2,900

Windsor, VT Homes

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  • /42

    $435,000 Sold Apr 01, 2025

    • 1,514 Sq Ft
    • $287/SF
    • 10 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1969

    773 Hale Hollow Rd, Plymouth, VT 05056

    If you are looking for a home out in the country yet convenient to world class ski resorts, golf, lakes and quintessential villages...this home is for you! Situated on a quiet road with beautiful views the house has two spacious living areas with many windows letting in the natural light. There's a stone hearth and woodstove making it warm and cozy for chilly VT evenings. The dine-in kitchen

    Lorien Kelly Kelley Real Estate, Inc.

    773 Hale Hollow Rd, Plymouth, VT 05056
    • /37

      Est $1,177,591 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,949 Sq Ft

      326 Hall Cir, Woodstock, VT 05091

      326 Hall Cir, Woodstock, VT 05091
  • /50

    $945,000

    • 4 Beds
    • 2.5 Baths
    • 2,044 Sq Ft

    100 Pomfret Rd, Woodstock, VT 05091

    Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting.Inside, you’ll find a sun-drenched home featuring four

    Keri Cole Williamson Group Sothebys Intl. Realty

    100 Pomfret Rd, Woodstock, VT 05091
  • /39

    $410,000 Sold Apr 01, 2025

    • 1,052 Sq Ft
    • $390/SF
    • 97 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1930

    6 Highland Ave, Woodstock, VT 05091

    A rare opportunity for Woodstock! An affordable Woodstock Village cottage! The advantage of contemporary solar powered energy efficiency, with connection to an energy storing Tesla battery! The property further benefits from valuable infrastructure components of the municipal sewer system and the Woodstock Aqueduct Water Company! An attractive interior features wood flooring throughout! A large

    John Wetmore Wetmore Real Estate

    6 Highland Ave, Woodstock, VT 05091
    • /30

      Est $1,635,000 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
  • /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
  • /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

      Est $1,217,287 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
  • /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
  • /24

    $230,000 Sold Mar 26, 2025

    • 856 Sq Ft
    • $269/SF
    • 3 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1984

    29 Heritage Condos Unit 29D, Woodstock, VT 05091

    OPEN HOUSE CANCELLED.A desirable 1 bedroom condo in Woodstock! Just a short distance from the high school, Farmer's Market, and Thompson Senior Center and only a 3 minute drive from the Woodstock town green and less than 12 minutes to Saskadena Six for skiing. The condo association takes care of all the exterior maintenance (minus clearing off the balcony), and provides interior lockable storage

    Franchesca Collins Hall Collins Real Estate Group

    29 Heritage Condos Unit 29D, 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
  • /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
  • /43

    $700,000 Sold Feb 14, 2025

    • 2,616 Sq Ft
    • $268/SF
    • 15 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    944 College Hill Rd, Woodstock, VT 05091

    PRIVATE- Cape Cod Home less than a mile to Historic Woodstock Village! This generous sized home consisting of 2616 squ ft. sits on 3.62 secluded acres. Built in 1988 and first time on the market- this home has been well maintained with an abundance of light, generous proportioned rooms with handsome hardwood floors. First floor consists of kitchen with quartz counters and soft neutral toned

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    944 College Hill Rd, Woodstock, VT 05091
    • /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
  • /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
  • /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
    • /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
  • /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
  • /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

      Est $2,336,340 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
  • /43

    $1,395,000

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

    15 Central St, Woodstock, VT 05091

    15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building

    Laird Bradley Williamson Group Sothebys Intl. Realty

    15 Central St, 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
    • /32

      Est $540,777 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,100 Sq Ft

      35 White Loop Unit B-102, Ludlow, VT 05149

      35 White Loop Unit B-102, Ludlow, VT 05149
  • /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
  • /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
    • /34

      Est $585,073 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,196 Sq Ft

      1782 South Rd, Woodstock, VT 05091

      1782 South Rd, 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
  • /14

    $220,000 Sold Jan 08, 2025

    • 1,120 Sq Ft
    • $196/SF
    • 32 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1985

    2176 Bridgewater Center Rd, Bridgewater Corners, VT 05035

    Welcome to this delightful 3-bedroom, 1-bath ranch-style home nestled in the heart of scenic Bridgewater, Vermont. Perfectly situated on a quiet country road, this home offers the quintessential Vermont lifestyle with fresh air, and plenty of outdoor space. The single-level layout is ideal for easy living, featuring a spacious living room with large windows that let in plenty of natural light.

    Katie Ladue Gilbert KW Vermont Woodstock

    2176 Bridgewater Center Rd, Bridgewater Corners, VT 05035
    • /33

      Est $545,000 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
  • /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
  • /28

    $270,000 Sold Jan 07, 2025

    • 1,328 Sq Ft
    • $203/SF
    • 72 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    823 Goldcoast Rd, Bridgewtr Cor, VT 05035

    Highly desired Bridgewater location on Gold Coast Road minutes to the Killington Skyeship Gondola & Base Lodge, and the beautiful Village of Woodstock. Close to VAST snowmobile trails, and endless hiking/mountain biking trails. Five minutes to the legendary Long Trail Brewery. This 3 bedroom, 2 full bath home is set on 2.6 tranquil, well-maintained acres. The home has an eat in kitchen, spacious

    Marni Rieger KW Vermont-Killington

    823 Goldcoast Rd, Bridgewtr Cor, VT 05035
    • /39

      Est $1,772,086 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,032 Sq Ft

      343 Spruce Way, Woodstock, VT 05091

      343 Spruce Way, 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
  • /60

    $1,499,000 Sold Jan 06, 2025

    • 3,001 Sq Ft
    • $500/SF
    • 181 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1985

    1133 Atwood Ln, Woodstock, VT 05091

    **Price Improvement**Beautiful country contemporary home offers the best of Vermont living.Private yet convenient,just 6 miles from Woodstock Village and within 30 min. drive to DHMC,Dartmouth College,& Upper Valley shopping, dining, arts and amenities.Set on 28.6 acres,the property feels like a private sanctuary w/ stunning views and southern exposure.Inside,warm wood floors & finishes flow

    Tambrey Vutech KW Vermont Woodstock

    1133 Atwood Ln, Woodstock, VT 05091
    • /40

      Est $438,723 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,374 Sq Ft

      1880 South Rd, Woodstock, VT 05091

      1880 South Rd, Woodstock, VT 05091
  • /10

    $129,000

    • Land
    • 3.00 Acres
    • $43,000 per Acre

    0 Goldcoast Rd, Bridgewater, VT 05034

    Come see this beautiful piece of Vermont!! Conveniently located in the town of Bridgewater that boasts no zoning. Enjoy all the outdoor adventures that Vermont has to offer nearby, minutes to world class skiing and riding, mountain biking, surrounded by snowmobiling trails, golf, Long Trail Brewery, Plymouth’s trio of lakes, and the quintessential Vermont town of Woodstock. Visualize your own

    Will Spanos KW Vermont-Killington

    0 Goldcoast Rd, Bridgewater, VT 05034
  • /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
    • /26

      Est $1,428,193 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,043 Sq Ft

      76 Grove Hill Rd, Woodstock, VT 05091

      76 Grove Hill Rd, Woodstock, VT 05091
  • /28

    $239,000

    • 3 Beds
    • 1,984 Sq Ft

    18 Oak Chapel Rd, Bridgewater, VT 05035

    Discover the potential of this unique fixer-upper property nestled on 0.64 acres, featuring not one, but two distinct buildings awaiting your vision.Step into the main 3-bedroom white house, a fixer-upper's dream filled with endless possibilities. The front porch offers a seasonal retreat with stunning Vermont mountain views - envision it transformed into a year-round haven with a few

    Chelsea Bevis KW Vermont Woodstock

    18 Oak Chapel Rd, Bridgewater, VT 05035
  • /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

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