Windsor, VT Homes

/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
/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

/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

/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
/40
$740,000 Sold Aug 18, 2025
- 2,688 Sq Ft
- $275/SF
- 67 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1975
339 Gully Rd, Woodstock, VT 05091

Peaceful Gully Road Retreat. Just minutes from Woodstock Village.Set on 5.1 private acres along quiet and desirable Gully Road, this beautifully updated four-bedroom, two and one-half bath home offers the perfect blend of peaceful country living and convenient proximity to Woodstock shops, restaurants, and schools.The main level features a light-filled, open-concept layout with a dramatic

Derek Cosentino Four Seasons Sotheby's Int'l Realty

339 Gully Rd, Woodstock, VT 05091

/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

/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
/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

/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
/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

/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
/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

/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

/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
/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

/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

/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
/36
$860,000 Sold Aug 11, 2025
- 2,330 Sq Ft
- $369/SF
- 367 Days On Market
- 4 Beds
- 1 Bath
- Built 1865
61 Putnam Rd, Bridgewater Corners, VT 05035

Enjoy a peaceful, park-like setting in the Broad Brook valley at one of Bridgewater’s most iconic farmhouses. Both floors of the home feature large rooms, high ceilings, and beautiful wide-board flooring. The main floor has a large eat-in kitchen with connected butler’s pantry/ mudroom, spacious formal dining room with views, living room, parlor, and a bedroom with a bath just outside the door.

Geoff Eckler Real Broker LLC

61 Putnam Rd, Bridgewater Corners, VT 05035

/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

/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
/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

/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

/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
/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

/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

/57
$985,000
- 3 Beds
- 2 Baths
- 2,760 Sq Ft
616 Rose Hill Rd, Woodstock, VT 05091

This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house

Carol Wood Williamson Group Sothebys Intl. Realty

616 Rose Hill 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

/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

/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
/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

/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

/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
/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

/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
$975,000
- 3 Beds
- 3 Baths
- 1,656 Sq Ft
509 Church Hill Rd, Wood Stock, VT 05091

Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

Carol Wood Williamson Group Sothebys Intl. Realty

509 Church Hill Rd, Wood Stock, 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

/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

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