36,189

Windsor County, VT Homes

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  • /32

    $370,000 Sold Dec 12, 2025

    109 Okemo Ridge Rd Unit C201, Ludlow, VT 05149

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft
    • Built 1984

    Last Sold Summary

    • $578/SF
    • 32 Days On Market

    Current Estimated Value $374,554

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

    109 Okemo Ridge Rd Unit C201, Ludlow, VT 05149
    • /38

      Est $1,003,838 Not Listed For Sale

      1432 Union Village Rd, Norwich, VT 05055

      • 4 Beds
      • 3.5 Baths
      • 3,888 Sq Ft
      • Built 1850
      1432 Union Village Rd, Norwich, VT 05055

      Last Sold Summary

      • 51% Above List Price
      • $171/SF
      • 30 Days On Market

      Last Sold Price $665,000

      Last Listing Agent Jane Darrach Martha E. Diebold/Hanover

  • /42

    $429,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    1979 N Hill Rd, Chester, VT 05143

    Welcome to this attractive Andover Contemporary home, perfectly suited for year-round living or as a Vermont vacation retreat. Built in 2005, this 3 bedroom, 2 bath residence offers modern comfort in a peaceful country setting on 2.1 acres while being just minutes from Okemo Mountain Resort and close to scenic snowmobile trails—ideal for outdoor enthusiasts in every season. The inviting

    Geralyn Donohue Engel & Völkers Okemo

    1979 N Hill Rd, Chester, VT 05143
  • /28

    $197,700 Sold Jul 07, 2025

    93 Litchfield St, Springfield, VT 05156

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1941

    Last Sold Summary

    • 1% Below List Price
    • $309/SF
    • 47 Days On Market

    Current Estimated Value $201,865

    Last Listing Agent Debra Staniscia Four Seasons Sotheby's Int'l Realty

    93 Litchfield St, Springfield, VT 05156
    • /17

      Est $83,850 Not Listed For Sale

      35 Depot St, Chester, VT 05143

      • 4 Beds
      • Built 1880
      35 Depot St, Chester, VT 05143

      Last Sold Summary

      • 12% Above List Price
      • $13/SF
      • 68 Days On Market

      Last Sold Price $75,000

      Last Listing Agent Debra Staniscia Four Seasons Sotheby's Int'l Realty

  • /17

    $53,000

    • Land
    • 1.5 Acres
    • $35,333 per Acre

    2-66 Goshawk Dr, Plymouth, VT 05056

    Dreaming of building your own Vermont-style home but hoping to find an affordable parcel? This lot at Hawk Resort is the perfect opportunity. With power and other utilities already on site and the ability to connect to the community septic system, you’ll be well on your way to breaking ground on your dream home. Tucked among the trees in a peaceful natural setting, this property offers privacy

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    2-66 Goshawk Dr, Plymouth, VT 05056
  • /26

    $325,000 Sold Aug 15, 2025

    38 Cardinal Dr, Hartford, VT 05001

    • 4 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • Built 1930

    Last Sold Summary

    • 11% Below List Price
    • $243/SF
    • 6 Days On Market

    Last Listing Agent Josh Hunt Snyder Donegan Real Estate Group

    38 Cardinal Dr, Hartford, VT 05001
    • /6

      Est $73,941 Not Listed For Sale

      600 Kendricks Corner Rd, Perkinsville, VT 05151

      600 Kendricks Corner Rd, Perkinsville, VT 05151

      Last Sold Summary

      • 1% Below List Price
      • 16 Days On Market

      Last Sold Price $75,000

      Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

  • /25

    $115,000

    • Land
    • 10 Acres
    • $11,500 per Acre

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

    Ten-acre wooded parcel with potential views located near the top of Great Roaring Brook Rd. The topography is rolling too steep with multiple buildings sites, rock crop outs, and streams throughout. A wonderful opportunity to design and build your Vermont dream home. Located between Ludlow and Woodstock with equal distance to Killington and Okemo Ski areas. Close to Lake Rescue and Echo Lake for

    Terry Davis Williamson Group Sothebys Intl. Realty

    S-1C Great Roaring Brook Rd, Plymouth, VT 05056
  • /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 $1,114,932

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

    51 Alpine Way Unit A2, Ludlow, VT 05149
    • /17

      Not Listed For Sale

      00 Hemlock Hill Dr, Ludlow, VT 05149

      00 Hemlock Hill Dr, Ludlow, VT 05149

      Last Sold Summary

      • 1,056 Days On Market

      Last Sold Price $275,000

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

  • /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 Rogala 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
    • /33

      Not Listed For Sale

      111 Lakeland Dr Unit B, Hartford, VT 05001

      • 3 Beds
      • 2 Baths
      • 1,346 Sq Ft
      • Built 1982
      111 Lakeland Dr Unit B, Hartford, VT 05001

      Last Sold Summary

      • $353/SF
      • 2 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  • /3

    $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 $266,995

    Last Listing Agent Kevin Holmes Blue Slate Realty

    338 Us Route 5 S, Windsor, VT 05089
    • /39

      Not Listed For Sale

      122 Parrish View Rd, West Windsor, VT 05037

      • 2 Beds
      • 2.5 Baths
      • 1,400 Sq Ft
      • Built 2007
      122 Parrish View Rd, West Windsor, VT 05037

      Last Sold Summary

      • $439/SF
      • 47 Days On Market

      Last Sold Price $614,000

      Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  • /42

    $79,000

    • 1 Bed
    • 2 Baths
    • 775 Sq Ft

    211/213 Qtr I Jackson Gore Inn, Ludlow, VT 05149

    Welcome to effortless mountain living in this spacious 1-bedroom, 2-bathroom unit at the premier Jackson Gore Inn at Okemo Mountain Resort. Boasting slope views, a lockout design, and room to comfortably sleep up to 8 guests, this is the perfect blend of personal getaway with rental opportunities.The well-designed floor plan features a full kitchen, dining area, and cozy living room with a gas

    Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

    211/213 Qtr I Jackson Gore Inn, 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 $495,798

    Last Listing Agent Cheryl Herrmann RE/MAX Group One Realtors

    33 Barber Ln, Hartland, VT 05048
    • /28

      Not Listed For Sale

      238 South St, Hartford, VT 05088

      • 3 Beds
      • 1.5 Baths
      • 1,170 Sq Ft
      • Built 1883
      238 South St, Hartford, VT 05088

      Last Sold Summary

      • $346/SF
      • 5 Days On Market

      Last Sold Price $405,000

      Last Listing Agent Rowan Carroll Coldwell Banker LIFESTYLES - Hanover

  • /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 $424,452

    Last Listing Agent Rachael Rogala Lange & Lange

    317 Bailey Hill Rd, Cavendish, VT 05153
    • /19

      Not Listed For Sale

      976 Hard Rd Unit 2, Hartford, VT 05001

      • 2 Beds
      • 3.5 Baths
      • 1,426 Sq Ft
      • Built 1972
      976 Hard Rd Unit 2, Hartford, VT 05001

      Last Sold Summary

      • $219/SF
      • 11 Days On Market

      Last Sold Price $312,000

      Last Listing Agent Tyler Hall BHHS Verani Upper Valley

  • /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
  • /23

    $85,000 Sold May 28, 2025

    323 Hooper Hollow Rd, Bethel, VT 05032

    • 2 Beds
    • 0.5 Baths
    • 728 Sq Ft
    • Built 2013

    Last Sold Summary

    • $117/SF
    • 5 Days On Market

    Current Estimated Value $87,986

    Last Listing Agent Eric Kenyon Rural Vermont Real Estate

    323 Hooper Hollow Rd, Bethel, VT 05032
    • /48

      Est $370,772 Not Listed For Sale

      32 Route 103 S Unit F3, Ludlow, VT 05149

      • 3 Beds
      • 2 Baths
      • 1,125 Sq Ft
      • Built 1984
      32 Route 103 S Unit F3, Ludlow, VT 05149

      Last Sold Summary

      • 12% Below List Price
      • $373/SF
      • 14 Days On Market

      Last Sold Price $420,000

      Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

  • /47

    $8,000,000

    • 3 Beds
    • 3.5 Baths
    • 5,384 Sq Ft

    115 Eastman Rd, Woodstock, VT 05091

    Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

    Keri Cole Williamson Group Sothebys Intl. Realty

    115 Eastman Rd, Woodstock, VT 05091
  • /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
    • /40

      Est $664,107 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% Below List Price
      • $212/SF
      • 9 Days On Market

      Last Sold Price $729,000

      Last Listing Agent Frank Provance Diamond Realty

  • /31

    $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 Realty

    29 Markham Ln, Weston, VT 05161
  • /43

    $400,000 Sold Apr 25, 2025

    3057 Vt Route 11 E, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Below List Price
    • $222/SF
    • 106 Days On Market

    Current Estimated Value $424,121

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    3057 Vt Route 11 E, Chester, VT 05143
    • /4

      Est $809,356 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

      • 3% Below List Price
      • $573/SF
      • 1 Day On Market

      Last Sold Price $835,000

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

  • /37

    $55,000

    • 1 Bath
    • 390 Sq Ft

    212 QIII Jackson Gore Inn Unit 212 QIII, Ludlow, VT 05149

    Jackson Gore Inn at Okemo Mountain Resort. Quarter Share Ownership, Unit 212 Quarter III is a true four-season destination offering a rare combination of slope-side convenience, year-round recreation, and resort-style amenities. With quarter-share ownership, you can enjoy the benefits of mountain living without the full-time commitment. This studio condominium is located in the Jackson Gore Inn

    Kevin Barnes William Raveis Real Estate Vermont Properties

    212 QIII Jackson Gore Inn Unit 212 QIII, Ludlow, VT 05149
  • /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 $424,602

    Last Listing Agent Jacob Barnes EXP Realty

    4 Twine Hill Rd, Ludlow, VT 05149
    • /36

      Not Listed For Sale

      267 Okemo Trailside Unit 29 B, Ludlow, VT 05149

      • 3 Beds
      • 2.5 Baths
      • 1,660 Sq Ft
      • Built 1983
      267 Okemo Trailside Unit 29 B, Ludlow, VT 05149

      Last Sold Summary

      • $548/SF
      • 6 Days On Market

      Last Sold Price $910,000

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

  • /20

    $169,000

    • Land
    • 0.52 Acre
    • $325,000 per Acre

    71 S Windsor St, Royalton, VT 05068

    Centrally located, in the picturesque village of South Royalton, is a building lot with multifaceted potential! The desirable attributes of both the ability for connection to the municipal sewer and connection to the municipal water system could present the opportunity for multi-unit residential construction! An extensive level lawn area makes visualizing prospective building sites a simple

    John Wetmore Wetmore Real Estate

    71 S Windsor St, 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 $868,749

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

    151 Smokerise, Ludlow, VT 05149
    • /3

      Not Listed For Sale

      00 Weed Rd, Hartland, VT 05049

      00 Weed Rd, Hartland, VT 05049

      Last Sold Summary

      • 15 Days On Market

      Last Sold Price $500,000

      Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

  • /39

    $415,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft

    5 Brownsville Rd, Hartland, VT 05048

    Formerly Hartland Schoolhouse #11, this charming antique brick colonial in a village location, is just a 6 minute drive from an I-91 entrance/exit. Beautiful natural light in the 3 bedrooms, 2 baths. Indian shutters, lovely old wood floors and moldings and a surprisingly open floor plan. A very easy commute to Dartmouth College or Dartmouth Health.

    Jane Darrach Martha E. Diebold/Hanover

    5 Brownsville Rd, Hartland, VT 05048
  • /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 $576,333

    Last Listing Agent Frank Provance Diamond Realty

    12 Commonwealth Ave, Ludlow, VT 05149

Showing Results 241 - 280, Page 7 of 18

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