Windsor, VT Homes in ZIP Code 05091

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  /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
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  /14

  $1,900 per month

  • Studio - 3 Beds
  • 1 Bath
  • 450 Sq Ft
  • Condo for Rent

  156 Fairview Terrace Unit D, White River Junction, VT 05001

  This fully furnished loft apartment has a bedroom, a sleeping loft, a dining/living room, a full bath, but it doesn't have a kitchen - while it may not be ideal if you are looking for a full-year lease, it's absolutely perfect for short and medium term stays. It's located in a residential neighborhood next to downtown White River Junction, between Dartmouth College and West Lebanon shopping area,

  156 Fairview Terrace Unit D, White River Junction, VT 05001
• 

  

  

  /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
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  /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
• 

  

  /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
• 

  

  /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
• 

  

  /23

  Not Listed For Sale

  0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091

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

  

  /40

  $2,299,000

  • 6 Beds
  • 6 Baths
  • 7,619 Sq Ft

  5518 Vermont 12, Woodstock, VT 05091

  An historic brick residence prominently located in an affluent and growing community! Conveniently situated within walking distance to the Elementary School, to year round recreation on beloved Silver Lake and to the classic Barnard General Store. All the amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round cultural events

  John Wetmore Wetmore Real Estate

  5518 Vermont 12, Woodstock, VT 05091
• 

  

  /42

  $429,000 Sold Jul 16, 2025

  • 748 Sq Ft
  • $574/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1976

  3450 N Perry Rd, Barnard, VT 05031

  This charming log home features an open kitchen/dining/living room with three cozy bedrooms, two full bathrooms, and a family room, perfect for comfortable living. The rustic wooden interior and warm atmosphere create a welcoming space for family and friends. Each floor has a propane wood stove for ambiance and extra warmth on those chilly winter nights, while a large wrap-around deck is perfect

  Susan Hickey Snyder Donegan Real Estate Group

  3450 N Perry Rd, Barnard, VT 05031
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  /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
• 

  

  /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
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  /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
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  /38

  $1,999,000

  • 6 Beds
  • 6 Baths
  • 7,619 Sq Ft

  5518 Vt Route 12, Barnard, VT 05031

  An historic brick residence prominently located in an affluent and growing community! Conveniently situated within walking distance to the Elementary School, to year round recreation on beloved Silver Lake and to the classic Barnard General Store. All of the well known amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round

  John Wetmore Wetmore Real Estate

  5518 Vt Route 12, Barnard, VT 05031
• 

  

  /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
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  /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
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  /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 $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
• 

  

  /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
• 

  

  /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
• 

  

  /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
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  /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
• 

  

  /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
• 

  

  /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 $1,781,111 Not Listed For Sale

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

  2 Border Ln, Woodstock, VT 05091

  2 Border Ln, Woodstock, VT 05091
• 

  

  /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
• 

  

  /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
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  /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
• 

  

  /28

  $249,000 Open Sat 10AM - 12PM

  • 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
• 

  

  /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
• 

  

  /14

  $249,000

  • Land
  • 6 Acres
  • $38,308 per Acre

  5518 Vt Route 12, Barnard, VT 05031

  A pastoral parcel of land with the benefit a truly mesmerizing private pond! The location is great! Recreation on pristine Silver Lake and shopping in the beloved Barnard General Store are just a few minutes away from this peaceful Barnard Village acreage! One obvious building site would take advantage of views of the pond. Other possible sites certainly are presented within the extended open

  John Wetmore Wetmore Real Estate

  5518 Vt Route 12, Barnard, VT 05031
• 

  

  /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

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