3,359

Windsor, VT Homes in ZIP Code 05091

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    • /29

      Est $669,729 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,350 Sq Ft

      64 Fowler Rd Unit Q103, Ludlow, VT 05149

      64 Fowler Rd Unit Q103, Ludlow, VT 05149
  • /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
  • /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
    • /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
  • /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
  • /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
    • /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
  • /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
    • /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
  • /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
    • /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
  • /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
    • /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
  • /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
    • /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
  • /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
    • /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
  • /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
    • /39

      Est $744,935 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,943 Sq Ft

      629 N Bridgewater Rd, Bridgewater, VT 05034

      629 N Bridgewater Rd, Bridgewater, VT 05034
    • /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
    • /22

      Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,882 Sq Ft

      433 Fairbanks Turn, Hartford, VT 05059

      433 Fairbanks Turn, Hartford, VT 05059
    • /13

      Not Listed For Sale

      0 Vermont 12 Unit 4914573, Barnard, VT 05031

      0 Vermont 12 Unit 4914573, Barnard, VT 05031
    • /9

      Est $427,500 Not Listed For Sale

      253 Garvin Hill Rd, Hartland, VT 05048

      253 Garvin Hill Rd, Hartland, VT 05048
    • /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
    • /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
    • /40

      Est $348,426 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
    • /39

      Est $1,036,062 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,894 Sq Ft

      13 River St, Woodstock, VT 05091

      13 River St, Woodstock, VT 05091
    • /37

      Est $1,046,844 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,344 Sq Ft

      1075 Barber Hill Rd, Woodstock, VT 05091

      1075 Barber Hill Rd, Woodstock, VT 05091
    • /40

      Est $419,243 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,457 Sq Ft

      1176 W Woodstock Rd, Woodstock, VT 05091

      1176 W Woodstock Rd, Woodstock, VT 05091
    • /40

      Est $1,940,125 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,610 Sq Ft

      2018 Church Hill Rd, Woodstock, VT 05091

      2018 Church Hill Rd, Woodstock, VT 05091
    • /39

      Est $1,414,583 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 5,148 Sq Ft

      268 Willow Brook Rd, Woodstock, VT 05091

      268 Willow Brook Rd, Woodstock, VT 05091
    • /36

      Est $2,163,257 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,163 Sq Ft

      587 College Hill Rd, Woodstock, VT 05091

      587 College Hill Rd, Woodstock, VT 05091
    • /39

      Est $1,528,898 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 3,380 Sq Ft

      113 Prosper Rd, Woodstock, VT 05091

      113 Prosper Rd, Woodstock, VT 05091
    • /35

      Est $881,761 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,200 Sq Ft

      295 Mecawee Rd, Woodstock, VT 05091

      295 Mecawee Rd, Woodstock, VT 05091
    • /40

      Est $1,009,432 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,331 Sq Ft

      11 College Hill Rd, Woodstock, VT 05091

      11 College Hill Rd, Woodstock, VT 05091
    • /18

      Not Listed For Sale

      0 Eastman Unit 4959490, Barnard, VT 05031

      0 Eastman Unit 4959490, Barnard, VT 05031
    • /6

      Est $67,532 Not Listed For Sale

      1092 Sessions Meadow, Woodstock, VT 05091

      1092 Sessions Meadow, Woodstock, VT 05091
    • /40

      Est $2,134,003 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,759 Sq Ft

      170 Grove Hill Rd, Woodstock, VT 05091

      170 Grove Hill Rd, Woodstock, VT 05091
    • /33

      Est $595,633 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,893 Sq Ft

      2356 Fletcher Hill Rd, Woodstock, VT 05091

      2356 Fletcher Hill Rd, Woodstock, VT 05091
    • /34

      Est $381,278 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,068 Sq Ft

      2622 South Rd, Woodstock, VT 05091

      2622 South Rd, Woodstock, VT 05091

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