2,759

Windsor, VT Homes

Section Image
  • 1522 Barnard Rd, Woodstock, VT 05091
    1522 Barnard Rd, Woodstock, VT 05091
    1522 Barnard Rd, Woodstock, VT 05091
    /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
  • 36 Happy Valley Rd, Woodstock, VT 05091
    36 Happy Valley Rd, Woodstock, VT 05091
    36 Happy Valley Rd, Woodstock, VT 05091
    /23

    $1,995 per month

    • 1 Bed
    • 1 Bath
    • 1,200 Sq Ft
    • Apartment for Rent

    36 Happy Valley Rd, Woodstock, VT 05091

    Lovely one bedroom unit in a Historic home, located in the Hamlet of Woodstock Vermont. Space is fully furnished or you may request it to be unfurnished if necessary. If you need a quiet place to come on the weekends, ski for the winter or simply have a new home this is your place. Heat, Electric, Water, Sewer, Trash, On site Parking, snow removal all included in rent.NO Pets, NO

    Gail Childs Covered Bridge RE

    36 Happy Valley Rd, Woodstock, VT 05091
  • 294 Barberry Hill Rd, Woodstock, VT 05091
    294 Barberry Hill Rd, Woodstock, VT 05091
    294 Barberry Hill Rd, Woodstock, VT 05091
    /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
    • 433 Cowdrey Path, Woodstock, VT 05091
      433 Cowdrey Path, Woodstock, VT 05091
      433 Cowdrey Path, Woodstock, VT 05091
      /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
  • 39 Elm St Unit B, Woodstock, VT 05091
    39 Elm St Unit B, Woodstock, VT 05091
    39 Elm St Unit B, 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
  • 4 River St, Woodstock, VT 05091
    4 River St, Woodstock, VT 05091
    4 River St, 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
    • 0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091
      0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091
      0 Carlton Hill Rd Unit 4670150, 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
  • 61 Academy Cir, Woodstock, VT 05071
    61 Academy Cir, Woodstock, VT 05071
    61 Academy Cir, Woodstock, VT 05071
    /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
  • 11 College Hill Rd, Woodstock, VT 05091
    11 College Hill Rd, Woodstock, VT 05091
    11 College Hill Rd, Woodstock, VT 05091
    /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
    • 7 Golf Ave, Woodstock, VT 05091
      7 Golf Ave, Woodstock, VT 05091
      7 Golf Ave, 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
  • 187 Dana Rd, Woodstock, VT 05091
    187 Dana Rd, Woodstock, VT 05091
    187 Dana Rd, Woodstock, VT 05091
    /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
  • 119 English Mills Way, Woodstock, VT 05091
    119 English Mills Way, Woodstock, VT 05091
    119 English Mills Way, 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
    • 12 High St, Woodstock, VT 05091
      12 High St, Woodstock, VT 05091
      12 High St, 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
  • 441 Spruce Way, Woodstock, VT 05091
    441 Spruce Way, Woodstock, VT 05091
    441 Spruce Way, 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
  • 608 Fletcher Hill Rd, Woodstock, VT 05091
    608 Fletcher Hill Rd, Woodstock, VT 05091
    608 Fletcher Hill Rd, Woodstock, VT 05091
    /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
    • 39 South St, Woodstock, VT 05091
      39 South St, Woodstock, VT 05091
      39 South St, Woodstock, VT 05091
      /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
  • 1782 Randall Rd, Woodstock, VT 05091
    1782 Randall Rd, Woodstock, VT 05091
    1782 Randall Rd, 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
  • 85 Townhouse Way Unit 18, Woodstock, VT 05091
    85 Townhouse Way Unit 18, Woodstock, VT 05091
    85 Townhouse Way Unit 18, 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
    • 37 South St, Woodstock, VT 05091
      37 South St, Woodstock, VT 05091
      37 South St, Woodstock, VT 05091
      /27

      Est $713,457 Not Listed For Sale

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

      37 South St, Woodstock, VT 05091

      37 South St, Woodstock, VT 05091
  • 7 Slayton Terrace, Woodstock, VT 05091
    7 Slayton Terrace, Woodstock, VT 05091
    7 Slayton Terrace, 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
  • 22 Orchard Hill Rd, Woodstock, VT 05091
    22 Orchard Hill Rd, Woodstock, VT 05091
    22 Orchard Hill Rd, Woodstock, VT 05091
    /54

    $1,500,000 Sold Jun 09, 2025

    • 3,012 Sq Ft
    • $498/SF
    • 68 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1971

    22 Orchard Hill Rd, Woodstock, VT 05091

    LICHENVALE at 22 Orchard Hill Road in Pomfret is a traditional Royal Barry Wills designed cape situated to capture sweeping views south down the Pomfret Valley to Mt. Tom, and the hills surrounding Woodstock Village. The well-cared for dwelling is naturally landscaped with mature gardens, and stone walls and sited on a level plateau at the margins of an open meadow below and the forested hillside

    Laird Bradley Williamson Group Sothebys Intl. Realty

    22 Orchard Hill Rd, Woodstock, VT 05091
    • 10 Linden Hill, Woodstock, VT 05091
      10 Linden Hill, Woodstock, VT 05091
      10 Linden Hill, Woodstock, VT 05091
      /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
  • 19 Church St Unit EX, Woodstock, VT 05091
    19 Church St Unit EX, Woodstock, VT 05091
    19 Church St Unit EX, 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
  • 13 Golf Ave, Woodstock, VT 05091
    13 Golf Ave, Woodstock, VT 05091
    13 Golf Ave, 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
    • 28 The Green Unit 30, Woodstock, VT 05091
      28 The Green Unit 30, Woodstock, VT 05091
      28 The Green Unit 30, 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
  • 687 S Perry Rd, Woodstock, VT 05091
    687 S Perry Rd, Woodstock, VT 05091
    687 S Perry Rd, Woodstock, VT 05091
    /54

    $1,690,000

    • 5 Beds
    • 4.5 Baths
    • 4,617 Sq Ft

    687 S Perry Rd, Woodstock, VT 05091

    Privately sited on a knoll to capture sweeping North Westerly views, this expanded Classic Cape has been lovingly stewarded and tastefully updated over the years. Enter through the formal foyer with wainscot, or a convenient mudroom with powder room. Superior craftsmanship throughout featuring a beautifully appointed chef's kitchen with Viking range-top, wall ovens and best quality appliances,

    Danny Kogut Williamson Group Sothebys Intl. Realty

    687 S Perry Rd, Woodstock, VT 05091
  • 484 Carlton Hill Rd, Woodstock, VT 05091
    484 Carlton Hill Rd, Woodstock, VT 05091
    484 Carlton Hill Rd, 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
    • 2 Border Ln, Woodstock, VT 05091
      2 Border Ln, Woodstock, VT 05091
      2 Border Ln, Woodstock, VT 05091
      /40

      Est $1,781,111 Not Listed For Sale

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

      2 Border Ln, Woodstock, VT 05091

      2 Border Ln, Woodstock, VT 05091
  • 15 Hathorn Hill Street Extension, Woodstock, VT 05091
    15 Hathorn Hill Street Extension, Woodstock, VT 05091
    15 Hathorn Hill Street Extension, 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
  • 19 Linden Hill St, Woodstock, VT 05091
    19 Linden Hill St, Woodstock, VT 05091
    19 Linden Hill 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
    • 1 Border Ln, Woodstock, VT 05091
      1 Border Ln, Woodstock, VT 05091
      1 Border Ln, Woodstock, VT 05091
      /40

      Est $587,072 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
  • 2 Maple St, Woodstock, VT 05091
    2 Maple St, Woodstock, VT 05091
    2 Maple St, 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
  • 132 Riverbend Way, Woodstock, VT 05091
    132 Riverbend Way, Woodstock, VT 05091
    132 Riverbend Way, 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
    • 11 College Hill Rd, Woodstock, VT 05091
      11 College Hill Rd, Woodstock, VT 05091
      11 College Hill Rd, 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
  • 42 Heritage Condo Way Unit 16, Woodstock, VT 05091
    42 Heritage Condo Way Unit 16, Woodstock, VT 05091
    42 Heritage Condo Way Unit 16, 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
  • 105 Happy Valley Rd, Woodstock, VT 05091
    105 Happy Valley Rd, Woodstock, VT 05091
    105 Happy Valley Rd, Woodstock, VT 05091
    /40

    $575,000 Sold May 09, 2025

    • 1,700 Sq Ft
    • $338/SF
    • 274 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1848

    105 Happy Valley Rd, Woodstock, VT 05091

    PRICE REDUCTION!! A Quintessential Historic 3 Bedroom, 1,700 sq/ft. Home in Woodstock's coveted Taftsville Village. The "Levi D. Hall House" was built in 1848 by D. Taft & Sons and has been a loved and well-maintained home by the same family for nearly 70 years. Enter into beautiful natural light and a home in pristine condition throughout. The classic country kitchen has high ceilings with

    John Bassette Bassette Real Estate Group

    105 Happy Valley Rd, Woodstock, VT 05091
    • 3 Church St, Woodstock, VT 05091
      3 Church St, Woodstock, VT 05091
      3 Church St, Woodstock, VT 05091
      /39

      Est $3,387,678 Not Listed For Sale

      • 10 Beds
      • 15 Baths
      • 10,206 Sq Ft

      3 Church St, Woodstock, VT 05091

      3 Church St, Woodstock, VT 05091
  • 56 Heritage Condo Way Unit 9, Woodstock, VT 05091
    56 Heritage Condo Way Unit 9, Woodstock, VT 05091
    56 Heritage Condo Way Unit 9, Woodstock, VT 05091
    /18

    $239,500

    • 1 Bed
    • 1 Bath
    • 856 Sq Ft

    56 Heritage Condo Way Unit 9, Woodstock, VT 05091

    Lots of upgrades to this quiet, two level condo, with lovely views off back baloney. Bonus- new mini split heat pump providing both air conditioning and heat. Kitchen has some upgraded as well with a new dishwasher. This open floor concept condo provides lots of natural sunlight. Cozy up in the living room/dining room and read a book during the winter months overlooking the spacious

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    56 Heritage Condo Way Unit 9, Woodstock, VT 05091
  • 3086 South Rd, Woodstock, VT 05091
    3086 South Rd, Woodstock, VT 05091
    3086 South Rd, Woodstock, VT 05091
    /20

    $2,900,000 Sold May 05, 2025

    • 3,550 Sq Ft
    • $817/SF
    • 0 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1986

    3086 South Rd, Woodstock, VT 05091

    Beautifully and extensively renovated residence, newer construction barn-garage with five overhead doors and an attached one-bedroom apartment (ADU). The land component offers over a mile of private trails perfect for walking, horseback, snowshoeing and biking, including a coursing stream with waterfalls, open meadows, a sledding hill and beautiful landscaping. Detached screened porch and stone

    John Snyder Snyder Donegan Real Estate Group

    3086 South Rd, Woodstock, VT 05091
    • 26 River St, Woodstock, VT 05091
      26 River St, Woodstock, VT 05091
      26 River St, Woodstock, VT 05091
      /40

      Est $1,580,609 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 3,719 Sq Ft

      26 River St, Woodstock, VT 05091

      26 River St, Woodstock, VT 05091

Showing Results 1 - 40, Page 1 of 18

Vermont Windsor County Woodstock

Real Estate & Homes

Home Trends in Woodstock, VT

On average, homes in Woodstock, VT sell after 119 days on the market compared to the national average of 70 days. The median sale price for homes in Woodstock, VT over the last 12 months is $700,000, down 20% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$700,000
Median Single Family Sale Price
$1,185,000
Median Townhouse Sale Price
$358,000
Median 1 Bedroom Sale Price
$249,000
Average Price Per Sq Ft
$479
Number of Homes for Sale
9
Last 12 months Home Sales
45
Months of Supply
2.40
Median List Price
$985,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-20%
How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group