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 4-bedroom, 6-bathroom home nestled on a quiet country road in sought-after Reading, VT—just 4 miles from South Woodstock and close to the Green Mountain Horse Association. With Okemo Mountain only 30 minutes away and Killington just 35 minutes, plus world-class golf, biking trails and summer pastime amenities, this location is a four-season playground! This expansive home

  

  Susan Hickey

  Snyder Donegan Real Estate Group

  (802) 536-6644

  77 Newton Rd, Reading, VT 05062
• 

  

  

  /15

  $2,595 per month

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Townhouse for Rent

  2 Townhouse Way, Woodstock, VT 05091

  Available November 1 2025 through April 30th 2026Fully Furnished. All utilities plus internet included - you write one check each month.Hello Lovers of Vermont Fall and Winter! Here is your chance to escape the hustle and bustle of your busy life in Vermont's premier village of Woodstock! This Townhouse is peaceful and private, with all the amenities to keep you in comfort AND quick

  Matt DePrizio Covered Bridge RE

  2 Townhouse Way, Woodstock, VT 05091
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  /33

  $776,000 Sold Aug 25, 2025

  • 2,552 Sq Ft
  • $304/SF
  • 6 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1984

  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
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  /40

  Est $1,410,277 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
• 

  

  

  /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
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  /40

  $2,425,000 Sold Aug 15, 2025

  • 5,017 Sq Ft
  • $483/SF
  • 0 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2003

  739 Westerdale Rd, Woodstock, VT 05091

  Absolutely stunning, newly renovated residence, privately situated towards the end of a quiet town road in Woodstock, in an area of other substantial homes. Lovely mountain views and 10+ acres of privacy. The present owners have completed over $1 million in documented renovations in the past three years, including a fabulous new gourmet kitchen, powder bath, new bamboo flooring throughout the

  John Snyder Snyder Donegan Real Estate Group

  739 Westerdale Rd, Woodstock, VT 05091
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  /39

  Est $1,072,540 Not Listed For Sale

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

  433 Cowdrey Path, Woodstock, VT 05091

  433 Cowdrey Path, Woodstock, VT 05091
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  /43

  $2,600,000

  • 4 Beds
  • 3.5 Baths
  • 3,998 Sq Ft

  2 Pleasant St, Woodstock, VT 05091

  2 PLEASANT STREET- This stately brick Federal is a historic landmark property in the heart of Woodstock Village, home to many storied families in the town and state’s history, notably Julius Converse, Governor of Vermont in 1872, and Laurance Rockefeller. Though it has been well-renovated and maintained over the years, it retains many of its historic features to beautifully blend modern

  David Donegan Snyder Donegan Real Estate Group

  2 Pleasant St, Woodstock, VT 05091
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  /55

  $1,145,000 Sold Aug 15, 2025

  • 2,710 Sq Ft
  • $423/SF
  • 5 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2020

  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
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  /3

  Not Listed For Sale

  00 Weed Rd, Hartland, VT 05049

  00 Weed Rd, Hartland, VT 05049
• 

  

  /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
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  /26

  $480,000 Sold Aug 15, 2025

  • 930 Sq Ft
  • $516/SF
  • 98 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1860

  11A Prospect St, Woodstock, VT 05091

  Walk to everything Woodstock village has to offer from this sunny condo! Within an easy stroll of the Woodstock Inn, downtown restaurants, farmer's markets, and the Marsh Billings Rockefeller National Park, 11A Prospect is ideal for enjoying the charms of village living. Elevated above the Route 4 on a bucolic neighborhood side street, this well-kept home offers historic details with modern

  Keri Cole Williamson Group Sothebys Intl. Realty

  11A Prospect St, Woodstock, VT 05091
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  /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
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  /44

  $1,700,000 Sold Aug 15, 2025

  • 2,423 Sq Ft
  • $702/SF
  • 177 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2007

  2090 Randall Rd, Woodstock, VT 05091

  Constructed in 2007 with a nod to the Gothic Style Vermont Farmhouse vernacular, this beautifully composed country home creatively integrates curated period detail with modern conveniences and systems. Conveniently located at the end of a picturesque tree lined dirt road just minutes from the Villages of both Woodstock and South Woodstock offering privacy and tranquility. The interior spaces of

  Danny Kogut Williamson Group Sothebys Intl. Realty

  2090 Randall Rd, Woodstock, VT 05091
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  /40

  Est $591,851 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,980 Sq Ft

  21 Sportsmen Cove, Hartland, VT 05048

  21 Sportsmen Cove, Hartland, VT 05048
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  /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
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  /52

  $545,000 Sold Aug 06, 2025

  • 1,344 Sq Ft
  • $406/SF
  • 53 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1944

  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
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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
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  /40

  $1,295,000

  • 4 Beds
  • 3 Baths
  • 3,089 Sq Ft

  16 Church St, Woodstock, VT 05091

  16 Church has the most stunning view of the river from any house in the village that we have seen, perched up above a series of river rapids so the sounds of the river during the day or in the evening are incredibly peaceful and relaxing. Plus, 16 Church is privately nestled in, like a secret hideaway, yet steps to the village green (and a level walk to/from). And more unusual for the village,

  John Snyder Snyder Donegan Real Estate Group

  16 Church St, Woodstock, VT 05091
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  /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
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  /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
• 

  

  /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
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  /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
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  /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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  /59

  $1,750,000

  • 5 Beds
  • 4 Baths
  • 3,862 Sq Ft

  699 Spear Cemetery Rd, Reading, VT 05062

  Situated amongst the finest equine estates in the region, Tuacknback Farm is an iconic landmark, best known as the most popular hold along the famed Vermont 100 ride. Located on a scenic country road, accessing the most extensive trail systems in New England, the entire property was impeccably orchestrated for ease with direct walk-in access to the connected stable and hay loft, and a wide

  Danny Kogut Williamson Group Sothebys Intl. Realty

  699 Spear Cemetery Rd, Reading, VT 05062
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  /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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  /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
• 

  

  /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
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  /52

  $564,000 Sold Jul 28, 2025

  • 1,792 Sq Ft
  • $315/SF
  • 93 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2007

  551 Vermont 12, Hartland, VT 05048

  New price! Make this beautiful, spacious hillside home with gorgeous views your own! Easy access to Woodstock, Lebanon and Hanover. Hartland VT has no zoning and school choice for high school. 2.68 acres offers very nice privacy, located at the end of a long driveway. This 2007 built raised ranch is in excellent condition. With new construction homes being scarce, this residence is like new! This

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  551 Vermont 12, Hartland, VT 05048
• 

  

  /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
• 

  

  /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
• 

  

  /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
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  /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
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  /60

  $1,750,000

  • 3 Beds
  • 2.5 Baths
  • 5,422 Sq Ft

  2334 South Rd, Woodstock, VT 05091

  Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire

  Danny Kogut Williamson Group Sothebys Intl. Realty

  2334 South Rd, Woodstock, VT 05091
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  /40

  $525,000 Sold Jul 18, 2025

  • 2,023 Sq Ft
  • $260/SF
  • 164 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1988

  988 Jenne Rd, Reading, VT 05062

  Located on one of Vermont’s most photographed roads, this iconic Vermont home offers unmatched views from broad windows, which create a warm, sun-soaked interiors. Master craftsmanship is seen throughout the house, from the stunning floors to the designer built-ins. The living room, kitchen, and dining room share an open plan centered around a magnificent stone fireplace. Sliders lead to outdoor

  Jennifer Kirkman KW Vermont Woodstock

  988 Jenne Rd, Reading, VT 05062
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  /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
• 

  

  /60

  $1,349,000

  • 4 Beds
  • 4 Baths
  • 2,869 Sq Ft

  484 Route 12, Hartland, VT 05048

  South facing end of the road retreat, with long views! Equally appealing are expansive western views, for dynamic sunsets! Equestrian amenities of small horse barn, fenced paddocks and direct access to trails! This welcoming residence is certainly unique! A cape style home, with contemporary open floor plan, dramatic windows and a wide deck is seamlessly married to a rustic log cabin, with true

  John Wetmore Wetmore Real Estate

  484 Route 12, Hartland, VT 05048
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  /36

  $440,000 Sold Jul 15, 2025

  • 1,032 Sq Ft
  • $426/SF
  • 116 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  215 Densmore Hill Rd, Hartland, VT 05048

  Midway between Woodstock and South Woodstock you'll find this charming, private, log home. Sited on a 5 +/- acre wooded parcel, with a porch, and deck that are perfect for outdoor dining, and listening to the brook on quiet summer evenings. Inside, there's an open-concept living room and dining area for gathering; with a cozy (gas) fireplace, a cathedral ceiling and a wall of windows providing

  Sue Starr-Adams EXP Realty

  215 Densmore Hill Rd, Hartland, VT 05048
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  /40

  Est $1,910,235 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 3,997 Sq Ft

  2 Border Ln, Woodstock, VT 05091

  2 Border Ln, Woodstock, VT 05091

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