36,326

Windsor County, VT Homes

Section Image
    • /29

      Est $337,227 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

      • 4% Above List Price
      • $286/SF
      • 18 Days On Market
      • Last Sold Price $325,000
      • Oct 04, 2024

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  • /26

    $465,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    57 Townhouse Way Unit 9, Woodstock, VT 05091

    This beautiful Woodstock West Townhouse offers effortless, low-maintenance living in one of Vermont’s most charming four-season destinations. The main level welcomes you with a cozy living area centered around a fireplace, creating the perfect space to unwind. A sun-filled kitchen and dining area flow seamlessly onto a private deck—ideal for relaxing or entertaining. Upstairs, two generously

    Mary Mayhew Snyder Donegan Real Estate Group

    57 Townhouse Way Unit 9, Woodstock, VT 05091
  • /47

    $354,000 Sold Jan 09, 2026

    113 Hanover St, White River Junction, VT 05001

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1974

    Last Sold Summary

    • 6% Below List Price
    • $410/SF
    • 21 Days On Market

    Current Estimated Value $352,198

    Last Listing Agent Alex DeFelice The Clerkin Agency, P.C.

    113 Hanover St, White River Junction, VT 05001
    • /37

      Est $789,342 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

      • 32% Above List Price
      • $165/SF
      • 19 Days On Market
      • Last Sold Price $600,000
      • Sep 27, 2024

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

  • /50

    $325,000 Under Contract

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

    2218 Main St, Cavendish, VT 05142

    Terrific village home with bright, open living spaces! This property offers the perfect backdrop for sun-drenched days, featuring charming gingerbread trim and a unique, versatile room above the porch. As you enter through the welcoming sunroom, you’ll immediately enjoy the airy, open layout that connects the sunroom, dining room, and kitchen—perfect for breezy, seasonal gatherings. The first

    Jill Lawrence The Real Estate Collaborative

    2218 Main St, Cavendish, VT 05142
  • /6

    $90,000 Sold Sep 26, 2025

    36 Chestnut St, Hartford, VT 05001

    • Land
    • 28,314 Sq Ft
    • $138,462 per Acre

    Last Sold Summary

    • 28% Below List Price
    • 346 Days On Market

    Last Listing Agent Alex DeFelice The Clerkin Agency, P.C.

    36 Chestnut St, Hartford, VT 05001
    • /34

      Est $303,668 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

      • 15% Above List Price
      • $169/SF
      • 4 Days On Market
      • Last Sold Price $265,200
      • Jul 07, 2023

      Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

  • /59

    $275,000 Pending

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

    54 Twitchell Settlement, Rochester, VT 05767

    PRICE REDUCTION TODAY - NOW OFFERED AT $325,000 (PREVIOUSLY $410,000). Set in Rochester, this chalet-style single family home pairs a dramatic vaulted great room with cathedral ceilings and an arched window wall that pours in natural light and captures seasonal mountain views. The setting spans 3.20 acres with a mix of open field and wooded privacy, giving you room to spread out while enjoying a

    Nick Sicard EXP Realty

    54 Twitchell Settlement, Rochester, VT 05767
  • /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
    • /29

      Est $435,281 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

      • 26% Above List Price
      • $172/SF
      • 37 Days On Market
      • Last Sold Price $345,000
      • Oct 06, 2023

      Last Listing Agent Dana Haley Real Broker LLC

  • /60

    $925,000

    • 6 Beds
    • 7.5 Baths
    • 5,588 Sq Ft

    726 E Ash Rd, Plymouth, VT 05056

    Nestled on a 3-acre private lot at Hawk Resort in Vermont’s Lakes Region, this expansive custom residence offers an exceptional mountain retreat. Thoughtfully designed across four levels--each accessible by elevator--the home provides outstanding separation of space, perfect for hosting family and guests.Designed by architect Robert Carl Williams, the home showcases signature craftsmanship,

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    726 E Ash Rd, Plymouth, VT 05056
  • /32

    $310,000 Sold Jun 26, 2025

    359 S Mountain Rd, Perkinsville, VT 05151

    • 3 Beds
    • 1.5 Baths
    • 1,732 Sq Ft
    • Built 1963

    Last Sold Summary

    • 6% Below List Price
    • $179/SF
    • 5 Days On Market

    Current Estimated Value $320,037

    Last Listing Agent Daniel Preston KW Vermont Woodstock

    359 S Mountain Rd, Perkinsville, VT 05151
    • /40

      Est $337,300 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
      • Nov 10, 2023

      Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

  • /53

    $540,000

    • 1 Bed
    • 2 Baths
    • 957 Sq Ft

    717/719 Q1-4 Jackson Gore Adams House Unit 717/719 Q1-4, Ludlow, VT 05149

    Located in the heart of Jackson Gore at Okemo Mountain Resort, Adams House 717/719 Q1–4 presents a rare opportunity to own 100% interest in a traditionally quarter-share residence—all four quarters conveyed together, offering full ownership with excellent rental flexibility. This turn-key, ski-on/ski-off residence is being sold fully furnished, allowing a new owner to step right into the winter

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    717/719 Q1-4 Jackson Gore Adams House Unit 717/719 Q1-4, Ludlow, VT 05149
  • /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
    • /27

      Est $854,705 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

      • 55% Above List Price
      • $154/SF
      • 47 Days On Market
      • Last Sold Price $550,000
      • Oct 19, 2023

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /43

    $359,000

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft

    919 Vt Route 100 S, Rochester, VT 05767

    Set on a sun-drenched, level lot, this beautifully updated ranch offers effortless living with modern upgrades throughout. Recent improvements include new electrical and heating systems, a water heater, insulation, siding, doors, and double-pane windows—providing both comfort and efficiency. Inside, you’ll find warm hardwood floors, recessed lighting, and a spacious, inviting kitchen perfect for

    Christopher King King Real Estate

    919 Vt Route 100 S, Rochester, VT 05767
  • /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
    • /36

      Est $492,597 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

      • 7% Above List Price
      • $154/SF
      • 325 Days On Market
      • Last Sold Price $460,000
      • Apr 18, 2025

      Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  • /43

    $875,000

    • 2 Beds
    • 2 Baths
    • 1,820 Sq Ft

    860 Yale Heights Rd, Windsor, VT 05089

    This impeccably orchestrated cottage style contemporary home was crafted by Ennis Builders in 2006 with an eye to meticulous detail. The sweeping cherry spiral staircase, beautiful stonework and superior fit and finish imbue a quality of workmanship that reflects throughout the home. The main level features an open-concept kitchen with maple butcher block counters, and quality stainless steel

    Danny Kogut Williamson Group Sothebys Intl. Realty

    860 Yale Heights Rd, Windsor, VT 05089
  • /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 $658,473

    Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

    28 Webster Rd, Hartland, VT 05048
    • /39

      Est $801,893 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

      • 96% Above List Price
      • $390/SF
      • 97 Days On Market
      • Last Sold Price $410,000
      • Apr 01, 2025

      Last Listing Agent John Wetmore Wetmore Real Estate

  • /49

    $950,000 Pending

    • 3 Beds
    • 3 Baths
    • 3,236 Sq Ft

    746 Pattrell Rd, Norwich, VT 05055

    Perched on a quiet hillside road in Norwich, this mid-century gem offers something unique - extraordinary easterly views and a home that's been thoughtfully updated to enjoy them. The main level sets the tone. A newly redesigned mudroom and laundry room greets you at the door, with radiant floors and plenty of space to shed coats, boots, and gear before stepping into a stunning kitchen remodel

    Leah McLaughry Four Seasons Sotheby's Int'l Realty

    746 Pattrell Rd, Norwich, VT 05055
  • /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 $386,661

    Last Listing Agent Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

    32 Ascutney St, Windsor, VT 05089
    • /37

      Est $905,023 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

      • 3% Below List Price
      • $519/SF
      • 14 Days On Market
      • Last Sold Price $935,000
      • Sep 27, 2024

      Last Listing Agent Marni Rieger KW Vermont-Killington

  • /32

    $445,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 2,074 Sq Ft

    259 Jay Hill Rd, Hartford, VT 05001

    Bright, easy to maintain and furnished 3 bedroom, 3 bath house with all that Quechee Lakes has to offer. This home includes newer floors. kitchen appliances, 2 remodeled bathrooms, a whole house generator, and a garage with an electric car charger. Enjoy the outdoors with a large deck and an electric dog fence around the whole house.

    Sandra Dell KW Coastal and Lakes & Mountains Realty/Hanover

    259 Jay Hill Rd, Hartford, VT 05001
  • /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
    • /38

      Est $583,191 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

      • 23% Above List Price
      • $466/SF
      • 83 Days On Market
      • Last Sold Price $475,000
      • Jan 02, 2024

      Last Listing Agent Holly Hall Hall Collins Real Estate Group

  • /46

    $540,000

    • 1 Bed
    • 2 Baths
    • 1,112 Sq Ft

    193 Jackson Gore Unit 639/641, Ludlow, VT 05149

    Escape to mountain luxury with this fully furnished 1-bedroom, 2-bathroom condo located in the heart of the premier Okemo ski resort at Jackson Gore. Perfectly positioned just steps from the slopes, this stylish retreat offers the ultimate blend of comfort, convenience and year round adventure. The open-concept living space features a cozy gas fireplace and large windows with mountains views. The

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

    193 Jackson Gore Unit 639/641, 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 $308,454

    Last Listing Agent Susan Bellville Bellville Realty

    122 Summer St, Springfield, VT 05156
    • /39

      Est $3,545,484 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

      • 9% Above List Price
      • $319/SF
      • 345 Days On Market
      • Last Sold Price $3,255,000
      • Aug 15, 2023

      Last Listing Agent Story Jenks LandVest, Inc/Woodstock

  • /53

    $359,900 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,608 Sq Ft

    531 Main St, Chester, VT 05143

    Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area

    Katherine Burns William Raveis Real Estate Vermont Properties

    531 Main St, Chester, VT 05143
  • /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
    • /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
      • Sep 29, 2023

      Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

  • /20

    $239,000

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft

    574 Willard Rd Unit 4A, Quechee, VT 05059

    Experience the ultimate Vermont lifestyle in this stunning end-unit condominium, where modern elegance meets trailside serenity. This home offers a rare sense of privacy, featuring a spacious deck that wraps around the the condo, providing a front-row seat to the soothing sounds of the nearby brook and the quiet beauty of the surrounding woods. Inside, the residence is completely move-in ready

    Linda Hicks Quechee Lakes Real Estate Center

    574 Willard Rd Unit 4A, Quechee, VT 05059
  • /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 $308,530

    Last Listing Agent Susanne Pacilio Martha E. Diebold/Hanover

    942 Christian St, White River Junction, VT 05001
    • /29

      Est $750,404 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

      • 32% Above List Price
      • $445/SF
      • 84 Days On Market
      • Last Sold Price $570,000
      • Jun 07, 2024

      Last Listing Agent Herb Hart Quechee Lakes Real Estate Center

  • /12

    $137,000

    • Land
    • 5.39 Acres
    • $25,417 per Acre

    0 Woodlawn Dr Unit 2 & 3 5063379, Hartford, VT 05001

    5.39+/- acre Parcels of land (when combined) in HARTFORD / WHITE RIVER JUNCTION, VT. located on Woodlawn Drive just off the VA Cut Off Road! If you've been having a hard time finding the right home in this very tight housing market or if you've been dreaming about new construction in the Hartford / Upper Valley area than look no further. These building lots are conveniently located only 1 mile

    Alex DeFelice The Clerkin Agency, P.C.

    0 Woodlawn Dr Unit 2 & 3 5063379, Hartford, 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
    • /42

      Est $1,578,006 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

      • $361/SF
      • 79 Days On Market
      • Last Sold Price $1,580,000
      • Dec 30, 2024

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

Showing Results 641 - 680, Page 17 of 18

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