36,189

Windsor County, VT Homes

Section Image
    • /29

      Est $331,473 Not Listed For Sale

      201 Hill Top Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,137 Sq Ft
      • Built 1983
      201 Hill Top Rd, Chester, VT 05143

      Last Sold Summary

      • 2% Above List Price
      • $286/SF
      • 18 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  • /5

    $215,000 Pending

    • 2,381 Sq Ft

    3 Olney Rd, North Springfield, VT 05150

    FULLY LEASED BUILDING WITH 4 1 BR APARTMENTS JUST 5 MINUTES AWAY FROM SPRINGFIELD INDUSTRIAL PARK. GOOD UPSIDE WITH BELOW MARKET RENTS.

    Don Chabot Town and Country Realty

    3 Olney Rd, North Springfield, VT 05150
  • /2

    $365,000 Sold May 15, 2025

    32 Ascutney St, Windsor, VT 05089

    • 4 Beds
    • 3 Baths
    • 1,998 Sq Ft
    • Built 1919

    Last Sold Summary

    • 3% Above List Price
    • $183/SF
    • 0 Days On Market

    Current Estimated Value $386,732

    Last Listing Agent Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

    32 Ascutney St, Windsor, VT 05089
    • /37

      Est $773,163 Not Listed For Sale

      488 Andover Rd, Ludlow, VT 05149

      • 5 Beds
      • 4 Baths
      • 3,641 Sq Ft
      • Built 1920
      488 Andover Rd, Ludlow, VT 05149

      Last Sold Summary

      • 29% Above List Price
      • $165/SF
      • 19 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  • /19

    $27,500

    • Land
    • 1.98 Acres
    • $13,889 per Acre

    2-47 E Ash Rd, Plymouth, VT 05056

    Nice building lot within Hawk Resort. Some flat areas with potential westerly views. Electric and high speed internet is at street and there is the option to hook into community septic. Nestled in the scenic lakes region, halfway between Killington and Okemo, Hawk offers a prime location for outdoor enthusiasts. Whether you're hitting the slopes, exploring the trails, or simply enjoying the

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    2-47 E Ash Rd, Plymouth, VT 05056
  • /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
    • /34

      Est $315,903 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

      • 19% Above List Price
      • $169/SF
      • 4 Days On Market

      Last Sold Price $265,200

      Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

  • /60

    $1,350,000 Under Contract

    • 11 Beds
    • 11 Baths
    • 6,069 Sq Ft

    86 Main St, Ludlow, VT 05149

    Turnkey Village Inn and Restaurant in the heart of Ludlow, Vt. only steps to Okemo Mountain Ski Resort. This fully furnished and equipped property includes 9 guest rooms with private baths, a 2 bedroom, 2 bathroom owner’s apartment, and a former wine bar/restaurant space ready to relaunch with all FF&E included. Historic charm throughout, wood floors, fireplaces, and original detail-paired with

    John Napier TPW Real Estate

    86 Main St, Ludlow, VT 05149
  • /17

    $307,000 Sold May 16, 2025

    122 Summer St, Springfield, VT 05156

    • 4 Beds
    • 1.5 Baths
    • 1,972 Sq Ft
    • Built 1905

    Last Sold Summary

    • 16% Below List Price
    • $156/SF
    • 216 Days On Market

    Current Estimated Value $309,112

    Last Listing Agent Susan Bellville Bellville Realty

    122 Summer St, Springfield, VT 05156
    • /29

      Est $403,610 Not Listed For Sale

      21 Dell Rd, Springfield, VT 05156

      • 3 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 1950
      21 Dell Rd, Springfield, VT 05156

      Last Sold Summary

      • 17% Above List Price
      • $172/SF
      • 37 Days On Market

      Last Sold Price $345,000

      Last Listing Agent Dana Haley Real Broker LLC

  • /57

    $995,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,585 Sq Ft

    117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149

    Ledgewood on Okemo, a spacious condominium located in one of the most sought-after communities on Okemo Mountain. This property offers an abundance of space, featuring two en-suites and two additional bedrooms. The expansive great room opens to a large family kitchen with two breakfast bars, providing ample seating for the whole family. You'll also appreciate the private ski-in/ski-out access and

    Katherine Burns William Raveis Real Estate Vermont Properties

    117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149
  • /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 $321,504

    Last Listing Agent Susanne Pacilio Martha E. Diebold/Hanover

    942 Christian St, White River Junction, VT 05001
    • /40

      Est $335,223 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

      • 25% Above List Price
      • $119/SF
      • 34 Days On Market

      Last Sold Price $269,000

      Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

  • /41

    $579,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 3,080 Sq Ft

    1631 Christian St, White River Junction, VT 05001

    Extraordinary views and modern efficiency define this extensively renovated smart home on Christian Street in Wilder, VT. Ideally located just 6 minutes to Dartmouth College and 14 minutes to Dartmouth Health, this property offers both convenience and exceptional functionality. Recent major upgrades include a completely new kitchen, updated bathrooms, new furnace, upgraded 200-amp electrical

    Gerry Stark RE/MAX Upper Valley

    1631 Christian St, White River Junction, VT 05001
  • /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
    • /27

      Est $1,118,386 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

      • 103% Above List Price
      • $154/SF
      • 47 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /16

    $252,000

    • 2 Beds
    • 1.5 Baths
    • 1,048 Sq Ft

    205 Woodhaven Dr Unit 4, White River Junction, VT 05001

    Set in a centrally located neighborhood just minutes to Hanover, Lebanon, Dartmouth College, Dartmouth Health, I-91, shopping, dining, and recreation, this property offers exceptional accessibility while maintaining a peaceful residential feel.The main level features an airlock entry with closet, living area with a deck, an efficient kitchen, dining area, and a convenient half bath for

    Jill Harlow Coldwell Banker LIFESTYLES - Hanover

    205 Woodhaven Dr Unit 4, White River Junction, VT 05001
  • /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 $1,784,161

    Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

    2090 Randall Rd, Woodstock, VT 05091
    • /37

      Est $794,547 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

      • 15% Below List Price
      • $519/SF
      • 14 Days On Market

      Last Sold Price $935,000

      Last Listing Agent Marni Rieger KW Vermont-Killington

  • /60

    $200,000

    • Land
    • 6.63 Acres
    • $30,166 per Acre

    00 Vermont 103, Andover, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

    Rachael Rogala Lange & Lange

    00 Vermont 103, Andover, VT 05143
  • /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
    • /38

      Est $572,755 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

      • 21% Above List Price
      • $466/SF
      • 83 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Holly Hall Hall Collins Real Estate Group

  • /23

    $750,000

    • Land
    • 2.07 Acres
    • $362,319 per Acre

    Lot 1 Timber Creek Rd, Ludlow, VT 05149

    Timber Creek on Okemo offers a rare opportunity to build in one of Okemo’s premier on-mountain communities. This residential lot is ideally located with easy access to SouthFace Village, giving owners the ability to enjoy the sunny side of the mountain with convenient slope access and year-round resort-style amenities.Ownership includes access to SouthFace Village amenities, including a ski

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    Lot 1 Timber Creek Rd, 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 $744,248

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

    104 Spruce Ln, Ludlow, VT 05149
    • /27

      Est $745,033 Not Listed For Sale

      37 South St, Woodstock, VT 05091

      • 3 Beds
      • 2 Baths
      • 1,660 Sq Ft
      • Built 1900
      37 South St, Woodstock, VT 05091

      Last Sold Summary

      • 35% Above List Price
      • $331/SF
      • 4 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Jennifer Falvey KW Vermont Woodstock

  • /18

    $299,900

    • 2 Beds
    • 1.5 Baths
    • 1,496 Sq Ft

    105 Williams Ln Unit C, Quechee, VT 05059

    Adorable and well maintained 2 bedroom with loft and 1.5 bathroom condo located on top of the Quechee Ski Hill. Very short walk to the ski trail from your front door. The condo is fully furnished and "turn key". The owners only plan to take some small personal belongings and some artwork. Recent improvements include new gas fireplace, new stackable washer/dryer, new hot water heater and new bed

    Shane Vahey New England Real Estate Advisors, LLC

    105 Williams Ln Unit C, Quechee, VT 05059
  • /29

    $440,000 Sold Jun 30, 2025

    210 Hanover St, White River Junction, VT 05001

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Above List Price
    • $305/SF
    • 76 Days On Market

    Current Estimated Value $467,746

    Last Listing Agent Jill Harlow Coldwell Banker LIFESTYLES - Hanover

    210 Hanover St, White River Junction, VT 05001
    • /39

      Est $3,514,654 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

      • 8% Above List Price
      • $319/SF
      • 345 Days On Market

      Last Sold Price $3,255,000

      Last Listing Agent Story Jenks LandVest, Inc/Woodstock

  • /41

    $845,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 1,714 Sq Ft

    403 Horse Shoe Way, Woodstock, VT 05071

    Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

    Danny Kogut Williamson Group Sothebys Intl. Realty

    403 Horse Shoe Way, Woodstock, VT 05071
  • /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
    • /40

      Est $1,523,210 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

      • 38% Above List Price
      • $296/SF
      • 102 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

  • /60

    $825,000 Under Contract

    • 5 Beds
    • 5 Baths
    • 3,886 Sq Ft

    3961 Hartland Hill Rd, Woodstock, VT 05091

    NEW PRICE! This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor

    Tambrey Vutech KW Vermont Woodstock

    3961 Hartland Hill Rd, Woodstock, VT 05091
  • /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 $259,345

    Last Listing Agent Ara Cardew BHG Masiello Keene

    6 Blodgett Ln, Hartland, VT 05048
    • /29

      Est $774,815 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

      • 36% Above List Price
      • $445/SF
      • 84 Days On Market

      Last Sold Price $570,000

      Last Listing Agent Herb Hart Quechee Lakes Real Estate Center

  • /60

    $599,000

    • 4 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    5100 Route 100, Plymouth, VT 05056

    (Das Grünebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

    Marni Rieger KW Vermont-Killington

    5100 Route 100, Plymouth, VT 05056
  • /2

    $215,000 Sold Aug 29, 2025

    234 Harvard St, Springfield, VT 05156

    • 3 Beds
    • 1 Bath
    • 1,556 Sq Ft
    • Built 1918

    Last Sold Summary

    • 8% Above List Price
    • $138/SF
    • 6 Days On Market

    Last Listing Agent Isabella Luhrs BHG Masiello Keene

    234 Harvard St, Springfield, VT 05156
    • /42

      Est $1,554,169 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

      • 2% Below List Price
      • $361/SF
      • 79 Days On Market

      Last Sold Price $1,580,000

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /37

    $389,000

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

    221 Spring St, Stockbridge, VT 05772

    This charming rustic chalet in the desirable Highwood community, just minutes from Killington and Pico ski resorts, checks all the boxes for a cozy mountain getaway—vaulted ceilings, exposed beams, a classic fieldstone fireplace, and wide pine floors set in a peaceful wooded setting. The efficient footprint is ideal for small groups and intimate gatherings, yet with three bedrooms, a quirky

    Kyle Kershner Killington Pico Realty

    221 Spring St, Stockbridge, VT 05772
  • /38

    $595,000 Sold Jul 18, 2025

    20 Plumley Ave, Ludlow, VT 05149

    • 6 Beds
    • 5 Baths
    • 4,004 Sq Ft
    • Built 1908

    Last Sold Summary

    • 12% Below List Price
    • $149/SF
    • 183 Days On Market

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

    20 Plumley Ave, Ludlow, VT 05149
    • /40

      Est $783,591 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

      • 17% Below List Price
      • $579/SF
      • 15 Days On Market

      Last Sold Price $945,000

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

Showing Results 641 - 680, Page 17 of 18

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