1,309

Windsor, VT Homes

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  • /59

    $3,300,000

    • 4 Beds
    • 5 Baths
    • 5,000 Sq Ft

    1279 Old Bridgewater Hill Rd, Bridgewater, VT 05035

    Asa Greene traveled to Vermont in 1783 to establish a farm in the high hills in Bridgewater after serving in the American Revolution. 242 Years later the farmhouse still stands at the end of Old Bridgewater Hill Road after nearly 50 years of careful restoration and renovations made to accommodate an active, growing family. Creatively blending old & new the farmhouse takes advantage of an

    Laird Bradley Williamson Group Sothebys Intl. Realty

    1279 Old Bridgewater Hill Rd, Bridgewater, VT 05035
  • /24

    $3,850 per month

    • 4 Beds
    • 3.5 Baths
    • 2,225 Sq Ft
    • House for Rent

    1802 Vt 100a, Plymouth, VT 05056

    This property at 1802 VT 100A features 4 bedrooms and 3.5 bathrooms, offering a total of 2,225 square feet of living space. An additional room could be converted to a fifth bedroom. This charming home is available for long-term lease starting Sept. 1 (or possibly earlier) and offers a perfect blend of rustic character and modern comfort. The great room provides ample space for relaxation and

    1802 Vt 100a, Plymouth, VT 05056
  • /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
    • /34

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      7429 Us Route 4, Bridgewater, VT 05034

      7429 Us Route 4, Bridgewater, VT 05034
  • /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
  • /10

    $130,000 Sold Jun 18, 2025

    • Land
    • 50 Acres
    • $2,600 per Acre
    • 236 Days On Market

    00 Route 100a, Plymouth, VT 05056

    Raw land ready for your Vermont dreams to begin. Looking to build your cabin in the woods away from it all? This could be your spot! With some imagination this 50 acre wooded parcel of pristine Vermont land could be many things. Bordered by the Coolidge State Forest this is a paradise for hiking or exploring the forest. Nearby watersports, biking and golf add to the list of activities. If larger

    Elevations Team Real Broker LLC

    00 Route 100a, Plymouth, VT 05056
    • /37

      Est $540,030 Not Listed For Sale

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

      18 Town Line Rd, Plymouth, VT 05056

      18 Town Line Rd, Plymouth, VT 05056
  • /40

    $1,650,000

    • 4 Beds
    • 3 Baths
    • 2,619 Sq Ft

    441 Spruce Way, Woodstock, VT 05091

    441 SPRUCE WAY - Easily accessible to the village, yet tucked away on over 24 acres is this unique, modern/contemporary residence designed by Boston architect Ken McKinzie and sited perfectly to take in south-facing long range mountain views. The house was designed to be perfect for two, with the primary bedroom suite on the main living level, yet with two bedrooms and a bath at the other end of

    John Snyder Snyder Donegan Real Estate Group

    441 Spruce Way, Woodstock, VT 05091
  • /49

    $390,000 Sold Jun 05, 2025

    • 2,534 Sq Ft
    • $154/SF
    • 216 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1980

    732 Bridgewater Center Rd, Bridgewater Corners, VT 05035

    Nestled in the scenic town of Bridgewater, Vermont, just 9 minutes from Killington Ski Resort and 25 minutes from Okemo, this charming 2-unit single-family home on 1 acre is a unique mountain retreat and a proven rental success. One of the standout features is the thoroughly renovated first-floor kitchen, which boasts elegant marble countertops and ample counter space, perfect for cooking family

    Jeremy Collins Ridgeline Real Estate

    732 Bridgewater Center Rd, Bridgewater Corners, VT 05035
    • /27

      Est $545,711 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,176 Sq Ft

      2908 Route 100a, Plymouth, VT 05056

      2908 Route 100a, Plymouth, VT 05056
  • /60

    $1,950,000

    • 4 Beds
    • 6.5 Baths
    • 4,562 Sq Ft

    73 Laber Rd, Bridgewater Corners, VT 05035

    Experience elevated Vermont living with this exceptional mountaintop estate, thoughtfully designed for both comfort and flexibility. Set on nearly 30 private acres, the residence combines timeless architectural style with expansive interiors and truly breathtaking panoramic views—including sightlines to 4,000-foot peaks and Killington’s ski trails.Inside, you’ll find a rare level of

    Keri Cole Williamson Group Sothebys Intl. Realty

    73 Laber Rd, Bridgewater Corners, VT 05035
  • /17

    $86,500 Sold May 16, 2025

    • 1,120 Sq Ft
    • $77/SF
    • 86 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2011

    132 Riverbend Way, Woodstock, VT 05091

    Wonderful Woodstock location!!! 3 bedroom single wide mobile home ready for the new owner! Open concept kitchen and living room with plenty of closet space. Outside there is a large storage shed, a front porch and a deck under the tree. This home sits on a large corner lot! Only 13 miles to I-89!!

    Jenna Luce RE/MAX Upper Valley

    132 Riverbend Way, Woodstock, VT 05091
    • /35

      Est $631,488 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,920 Sq Ft

      139 Jennes Rd, Bridgewater Corners, VT 05035

      139 Jennes Rd, Bridgewater Corners, VT 05035
  • /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
  • /40

    $2,500,000 Sold May 02, 2025

    • 3,562 Sq Ft
    • $702/SF
    • 646 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1979

    2051 Goldcoast Rd, Bridgewater, VT 05091

    Peace. Tranquility. Big views. Located in the Chateauguay No Town Conservation Area near Woodstock, Wolfstar offers a haven with breathtaking views of the Green Mountains. Meticulously reenvisioned in 2008 by Vermont architect David Beilman, this 15-acre property, cherished as a second home for 35 years, provides complete privacy and understated luxury.The 3,562 sq ft shingle-style home

    Story Jenks LandVest, Inc/Woodstock

    2051 Goldcoast Rd, Bridgewater, VT 05091
    • /12

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,673 Sq Ft

      391 Phelps Rd, Woodstock, VT 05091

      391 Phelps Rd, Woodstock, VT 05091
  • /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
  • /50

    $1,275,000 Sold Apr 02, 2025

    • 2,584 Sq Ft
    • $493/SF
    • 72 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1985

    1075 Westerdale Rd, Woodstock, VT 05091

    This lovingly maintained property with mountain views has been enjoyed by a single family since its construction in 1985. The open-concept layout is anchored by a stone Rumford fireplace, which along with the southern exposure warms the large easy-to-keep space. The first floor master boasts ample storage with a sliding door for quick access to the grounds. Across from the main house via a

    Keri Cole Williamson Group Sothebys Intl. Realty

    1075 Westerdale Rd, Woodstock, VT 05091
    • /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
  • /35

    $399,000

    • 3 Beds
    • 3.5 Baths
    • 2,038 Sq Ft

    1497 Route 100a, Plymouth, VT 05056

    Talk about a convenient location! Central to Killington, Woodstock, and Ludlow. This home is absolutely suitable for full time living or vacation usage. Once upon a time, this was an old schoolhouse. Since then, it was reborn as a home. The floorplan is tremendously flexible with a den/office/TV room upstairs and down along with bedrooms both upstairs and down. A couple of really nice bay

    Betty McEnaney Diamond Realty

    1497 Route 100a, Plymouth, VT 05056
  • /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
    • /39

      Est $1,772,086 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 4,216 Sq Ft

      343 Spruce Way, Woodstock, VT 05091

      343 Spruce Way, Woodstock, VT 05091
  • /34

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,489 Sq Ft

    6852 Us Route 4, Bridgewater, VT 05034

    This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

    Laird Bradley Williamson Group Sothebys Intl. Realty

    6852 Us Route 4, Bridgewater, VT 05034
  • /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

      • 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
  • /32

    $80,000

    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft

    185 Riverbend Way, Woodstock, VT 05091

    Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first home, vacation getaway, or investment, this property is also

    Mendi Michael Engel & Völkers Okemo

    185 Riverbend Way, Woodstock, VT 05091
  • /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
    • /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
  • /24

    $550,000

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft

    2179 U S 4, Bridgewater, VT 05035

    Looking for the tranquility of rural life? Charming, well built, vacation cabin, off the grid, on 30+ acres, with stunning views of Killington. Cabin has 2 bedrooms, 1 bath and a loft, 80% finished including roughed-in bath. Perfect get away from the bothers and troubles of the world, high above the valley with great views of the nearby mountains. Beautiful wood floors, full kitchen and lovely

    John MacGovern Dark Horse Realty

    2179 U S 4, Bridgewater, VT 05035
  • /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
    • /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
  • /54

    $985,000

    • 3 Beds
    • 3 Baths
    • 1,920 Sq Ft

    72 Oakridge Way, Woodstock, VT 05091

    PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you’ll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot.

    Nancy Greenwood Watson Realty & Associates

    72 Oakridge Way, 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
    • /14

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,008 Sq Ft

      74 Upper Rd, Bridgewater Corners, VT 05035

      74 Upper Rd, Bridgewater Corners, VT 05035
  • /44

    $795,000

    • 4 Beds
    • 2 Baths
    • 2,496 Sq Ft

    410 Upper Rd, Bridgewater Corners, VT 05035

    This 1892 Farmhouse offers two fully furnished and equipped 2-bedroom residences and is located midway between historic Woodstock Vermont and the Killington and Okemo Mt. ski areas, just 15- and 30-minutes' drive away, respectively. The property is privately sited above the Ottauquechee (an Abenaki name translated as 'Bright Water') River and directly across from Long Trial Brewing where a main

    Laird Bradley Williamson Group Sothebys Intl. Realty

    410 Upper Rd, Bridgewater Corners, VT 05035
  • /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
    • /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
  • /60

    $859,000

    • 7 Beds
    • 7 Baths
    • 4,581 Sq Ft

    7137 Us Route 4, Bridgewater, VT 05034

    The historic Bridgewater Inn consists of a 3-bedroom, 3-bath spacious home excellent for families or groups. The home has two covered porches, a large eat-in kitchen, living room with gas fireplace and two game rooms. The house has new furniture, paint and floors along with new flush mounted mini splits.Attached are 4 turnkey suites with entrances separate form the home. The property is

    Laura Derderian Killington Valley Real Estate

    7137 Us Route 4, Bridgewater, VT 05034
  • /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
    • /40

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,472 Sq Ft

      19 Broad Brook Dr, Bridgewater, VT 05035

      19 Broad Brook Dr, Bridgewater, VT 05035

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