2,904

Windsor, VT Homes

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  • /59

    $1,850,000

    • 4 Beds
    • 6 Baths
    • 4,764 Sq Ft

    77 Newton Rd, Reading, VT 05062

    Welcome to this private property on a quiet country road in desirable Reading, VT, just 4 miles from South Woodstock. Only 30 minutes to Okemo Mountain Resort and 35 minutes to Killington Ski Area! This spacious 4-bedroom, 6-bathroom home comfortably sleeps 12. This home was made for entertaining! The updated kitchen features high-end appliances, leading to a dining area. Off the kitchen, an

    Agent Photo

    Susan Hickey

    Snyder Donegan Real Estate Group

    (802) 536-6644

    77 Newton Rd, Reading, VT 05062
  • /34

    $679,000 Sold Aug 04, 2025

    • 2,128 Sq Ft
    • $319/SF
    • 49 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1968

    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
    • /40

      Est $1,433,544 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,440 Sq Ft

      4946 South Rd, South Woodstock, VT 05071

      4946 South Rd, South Woodstock, VT 05071
  • /49

    $1,595,000

    • 5 Beds
    • 3.5 Baths
    • 3,648 Sq Ft

    1522 Barnard Rd, Woodstock, VT 05091

    Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef’s kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces—wood-burning, brick, and gas-ready—provide cozy warmth throughout. Upstairs, find 3–4 bedrooms including one with its own fireplace, plus a private guest room or

    Keri Cole Williamson Group Sothebys Intl. Realty

    1522 Barnard Rd, Woodstock, VT 05091
  • /37

    $685,000 Sold Aug 04, 2025

    • 1,600 Sq Ft
    • $428/SF
    • 60 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1985

    258 Densmore Hill Rd, Hartland, VT 05048

    Centrally located just 10 min from both Woodstock Village and Hartland Four Corners, this lovely, secluded contemporary home features bright, tidy sun- filled rooms with open concept kitchen/dining, pine plank flooring, comfortable living room with wood stove. Two step-out decks overlooking beautiful woodland plantings. Partially finished walk out lower level with ensuite bedroom. Easy access to

    Danny Kogut Williamson Group Sothebys Intl. Realty

    258 Densmore Hill Rd, Hartland, VT 05048
    • /39

      Est $1,152,009 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,507 Sq Ft

      433 Cowdrey Path, Woodstock, VT 05091

      433 Cowdrey Path, Woodstock, VT 05091
  • /48

    $1,749,000

    • 3 Beds
    • 3.5 Baths
    • 3,294 Sq Ft

    39 Elm St Unit B, Woodstock, VT 05091

    The Richmond House – Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a distinguished brick Federal with a softly weathered, rose-hued patina and elegant architectural details. Set on over an acre behind a classic white picket fence, this historic property—reimagined under the direction of Laurence Rockefeller—comprises three luxurious residences

    Zoe Hathorn Washburn Snyder Donegan Real Estate Group

    39 Elm St Unit B, Woodstock, VT 05091
  • /37

    $925,000 Sold Jul 31, 2025

    • 1,636 Sq Ft
    • $565/SF
    • 68 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1847

    4 River St, Woodstock, VT 05091

    This impeccably restored 1847 Woodstock village cape set upon a captivating river front landscape is truly magical! The complete and meticulous efficiency upgrades and renovations combined with the perfect village location offers an incomparable opportunity for those buyers coveting a village location. All new windows and red birch floors set the stage for the interior design. The sun-filled

    Mary Mayhew Snyder Donegan Real Estate Group

    4 River St, Woodstock, VT 05091
    • /23

      Not Listed For Sale

      0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091

      0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091
  • /40

    $3,500,000

    • 6 Beds
    • 6 Baths
    • 5,433 Sq Ft

    61 Academy Cir, Woodstock, VT 05071

    Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

    Carol Wood Williamson Group Sothebys Intl. Realty

    61 Academy Cir, Woodstock, VT 05071
  • /52

    $1,320,000 Sold Jul 25, 2025

    • 3,305 Sq Ft
    • $399/SF
    • 85 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1919

    11 College Hill Rd, Woodstock, VT 05091

    Welcome to 11 College Hill Road - Situated in the heart of Woodstock Village, this classic 1919 Gambrel offers space, charm, and incredible views of both the Ottauquechee River and the town's beloved Mount Tom. This beautifully maintained home is perched perfectly above the river with over a half an acre of landscaped outdoor space, including 50 feet of river frontage, mature fruit trees, and

    Zoe Hathorn Washburn Snyder Donegan Real Estate Group

    11 College 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
  • /22

    $645,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,468 Sq Ft

    187 Dana Rd, Woodstock, VT 05091

    This delightful gambrel cape offers a wonderful combination of thoughtful and charming updates, energy efficient upgrades, and a coveted and convenient location! An intelligent interior design offers an all-season functional flow for everyday living as well as entertaining. Step inside by way of a spacious entryway/mudroom that also has direct entry from the attached garage. One will find the

    Mary Mayhew Snyder Donegan Real Estate Group

    187 Dana Rd, Woodstock, VT 05091
  • /41

    $1,075,000 Sold Jul 15, 2025

    • 3,060 Sq Ft
    • $351/SF
    • 353 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1985

    119 English Mills Way, Woodstock, VT 05091

    An expansive 5 bedroom home, in a private location, conveniently just a few minutes drive from Woodstock Village! Among often sought amenities are a ground floor primary bedroom suite with private bath, a dramatic great room with cathedral ceiling and wood burning fireplace, a generously sized lower level in-law/guest suite with kitchen, dining, living room and bedroom with bath, 3 additional

    John Wetmore Wetmore Real Estate

    119 English Mills Way, Woodstock, VT 05091
    • /27

      Est $827,352 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,579 Sq Ft

      7 Golf Ave, Woodstock, VT 05091

      7 Golf Ave, Woodstock, VT 05091
  • /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
  • /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
    • /30

      Est $973,995 Not Listed For Sale

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

      12 High St, Woodstock, VT 05091

      12 High St, Woodstock, VT 05091
  • /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
  • /28

    $882,500 Sold Jun 18, 2025

    • 1,616 Sq Ft
    • $546/SF
    • 111 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    46 Stewart Ln Unit P-304, Ludlow, VT 05149

    Winterplace on Okemo Mountain – A One-of-a-Kind Opportunity! Discover the ultimate mountain retreat at Winterplace, one of Okemo's most sought-after condominium complexes. This exceptional top-floor, 3-bedroom plus loft condominium has been beautifully remodeled, blending modern comfort with classic alpine charm. The expanded loft has been transformed into a spacious second living area, perfect

    Katherine Burns William Raveis Real Estate Vermont Properties

    46 Stewart Ln Unit P-304, Ludlow, VT 05149
    • /38

      Est $553,300 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,020 Sq Ft

      39 South St, Woodstock, VT 05091

      39 South St, Woodstock, VT 05091
  • /37

    $1,185,000

    • 4 Beds
    • 3 Baths
    • 2,785 Sq Ft

    1782 Randall Rd, Woodstock, VT 05091

    This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

    Wade Treadway Wade I Treadway Real Estate

    1782 Randall Rd, Woodstock, VT 05091
  • /31

    $475,000 Sold Jun 16, 2025

    • 2,091 Sq Ft
    • $227/SF
    • 29 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1978

    85 Townhouse Way Unit 18, Woodstock, VT 05091

    Fully furnished and equipped condo nestled in a small quiet community just 5 minutes from historic Woodstock. This is an end unit in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. New windows throughout. Spacious living room anchored by a wood burning fireplace with hardwood floors. A couple of steps down takes you

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    85 Townhouse Way Unit 18, Woodstock, VT 05091
    • /27

      Est $695,515 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,660 Sq Ft

      37 South St, Woodstock, VT 05091

      37 South St, Woodstock, VT 05091
  • /41

    $1,495,000

    • 4 Beds
    • 2.5 Baths
    • 2,532 Sq Ft

    7 Slayton Terrace, Woodstock, VT 05091

    A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

    Keri Cole Williamson Group Sothebys Intl. Realty

    7 Slayton Terrace, 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
    • /31

      Est $974,978 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,970 Sq Ft

      10 Linden Hill, Woodstock, VT 05091

      10 Linden Hill, Woodstock, VT 05091
  • /27

    $1,200,000

    • 5 Beds
    • 4.5 Baths
    • 2,686 Sq Ft

    19 Church St Unit EX, Woodstock, VT 05091

    Bright and spacious five bedroom, five bath in-village residence with Ottauquechee River frontage and less than 1-minute walk to the Woodstock Green. 2-car attached garage enters into the kitchen via a mud-laundry room. Eat-in kitchen with stainless appliances, granite countertops and a large sunny bay window leads to the formal dining room, and also opens to the patio, perfect for entertaining

    John Snyder Snyder Donegan Real Estate Group

    19 Church St Unit EX, Woodstock, VT 05091
  • /32

    $700,000 Sold May 30, 2025

    • 1,520 Sq Ft
    • $461/SF
    • 0 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1880

    13 Golf Ave, Woodstock, VT 05091

    Charming circa 1880 cape in Woodstock Village! Located on a quiet dead-end street across from Mt Peg trail head... Walk to all of towns amenities, shops, restaurants and events on Historic Woodstock Green. Championship golf, fly fishing and skiing near by. This lovely antique cottage has hardwood floors through out, open kitchen with first floor laundry. Adjacent is sitting area and dining.

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    13 Golf Ave, Woodstock, VT 05091
    • /40

      Est $1,701,467 Not Listed For Sale

      • 6 Beds
      • 6 Baths
      • 3,892 Sq Ft

      28 The Green Unit 30, Woodstock, VT 05091

      28 The Green Unit 30, Woodstock, VT 05091
  • /34

    $2,199,000

    • 4 Beds
    • 3.5 Baths
    • 3,564 Sq Ft

    15 Hathorn Hill Street Extension, Woodstock, VT 05091

    An incredibly rare combination of in-Village and country living. 4+ acres and privacy with a pond and heated in-ground pool, yet walk-to-the Green. The residence, designed and built by the well-respected design-build firm Ambrose Construction, offers modern amenities, appliances and construction with a “Vermont Farmhouse” aesthetic. The vaulted ceiling timber frame great-gathering room has

    John Snyder Snyder Donegan Real Estate Group

    15 Hathorn Hill Street Extension, Woodstock, VT 05091
  • /36

    $1,800,000 Sold May 23, 2025

    • 4,100 Sq Ft
    • $439/SF
    • 61 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 2008

    484 Carlton Hill Rd, Woodstock, VT 05091

    Make this unique Adirondack-style home, with its rich stone and timber frame, and perfect location along the banks of the Ottauquechee River, your new Vermont retreat. Every window offers a stunning view of Mt. Tom, and the rushing river, making it a nature lover's paradise. The fieldstone fireplace soars two stories high in the great room, which is flooded with natural light through expansive

    Jennifer Kirkman KW Vermont Woodstock

    484 Carlton Hill Rd, Woodstock, VT 05091
    • /40

      Est $1,910,235 Not Listed For Sale

      • 4 Beds
      • 6 Baths
      • 5,897 Sq Ft

      2 Border Ln, Woodstock, VT 05091

      2 Border Ln, Woodstock, VT 05091
  • /59

    $1,745,000

    • 2 Beds
    • 3 Baths
    • 2,106 Sq Ft

    7 North St, Woodstock, VT 05091

    Stunning Renovated Antique Cape in the Heart of Woodstock Village!Tucked away on over an acre of beautifully landscaped land directly abutting the Marsh-Billings-Rockefeller National Park, this fully renovated antique Cape offers the rare combination of historic charm, modern efficiency, and unbeatable walkability. Located in the heart of Woodstock Village, you can stroll to the village

    Keri Cole Williamson Group Sothebys Intl. Realty

    7 North St, Woodstock, VT 05091
  • /49

    $875,000 Sold May 16, 2025

    • 2,034 Sq Ft
    • $430/SF
    • 19 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1992

    19 Linden Hill St, Woodstock, VT 05091

    Perched along scenic Linden Hill, this stunning village home offers exceptional privacy, comfort, and spacious interiors. A paved driveway leads to a one-car garage with a covered entrance, ensuring effortless access in all seasons.Inside, a generous mudroom provides a practical transition into the inviting living room, featuring a cozy propane fireplace, or the well-appointed kitchen with sleek

    Holly Hall Hall Collins Real Estate Group

    19 Linden Hill St, Woodstock, VT 05091
    • /40

      Est $576,510 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,368 Sq Ft

      1 Border Ln, Woodstock, VT 05091

      1 Border Ln, Woodstock, VT 05091
  • /55

    $1,095,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft

    2 Maple St, Woodstock, VT 05091

    Located in the Heart of Woodstock Village- fantastic location at the foot of the Mtn Peg trail system with easy access to Vail field and all of towns amenities. This beautifully renovated home is completely new. Handsome farmhouse vernacular style home with traditional slate floors, sliding barn doors and wood floors throughout first floor with an open concept for entertaining and all new

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    2 Maple St, Woodstock, VT 05091
  • /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
    • /40

      Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,305 Sq Ft

      11 College Hill Rd, Woodstock, VT 05091

      11 College Hill Rd, Woodstock, VT 05091
  • /28

    $249,000

    • 1 Bed
    • 1 Bath
    • 816 Sq Ft

    42 Heritage Condo Way Unit 16, Woodstock, VT 05091

    OPEN HOUSE SAT AUG 2 FROM 10 - 12 Located less than 2 miles from the Woodstock Village Green, this immaculately maintained and move-in-ready condo offers comfort and convenience in a peaceful setting. Just eight steps down from the front foyer, the unit opens into a thoughtfully designed space ideal for single-level living.Inside, you’ll find laminate flooring throughout and a cozy

    Franchesca Collins Hall Collins Real Estate Group

    42 Heritage Condo Way Unit 16, Woodstock, VT 05091

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