Windsor County, VT Homes

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  /60

  $220,000 Sold Nov 07, 2025

  442 Vermont 103, Chester, VT 05143

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft
  • Built 1941

  Last Sold Summary

  • 8% Below List Price
  • $215/SF
  • 70 Days On Market

  Last Listing Agent Rachael Rogala Lange & Lange

  442 Vermont 103, Chester, VT 05143
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  /39

  Est $3,565,454 Not Listed For Sale

  • 10 Beds
  • 15 Baths
  • 10,206 Sq Ft

  3 Church St, Woodstock, VT 05091

  3 Church St, Woodstock, VT 05091
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  /44

  $79,500

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149

  368/370 Qtr. IV~Enjoy two coveted winter weeks —including Christmas and New Year’s(2025-26)—at this spacious 1-bedroom, 2-bathroom lockout unit at the Jackson Gore Inn at Okemo. Located on the third floor and just steps from the Round House, this unit offers beautiful valley views and ideal proximity to lifts, pools, and dining. Unit C Features: 1 bedroom, sleeps eight, lock-out capabilities, 2

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

  368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149
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  /53

  $482,500 Sold Nov 12, 2025

  1612 Hartford Ave, Hartford, VT 05001

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft
  • Built 1880

  Last Sold Summary

  • 12% Above List Price
  • $359/SF
  • 5 Days On Market

  Last Listing Agent Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  1612 Hartford Ave, Hartford, VT 05001
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  /40

  Est $1,386,151 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 3,719 Sq Ft

  26 River St, Woodstock, VT 05091

  26 River St, Woodstock, VT 05091
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  /17

  $85,000

  • Land
  • 11.51 Acres
  • $7,385 per Acre

  00 Chaos Turnpike, Cavendish, VT 05142

  NOT QUITE off the Grid Hideaway (Verizon 1-4 G) Just down the country lane to Knapp Ponds/Knapp Brook Wildlife Management Area. Forgotten by the owners for the last 30 years, this lot has a mix of timber, stone wall & sloping mountain terrain. 475 feet frontage along the Class 3 road and only a short hike to the ponds. Boat ramps for fishing and hunting access.

  Alexandra Eatmon Kelley Real Estate, Inc.

  00 Chaos Turnpike, Cavendish, VT 05142
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  /24

  $549,900 Sold Dec 02, 2025

  2179 U S 4, Bridgewater, VT 05035

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 2021

  Last Sold Summary

  • $546/SF
  • 92 Days On Market

  Last Listing Agent John MacGovern Dark Horse Realty

  2179 U S 4, Bridgewater, VT 05035
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  /29

  Est $698,070 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  42 River St, Woodstock, VT 05091

  42 River St, Woodstock, VT 05091
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  /28

  $93,999 Under Contract

  • 3 Beds
  • 2 Baths
  • 880 Sq Ft

  32 Oak Ln, Springfield, VT 05156

  Welcome to 32 Oak Lane, Springfield VT 05156, where modern comfort meets affordability in Windy Hill Acres Park! This brand-new Dias model manufactured home offers 3 bedrooms, 2 bathrooms, and 880 sq. ft. (14 x 66 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  32 Oak Ln, Springfield, VT 05156
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  /2

  $190,000 Sold Jul 15, 2025

  66 Mount Vernon St, Springfield, VT 05156

  • 4 Beds
  • 1.5 Baths
  • 1,502 Sq Ft
  • Built 1860

  Last Sold Summary

  • 6% Above List Price
  • $126/SF
  • 40 Days On Market

  Current Estimated Value $185,066

  Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  66 Mount Vernon St, Springfield, VT 05156
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  /40

  Est $820,577 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  25 Slayton Terrace, Woodstock, VT 05091

  25 Slayton Terrace, Woodstock, VT 05091
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  /7

  $186,000

  • 6 Beds
  • 4 Baths
  • 2,304 Sq Ft

  51 Merrill St, Springfield, VT 05156

  This great property has so much to offer! With a large and expansive bottom floor unit featuring 3 bedrooms and 2 bathrooms with in unit laundry and a primary suite. Moving upstairs there is a great 2 bedroom 1 bathroom unit and adjacent to that unit is a 1 bed 1 bath unit. With an updated roof in 2020 and a newer heating unit that was put in in 2017.

  Thaddeus Abare Barrett and Valley Associates Inc.

  51 Merrill St, Springfield, VT 05156
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  /2

  $1,175,000 Sold Jun 30, 2025

  101 Ledgewood Rd Unit G3/G4 Garage, Ludlow, VT 05149

  • 4 Beds
  • 3.5 Baths
  • 2,854 Sq Ft
  • Built 1993

  Last Sold Summary

  • 6% Below List Price
  • $412/SF
  • 0 Days On Market

  Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

  101 Ledgewood Rd Unit G3/G4 Garage, Ludlow, VT 05149
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  /40

  Est $986,314 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,136 Sq Ft

  77 Central St, Woodstock, VT 05091

  77 Central St, Woodstock, VT 05091
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  /35

  $998,000

  • Land
  • 101 Acres
  • $9,881 per Acre

  0 Newton Ln Unit 3 5045699, Hartford, VT 05001

  110 Acres of Pastoral Beauty with Mountain Views in Hartford and Norwich, Vermont. This rare 110-acre parcel, 101 acres in Hartford and nine in Norwich (see separate MLS listing #5045705), offers rolling meadows, mature hardwoods, and long mountain views in the heart of the Upper Valley. The elevated, west-facing setting is filled with natural light and classic Vermont charm, with open pastures

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  0 Newton Ln Unit 3 5045699, Hartford, VT 05001
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  /28

  $212,000 Sold Oct 17, 2025

  30 Pond St Unit 8, Ludlow, VT 05149

  • 2 Beds
  • 2 Baths
  • 780 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Below List Price
  • $272/SF
  • 38 Days On Market

  Last Listing Agent Frank Provance Diamond Realty

  30 Pond St Unit 8, Ludlow, VT 05149
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  /40

  Est $3,158,040 Not Listed For Sale

  • 7 Beds
  • 4.5 Baths
  • 5,306 Sq Ft

  4 Bond St, Woodstock, VT 05091

  4 Bond St, Woodstock, VT 05091
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  /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
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  /40

  $1,850,000 Sold Jun 06, 2025

  109 Windy Ln, Pomfret, VT 05067

  • 5 Beds
  • 4 Baths
  • 3,336 Sq Ft
  • Built 1970

  Last Sold Summary

  • $555/SF
  • 0 Days On Market

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  109 Windy Ln, Pomfret, VT 05067
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  /35

  Not Listed For Sale

  • 7 Beds
  • 5.5 Baths
  • 6,472 Sq Ft

  3 Bond St, Woodstock, VT 05091

  3 Bond St, Woodstock, VT 05091
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  /50

  $425,000 Open Sun 11AM - 1PM

  • 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
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  /55

  $1,000,000 Sold Sep 26, 2025

  134 Lawrence Hill Rd, Weston, VT 05161

  • 3 Beds
  • 5 Baths
  • 4,849 Sq Ft
  • Built 1996

  Last Sold Summary

  • 16% Below List Price
  • $206/SF
  • 26 Days On Market

  Last Listing Agent Kathy Snyder

  134 Lawrence Hill Rd, Weston, VT 05161
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  /40

  Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,488 Sq Ft

  28 Pleasant St, Woodstock, VT 05091

  28 Pleasant St, Woodstock, VT 05091
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  /15

  $199,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,465 Sq Ft

  2314 Main St, Cavendish, VT 05142

  A little vision, a little elbow grease and some paint and this home will once again be the village stunner it once was. Beautiful wood floors, antique features like built in bookcases and nooks, solid doors and large spacious rooms make this home a no brainer for anyone looking for space and Vermont charm.Close to everything you need....Singleton's store for smoked meats, groceries, deli

  Lisa Kelley Cummings & Co

  2314 Main St, Cavendish, VT 05142
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  /44

  $450,000 Sold Jul 08, 2025

  230 Bentley Rd, Hartford, VT 05001

  • 3 Beds
  • 2 Baths
  • 1,761 Sq Ft
  • Built 1980

  Last Sold Summary

  • 6% Below List Price
  • $256/SF
  • 87 Days On Market

  Last Listing Agent Heather Ashline BHHS Verani Upper Valley

  230 Bentley Rd, Hartford, VT 05001
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  /38

  Est $274,458 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 955 Sq Ft

  87 Kennedy Dr, Windsor, VT 05089

  87 Kennedy Dr, Windsor, VT 05089
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  /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
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  /19

  $180,000 Sold Dec 15, 2025

  798 Vermont 14, Sharon, VT 05065

  • Land
  • 11 Acres
  • $16,364 per Acre

  Last Sold Summary

  • 40% Below List Price
  • 73 Days On Market

  Last Listing Agent Holly Hall Hall Collins Real Estate Group

  798 Vermont 14, Sharon, VT 05065
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  /17

  Est $214,975 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft

  93 Weston Heights, Windsor, VT 05089

  93 Weston Heights, Windsor, VT 05089
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  /6

  $239,000

  • 2 Beds
  • 1 Bath
  • 1,190 Sq Ft

  442 E Woodstock Rd Unit 4A, Woodstock, VT 05091

  Airy, tranquil and quiet, this former yoga studio space has been converted into a two bedroom condo. Sweeping views through the Palladian window, large living area with soaring vaulted ceiling, newer kitchen with granite counters and newer bath with walk in shower. Spacious entry can accommodate bikes, skis and more. Walking distance to shops, restaurants, entertainment and recreation in the

  Jane Darrach Martha E. Diebold/Hanover

  442 E Woodstock Rd Unit 4A, Woodstock, VT 05091
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  /43

  $612,500 Sold Oct 20, 2025

  108 Heritage Heights, Stockbridge, VT 05772

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1988

  Last Sold Summary

  • 12% Below List Price
  • $430/SF
  • 84 Days On Market

  Last Listing Agent Katie McFadden RE/MAX North Professionals

  108 Heritage Heights, Stockbridge, VT 05772
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  /26

  Est $190,449 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,452 Sq Ft

  1092 Weeden Hill Rd, Windsor, VT 05089

  1092 Weeden Hill Rd, Windsor, VT 05089
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  /44

  $549,000

  • 1 Bed
  • 1.5 Baths
  • 1,044 Sq Ft

  144 Lodge Rd Unit 5, Ludlow, VT 05149

  Slopeside at SouthFace Village Okemo! This may be the nicest one-bedroom condominium currently available on Okemo Mountain. Immaculate and barely used, it comfortably sleeps six and is offered fully furnished, move-in ready for your mountain escape. The interior features stylish quartz countertops, hardwood flooring, built-in shelving, and energy-efficient appliances. Ductless mini-splits provide

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  144 Lodge Rd Unit 5, Ludlow, VT 05149
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  /53

  $1,375,000 Sold Jul 15, 2025

  176 Upper Pasture Rd, Norwich, VT 05055

  • 4 Beds
  • 3.5 Baths
  • 3,478 Sq Ft
  • Built 1981

  Last Sold Summary

  • $395/SF
  • 104 Days On Market

  Current Estimated Value $1,364,592

  Last Listing Agent Patricia Greene Coldwell Banker LIFESTYLES - Hanover

  176 Upper Pasture Rd, Norwich, VT 05055
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  /29

  Est $298,128 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft

  74 Union St, Windsor, VT 05089

  74 Union St, Windsor, VT 05089
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  /36

  $424,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 1,832 Sq Ft

  473 Taylor Dr, Windsor, VT 05089

  Conveniently located from Interstate 91 and Route 5 in the Taylor Drive neighborhood sits a tidy cape home ready for its new owners. Many choices for bedrooms including a downstairs primary suite currently used as a den and 3 bedrooms upstairs for use as such or perhaps office and music space. The kitchen has been thoughtfully updated and the open concept between kitchen, living and dining

  Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

  473 Taylor Dr, Windsor, VT 05089
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  /60

  $1,450,000 Sold Dec 24, 2025

  44 John Deere Dr, Ludlow, VT 05149

  • 4 Beds
  • 4 Baths
  • 5,838 Sq Ft
  • Built 2007

  Last Sold Summary

  • $248/SF
  • 44 Days On Market

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

  44 John Deere Dr, Ludlow, VT 05149
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  /18

  Est $207,659 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,514 Sq Ft

  159 State St, Windsor, VT 05089

  159 State St, Windsor, VT 05089
• 

  

  /60

  $3,350,000

  • 6 Beds
  • 4.5 Baths
  • 5,657 Sq Ft

  400 Ruusunen Rd, Springfield, VT 05156

  Wild Trails Farm offers unparalleled privacy, encompassing 436 acres of natural splendor. At the heart of this retreat is a 5,600+ sq ft lodge that is both luxurious and eco-friendly, powered by solar and geothermal. It features 6 spacious bedrooms, 4.5 bathrooms, a gourmet kitchen with dual dining areas, common rooms, and sauna. The 2-car garage is currently utilized as a yoga studio, but could

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  400 Ruusunen Rd, Springfield, VT 05156
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  /49

  $455,500 Sold Sep 30, 2025

  281 Evergreen Terrace, Springfield, VT 05156

  • 4 Beds
  • 2 Baths
  • 2,040 Sq Ft
  • Built 1974

  Last Sold Summary

  • 1% Above List Price
  • $223/SF
  • 37 Days On Market

  Last Listing Agent Carol Cole BHG Masiello Brattleboro

  281 Evergreen Terrace, Springfield, VT 05156

Showing Results 561 - 600, Page 15 of 18