Windsor County, VT Homes

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  /37

  $600,000 Sold May 09, 2025

  43 Lee Way, Andover, VT 05143

  • 3 Beds
  • 3 Baths
  • 2,076 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $289/SF
  • 575 Days On Market

  Last Listing Agent Britt Wohler

  43 Lee Way, Andover, VT 05143
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  /38

  Est $418,525 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  515 North Rd, Bethel, VT 05032

  515 North Rd, Bethel, VT 05032
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  /47

  $379,900

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft

  1001 Woodstock Rd, White River Junction, VT 05001

  Wonderful Ranch style home situated on a 2.5+/- acre in town lot and conveniently located only minutes from the bustling arts and theatre district of downtown White River Junction, VT. This home radiates warmth and hospitality and could be perfect for buyers looking for single level living! This two bedroom, (possible 3 bedroom,) two bath home is a rare opportunity to own a more affordable home

  Alex DeFelice The Clerkin Agency, P.C.

  1001 Woodstock Rd, White River Junction, VT 05001
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  /9

  $68,000 Sold Nov 06, 2025

  0 Porter Rd, Barnard, VT 05032

  • Land
  • 33.8 Acres
  • $2,012 per Acre

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Susan Hickey Snyder Donegan Real Estate Group

  0 Porter Rd, Barnard, VT 05032
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  /29

  Est $342,498 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,137 Sq Ft

  201 Hill Top Rd, Chester, VT 05143

  201 Hill Top Rd, Chester, VT 05143
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  /52

  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 4,177 Sq Ft

  166 Woods Rd W, Ludlow, VT 05149

  Perched high on the hillside, this home offers expansive views of the lakes and mountains. Located at the end of a quiet road in the Farm Ridge Community just under 5 miles from the base of Okemo Mountain and 4 miles to Plymouth State Park for boating and swimming in the warmer months. The maintained trails on it's 16.15 acres makes it easy to explore, while the deck is a perfect place to relax,

  Jessica Citera Cummings & Co

  166 Woods Rd W, Ludlow, VT 05149
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  /52

  $390,000 Sold Oct 29, 2025

  2680 Hartford Ave Unit 15, White River Junction, VT 05001

  • 2 Beds
  • 2.5 Baths
  • 1,682 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $232/SF
  • 3 Days On Market

  Last Listing Agent Jaime Durell BHHS Verani Upper Valley

  2680 Hartford Ave Unit 15, White River Junction, VT 05001
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  /40

  Est $743,427 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,040 Sq Ft

  201 Spruce Dr, Chester, VT 05143

  201 Spruce Dr, Chester, VT 05143
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  /16

  $390,000

  • 3 Beds
  • 1 Bath
  • 1,620 Sq Ft

  181 Banister Rd, Windsor, VT 05089

  Over 10 acres of beautiful fields and pasture with long range views and stone walls lining the property. Mature trees dot the perimeter and a lovely stream runs along the roadside. There is a multilevel functioning barn with water and electricity and a small gated paddock off to the side. Located in the heart of Horse Country, this would be and ideal equestrian property or a great place to raise

  Dan Noble Snyder Donegan Real Estate Group

  181 Banister Rd, Windsor, VT 05089
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  /31

  $415,000 Sold Jun 05, 2025

  121 Truell Rd, White River Junction, VT 05001

  • 3 Beds
  • 1.5 Baths
  • 1,791 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $232/SF
  • 53 Days On Market

  Current Estimated Value $418,300

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

  121 Truell Rd, White River Junction, VT 05001
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  /37

  Est $677,301 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,641 Sq Ft

  488 Andover Rd, Ludlow, VT 05149

  488 Andover Rd, Ludlow, VT 05149
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  /7

  $120,000

  • Land
  • 3.6 Acres
  • $33,333 per Acre

  263 High Ridge Rd, Cavendish, VT 05142

  Scenic Proctorsville Opportunity!Discover two parcels totaling 3.6 acres, perfectly perched on a beautiful hill. From this elevated setting, enjoy stunning views of Okemo Mountain’s ski trails (only 10 mins away), already impressive, with even greater ridgeline vistas possible through selective clearing. The land is a beautiful mix of open and wooded areas, offering both natural privacy and

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

  263 High Ridge Rd, Cavendish, VT 05142
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  /39

  $525,000 Sold Mar 11, 2025

  557 Willard Rd Unit 5182, Hartford, VT 05059

  • 3 Beds
  • 2.5 Baths
  • 1,865 Sq Ft
  • Built 1976

  Last Sold Summary

  • 4% Below List Price
  • $282/SF
  • 4 Days On Market

  Last Listing Agent Derek Cosentino Four Seasons Sotheby's Int'l Realty

  557 Willard Rd Unit 5182, Hartford, VT 05059
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  /34

  Est $311,703 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  82 Wellwood Orchard Rd, Springfield, VT 05156

  82 Wellwood Orchard Rd, Springfield, VT 05156
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  /54

  $995,000

  • 5 Beds
  • 4 Baths
  • 3,063 Sq Ft

  152 Town Farm Rd, Ludlow, VT 05149

  Welcome to your dream getaway! Add your "decorating" touches to this newly built "South Hill" home. This 5-bedroom, 4-bathroom country home combines timeless craftsmanship with modern comfort, just minutes from Okemo. Step inside to the inviting, open floor plan where natural light pours in. Open concept includes the kitchen, dining, and living areas—a perfect space for entertaining. The kitchen

  Joseph Karl William Raveis Real Estate Vermont Properties

  152 Town Farm Rd, Ludlow, VT 05149
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  /42

  $395,000 Sold Nov 07, 2025

  1093 Middle Hollow Rd, Rochester, VT 05767

  • 4 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • Built 1970

  Last Sold Summary

  • 1% Below List Price
  • $239/SF
  • 10 Days On Market

  Last Listing Agent Kyle Kershner Killington Pico Realty

  1093 Middle Hollow Rd, Rochester, VT 05767
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  /29

  Est $377,541 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  21 Dell Rd, Springfield, VT 05156

  21 Dell Rd, Springfield, VT 05156
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  /60

  $3,650,000

  • 5 Beds
  • 4 Baths
  • 5,181 Sq Ft

  348 Turtle Hill Rd, Ludlow, VT 05149

  Built over the course of two years and completed in 2023, this nearly new custom timberframe home showcases exceptional craftsmanship and fine attention to detail. Privately sited on over 13 acres, the property offers sweeping, panoramic views of southern Vermont's mountains and valleys; vistas that are truly second to none. The home's architectural highlights include hand-hewn Douglas fir beams

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  348 Turtle Hill Rd, Ludlow, VT 05149
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  /15

  $55,000 Sold Feb 11, 2025

  Lot 3 Peavine Blvd, Bethel, VT 05032

  • Land
  • 4 Acres
  • $13,750 per Acre

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Terry Davis Williamson Group Sothebys Intl. Realty

  Lot 3 Peavine Blvd, Bethel, VT 05032
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  /40

  Est $312,244 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,264 Sq Ft

  305 Summer St, Springfield, VT 05156

  305 Summer St, Springfield, VT 05156
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  /60

  $799,000

  • 4 Beds
  • 2 Baths
  • 2,516 Sq Ft

  14 Gill Terrace, Ludlow, VT 05149

  Effortless Style Meets Vermont Village Living Sweeping arches, sun-soaked spaces, and vintage charm, this Ludlow Village home is the perfect blend of character and modern comfort. Lovingly cared for over 33 years, it's been thoughtfully renovated to keep the history intact while adding all the upgrades you want. Wake up to southern light streaming into your sunroom, sip coffee on the elevated

  Diane Rousseau Four Seasons Sotheby's Int'l Realty

  14 Gill Terrace, Ludlow, VT 05149
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  /42

  $77,000 Sold Jul 10, 2025

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

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $99/SF
  • 69 Days On Market

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

  211/213 Qtr I Jackson Gore Inn, Ludlow, VT 05149
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  /27

  Est $1,069,013 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,579 Sq Ft

  7 Golf Ave, Woodstock, VT 05091

  7 Golf Ave, Woodstock, VT 05091
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  /40

  $799,000

  • 7 Beds
  • 6 Baths
  • 5,028 Sq Ft

  52 Upper, Bridgewater, VT 05035

  A "turn-key" commercial opportunity in a highly visible location! Being well situated between the world class skiing of Killington and the numerous amenities of historic Woodstock Village entrepreneurial dreams for this diverse property can easily take flight! Within this classic New England style structure are a professionally appointed and immaculate commercial kitchen, spacious dining rooms,

  John Wetmore Wetmore Real Estate

  52 Upper, Bridgewater, VT 05035
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  /42

  $340,000 Sold Jun 23, 2025

  4729 Us Route 5 S, Perkinsville, VT 05151

  • 3 Beds
  • 1.5 Baths
  • 1,842 Sq Ft
  • Built 1972

  Last Sold Summary

  • 5% Above List Price
  • $185/SF
  • 39 Days On Market

  Current Estimated Value $323,926

  Last Listing Agent Ross Doody Century 21 Highview Realty

  4729 Us Route 5 S, Perkinsville, VT 05151
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  /37

  Est $834,715 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  13 High St, Woodstock, VT 05091

  13 High St, Woodstock, VT 05091
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  /17

  $149,000

  • Land
  • 1.83 Acres
  • $81,421 per Acre

  00 Raymond Rd, Ludlow, VT 05149

  LAND PARCEL WITH LAKE RESCUE ACCESS....This parcel is the last undeveloped lot available that has lake access, shared with a small association, SUNNY VALLEY, with only (8) properties. The building envelope is level and power is at the road. The lot overlooks a pretty meadow with undeveloped woodlands as a backdrop. The Sunny Valley privileges at Lake Rescue include (2) deck platforms overlooking

  Roger Danyew Diamond Realty

  00 Raymond Rd, Ludlow, VT 05149
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  /33

  $313,000 Sold Oct 02, 2025

  85 Slawson Rd, Weston, VT 05161

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $313/SF
  • 26 Days On Market

  Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

  85 Slawson Rd, Weston, VT 05161
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  /38

  Est $516,518 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft

  39 South St, Woodstock, VT 05091

  39 South St, Woodstock, VT 05091
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  /14

  $159,000 Under Contract

  • Land
  • 11.63 Acres
  • $13,672 per Acre

  Lot 10 S Hill Rd, Stockbridge, VT 05772

  Embrace the beauty of Vermont living on this picturesque 11.63-acre parcel in the heart of the Green Mountains. Bordered by a year-round brook, this beautiful, wooded property captures the essence of classic Vermont charm. With easy access from a town-maintained road, a roughed-in driveway, and a partially cleared homesite, the groundwork is already in place for your dream 3-bedroom home. Unlike

  Kyle Kershner Killington Pico Realty

  Lot 10 S Hill Rd, Stockbridge, VT 05772
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  /22

  $200,000 Sold Aug 01, 2025

  20 Smith St, Springfield, VT 05156

  • 3 Beds
  • 2 Baths
  • 1,083 Sq Ft
  • Built 1950

  Last Sold Summary

  • $185/SF
  • 37 Days On Market

  Current Estimated Value $194,481

  Last Listing Agent Patrick Kelley Four Seasons Sotheby's Int'l Realty

  20 Smith St, Springfield, VT 05156
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  /31

  Est $1,093,712 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  10 Linden Hill, Woodstock, VT 05091

  10 Linden Hill, Woodstock, VT 05091
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  /22

  $239,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  75 Whitney Rd, Springfield, VT 05156

  This well-maintained home is located in a quiet, private, country setting. Recent updates include fresh interior paint, new carpeting throughout, and a brand new hot water tank. The open-concept living area offers a functional layout that’s great for everyday living. An oversized first-floor laundry room adds flexibility and could also be used for storage, or other needs. The home offers a

  Thaddeus Abare Barrett and Valley Associates Inc.

  75 Whitney Rd, Springfield, VT 05156
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  /52

  $1,470,000 Sold Sep 05, 2025

  7511 Woodstock Rd, Hartford, VT 05001

  • 4 Beds
  • 3 Baths
  • 3,311 Sq Ft
  • Built 1983

  Last Sold Summary

  • 8% Below List Price
  • $444/SF
  • 66 Days On Market

  Last Listing Agent Richard Higgerson Higgerson & Company

  7511 Woodstock Rd, Hartford, VT 05001
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  /40

  Est $1,610,598 Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 3,892 Sq Ft

  28 The Green Unit 30, Woodstock, VT 05091

  28 The Green Unit 30, Woodstock, VT 05091
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  /59

  $410,000

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

  54 Twitchell Settlement, Rochester, VT 05767

  "Nestled on over three private acres, this Vermont retreat exudes rustic charm and modern comfort. The soaring cathedral ceilings and floor-to-ceiling arched windows in the great room flood the space with natural light, creating a warm and inviting atmosphere. The open-concept layout seamlessly connects the kitchen, dining, and living areas, ideal for gatherings or quiet moments by the pellet

  Nick Sicard EXP Realty

  54 Twitchell Settlement, Rochester, VT 05767
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  /60

  $825,000 Sold Nov 14, 2025

  226 Trailside Rd Unit 47-C, Ludlow, VT 05149

  • 4 Beds
  • 2.5 Baths
  • 2,610 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Below List Price
  • $316/SF
  • 45 Days On Market

  Last Listing Agent Frank Provance Diamond Realty

  226 Trailside Rd Unit 47-C, Ludlow, VT 05149
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  /40

  Est $1,905,760 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 3,997 Sq Ft

  2 Border Ln, Woodstock, VT 05091

  2 Border Ln, Woodstock, VT 05091
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  /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
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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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