Windsor, VT Homes

• 

  

  

  /40

  Est $1,164,310 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  8 Garvin Hill Rd, Woodstock, VT 05091

  8 Garvin Hill Rd, Woodstock, VT 05091
• 

  

  

  /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

  $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 $551,305 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,472 Sq Ft

  140 Cream Pot Rd, Hartland, VT 05048

  140 Cream Pot Rd, Hartland, VT 05048
• 

  

  

  /9

  $275,000

  • Land
  • 0.43 Acre
  • $639,535 per Acre

  1054 W Woodstock Rd, Woodstock, VT 05091

  Ideally located parcel across West Woodstock Road from the Woodstock Farmers Market and 500 yards from the entry to Woodstock Union Middle & High School. Public water and sewer available with access off Prosper Road near the junction of US Road Route 4/West Woodstock Road. Building plans available. Multi-unit housing development potential in zero vacancy environment.

  Laird Bradley Williamson Group Sothebys Intl. Realty

  1054 W Woodstock 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
• 

  

  /39

  Est $806,403 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,263 Sq Ft

  200 Garvin Hill Rd, Woodstock, VT 05091

  200 Garvin Hill Rd, Woodstock, VT 05091
• 

  

  /31

  $729,000

  • 3 Beds
  • 3 Baths
  • 1,550 Sq Ft

  13 Slayton Terrace, Woodstock, VT 05091

  Charming cottage located in the heart of historic Woodstock Village with walking distance to all the shops, restaurants and town theatre. Mtn Peg walking trails just a 2 minute walk from front door for those hiking enthusiasts. This home is filled with an abundance of natural sunlight and features all hardwood floors throughout. New kitchen with butcher block counters, stainless appliances,

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  13 Slayton Terrace, 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
• 

  

  /24

  Est $377,948 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,641 Sq Ft

  141 Cream Pot Rd, Hartland, VT 05048

  141 Cream Pot Rd, Hartland, VT 05048
• 

  

  /4

  $84,900

  • Land
  • 3.80 Acres
  • $22,342 per Acre

  14 Hartland Hill Rd, Hartland, VT 05048

  Owner Will Consider Financing – Ask for Details!3.8 Acres of Wooded Serenity in Hartland, VTDiscover the perfect balance of privacy and convenience with this beautiful 3.8-acre wooded parcel tucked away in the quiet countryside of Hartland, Vermont. Set off the beaten path, this peaceful retreat offers a sense of seclusion while being just minutes from the vibrant communities of

  Kris Pettee EXP Realty

  14 Hartland Hill Rd, Hartland, VT 05048
• 

  

  /37

  $975,000 Sold Jan 10, 2025

  • 2,944 Sq Ft
  • $331/SF
  • 28 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1994

  828 Deerbrook Way, Woodstock, VT 05091

  A gem of a property on 12 spectacular, mostly wooded, acres in the desirable Deerbrook Way area of Woodstock. Four+ miles to all the amenities of Woodstock Village and 8 miles to the Skyship Gondola at Killington. Built in 1994, this custom designed red oak Post and Beam Contemporary provides everything you would want in a primary residence or a get away vacation retreat. Situated on a 12+ acre

  Stan Butler Four Seasons Sotheby's Int'l Realty

  828 Deerbrook Way, Woodstock, VT 05091
• 

  

  /40

  Est $1,012,803 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 2,555 Sq Ft

  3090 South Rd, Woodstock, VT 05091

  3090 South 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
• 

  

  /47

  $925,000 Sold Jan 08, 2025

  • 2,000 Sq Ft
  • $462/SF
  • 42 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1850

  3894 Rush Meadow Rd, West Windsor, VT 05089

  Located in the premiere Rush Meadow region of West Windsor in the heart of horse country, this magical, pastoral property checks every box: spectacular established perennial beds, including extensive banks of show-stopping lilacs; spring-fed swimming pond with dock; expansive meadow and trails for hiking, snowshoeing and cross country skiing; seasonal and year-round brooks with heavy duty

  Danny Kogut Williamson Group Sothebys Intl. Realty

  3894 Rush Meadow Rd, West Windsor, VT 05089
• 

  

  /30

  Est $1,388,485 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,218 Sq Ft

  2409 South Rd, Woodstock, VT 05091

  2409 South 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
• 

  

  /42

  $1,580,000 Sold Dec 30, 2024

  • 4,378 Sq Ft
  • $361/SF
  • 79 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1886

  33 River St, Woodstock, VT 05091

  BEAUTIFULLY renovated rare antique residence in the heart of historic Woodstock! Located in a premiere neighborhood within walking distance to all of towns amenities, hiking on Mtn Tom in your backyard. Situated on a very large lot featuring an in-ground pool accented with arbor and pool house. Lovely perennial gardens and large backyard for those seeking a vegetable garden or room for

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  33 River St, Woodstock, VT 05091
• 

  

  /40

  Est $1,321,751 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,668 Sq Ft

  513 Deer Brook Way, Woodstock, VT 05091

  513 Deer Brook Way, Woodstock, VT 05091
• 

  

  /48

  $795,000

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft

  25 Linden Hill St, Woodstock, VT 05091

  This classic early 20th Century farmhouse with 3 sunny bedrooms and two baths is sited on a quiet Village Street uphill above the Woodstock Elementary School and across from the public playground at Vail Field and the Woodstock Country Club golf course. The home has benefitted from the thoughtful additions of an eat-in kitchen and a front porch where you can enjoy long summer evenings. A

  Laird Bradley Williamson Group Sothebys Intl. Realty

  25 Linden Hill St, Woodstock, VT 05091
• 

  

  /32

  $692,000 Sold Dec 19, 2024

  • 2,527 Sq Ft
  • $274/SF
  • 195 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1890

  1207 Church Hill Rd, Woodstock, VT 05091

  Historic Vermont cape house with easy access, only a mile to the Woodstock village center. There is a lot of history and character with beautiful old wood floors and beams. A covered walkway from the attached two-car garage comes into a mud-entry room and right into the classic farmhouse kitchen. Off the kitchen is a generous pantry/laundry room and a bath with shower. The spacious family

  John Snyder Snyder Donegan Real Estate Group

  1207 Church Hill Rd, Woodstock, VT 05091
• 

  

  /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
• 

  

  /60

  $2,450,000

  • 4 Beds
  • 3.5 Baths
  • 5,573 Sq Ft

  851 Riverside Park Rd, Woodstock, VT 05091

  "All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers

  Richard Higgerson Higgerson & Company

  851 Riverside Park Rd, Woodstock, VT 05091
• 

  /2

  $2,850,000 Sold Dec 16, 2024

  • 6,403 Sq Ft
  • $445/SF
  • 158 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1976

  2055 Church Hill Rd, Woodstock, VT 05091

  Nestled among verdant rolling hills, High Birch is located in one of the area’s most desirable regions at the midpoint between Woodstock and South Woodstock Villages. Designed in 1976 by prominent New York architect Lewis Davis, of Davis, Brody and Bond renowned for his modernist skyscrapers that impacted the skyline of New York City, the home contrasts sleek interior spaces to the surrounding

  Danny Kogut Williamson Group Sothebys Intl. Realty

  2055 Church Hill Rd, Woodstock, VT 05091
• 

  

  /40

  Est $1,452,984 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
• 

  

  /6

  $54,900

  • Land
  • 29 Acres
  • $1,893 per Acre

  0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464

  These 29 acres, per PVA map, are located in southern Magoffin County in Royalton, Kentucky, with the acreage running along both sides of RT 7. The property is located in the Salt Lick area outside Royalton and includes property on both sides of Salt Lick Road as well. The property is undeveloped but electric and public water are available. For those with visions of homesteading, the Licking River

  Doug Wireman First Choice Realty & Assoc.

  0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464
• 

  

  /48

  $1,195,000 Sold Dec 12, 2024

  • 2,058 Sq Ft
  • $581/SF
  • 15 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  5274 W Woodstock Rd, Woodstock, VT 05091

  This stunner of a farmhouse is a spectacular example of vision, craftsmanship, and a commitment to the finest materials including standing seamed roofs and fully updated systems.  The recently installed custom iron doors provide Architectural Digest design aesthetic. The chef’s kitchen showcases a stainless six burner stove along with the quietest Bosch dishwasher available, built-in Bosch

  Keri Cole Williamson Group Sothebys Intl. Realty

  5274 W Woodstock Rd, Woodstock, VT 05091
• 

  

  /10

  Est $207,809 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  1514 Stone Chimney Rd, Reading, VT 05062

  1514 Stone Chimney Rd, Reading, VT 05062
• 

  

  /19

  $275,000

  • Land
  • 5.00 Acres
  • $55,000 per Acre

  95 Jenne Rd, Hartland, VT 05048

  5 acres of peacefully quiet land that are situated in an area well known to the equestrian community! Both the surrounding neighbors, on this seldom traveled country road, and numerous other properties in this broad community present as substantial privately sited homes. As you meander up Jenne Road to reach the parcel the classic large maple trees that typify the borders of pastoral Vermont

  John Wetmore Wetmore Real Estate

  95 Jenne Rd, Hartland, VT 05048
• 

  

  /34

  $875,000 Sold Dec 10, 2024

  • 1,590 Sq Ft
  • $550/SF
  • 12 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1880

  5 Mountain Ave Unit 4, Woodstock, VT 05091

  ICONIC. Just a stroll across Woodstock's famed covered bridge, this historic property is home to five unique condominiums - premier among them is this gracious, bright, and fully renovated two-bedroom home. With beamed nine-foot ceilings, a true turret (complete with curved glass!), a handsome den, spacious bedrooms, private laundry, and dedicated garage parking, this gorgeous condo is equally

  Keri Cole Williamson Group Sothebys Intl. Realty

  5 Mountain Ave Unit 4, Woodstock, VT 05091
• 

  

  /40

  Est $2,164,819 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,864 Sq Ft

  26 The Green, Wood Stock, VT 05091

  26 The Green, Wood Stock, VT 05091
• 

  

  /13

  $1,789,000

  • Land
  • 100 Acres
  • $17,890 per Acre

  5000 Vermont 106, Reading, VT 05062

  Beautiful building lot of approximately 100 acres just 5 mins to South Woodstock, and privately situated with a driveway entrance directly on VT 106 for easy access. The parcel includes woods roads and trails, ancient stone walls, brooks, ponds and some cleared areas as potential future building sites with lovely southern exposure and long-range views of distant hills. The property contains two

  John Snyder Snyder Donegan Real Estate Group

  5000 Vermont 106, Reading, VT 05062
• 

  

  /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
• 

  

  /34

  Est $969,082 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,784 Sq Ft

  20 Lincoln St, Woodstock, VT 05091

  20 Lincoln St, Woodstock, VT 05091
• 

  

  /14

  $845,000

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  234 Randall Rd, Wood Stock, VT 05091

  Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm

  Wade Treadway Wade I Treadway Real Estate

  234 Randall Rd, Wood Stock, VT 05091
• 

  

  /33

  $725,000 Sold Nov 15, 2024

  • 3,794 Sq Ft
  • $191/SF
  • 156 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1987

  781 Silver Hill Rd, West Windsor, VT 05089

  Beautifully constructed Davis Timber frame home in the desirable Silver Hill region of West Windsor. Spacious, bright rooms connect beautifully to private outdoor deck and screened porch overlooking a large swimming pond. The generous living room runs front to back anchored by a beautiful stone fireplace with warm golden hardwood floors, and exposed beam structure. The open concept kitchen offers

  Danny Kogut Williamson Group Sothebys Intl. Realty

  781 Silver Hill Rd, West Windsor, VT 05089
• 

  

  /34

  Est $650,416 Not Listed For Sale

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

  1782 South Rd, Woodstock, VT 05091

  1782 South Rd, Woodstock, VT 05091
• 

  

  /48

  $7,250,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 5,087 Sq Ft

  412 Skyland Ln, Woodstock, VT 05091

  Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 65 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains

  Story Jenks LandVest, Inc/Woodstock

  412 Skyland Ln, Woodstock, VT 05091
• 

  

  /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
• 

  

  /26

  Est $601,316 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,059 Sq Ft

  11 Church St Unit 2, Woodstock, VT 05091

  11 Church St Unit 2, Woodstock, VT 05091

Showing Results 81 - 120, Page 3 of 18