36,490

Windsor County, VT Homes

Section Image
  • /39

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft

    76 Goldthwaite Rd, Chester, VT 05143

    Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal-style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

    Gary Coger Four Seasons Sotheby's Int'l Realty

    76 Goldthwaite Rd, Chester, VT 05143
  • /51

    $1,085,000

    Sold Sep 18, 2025

    51 Alpine Way Unit A2, Ludlow, VT 05149

    • 3 Beds
    • 3.5 Baths
    • 1,897 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Below List Price
    • $572/SF
    • 4 Days On Market

    Current Estimated Value $1,152,273

    Last Listing Agent Boris Lavanovich Mary W. Davis Realtor & Assoc., Inc.

    51 Alpine Way Unit A2, Ludlow, VT 05149
    • /40

      Est $666,687

      Not Listed For Sale

      621 Main St, Proctorsville, VT 05153

      • 5 Beds
      • 5 Baths
      • 3,434 Sq Ft
      • Built 1787
      621 Main St, Proctorsville, VT 05153

      Last Sold Summary

      • 9 Days On Market

  • /36

    $95,000

    • 2 Beds
    • 2 Baths
    • 1,025 Sq Ft

    224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149

    Experience Vermont's Premier Mountain Living Without Full Ownership Costs. Step directly onto Okemo's slopes from your slopeside retreat at Jackson Gore. This condo-tel quarter-share gives you deeded ownership of 13 weeks annually (25% of the year)—at a fraction of the cost of whole ownership. You own one of four deeded interests in this unit. You receive every fourth week on a rotating schedule,

    Rachael Lange Lange & Lange

    224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149
  • /34

    $2,210,000

    Sold Sep 24, 2025

    15 Hathorn Hill Street Extension, Woodstock, VT 05091

    • 4 Beds
    • 3.5 Baths
    • 3,564 Sq Ft
    • Built 2009

    Last Sold Summary

    • 1% Above List Price
    • $620/SF
    • 68 Days On Market

    Last Listing Agent John Snyder Snyder Donegan Real Estate Group

    15 Hathorn Hill Street Extension, Woodstock, VT 05091
    • /4

      Est $906,610

      Not Listed For Sale

      160 Solitude Rd Unit L104, Ludlow, VT 05149

      • 3 Beds
      • 2.5 Baths
      • 1,456 Sq Ft
      • Built 1998
      160 Solitude Rd Unit L104, Ludlow, VT 05149

      Last Sold Summary

      • 1 Day On Market

  • /12

    $199,000

    • Land
    • 29 Acres
    • $6,862 per Acre

    00 Vermont 12, Barnard, VT 05031

    A beautiful and private 29 acre building lot on a mountainside in an area of Barnard populated by estate properties. A road to the potential building site is in and soil testing for septic will be completed as soon as snow clears. Views of the valley and local mountains currently cleared and can be expanded with additional clearing. The location is a short drive to Woodstock, a shorter drive to

    Stan Butler Four Seasons Sotheby's Int'l Realty

    00 Vermont 12, Barnard, VT 05031
  • /11

    $240,000

    Sold Jul 21, 2025

    338 Us Route 5 S, Windsor, VT 05089

    • 6 Beds
    • 2 Baths
    • 2,504 Sq Ft
    • Built 1840

    Last Sold Summary

    • $96/SF
    • 7 Days On Market

    Current Estimated Value $242,470

    Last Listing Agent Kevin Holmes Blue Slate Realty

    338 Us Route 5 S, Windsor, VT 05089
    • /3

      Not Listed For Sale

      00 Weed Rd, Hartland, VT 05049

      00 Weed Rd, Hartland, VT 05049

      Last Sold Summary

      • 15 Days On Market

  • /34

    $100,000

    • 2 Beds
    • 3 Baths
    • 1,367 Sq Ft

    506/508 Qtr I Adams House, Ludlow, VT 05149

    Adams House Unit 506/508 QII: Quarter ownership. This 2 Bedroom, 3 Bathroom lock-out style unit that sleeps 8 in Adams House is in an excellent location. When you park in the heated garage, you find yourself only steps away from the unit which is located on the first floor. A very short walk down the hall and you pass the owners locker location. The gas fireplace will warm your spirits and make

    Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

    506/508 Qtr I Adams House, Ludlow, VT 05149
  • /42

    $450,000

    Sold Jul 07, 2025

    33 Barber Ln, Hartland, VT 05048

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft
    • Built 2008

    Last Sold Summary

    • 3% Above List Price
    • $207/SF
    • 7 Days On Market

    Current Estimated Value $481,109

    Last Listing Agent Cheryl Herrmann RE/MAX Group One Realtors

    33 Barber Ln, Hartland, VT 05048
    • /40

      Not Listed For Sale

      954 E Ash Rd Unit L-17, Plymouth, VT 05056

      • 4 Beds
      • 3.5 Baths
      • 1,660 Sq Ft
      • Built 1986
      954 E Ash Rd Unit L-17, Plymouth, VT 05056

      Last Sold Summary

      • 18 Days On Market

  • /3

    $175,000

    • Land
    • 12.51 Acres
    • $13,989 per Acre

    377 Coach Rd, Chester, VT 05143

    Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    377 Coach Rd, Chester, VT 05143
  • /54

    $402,060

    Sold Aug 14, 2025

    317 Bailey Hill Rd, Cavendish, VT 05153

    • 3 Beds
    • 2 Baths
    • 2,012 Sq Ft
    • Built 1992

    Last Sold Summary

    • 4% Below List Price
    • $200/SF
    • 5 Days On Market

    Current Estimated Value $416,629

    Last Listing Agent Rachael Lange Lange & Lange

    317 Bailey Hill Rd, Cavendish, VT 05153
    • /40

      Not Listed For Sale

      318 Ebbin Lockwood Way, Woodstock, VT 05071

      • 3 Beds
      • 3.5 Baths
      • 6,047 Sq Ft
      • Built 1970
      318 Ebbin Lockwood Way, Woodstock, VT 05071

      Last Sold Summary

      • 495 Days On Market

  • /44

    $729,000

    $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,018 Sq Ft

    51 High St, Ludlow, VT 05149

    Welcome to 51 High Street — an immaculate, turnkey village home just steps from the Okemo shuttle stop, offering effortless access to Okemo Mountain Resort and all that Ludlow has to offer. This inviting residence features five bedrooms and 2.5 baths, thoughtfully updated for comfortable year-round living. The renovated kitchen shines with classic soapstone countertops and a charming Jøtul

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    51 High St, Ludlow, VT 05149
  • /17

    $120,000

    Sold Jul 10, 2025

    Lot #6 Southern Pines Ln, Ludlow, VT 05149

    • Land
    • 4.44 Acres
    • $27,027 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 472 Days On Market

    Last Listing Agent Andre Menard Mary W. Davis Realtor & Assoc., Inc.

    Lot #6 Southern Pines Ln, Ludlow, VT 05149
    • /25

      Est $594,361

      Not Listed For Sale

      124 Village Ln, West Windsor, VT 05037

      • 3 Beds
      • 2 Baths
      • 1,442 Sq Ft
      • Built 2011
      124 Village Ln, West Windsor, VT 05037

      Last Sold Summary

      • 246 Days On Market

  • /36

    $500,000

    • 3 Beds
    • 3 Baths
    • 2,122 Sq Ft

    1138 Bethel Mountain Rd, Rochester, VT 05767

    Set on 4.7± acres along scenic Bethel Mountain Road, this mountain-view property offers the kind of Vermont experience that you're yearning for. With a swimming pond, expansive outdoor living spaces, detached three-car garage, and easy access to some of the state’s best outdoor recreation, this is a home designed to be enjoyed in every season. The setting is exceptional. Long-range mountain views

    William Brokhof Vermont Backcountry Real Estate

    1138 Bethel Mountain Rd, Rochester, VT 05767
  • /2

    $427,500

    Sold Oct 01, 2025

    4 Twine Hill Rd, Ludlow, VT 05149

    • 4 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 1956

    Last Sold Summary

    • 2% Below List Price
    • $251/SF
    • 30 Days On Market

    Current Estimated Value $480,916

    Last Listing Agent Jacob Barnes EXP Realty

    4 Twine Hill Rd, Ludlow, VT 05149
    • /18

      Not Listed For Sale

      574 Willard Rd Unit 3 F, Hartford, VT 05001

      • 2 Beds
      • 1 Bath
      • 900 Sq Ft
      • Built 1978
      574 Willard Rd Unit 3 F, Hartford, VT 05001

      Last Sold Summary

      • 57 Days On Market

  • /29

    $530,000

    • 3 Beds
    • 2.5 Baths
    • 4,020 Sq Ft

    28 Fairview Terrace, Royalton, VT 05068

    This 3-bedroom, 2.5-bath home is full of potential, with the option to create an auxiliary dwelling for added flexibility. The current owner saw the promise in this gem and has already invested in the important updates: fresh exterior paint, a brand-new septic system, a new roof, upgraded electrical, and other quality improvements. With much of the essential work complete, the next owner has the

    Wendie Wright Coldwell Banker LIFESTYLES - Hanover

    28 Fairview Terrace, Royalton, VT 05068
  • /39

    $825,000

    Sold Dec 04, 2025

    151 Smokerise, Ludlow, VT 05149

    • 3 Beds
    • 5 Baths
    • 4,532 Sq Ft
    • Built 1996

    Last Sold Summary

    • 6% Below List Price
    • $182/SF
    • 101 Days On Market

    Current Estimated Value $889,488

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

    151 Smokerise, Ludlow, VT 05149
    • /40

      Est $330,896

      Not Listed For Sale

      27 Kelly Rd, Stockbridge, VT 05772

      • 5 Beds
      • 2 Baths
      • 2,448 Sq Ft
      • Built 1930
      27 Kelly Rd, Stockbridge, VT 05772

      Last Sold Summary

      • 75 Days On Market

  • /13

    $215,000

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    122 Quechee Hollow Ln Unit 4E, Hartford, VT 05059

    Welcome to easy living in Quechee Lakes! This charming 2-bedroom condo offers a cozy, traditional style that feels warm and inviting from the moment you arrive. Neat, tidy, and well-maintained, it's the perfect retreat for year-round enjoyment or a convenient getaway. As part of the Quechee Lakes community, you'll have access to an outstanding array of amenities, including championship golf,

    Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

    122 Quechee Hollow Ln Unit 4E, Hartford, VT 05059
  • /48

    $540,000

    Sold Dec 12, 2025

    12 Commonwealth Ave, Ludlow, VT 05149

    • 9 Beds
    • 6 Baths
    • 5,054 Sq Ft
    • Built 1900

    Last Sold Summary

    • 6% Below List Price
    • $107/SF
    • 184 Days On Market

    Current Estimated Value $550,968

    Last Listing Agent Frank Provance Diamond Realty

    12 Commonwealth Ave, Ludlow, VT 05149
    • /60

      Est $3,437,655

      Not Listed For Sale

      4 Morning Star, Ludlow, VT 05149

      • 5 Beds
      • 6.5 Baths
      • 6,184 Sq Ft
      • Built 2004
      4 Morning Star, Ludlow, VT 05149

      Last Sold Summary

      • 237 Days On Market

  • /40

    $375,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    21 Dell Rd, Springfield, VT 05156

    Coming soon - showings start Monday May 18th by appointment. So much space! This property features a paved driveway leading to a two-car attached garage, plus a clever third-bay conversion that now serves as a spacious and convenient laundry room. Entering through the covered porch ensures you never have to shovel your way to the door, leading you directly into a kitchen with updated stainless

    Franchesca Collins Hall Collins Real Estate Group

    21 Dell Rd, Springfield, VT 05156
  • /22

    $270,000

    Sold May 22, 2026

    1299 Quechee Main St Unit 2E, Hartford, VT 05001

    • 2 Beds
    • 1.5 Baths
    • 1,063 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $254/SF
    • 85 Days On Market

    Last Listing Agent Linda Hicks Quechee Lakes Real Estate Center

    1299 Quechee Main St Unit 2E, Hartford, VT 05001
    • /40

      Est $588,997

      Not Listed For Sale

      21 Sportsmen Cove, Hartland, VT 05048

      • 3 Beds
      • 2 Baths
      • 1,980 Sq Ft
      • Built 2006
      21 Sportsmen Cove, Hartland, VT 05048

      Last Sold Summary

      • 19 Days On Market

  • /36

    $299,000

    • 2 Beds
    • 1 Bath
    • 750 Sq Ft

    29 Markham Ln, Weston, VT 05161

    This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally

    Catherine Cairns Maple Leaf Real Estate

    29 Markham Ln, Weston, VT 05161
  • /47

    $517,000

    Sold Dec 16, 2025

    127 Pleasant St, Cavendish, VT 05142

    • 4 Beds
    • 2 Baths
    • 2,300 Sq Ft
    • Built 1928

    Last Sold Summary

    • 6% Below List Price
    • $225/SF
    • 123 Days On Market

    Current Estimated Value $516,337

    Last Listing Agent Tyleen Murray Kelley Real Estate, Inc.

    127 Pleasant St, Cavendish, VT 05142
    • /3

      Est $447,862

      Not Listed For Sale

      1013 Malagash Rd, South Reading, VT 05153

      • 2 Beds
      • Built 2024
      1013 Malagash Rd, South Reading, VT 05153

      Last Sold Summary

      • 42 Days On Market

  • /4

    $169,000

    • Land
    • 15.4 Acres
    • $10,974 per Acre

    0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091

    Instant equity in Woodstock! Bring your vision to life on this exceptional parcel of raw land, nestled in one of Vermont’s most coveted and quintessential communities. Offered below its current town-assessed value and backed by a recent independent appraisal valuation, this property delivers significant instant equity from day one. Whether you envision a private, tucked-away country estate or a

    Chelsea Bevis KW Vermont Woodstock

    0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091
  • /19

    $243,000

    Sold Sep 03, 2025

    86 Webster Rd, Hartland, VT 05048

    • 3 Beds
    • 1 Bath
    • 940 Sq Ft
    • Built 1969

    Last Sold Summary

    • 3% Below List Price
    • $259/SF
    • 34 Days On Market

    Current Estimated Value $242,863

    Last Listing Agent Jim Bialowski BHG Masiello Keene

    86 Webster Rd, Hartland, VT 05048
    • /8

      Not Listed For Sale

      1028 Fairbanks Turn, Woodstock, VT 05091

      1028 Fairbanks Turn, Woodstock, VT 05091

      Last Sold Summary

      • 162 Days On Market

  • /36

    $515,000

    $20K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 4,933 Sq Ft

    2 Pine St, Windsor, VT 05089

    Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch

    Susan Bellville Bellville Realty

    2 Pine St, Windsor, VT 05089
  • /52

    $598,000

    Sold Oct 10, 2025

    2510 E Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 2,264 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $264/SF
    • 94 Days On Market

    Current Estimated Value $591,115

    Last Listing Agent Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
    • /26

      Est $275,053

      Not Listed For Sale

      71 Putnam Rd, Springfield, VT 05156

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 2020
      71 Putnam Rd, Springfield, VT 05156

      Last Sold Summary

      • 6 Days On Market

  • /12

    $79,000

    • Land
    • 2.53 Acres
    • $31,225 per Acre

    Lot #4 Meadow Rd, Ludlow, VT 05149

    Private 2.53+/- acre state approved building lot located at the end of a dead-end, private road. Positioned at the south end of Ludlow off East Hill Road, this lot offers easy access to town amenities and the Okemo Ski Area. Possible views of Okemo with clearing.

    Andre Menard Mary W. Davis Realtor & Assoc., Inc.

    Lot #4 Meadow Rd, Ludlow, VT 05149

Showing Results 281 - 320, Page 8 of 18

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