Windsor, VT Homes in ZIP Code 05071

• 

  

  

  /40

  $3,500,000

  • 6 Beds
  • 6 Baths
  • 5,433 Sq Ft

  61 Academy Cir, Woodstock, VT 05071

  Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

  Carol Wood Williamson Group Sothebys Intl. Realty

  61 Academy Cir, Woodstock, VT 05071
• 

  

  

  /51

  $1,300,000 Sold Jul 02, 2025

  • 4,228 Sq Ft
  • $307/SF
  • 91 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1980

  608 Fletcher Hill Rd, Woodstock, VT 05091

  Open House Sunday, April 13, 12:00 to 2:00 - Tucked away in the serene forests of Woodstock, Vermont, this beautifully remodeled 11-room home offers 4 bedrooms, 4 bathrooms, and 4,225 sq. ft. of luxurious living space on 5.4 private acres. The open-concept design is flooded with natural light, featuring a stunning chef’s kitchen with high-end stainless steel appliances, Vermont soapstone

  Sandy Reavill Real Broker LLC

  608 Fletcher Hill Rd, Woodstock, VT 05091
• 

  

  

  /40

  Est $1,410,277 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  4946 South Rd, South Woodstock, VT 05071

  4946 South Rd, South Woodstock, VT 05071
• 

  

  

  /42

  $8,000,000

  • 3 Beds
  • 3.5 Baths
  • 6,096 Sq Ft

  115 Eastman Rd, South Woodstock, VT 05071

  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

  115 Eastman Rd, South Woodstock, VT 05071
• 

  

  

  /40

  $750,000 Sold May 01, 2025

  • 1,840 Sq Ft
  • $408/SF
  • 43 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1970

  6963 South Rd, Woodstock, VT 05071

  Enchanting cottage perched on a private knoll with short range views. This property consist of 33 acres with a mixture of open meadow and woods for those looking for an afternoon of walking or snowshoeing. It is currently enrolled in the Current Use Forestry program. Stunning perennial gardens enhance the handsome stone walls and stone walk way to the residence. It's a Garden enthusiasts

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  6963 South Rd, Woodstock, VT 05071
• 

  

  /39

  Est $1,072,540 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,507 Sq Ft

  433 Cowdrey Path, Woodstock, VT 05091

  433 Cowdrey Path, Woodstock, VT 05091
• 

  

  /37

  $845,000

  • 2 Beds
  • 1.5 Baths
  • 1,714 Sq Ft

  403 Horse Shoe Way, Woodstock, VT 05071

  Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

  Danny Kogut Williamson Group Sothebys Intl. Realty

  403 Horse Shoe Way, Woodstock, VT 05071
• 

  

  /35

  $475,000 Sold Mar 27, 2025

  • 1,424 Sq Ft
  • $334/SF
  • 144 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1971

  378 Fletcher Hill Rd, South Woodstock, VT 05071

  Privately located, in desirable South Woodstock! A comfortable home with the benefit of great outside spaces providing the opportunity for recreation, gardening or entertaining! South Woodstock is well known for the potential of having wonderful access to miles of trails enjoyed by equestrians, hikers and snowmobilers. The numerous amenities of historic Woodstock Village are just minutes away!

  John Wetmore Wetmore Real Estate

  378 Fletcher Hill Rd, South Woodstock, VT 05071
• 

  

  /40

  Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 4,510 Sq Ft

  5798 South Rd, Woodstock, VT 05071

  5798 South Rd, Woodstock, VT 05071
• 

  

  /19

  $695,000

  • Land
  • 61 Acres
  • $11,474 per Acre

  0 Noah Wood Rd, Woodstock, VT 05071

  Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

  Dan Noble Snyder Donegan Real Estate Group

  0 Noah Wood Rd, Woodstock, VT 05071
• 

  

  /40

  $2,750,000 Sold Feb 13, 2025

  • 6,443 Sq Ft
  • $427/SF
  • 495 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1970

  318 Ebbin Lockwood Way, Woodstock, VT 05071

  Serene, private, contemporary: Sited on a ridge above South Woodstock village, the 54 acre property offers complete seclusion in an elegant setting with an extensive network of trails. The three bedroom main dwelling is sleek and elegant, with an open floor plan crafted to take in the beauty of the site with abundant use of organic material designed to integrate the design with the surrounding

  Story Jenks LandVest, Inc/Woodstock

  318 Ebbin Lockwood Way, Woodstock, VT 05071
• 

  

  /40

  Est $1,575,566 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,329 Sq Ft

  282 Fletcher Hill Rd, Woodstock, VT 05091

  282 Fletcher Hill Rd, Woodstock, VT 05091
• 

  

  /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
• 

  /2

  $1,175,000 Sold Jan 29, 2025

  • 2,660 Sq Ft
  • $442/SF
  • 186 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2014

  6453 South Rd, Woodstock, VT 05071

  Round Top Cottage is sited on a knoll just outside the village of South Woodstock on 20 acres, offering complete privacy and views of the rolling hills framing the Kedron Valley. This three-bedroom lodge, fully renovated in 2024, blends modern amenities with rustic elegance. The open floor plan features cathedral ceilings in the main living and dining area, creating an inviting space to gather

  Story Jenks LandVest, Inc/Woodstock

  6453 South Rd, Woodstock, VT 05071
• 

  

  /40

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,135 Sq Ft

  418 Fletcher Hill Rd, South Woodstock, VT 05071

  418 Fletcher Hill Rd, South Woodstock, VT 05071
• 

  

  /27

  $650,000

  • Land
  • 78 Acres
  • $8,366 per Acre

  0 Mecawee Rd, Woodstock, VT 05091

  Spectacular 77+ acre parcel on sought after Mecawee Rd. with a perfect combination of level, sloping and hilly terrain. There are multiple building sites including a large cleared area set back off the road with a driveway in place and utilities (electric & fiber optic) at the street. This past Fall, the Sellers went to great lengths to clear the land all the way down to the road opening up

  Dan Noble Snyder Donegan Real Estate Group

  0 Mecawee Rd, Woodstock, VT 05091
• 

  

  /40

  $4,205,000 Sold Jan 27, 2025

  • 5,939 Sq Ft
  • $708/SF
  • 121 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1797

  327 Fletcher Schoolhouse Rd, Woodstock, VT 05071

  ByBrook Farm: Reimagined, turnkey 1790s farmhouse set in one of Vermont's most loved valleys, perennial gardens, stone walls, a spring fed pond, a brook, and rolling meadows. Quiet luxury. Just outside the hamlet of South Woodstock on 25 acres, the 2-bedroom 4,667 sf farmhouse and the 2-bedroom 1,273 sf guest cottage are connected by a stone pathway through the gardens. In the recent renovations

  Story Jenks LandVest, Inc/Woodstock

  327 Fletcher Schoolhouse Rd, Woodstock, VT 05071
• 

  

  /37

  Est $3,079,598 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 4,700 Sq Ft

  592 Quinn Rd, Woodstock, VT 05091

  592 Quinn Rd, Woodstock, VT 05091
• 

  

  /58

  $549,000

  • Land
  • 20 Acres
  • $27,178 per Acre

  00 Long Hill Rd, Woodstock, VT 05071

  Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west.Located just minutes from

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  00 Long Hill Rd, Woodstock, VT 05071
• 

  

  /40

  $3,350,000 Sold Nov 22, 2024

  • 6,040 Sq Ft
  • $555/SF
  • 210 Days On Market

  • 6 Beds
  • 7 Baths
  • Built 1820

  486 Benedict Rd, South Woodstock, VT 05071

  "BENEDICT HILL" - sited on 38 acres on a quiet gravel road in a premier location in South Woodstock is this truly classic Vermont estate property. Excellent equestrian / horse potential with historic 5-stall barn and fencing for pastures/paddocks already in place. The land component is comprised of split-rail fence lined pastures, meadows, woodlands, giant maple trees, ancient stone walls and

  John Snyder Snyder Donegan Real Estate Group

  486 Benedict Rd, South Woodstock, VT 05071
• 

  

  /40

  Est $719,162 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,904 Sq Ft

  588 Kendall Rd, Woodstock, VT 05091

  588 Kendall Rd, Woodstock, VT 05091
• 

  

  /43

  $1,950,000

  • 5 Beds
  • 3.5 Baths
  • 3,502 Sq Ft

  4945 South Rd, Woodstock, VT 05071

  The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron

  Story Jenks LandVest, Inc/Woodstock

  4945 South Rd, Woodstock, VT 05071
• 

  

  /40

  $680,000 Sold Nov 13, 2024

  • 1,470 Sq Ft
  • $463/SF
  • 157 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1852

  5014 South Rd, Woodstock, VT 05071

  This charming 1852 Cape has been fully renovated with exquisite finishes. Warm honey-toned antique wide pine floors, soapstone counters with creamy cabinetry in kitchen accented with new stainless appliances. Open floor plan into a sunlit dining room. Enjoy a cup of hot cocoa and a good book curled up in front of the woodstove off the kitchen on a snowy winter day. The first floor also

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  5014 South Rd, Woodstock, VT 05071
• 

  

  /25

  Not Listed For Sale

  • 8 Beds
  • 5 Baths
  • 2,908 Sq Ft

  144 Town Farm Rd, Woodstock, VT 05071

  144 Town Farm Rd, Woodstock, VT 05071
• 

  

  /39

  $649,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,958 Sq Ft

  5851 South Rd, Woodstock, VT 05071

  This charming home is an amazing opportunity to own a piece of history in the lovely village of South Woodstock , Vermont. Starting its life as the garage and home of Clyde Wood it has evolved over time with the present owners into a beautiful , meticulous residence. Much attention to detail can be found in every room from wide pine flooring to cathedral ceiling in the great room. The home is

  Carol Wood Williamson Group Sothebys Intl. Realty

  5851 South Rd, Woodstock, VT 05071
• 

  

  /40

  $410,000 Sold Oct 11, 2024

  • 2,030 Sq Ft
  • $202/SF
  • 94 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  148 E Hill Rd Unit A, South Woodstock, VT 05071

  A rare opportunity to own an iconic, contemporary condo in the heart of South Woodstock's bucolic horse country. Less than a mile from the Kedron Valley Inn and Ransom Tavern and just six miles from Woodstock village, this extraordinary four-floor, light-filled, open-concept condo has been updated with thoughtful, longterm investments, including roofs and windows. Surrounded by pristine

  Keri Cole Williamson Group Sothebys Intl. Realty

  148 E Hill Rd Unit A, South Woodstock, VT 05071
• 

  

  /40

  Est $342,760 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 868 Sq Ft

  1747 Long Hill Rd, Woodstock, VT 05091

  1747 Long Hill Rd, Woodstock, VT 05091
• 

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 5,972 Sq Ft

  1862 Long Hill Rd, Woodstock, VT 05071

  1862 Long Hill Rd, Woodstock, VT 05071
• 

  

  /34

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,352 Sq Ft

  2646 Curtis Hollow Rd, Woodstock, VT 05071

  2646 Curtis Hollow Rd, Woodstock, VT 05071
• 

  

  /15

  Not Listed For Sale

  00 Bryant Rd Unit Lot 1, South Woodstock, VT 05071

  00 Bryant Rd Unit Lot 1, South Woodstock, VT 05071
• 

  

  /37

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft

  734 Curtis Hollow Rd, Woodstock, VT 05034

  734 Curtis Hollow Rd, Woodstock, VT 05034
• 

  

  /31

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,748 Sq Ft

  238 Cowdrey Path, Woodstock, VT 05071

  238 Cowdrey Path, Woodstock, VT 05071
• 

  

  /36

  Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,139 Sq Ft

  89 Academy Cir, Woodstock, VT 05071

  89 Academy Cir, Woodstock, VT 05071
• 

  

  /40

  Est $1,051,696 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,180 Sq Ft

  4980 South Rd, South Woodstock, VT 05071

  4980 South Rd, South Woodstock, VT 05071
• 

  

  /18

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,048 Sq Ft

  358 Cowdrey Path, South Woodstock, VT 05071

  358 Cowdrey Path, South Woodstock, VT 05071
• 

  

  /26

  Not Listed For Sale

  00 Curtis Hollow Rd, Woodstock, VT 05091

  00 Curtis Hollow Rd, Woodstock, VT 05091
• 

  

  /6

  Est $824,432 Not Listed For Sale

  • 4 Beds

  6656 South Rd, Woodstock, VT 05071

  6656 South Rd, Woodstock, VT 05071
• 

  

  /27

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,196 Sq Ft

  700 John Darling Rd, South Woodstock, VT 05071

  700 John Darling Rd, South Woodstock, VT 05071
• 

  

  /25

  Est $714,673 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,368 Sq Ft

  173 Peterkin Hill Rd, South Woodstock, VT 05071

  173 Peterkin Hill Rd, South Woodstock, VT 05071
• 

  

  /31

  Est $2,426,620 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 3,708 Sq Ft

  1239 Peterkin Hill Rd, South Woodstock, VT 05071

  1239 Peterkin Hill Rd, South Woodstock, VT 05071

Showing Results 1 - 40, Page 1 of 10