34,509

Windsor County, VT Homes

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  • /52

    $499,000

    $200K PRICE DROP
    • 2.5 Baths
    • 7,445 Sq Ft

    66 Duttonsville School Dr, Cavendish, VT 05142

    Where History Meets Possibility. An 1862 Schoolhouse Reimagined. Step back in time and into opportunity. Built in 1862, this remarkable historic schoolhouse has been lovingly preserved, its character and craftsmanship thoughtfully maintained while seamlessly supporting modern use.Since 1973, the building has served as the home of a thriving distribution business, proof of its adaptability,

    Agent Photo

    Gail Beardmore

    Engel & Völkers Okemo

    66 Duttonsville School Dr, Cavendish, VT 05142
  • /15

    Starting at $1,895 Per Month

    • 3 Beds

    8 Union St, Windsor, VT 05089

    8 Union St.

    8 Union St, Windsor, VT 05089
  • /33

    $405,000

    Sold May 08, 2026

    2680 Hartford Ave Unit 14, White River Junction, VT 05001

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft
    • Built 2004

    Last Sold Summary

    • 4% Above List Price
    • $243/SF
    • 3 Days On Market

    Current Estimated Value $396,119

    Last Listing Agent Liam McCarthy Coldwell Banker LIFESTYLES - Hanover

    2680 Hartford Ave Unit 14, White River Junction, VT 05001
    • /52

      Est $562,548

      Not Listed For Sale

      1613 W Woodstock Rd, Woodstock, VT 05091

      • 3 Beds
      • 1.5 Baths
      • 2,240 Sq Ft
      • Built 1944
      1613 W Woodstock Rd, Woodstock, VT 05091

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Holly Hall Hall Collins Real Estate Group

  • /2

    $99,000

    Under Contract
    • Land
    • 9.9 Acres
    • $10,000 per Acre

    00 Main St, Ludlow, VT 05149

    LOCATION LOCATION LOCATION....options are unlimited for this large ready to develop parcel. Okemo Mountain views, level (and mostly cleared) parcel with MAJOR ROAD FRONTAGE! You can't beat the spot or the wonderful mountain view!** One of the owners is a licensed Vermont Real Estate agent.

    Agent Photo

    Lisa Kelley

    Cummings & Co

    00 Main St, Ludlow, VT 05149
  • /20

    $2,300 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Condo for Rent

    50 Pleasant St Unit 2, Ludlow, VT 05149

    Property Id: 126632 3 Bedroom 2 Bath 2nd floor Apartment. Very bright and open. New dishwasher, washer and dryer. Fully furnished. Close to shopping and restaurants. On the shuttle route. Okemo base 2 miles away.

    50 Pleasant St Unit 2, Ludlow, VT 05149
  • /53

    $798,000

    Sold Oct 31, 2025

    392 Gully Rd, Woodstock, VT 05091

    • 2 Beds
    • 2 Baths
    • 1,308 Sq Ft
    • Built 2019

    Last Sold Summary

    • $610/SF
    • 28 Days On Market

    Current Estimated Value $781,992

    Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

    392 Gully Rd, Woodstock, VT 05091
    • /23

      Not Listed For Sale

      240 QIV 111 Jackson Gore Rd Unit 240 QIV, Ludlow, VT 05149

      • Studio
      • 1 Bath
      • 390 Sq Ft
      • Built 2003
      240 QIV 111 Jackson Gore Rd Unit 240 QIV, Ludlow, VT 05149

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Kevin Barnes William Raveis Real Estate Vermont Properties

  • /60

    $349,900

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,546 Sq Ft

    295 Spencer Hollow Rd, Springfield, VT 05156

    First time ever for sale! This delightful country home has been with the same family since it was built. Expanded cape style home is full of wonderful natural light, hardwood and tile floors, natural woodwork, built-in China cabinet, 3 bedrooms and full bath on the main floor and a fourth bedroom and 3/4 bath on the second floor along with a bonus room. Ceiling fans throughout the home keep the

    Agent Photo

    Julie Buffum

    Buffum Realty

    295 Spencer Hollow Rd, Springfield, VT 05156
  • /20

    $2,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,500 Sq Ft
    • House for Rent

    6 Alpine Dr, Ludlow, VT 05149

    Property Id: 126643 Very private mountain setting. True Vermont setting. FULLY FURNISHED Sleeps 6 Most pets allowed. SPRING AND SUMMER VACATION RENTAL NOT AVAILABLE FOR A LONG TERM RENTAL

    6 Alpine Dr, Ludlow, VT 05149
  • /60

    $625,000

    Sold Sep 11, 2025

    200 Peregrine Rd, Plymouth, VT 05056

    • 4 Beds
    • 4 Baths
    • 2,818 Sq Ft
    • Built 1995

    Last Sold Summary

    • 11% Below List Price
    • $222/SF
    • 108 Days On Market

    Current Estimated Value $705,899

    Last Listing Agent Marni Rieger KW Vermont-Killington

    200 Peregrine Rd, Plymouth, VT 05056
    • /23

      Not Listed For Sale

      240 QII 111 Jackson Gore Rd Unit 240 QII, Ludlow, VT 05149

      • Studio
      • 1 Bath
      • 390 Sq Ft
      • Built 2003
      240 QII 111 Jackson Gore Rd Unit 240 QII, Ludlow, VT 05149

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Kevin Barnes William Raveis Real Estate Vermont Properties

  • /60

    $500,000

    • 4 Beds
    • 4 Baths
    • 960 Sq Ft

    544 Vulture Mountain Rd, Stockbridge, VT 05772

    Welcome to Camp Treetops, a one-of-a-kind mountaintop estate perched high above the White River Valley. This fully operating, high-performing retreat conveys COMPLETELY FURNISHED and turnkey, with panoramic mountain and White River views, total privacy, and a proven income stream already in place.At its heart is the original Sears Roebuck kit hunting cabin, beautifully renovated with warm

    Agent Photo

    Jacob Barnes

    EXP Realty

    544 Vulture Mountain Rd, Stockbridge, VT 05772
  • /8

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft
    • Condo for Rent

    201 Union St Unit 201C, Springfield, VT 05156

    Property Id: 2507664 650 sf 1 bedroom apartment, large kitchen, with recently updated appliances, laminate flooring throughout the apartment. bedroom is has a large closet. Bath has a tub and shower with tile flooring. It has a large yard area for outdoor recreation. Apartment is located within walking distance to shopping, hospital, and K-12 schools, and churches also has public

    201 Union St Unit 201C, Springfield, VT 05156
  • /60

    $997,500

    Sold Nov 14, 2025

    2941 Twenty Mile Stream Rd, Cavendish, VT 05142

    • 4 Beds
    • 4.5 Baths
    • 4,420 Sq Ft
    • Built 1834

    Last Sold Summary

    • 19% Below List Price
    • $226/SF
    • 109 Days On Market

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    2941 Twenty Mile Stream Rd, Cavendish, VT 05142
    • /32

      Not Listed For Sale

      11 and 12 Boynton Rd, Weston, VT 05161

      11 and 12 Boynton Rd, Weston, VT 05161

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

  • /2

    $249,000

    Under Contract
    • 3,978 Sq Ft

    67 Valley St, Springfield, VT 05156

    Seller remarks: Building is structurally sound, vinyl siding, slate roof, plumbing & heating in working order. 2 units rented, 2 units ready for a facelift. Lots of square footage here. Seller has information on grant money available, up to $120,000 for rehabs. This could be your chance to get started in the rental business.

    Agent Photo

    Julie Buffum

    Buffum Realty

    67 Valley St, Springfield, VT 05156
  • /5

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    259 River St Extension Unit 3, Bethel, VT 05032

    Property Id: 2764669 Wonderful carriage house recently redone. It’s like your own house with private entrance. First floor open concept with washer and dryer, cute kitchen with stained glass in between the living room and kitchen. Hardwood in Living room dining area and tiled kitchen. Lovely staircase with stained glass on the landing going up to tiled bath with glass shower, bedroom and

    259 River St Extension Unit 3, Bethel, VT 05032
  • /2

    $273,000

    Sold Aug 07, 2026

    61 Kennedy Dr, Windsor, VT 05089

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1943

    Last Sold Summary

    • $271/SF
    • 0 Days On Market

    Current Estimated Value $240,082

    Last Listing Agent Allison Griep BHHS Verani Upper Valley

    61 Kennedy Dr, Windsor, VT 05089
    • /23

      Not Listed For Sale

      S-1D Great Roaring Brook Rd, Plymouth, VT 05056

      S-1D Great Roaring Brook Rd, Plymouth, VT 05056

      Last Sold Summary

      • 180 Days On Market

      Last Listing Agent Terry Davis Williamson Group Sothebys Intl. Realty

  • /23

    $199,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,767 Sq Ft

    165 Dutton Farm Rd, Springfield, VT 05156

    Bring your vision to this private 3-bedroom, 2-bath home with a bonus room, nestled in a sought-after location. Surrounded by nature, this property offers the peace and privacy you've been searching for while providing endless potential to make it your own. Enjoy beautiful views from the large living room windows, or venture outdoors to explore the near-by walking trails. Established herbs and

    Agent Photo

    Kirsten Dole

    Coldwell Banker LIFESTYLES - Hanover

    165 Dutton Farm Rd, Springfield, VT 05156
  • /20

    $1,650 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    50 Pleasant St Unit 3, Ludlow, VT 05149

    Property Id: 1784303 Third floor nicely furnished apartment. Short walk to restaurants and shopping. MUST MEET LANDLORD BEFORE LEASE. Tenant to pay oil and electric. Sorry no pets or smoking allowed. Very short walk to town. Great Ludlow village location. This is a spring and summer vacation rental. Please call with questions or to set up a showing.

    50 Pleasant St Unit 3, Ludlow, VT 05149
  • /60

    $475,000

    Sold Aug 27, 2025

    472 Main St, Chester, VT 05143

    • 5 Beds
    • 7 Baths
    • 5,546 Sq Ft
    • Built 1850

    Last Sold Summary

    • 5% Below List Price
    • $86/SF
    • 36 Days On Market

    Current Estimated Value $477,365

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    472 Main St, Chester, VT 05143
    • /17

      Not Listed For Sale

      00 Ellison Loop, Ludlow, VT 05149

      00 Ellison Loop, Ludlow, VT 05149

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

  • /58

    $1,350,000

    $50K PRICE DROP
    • 6 Beds
    • 5 Baths
    • 4,571 Sq Ft

    505 Deweys Mills Rd, Hartford, VT 05047

    The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the

    Agent Photo

    Jennifer Falvey

    KW Vermont Woodstock

    505 Deweys Mills Rd, Hartford, VT 05047
  • /10

    $1,400 Per Month

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft
    • Condo for Rent

    29 Cottage Ave Unit . 4, Springfield, VT 05156

    Property Id: 2792102 Apartment is located within walking distance to shopping, hospital, churches, and K-12 schools, also has public transportation available. Rent of $1,400.00 includes snow and trash removal, lawn care. Monthly income must be 3 times the monthly rent and we do back ground checks.

    29 Cottage Ave Unit . 4, Springfield, VT 05156
  • /36

    $655,000

    Sold Nov 24, 2025

    4 Stanton St, Woodstock, VT 05091

    • 4 Beds
    • 2.5 Baths
    • 2,124 Sq Ft
    • Built 1901

    Last Sold Summary

    • 18% Above List Price
    • $308/SF
    • 7 Days On Market

    Current Estimated Value $685,878

    Last Listing Agent Nan Carroll Coldwell Banker LIFESTYLES - Hanover

    4 Stanton St, Woodstock, VT 05091
    • /37

      Not Listed For Sale

      61 Davis Rd, Cavendish, VT 05153

      • 2 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1982
      61 Davis Rd, Cavendish, VT 05153

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Evan Russell Real Broker LLC

  • /2

    $54,900

    Pending
    • Land
    • 3 Acres
    • $18,300 per Acre

    00 Comstock Ave, Weathersfield, VT 05030

    3.00 +/- lot located just minutes from I91, Claremont, Windsor, Springfield and the upper valley. If you have been looking for an untouched piece of land this is your opportunity.

    Agent Photo

    Julie Buffum

    Buffum Realty

    00 Comstock Ave, Weathersfield, VT 05030
  • /10

    $1,875 Per Month

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • House for Rent

    291 Moses Ln, Royalton, VT 05068

    Property Id: 2498154 South Royalton 3 bedroom two bath nice lawn, fire pit to enjoy, storage. Unit can share roommate with approval, tenant pays all utilities. Walking distance to law school.

    291 Moses Ln, Royalton, VT 05068
  • /31

    $450,000

    Sold Oct 06, 2025

    151 Burton Rd, Weston, VT 05161

    • 4 Beds
    • 2 Baths
    • 1,715 Sq Ft
    • Built 1966

    Last Sold Summary

    • 9% Below List Price
    • $262/SF
    • 71 Days On Market

    Current Estimated Value $446,463

    Last Listing Agent Gary Coger Four Seasons Sotheby's Int'l Realty

    151 Burton Rd, Weston, VT 05161
    • /42

      Not Listed For Sale

      4150 Trebo Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,566 Sq Ft
      • Built 1995
      4150 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Alexandra Eatmon Kelley Real Estate, Inc.

  • /29

    $249,000

    • 3 Beds
    • 1 Bath
    • 1,203 Sq Ft

    42 Mark St, Springfield, VT 05156

    Delightful cape style home in a family friendly neighborhood. Large lot with detached single car garage, additional building for storage, lots of level space for a garden or to fence in. Home features a covered entry. This home has seen lots of updates thru its life including a newer roof, new wooden siding that has been freshly painted, interior of the home has also been freshly painted. Lots of

    Agent Photo

    Julie Buffum

    Buffum Realty

    42 Mark St, Springfield, VT 05156
  • /17

    $1,000 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    10 Mineral St Unit Keive House, Springfield, VT 05156

    Property Id: 2505999 Spacious 144sf rooms , Our rooms include electricity, heating, Wi-Fi, large living room, Kitchen with stove, refrigerator, and Micro wave. Keive House is convexly located to restaurants, shopping, schools, hospitals, and churches all within walking distance or you can take the bus that stops across the street. We take long term and short term rentals. To apply

    10 Mineral St Unit Keive House, Springfield, VT 05156
  • /59

    $1,625,000

    Sold Oct 24, 2025

    7 North St, Woodstock, VT 05091

    • 2 Beds
    • 3 Baths
    • 2,106 Sq Ft
    • Built 1880

    Last Sold Summary

    • 12% Below List Price
    • $772/SF
    • 111 Days On Market

    Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

    7 North St, Woodstock, VT 05091
    • /53

      Not Listed For Sale

      517-519 Jackson Gore Rd Unit 517-519 QTR I, Ludlow, VT 05149

      • 1 Bed
      • 2 Baths
      • 957 Sq Ft
      • Built 2003
      517-519 Jackson Gore Rd Unit 517-519 QTR I, Ludlow, VT 05149

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Frank Provance Diamond Realty

  • /43

    $419,900

    $5K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,982 Sq Ft

    176 Meadow Rd, Chester, VT 05143

    Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless

    Agent Photo

    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    176 Meadow Rd, Chester, VT 05143
  • /9

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • Condo for Rent

    59 Wall St Unit 4, Springfield, VT 05156

    Property Id: 2583239 Apartment is located within walking distance to shopping, hospital, and K-12 schools, and churches also has public transportation available. Rent of $1,600.00 includes heat, Hot water, snow and trash removal, lawn care. Monthly income must be 3 times the monthly rent and we do back ground checks.

    59 Wall St Unit 4, Springfield, VT 05156
  • /46

    $200,000

    Sold Jan 09, 2026

    713/715 Qtr I Adams House, Ludlow, VT 05149

    • 3 Beds
    • 3 Baths
    • 2,001 Sq Ft
    • Built 2007

    Last Sold Summary

    • 5% Below List Price
    • $100/SF
    • 13 Days On Market

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

    713/715 Qtr I Adams House, Ludlow, VT 05149
    • /54

      Not Listed For Sale

      228 Birch Landing Rd Unit 27, Plymouth, VT 05056

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft
      • Built 1985
      228 Birch Landing Rd Unit 27, Plymouth, VT 05056

      Last Sold Summary

      • 51 Days On Market

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

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