Windsor, VT Homes

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  /40

  Est $887,987 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,324 Sq Ft

  917 Carlton Hill Rd, Woodstock, VT 05091

  917 Carlton Hill Rd, Woodstock, VT 05091
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  /26

  $489,500 Pending

  • 2 Beds
  • 1.5 Baths
  • 930 Sq Ft

  11A Prospect St, Woodstock, VT 05091

  Walk to everything Woodstock village has to offer from this sunny condo! Within an easy stroll of the Woodstock Inn, downtown restaurants, farmer's markets, and the Marsh Billings Rockefeller National Park, 11A Prospect is ideal for enjoying the charms of village living. Elevated above the Route 4 on a bucolic neighborhood side street, this well-kept home offers historic details with modern

  Keri Cole Williamson Group Sothebys Intl. Realty

  11A Prospect St, Woodstock, VT 05091
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  /40

  $2,000,000 Sold Oct 07, 2024

  • 2,411 Sq Ft
  • $830/SF
  • 35 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2009

  1106 Church Hill Rd, Woodstock, VT 05091

  Travel a mile south of Woodstock Village on Church Hill Road and you’ll discover a rural refuge that combines seclusion with proximity to village life. Two dwellings, a modern home and a separate cottage sheltered by woodland are discreetly sited overlooking a sparkling two-acre spring-fed pond. Each residence offers three bedrooms and two baths with open floor plans and single level living. The

  Laird Bradley Williamson Group Sothebys Intl. Realty

  1106 Church Hill Rd, Woodstock, VT 05091
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  /40

  Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 6,799 Sq Ft

  587 Old River Rd, Woodstock, VT 05091

  587 Old River Rd, Woodstock, VT 05091
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  /34

  $679,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  294 Barberry Hill Rd, Woodstock, VT 05091

  Discover this delightful 3-bedroom, 2.5-bath home nestled on 1.8 acres at the end of a peaceful dead-end road. Conveniently located near Woodstock Middle/High School, the Thompson Senior Center, and the popular Woodstock Farmers’ Market.This home offers a spacious and functional layout, the welcoming mudroom features generous storage space and a laundry area cleverly tucked behind sliding

  Bonnie Bergeron Snyder Donegan Real Estate Group

  294 Barberry Hill Rd, Woodstock, VT 05091
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  /37

  $935,000 Sold Sep 27, 2024

  • 1,800 Sq Ft
  • $519/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  13 High St, Woodstock, VT 05091

  Prime Woodstock Village Location. Fabulous spot. Walk to everything in town from this absolutely adorable, renovated 3 bedroom/ 2 full bath home. Formally the town Blacksmith shop. This charming property has an open concept floor plan ideal for entertaining. Beautiful wood floors and loads of light throughout. Spacious smooth fenced in yard with frontage on the Kedron Brook. Sit on the deck and

  Marni Rieger KW Vermont-Killington

  13 High St, Woodstock, VT 05091
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  /38

  Est $1,181,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  506 Westerdale Rd, Woodstock, VT 05091

  506 Westerdale Rd, Woodstock, VT 05091
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  /44

  $1,800,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,423 Sq Ft

  2090 Randall Rd, Woodstock, VT 05091

  Constructed in 2007 with a nod to the Gothic Style Vermont Farmhouse vernacular, this beautifully composed country home creatively integrates curated period detail with modern conveniences and systems. Conveniently located at the end of a picturesque tree lined dirt road just minutes from the Villages of both Woodstock and South Woodstock offering privacy and tranquility. The interior spaces of

  Danny Kogut Williamson Group Sothebys Intl. Realty

  2090 Randall Rd, Woodstock, VT 05091
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  /27

  $375,000 Sold Sep 06, 2024

  • 1,666 Sq Ft
  • $225/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1920

  2411 Chateauguay Rd, Woodstock, VT 05091

  Extremely well maintained 3 bedroom / 1 bath home on 3.7+/- acres in Barnard. For those that enjoy to cook, you will love the nice size kitchen with its gas cooking stove, lots of cabinets and plenty of counterspace. If you need addition storage or space, you will enjoy the walk in pantry which offers a second sink, a freezer, more counterspace and cabinets. Serving as a laundry area as well, you

  Lisa Baldwin Coldwell Banker LIFESTYLES - Hanover

  2411 Chateauguay Rd, Woodstock, VT 05091
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  /6

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,620 Sq Ft

  7 Hathorn Hill Unit 7, Woodstock, VT 05091

  7 Hathorn Hill Unit 7, Woodstock, VT 05091
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  /40

  $695,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,584 Sq Ft

  3914 South Rd, Woodstock, VT 05091

  This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont’s changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level.

  Laird Bradley Williamson Group Sothebys Intl. Realty

  3914 South Rd, Woodstock, VT 05091
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  /28

  $835,000 Sold Sep 06, 2024

  • 3,394 Sq Ft
  • $246/SF
  • 37 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1971

  86 Willow Brook Rd, Woodstock, VT 05091

  This classic expanded Cape Style Home is located on a quiet dirt road within walking distance to The Village Green, and just steps to King Farm and the Mt Tom Trail system. Plenty of room to sprawl about in the generous common spaces. The living room has oversized windows and anchored by a brick fireplace flanked by built in book shelves with a propane stove insert. The dining room has a wood

  Danny Kogut Williamson Group Sothebys Intl. Realty

  86 Willow Brook Rd, Woodstock, VT 05091
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  /40

  Est $687,732 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  3256 South Rd, Woodstock, VT 05091

  3256 South Rd, Woodstock, VT 05091
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  /40

  $1,875,000 Pending

  • 10 Beds
  • 12 Baths
  • 7,769 Sq Ft

  2709 W Woodstock Rd, Woodstock, VT 05091

  INVESTMENT, MULTI-GENERATIONAL, MULTI FAMILY AND COMMERCIAL OPPORTUNITY .. priced below appraised value on land and buildings providing instant equity. Experience the charm of Woodstock, VT with its quaint Main Street and enjoy the proximity to Killington Resort, just a short drive away. This exceptional property offers a unique blend of natural beauty and year-round recreational opportunities,

  Susan Bishop Four Seasons Sotheby's Int'l Realty

  2709 W Woodstock Rd, Woodstock, VT 05091
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  /40

  $358,000 Sold Sep 03, 2024

  • 1,728 Sq Ft
  • $207/SF
  • 43 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1982

  21 Townhouse Way, Woodstock, VT 05091

  The location and setting for this spacious brick home makes it one of the most desirable neighborhoods in Woodstock. The setting is private surrounded by woods and open, landscaped gardens. An easy drive to the Woodstock Green and walkable to the Woodstock Middle and High Schools as well as the Union Arena. The eat in kitchen leads out to a lovely deck that offers a private setting for outdoor

  Carol Wood Williamson Group Sothebys Intl. Realty

  21 Townhouse Way, Woodstock, VT 05091
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  /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
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  /40

  $1,875,000 Pending

  • 10 Beds
  • 11 Baths
  • 7,769 Sq Ft

  2709 W Woodstock Rd, Woodstock, VT 05091

  INVESTMENT, MULTI-GENERATIONAL, MULTI FAMILY AND COMMERCIAL OPPORTUNITY .. priced below appraised value on land and buildings providing instant equity. Experience the charm of Woodstock, VT with its quaint Main Street and enjoy the proximity to Killington Resort, just a short drive away. This exceptional property offers a unique blend of natural beauty and year-round recreational opportunities,

  Susan Bishop Four Seasons Sotheby's Int'l Realty

  2709 W Woodstock Rd, Woodstock, VT 05091
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  /40

  $675,000 Sold Aug 23, 2024

  • 1,764 Sq Ft
  • $383/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  819 Pomfret Rd, Woodstock, VT 05091

  Traditional cape style home surrounded by beautiful hayfields and views of the Vermont countryside. This Immaculately maintained property has hardwood floors throughout and a Vermont Castings wood burning stove in the main living area. The kitchen is equipped with a large butcher block island, gas stove and ample counter space. On the main floor there is one bedroom with a full bath and a small

  Mia Parsons Douglas Elliman of Vermont LLC

  819 Pomfret Rd, Woodstock, VT 05091
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  /24

  Est $540,293 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,034 Sq Ft

  708 E Woodstock Rd, Woodstock, VT 05091

  708 E Woodstock Rd, Woodstock, VT 05091
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  /53

  $798,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,308 Sq Ft

  392 Gully Rd, Woodstock, VT 05091

  Built in 2019, this charming Cape-style home is nestled on five sunny, private acres just minutes from Woodstock Village. Thoughtfully designed and beautifully constructed, the home offers efficient, low-maintenance living in a coveted location. With excellent solar exposure, stunning sunset views, and lovely hillside scenery, it’s bright, warm, and welcoming year-round.The interior

  Keri Cole Williamson Group Sothebys Intl. Realty

  392 Gully Rd, Woodstock, VT 05091
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  /10

  $230,000 Sold Aug 16, 2024

  • 1,264 Sq Ft
  • $182/SF
  • 127 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1979

  139 Doe Hill Way, Woodstock, VT 05091

  What a prime location being just off the main road with great privacy and room to roam! This home features open, airy living space and potential for more with a family room and laundry in the lower level. The two sided deck is great for nature watching and provides great relaxation space at the end of the day. There's a lot of upside potential at this property and the location is very convenient

  Susan Bellville Bellville Realty

  139 Doe Hill Way, Woodstock, VT 05091
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  /40

  Est $1,545,988 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,080 Sq Ft

  612 Church Hill Rd, Woodstock, VT 05091

  612 Church Hill Rd, Woodstock, VT 05091
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  /24

  $629,500 Under Contract

  • 4 Beds
  • 1.5 Baths
  • 1,650 Sq Ft

  40 Pomfret Rd, Woodstock, VT 05091

  Welcome to Kingsley Cottage – A delightful and charming property situated in the pastoral landscape of the Prosper Valley in Woodstock. Meticulous energy efficiency upgrades of the property have been combined with an aesthetically sensitive preservation of the vintage charm. A spacious covered porch details the exterior envelope of the home – the perfect spot to enjoy outdoor dining,

  Mary Mayhew Snyder Donegan Real Estate Group

  40 Pomfret Rd, Woodstock, VT 05091
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  /14

  $678,000 Sold Oct 25, 2024

  • 1,656 Sq Ft
  • $409/SF
  • 0 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1947

  16 Pomfret Rd, Woodstock, VT 05091

  Mary Mayhew Snyder Donegan Real Estate Group

  16 Pomfret Rd, Woodstock, VT 05091
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  /8

  Not Listed For Sale

  • 9 Beds
  • 9 Baths
  • 6,980 Sq Ft

  387 Benedict Rd, Woodstock, VT 05071

  387 Benedict Rd, Woodstock, VT 05071
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  /33

  $768,500 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,552 Sq Ft

  3 Hathorn Hill St Unit 3, Woodstock, VT 05091

  Rare opportunity to own in Hathorn Hill Condos. Private, quiet with lovely fern grove and stonewalls with views to the East. This unit has an de-attached 2 bay garage with easy access to extra parking. Upper level consist of an open floor plan, abundance of natural light with slider doors across the front for nice views off balcony. Living room anchored by a handsome wood burning fireplace

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  3 Hathorn Hill St Unit 3, Woodstock, VT 05091
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  /2

  $287,500 Sold Oct 01, 2024

  • 1,408 Sq Ft
  • $204/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1954

  2454 South Rd, Woodstock, VT 05091

  Danny Kogut Williamson Group Sothebys Intl. Realty

  2454 South Rd, Woodstock, VT 05091
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  /15

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 934 Sq Ft

  13 Park View Way Unit 31, Woodstock, VT 05091

  13 Park View Way Unit 31, Woodstock, VT 05091
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  /52

  $549,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 2,240 Sq Ft

  1613 W Woodstock Rd, Woodstock, VT 05091

  OPEN HOUSE SUNDAY JUNE 15 FROM 12-3! Welcome to this turn-key, thoughtfully renovated home featuring a fully updated kitchen with granite countertops, stainless steel appliances, a gas stove, and a sliding glass door that opens to a covered porch—perfect for overlooking the spacious backyard. The main level offers a comfortable bedroom and a nearby full bath, while upstairs you'll find two

  Holly Hall Hall Collins Real Estate Group

  1613 W Woodstock Rd, Woodstock, VT 05091
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  /28

  Est $1,803,726 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,836 Sq Ft

  4411 Church Hill Rd, Woodstock, VT 05091

  4411 Church Hill Rd, Woodstock, VT 05091
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  /39

  $775,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  17 Golf Pond, Woodstock, VT 05091

  Nestled in the heart of the picturesque Village of Woodstock, this beautiful 3-bedroom, 2.5-bath home offers a perfect blend of classic Vermont charm and modern comfort. Overlooking a serene pond, the home boasts an open floor plan on the main level..Step inside to find warm wood floors throughout, a welcoming fireplace that anchors the spacious living area, a thoughtfully laid out kitchen

  Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  17 Golf Pond, Woodstock, VT 05091
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  /20

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,305 Sq Ft

  12 Linden Hill St, Woodstock, VT 05091

  12 Linden Hill St, Woodstock, VT 05091
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  /40

  $775,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  339 Gully Rd, Woodstock, VT 05091

  Peaceful Gully Road Retreat. Just minutes from Woodstock Village.Set on 5.1 private acres along quiet and desirable Gully Road, this beautifully updated four-bedroom, two and one-half bath home offers the perfect blend of peaceful country living and convenient proximity to Woodstock shops, restaurants, and schools.The main level features a light-filled, open-concept layout with a dramatic

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  339 Gully Rd, Woodstock, VT 05091
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  /17

  Est $1,315,941 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,798 Sq Ft

  4651 Cloudland Rd, Woodstock, VT 05091

  4651 Cloudland Rd, Woodstock, VT 05091
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  /39

  $649,000 Under Contract

  • 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
• 

  

  /25

  Not Listed For Sale

  • 8 Beds
  • 5 Baths
  • 3,748 Sq Ft

  144 Town Farm Rd, Woodstock, VT 05071

  144 Town Farm Rd, Woodstock, VT 05071
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  /39

  $1,499,000 Under Contract

  • Land
  • 4.57 Acres
  • $328,009 per Acre

  458 Woodstock Rd, Wood Stock, VT 05091

  It has been said that the highest and best use of this landmark Woodstock property would be a combination of constructing multiple residential units, in the private rear acreage, and commercial development, of the highly visible Route 4 road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village! This property

  John Wetmore Wetmore Real Estate

  458 Woodstock Rd, Wood Stock, VT 05091
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  /11

  Not Listed For Sale

  • 11 Beds
  • 5 Baths
  • 6,095 Sq Ft

  7465 U S 4, Woodstock, VT 05091

  7465 U S 4, Woodstock, VT 05091
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  /40

  Est $614,516 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,592 Sq Ft

  4662 W Woodstock Rd, Woodstock, VT 05091

  4662 W Woodstock Rd, Woodstock, VT 05091
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  /26

  Est $548,268 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,070 Sq Ft

  2456 Cox District Rd Unit 250.32.02.01, Woodstock, VT 05091

  2456 Cox District Rd Unit 250.32.02.01, Woodstock, VT 05091

Showing Results 121 - 160, Page 4 of 18