3 Beds
      • 2.5 Baths
      • 1,280 Sq Ft
      • Built 1890
      42 River St, Woodstock, VT 05091

      Last Sold Summary

      • 84 Days On Market

  • /33

    $235,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    110 Saint Hyacinth St, Bethel, VT 05032

    If you’re looking for move-in ready, efficient living, in a convenient location while also enjoying some privacy overlooking the White River, look no further than 110 Saint Hyacinth St in Bethel, VT. Extensive renovation work has been done to the structure and interior finishes. Almost the entire first floor is brand new from floor joists, flooring, and doors to walls and lighting. Not to mention

    Rachel Arsenault Williamson Group Sothebys Intl. Realty

    110 Saint Hyacinth St, Bethel, VT 05032
  • /47

    $695,000

    Sold Dec 23, 2025

    36 Lower IV Unit 48A, Ludlow, VT 05149

    • 4 Beds
    • 2.5 Baths
    • 1,844 Sq Ft
    • Built 1987

    Last Sold Summary

    • 10% Below List Price
    • $377/SF
    • 165 Days On Market

    Last Listing Agent Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    36 Lower IV Unit 48A, Ludlow, VT 05149
    • /42

      Est $1,591,522

      Not Listed For Sale

      33 River St, Woodstock, VT 05091

      • 4 Beds
      • 4 Baths
      • 4,378 Sq Ft
      • Built 1886
      33 River St, Woodstock, VT 05091

      Last Sold Summary

      • 79 Days On Market

  • /50

    $625,000

    • 3 Beds
    • 3 Baths
    • 1,376 Sq Ft

    97 Okemo Trailside Extension Unit 15 C, Ludlow, VT 05149

    Welcome home to Trailside 15C on Okemo. Fully renovated and sold turn-key furnished, this 3-bedroom, 3-bath Trailside condominium is designed for effortless mountain living. The well-thought-out floor plan maximizes space and comfort, featuring a sun-filled main level with vaulted ceilings, exposed beams, and an open-concept kitchen, living, and dining area that captures a classic Vermont vibe.

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    97 Okemo Trailside Extension Unit 15 C, Ludlow, VT 05149
  • /23

    $257,500

    Sold Nov 25, 2025

    6 Blodgett Ln, Hartland, VT 05048

    • 2 Beds
    • 1 Bath
    • 1,336 Sq Ft
    • Built 1925

    Last Sold Summary

    • 11% Below List Price
    • $193/SF
    • 45 Days On Market

    Current Estimated Value $250,000

    Last Listing Agent Ara Cardew BHG Masiello Keene

    6 Blodgett Ln, Hartland, VT 05048
    • /40

      Est $896,600

      Not Listed For Sale

      25 Slayton Terrace, Woodstock, VT 05091

      • 3 Beds
      • 1.5 Baths
      • 1,632 Sq Ft
      • Built 1925
      25 Slayton Terrace, Woodstock, VT 05091

      Last Sold Summary

      • 15 Days On Market

  • /17

    $149,000

    • Land
    • 1.83 Acres
    • $81,421 per Acre

    00 Raymond Rd, Ludlow, VT 05149

    LAND PARCEL WITH LAKE RESCUE ACCESS....This parcel is the last undeveloped lot available that has lake access, shared with a small association, SUNNY VALLEY, with only (8) properties. The building envelope is level and power is at the road. The lot overlooks a pretty meadow with undeveloped woodlands as a backdrop. The Sunny Valley privileges at Lake Rescue include (2) deck platforms overlooking

    Roger Danyew Diamond Realty

    00 Raymond Rd, Ludlow, VT 05149

Showing Results 641 - 680, Page 17 of 18

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