Windsor, VT Homes

/32
$692,000 Sold Dec 19, 2024
- 2,527 Sq Ft
- $274/SF
- 195 Days On Market
- 3 Beds
- 4 Baths
- Built 1890
1207 Church Hill Rd, Woodstock, VT 05091

Historic Vermont cape house with easy access, only a mile to the Woodstock village center. There is a lot of history and character with beautiful old wood floors and beams. A covered walkway from the attached two-car garage comes into a mud-entry room and right into the classic farmhouse kitchen. Off the kitchen is a generous pantry/laundry room and a bath with shower. The spacious family

John Snyder Snyder Donegan Real Estate Group

1207 Church Hill Rd, Woodstock, VT 05091

/40
Est $1,321,751 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,668 Sq Ft
513 Deer Brook Way, Woodstock, VT 05091

513 Deer Brook Way, Woodstock, VT 05091

/47
$8,000,000
- 3 Beds
- 3.5 Baths
- 5,384 Sq Ft
115 Eastman Rd, Woodstock, VT 05091

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 Williamson Group Sothebys Intl. Realty

115 Eastman Rd, Woodstock, VT 05091
/44
$470,000 Sold Dec 17, 2024
- 1,536 Sq Ft
- $306/SF
- 31 Days On Market
- 3 Beds
- 2 Baths
- Built 1971
2115 E Woodstock Rd, Woodstock, VT 05091

This charming Woodstock home, with river views & versatile floor plan offers two levels of thoughtfully designed living space. This property is a fantastic opportunity for a short-term rental investment or the perfect family getaway for ski season! Upon entering, you’ll immediately notice the attractive wood finishes & natural light, capturing the beauty of the surroundings. The home has 3

Isabella Luhrs BHG Masiello Keene

2115 E Woodstock Rd, Woodstock, VT 05091

/40
Not Listed For Sale
- 5 Beds
- 6 Baths
- 4,510 Sq Ft
5798 South Rd, Woodstock, VT 05071

5798 South Rd, Woodstock, VT 05071

/38
$690,000
- 4 Beds
- 3 Baths
- 2,557 Sq Ft
144 Butternut Ln, Woodstock, VT 05091

The Harry Emmons House an antique brick cape located in the village of Taftsville sited on an open flat village lot. Through the classic covered farm porch enter a gathering room with a brick fireplace, light-filled high ceilings, exposed beams in comfortably sized rooms, a country kitchen, sunny dining room, and a first-floor bedroom with dressing area. Moving upstairs, the second floor has two

Scott Monahan Williamson Group Sothebys Intl. Realty

144 Butternut Ln, Woodstock, VT 05091
/2
$2,850,000 Sold Dec 16, 2024
- 6,403 Sq Ft
- $445/SF
- 158 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1976
2055 Church Hill Rd, Woodstock, VT 05091

Nestled among verdant rolling hills, High Birch is located in one of the area’s most desirable regions at the midpoint between Woodstock and South Woodstock Villages. Designed in 1976 by prominent New York architect Lewis Davis, of Davis, Brody and Bond renowned for his modernist skyscrapers that impacted the skyline of New York City, the home contrasts sleek interior spaces to the surrounding

Danny Kogut Williamson Group Sothebys Intl. Realty

2055 Church Hill Rd, Woodstock, VT 05091

/40
Est $1,452,984 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,329 Sq Ft
282 Fletcher Hill Rd, Woodstock, VT 05091

282 Fletcher Hill Rd, Woodstock, VT 05091

/27
$650,000
- Land
- 78 Acres
- $8,366 per Acre
0 Mecawee Rd, Woodstock, VT 05091

Spectacular 77+ acre parcel on sought after Mecawee Rd. with a perfect combination of level, sloping and hilly terrain. There are multiple building sites including a large cleared area set back off the road with a driveway in place and utilities (electric & fiber optic) at the street. This past Fall, the Sellers went to great lengths to clear the land all the way down to the road opening up

Dan Noble Snyder Donegan Real Estate Group

0 Mecawee Rd, Woodstock, VT 05091
/48
$1,195,000 Sold Dec 12, 2024
- 2,058 Sq Ft
- $581/SF
- 15 Days On Market
- 2 Beds
- 2 Baths
- Built 1972
5274 W Woodstock Rd, Woodstock, VT 05091

This stunner of a farmhouse is a spectacular example of vision, craftsmanship, and a commitment to the finest materials including standing seamed roofs and fully updated systems. The recently installed custom iron doors provide Architectural Digest design aesthetic. The chef’s kitchen showcases a stainless six burner stove along with the quietest Bosch dishwasher available, built-in Bosch

Keri Cole Williamson Group Sothebys Intl. Realty

5274 W Woodstock Rd, Woodstock, VT 05091

/40
Est $2,164,819 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,864 Sq Ft
26 The Green, Wood Stock, VT 05091

26 The Green, Wood Stock, VT 05091

/9
$275,000
- Land
- 0.43 Acre
- $639,535 per Acre
1054 W Woodstock Rd, Woodstock, VT 05091

Ideally located parcel across West Woodstock Road from the Woodstock Farmers Market and 500 yards from the entry to Woodstock Union Middle & High School. Public water and sewer available with access off Prosper Road near the junction of US Road Route 4/West Woodstock Road. Building plans available. Multi-unit housing development potential in zero vacancy environment.

Laird Bradley Williamson Group Sothebys Intl. Realty

1054 W Woodstock Rd, Woodstock, VT 05091
/34
$875,000 Sold Dec 10, 2024
- 1,590 Sq Ft
- $550/SF
- 12 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1880
5 Mountain Ave Unit 4, Woodstock, VT 05091

ICONIC. Just a stroll across Woodstock's famed covered bridge, this historic property is home to five unique condominiums - premier among them is this gracious, bright, and fully renovated two-bedroom home. With beamed nine-foot ceilings, a true turret (complete with curved glass!), a handsome den, spacious bedrooms, private laundry, and dedicated garage parking, this gorgeous condo is equally

Keri Cole Williamson Group Sothebys Intl. Realty

5 Mountain Ave Unit 4, Woodstock, VT 05091

/34
Est $969,082 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,784 Sq Ft
20 Lincoln St, Woodstock, VT 05091

20 Lincoln St, Woodstock, VT 05091

/57
$1,895,000
- 3 Beds
- 2.5 Baths
- 2,688 Sq Ft
20 The Green, Woodstock, VT 05091

Stunning antique cape! Located in the 'heart' of Woodstock. Originally located on Central Street- this home was moved in the 1960's to this location and had an extensive renovation in 2011. The antique brick section was built in 1826- it boasts a spacious living room anchored with a large wood burning fireplace, original wide pine floors and lots of space for entertaining. Adjacent find a

Gretchjen Smith Williamson Group Sothebys Intl. Realty

20 The Green, Woodstock, VT 05091
/26
$1,115,000 Sold Nov 14, 2024
- 2,250 Sq Ft
- $496/SF
- 107 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2006
317 Bridgewater Hollow Road Extension Unit 7-035, Woodstock, VT 05091

If you are looking for a beautiful and quiet off-the-grid mountain retreat, look no further. This custom log home is situated on 106+ acres with incredible mountain views, brooks, pond, orchard, hiking trails, and abundant wildlife and it is just minutes from the Killington ski area and the charming town of Woodstock, VT. The interior of the home is best described as having the feeling of a

Kris Lippi Get Listed Realty

317 Bridgewater Hollow Road Extension Unit 7-035, Woodstock, VT 05091

/34
Est $650,416 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,300 Sq Ft
1782 South Rd, Woodstock, VT 05091

1782 South Rd, Woodstock, VT 05091

/31
$729,000
- 3 Beds
- 3 Baths
- 1,550 Sq Ft
13 Slayton Terrace, Woodstock, VT 05091

Charming cottage located in the heart of historic Woodstock Village with walking distance to all the shops, restaurants and town theatre. Mtn Peg walking trails just a 2 minute walk from front door for those hiking enthusiasts. This home is filled with an abundance of natural sunlight and features all hardwood floors throughout. New kitchen with butcher block counters, stainless appliances,

Gretchjen Smith Williamson Group Sothebys Intl. Realty

13 Slayton Terrace, Woodstock, VT 05091
/40
$680,000 Sold Nov 13, 2024
- 1,470 Sq Ft
- $463/SF
- 157 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1852
5014 South Rd, Woodstock, VT 05071

This charming 1852 Cape has been fully renovated with exquisite finishes. Warm honey-toned antique wide pine floors, soapstone counters with creamy cabinetry in kitchen accented with new stainless appliances. Open floor plan into a sunlit dining room. Enjoy a cup of hot cocoa and a good book curled up in front of the woodstove off the kitchen on a snowy winter day. The first floor also

Gretchjen Smith Williamson Group Sothebys Intl. Realty

5014 South Rd, Woodstock, VT 05071

/26
Est $601,316 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,059 Sq Ft
11 Church St Unit 2, Woodstock, VT 05091

11 Church St Unit 2, Woodstock, VT 05091

/35
$1,895,000
- 5 Beds
- 4.5 Baths
- 4,214 Sq Ft
10 College Hill Rd, Woodstock, VT 05091

10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in

John Snyder Snyder Donegan Real Estate Group

10 College Hill Rd, Woodstock, VT 05091
/18
$70,000 Sold Nov 01, 2024
- 1,124 Sq Ft
- $62/SF
- 141 Days On Market
- 2 Beds
- 2 Baths
- Built 1977
257 Riverbend Way, Woodstock, VT 05091

A wonderful opportunity in the amazing community of Woodstock, Vermont. Only 10 minutes to the charming Woodstock village is this Spacious 2-Bedroom Mobile Home located in Riverside MHP. This home offers an abundance of space and desirable features, making it an ideal retreat for those seeking comfort, convenience, and outdoor adventure. Two Bedrooms, Two Full Bathrooms With bedrooms located at

Heather Ashline BHHS Verani Upper Valley

257 Riverbend Way, Woodstock, VT 05091

/38
Est $1,493,397 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,350 Sq Ft
2876 Hartland Hill Rd, Woodstock, VT 05091

2876 Hartland Hill Rd, Woodstock, VT 05091

/43
$2,250,000
- 5 Beds
- 3.5 Baths
- 3,502 Sq Ft
4945 South Rd, Woodstock, VT 05071

The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron

Story Jenks LandVest, Inc/Woodstock

4945 South Rd, Woodstock, VT 05071
/30
$328,000 Sold Oct 24, 2024
- 1,152 Sq Ft
- $285/SF
- 139 Days On Market
- 3 Beds
- 1 Bath
- Built 1967
5770 Stage Rd, Woodstock, VT 05091

Three bedroom /1 bath wood frame ranch home with walkout lower level on 3.9+/- acres located in Barnard, Vermont. Only 0.6 miles up from the Barnard General Store, it is an easy walk to the general store, PO and Silver Lake. Owned by the same family for over 50 years, this home is simple but sweet and ideal for those looking for one level living. Facing south, you will find this home gets lots of

Lisa Baldwin Coldwell Banker LIFESTYLES - Hanover

5770 Stage Rd, Woodstock, VT 05091

/39
Est $1,724,417 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,216 Sq Ft
343 Spruce Way, Woodstock, VT 05091

343 Spruce Way, Woodstock, VT 05091

/48
$795,000
- 3 Beds
- 2 Baths
- 1,694 Sq Ft
25 Linden Hill St, Woodstock, VT 05091

This classic early 20th Century farmhouse with 3 sunny bedrooms and two baths is sited on a quiet Village Street uphill above the Woodstock Elementary School and across from the public playground at Vail Field and the Woodstock Country Club golf course. The home has benefitted from the thoughtful additions of an eat-in kitchen and a front porch where you can enjoy long summer evenings. A

Laird Bradley Williamson Group Sothebys Intl. Realty

25 Linden Hill St, Woodstock, VT 05091
/2
$650,000 Sold Oct 22, 2024
- 2,016 Sq Ft
- $322/SF
- 69 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1980
157 Deer Ridge Way, Woodstock, VT 05091

Welcome to this beautifully renovated 3-bedroom, 2.5 bathroom home situated on a private road just minutes from the Woodstock Village. This property has undergone extensive remodeling to provide modern comfort and style. The primary suite is featured with a heat pump for heating and cooling, a tastefully tiled bathroom with a heated floor, a walk-in closet, as well as a laundry room. The living

Andrew Kimbell Hall Collins Real Estate Group

157 Deer Ridge Way, Woodstock, VT 05091

/40
Est $452,447 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,574 Sq Ft
1880 South Rd, Woodstock, VT 05091

1880 South Rd, Woodstock, VT 05091

/60
$2,450,000
- 4 Beds
- 3.5 Baths
- 5,573 Sq Ft
851 Riverside Park Rd, Woodstock, VT 05091

"All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers

Richard Higgerson Higgerson & Company

851 Riverside Park Rd, Woodstock, VT 05091
/22
$131,000 Sold Oct 18, 2024
- 1,013 Sq Ft
- $129/SF
- 194 Days On Market
- 3 Beds
- 2 Baths
- Built 2023
7 Park View Way Unit 32, Woodstock, VT 05091

A wonderful opportunity for affordable living in the charming community of Woodstock Vermont. Need help with down payment Champlain Housing Trust may be able to help you, up to $30,000 in deferred loan program for qualified buyers. Home is on site after a long rainy summer ready for the new owner. 2023 Single Wide Mobile home 3 bedrooms 2 bath. Buyers application for Park approval under

Jenna Luce RE/MAX Upper Valley

7 Park View Way Unit 32, Woodstock, VT 05091

/33
Est $625,274 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,654 Sq Ft
4165 Hartland Hill Rd, Woodstock, VT 05091

4165 Hartland Hill Rd, Woodstock, VT 05091

/60
$1,850,000
- 4 Beds
- 3.5 Baths
- 5,000 Sq Ft
2706 E Woodstock Rd, Woodstock, VT 05091

INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, cafe, or retail store), Post Office (with current

John Bassette Bassette Real Estate Group

2706 E Woodstock Rd, Woodstock, VT 05091
/12
$475,000 Sold Oct 17, 2024
- Land
- 4.17 Acres
- $113,909 per Acre
- 64 Days On Market
0 Rose Hill Rd, Woodstock, VT 05091

Secluded and desirable. This parcel boasts privacy despite its unrivaled distance to the happenings of downtown Woodstock, Vermont and even closer proximity to Woodstock's Recreation Center. Break ground into the life you've always dreamed of. Piping has been brought in for town sewer and additional piping is ready for underground electricity to be installed. This 4.17 acre lot provides ample

Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

0 Rose Hill Rd, Woodstock, VT 05091

/26
Est $1,538,757 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 3,043 Sq Ft
76 Grove Hill Rd, Woodstock, VT 05091

76 Grove Hill Rd, Woodstock, VT 05091

/11
$579,000
- Land
- 6 Acres
- $89,628 per Acre
0 Barnard Rd, Woodstock, VT 05091

A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant

John Wetmore Wetmore Real Estate

0 Barnard Rd, Woodstock, VT 05091
/35
$595,000 Sold Oct 11, 2024
- 1,146 Sq Ft
- $519/SF
- 38 Days On Market
- 2 Beds
- 1 Bath
- Built 1950
93 Blackbriar Rd, Woodstock, VT 05091

Privately sited on 1.90 landscaped and wooded acres in downtown Woodstock, this newly renovated mid-century Bungalow offers the perfect combination of original charm, modern amenities, and locational convenience. Renovations were extensive and include new kitchen cabinets, countertops, appliances, and fixtures, bathroom tile shower enclosure, hearthstone for the wood-burning fireplace, and

David Donegan Snyder Donegan Real Estate Group

93 Blackbriar Rd, Woodstock, VT 05091

/37
Est $3,158,662 Not Listed For Sale
- 6 Beds
- 6.5 Baths
- 4,700 Sq Ft
592 Quinn Rd, Woodstock, VT 05091

592 Quinn Rd, Woodstock, VT 05091

/48
$7,250,000 New Construction
- 4 Beds
- 4.5 Baths
- 5,087 Sq Ft
412 Skyland Ln, Woodstock, VT 05091

Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 65 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains

Story Jenks LandVest, Inc/Woodstock

412 Skyland Ln, Woodstock, VT 05091
/37
$2,350,000 Sold Oct 11, 2024
- 3,925 Sq Ft
- $599/SF
- 70 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1910
182 Rose Hill Rd, Woodstock, VT 05091

This historic home was built in 1904 by John Cotton Dana for his family around 1904. The Danas were a prominent family in Woodstock . The Dana House , home of the Woodstock Historical Society, is a major landmark in Woodstock. The house has recently undergone a comprehensive renovation. The large open rooms ,enveloped with light and lovely views , create a sophisticated yet cozy setting. The

Carol Wood Williamson Group Sothebys Intl. Realty

182 Rose Hill Rd, Woodstock, VT 05091

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