Windsor, VT Homes

/39
Est $1,772,086 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

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/32
$80,000
- 3 Beds
- 2 Baths
- 1,008 Sq Ft
185 Riverbend Way, Woodstock, VT 05091

Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first home, vacation getaway, or investment, this property is also

Mendi Michael Engel & Völkers Okemo

185 Riverbend Way, Woodstock, VT 05091
/40
$750,000 Sold May 01, 2025
- 1,840 Sq Ft
- $408/SF
- 43 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1970
6963 South Rd, Woodstock, VT 05071

Enchanting cottage perched on a private knoll with short range views. This property consist of 33 acres with a mixture of open meadow and woods for those looking for an afternoon of walking or snowshoeing. It is currently enrolled in the Current Use Forestry program. Stunning perennial gardens enhance the handsome stone walls and stone walk way to the residence. It's a Garden enthusiasts

Gretchjen Smith Williamson Group Sothebys Intl. Realty

6963 South Rd, Woodstock, VT 05071

/40
Est $438,723 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,374 Sq Ft
1880 South Rd, Woodstock, VT 05091

1880 South Rd, 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
/50
$1,275,000 Sold Apr 02, 2025
- 2,584 Sq Ft
- $493/SF
- 72 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1985
1075 Westerdale Rd, Woodstock, VT 05091

This lovingly maintained property with mountain views has been enjoyed by a single family since its construction in 1985. The open-concept layout is anchored by a stone Rumford fireplace, which along with the southern exposure warms the large easy-to-keep space. The first floor master boasts ample storage with a sliding door for quick access to the grounds. Across from the main house via a

Keri Cole Williamson Group Sothebys Intl. Realty

1075 Westerdale Rd, Woodstock, VT 05091

/26
Est $1,428,193 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

/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
/35
$475,000 Sold Mar 27, 2025
- 1,424 Sq Ft
- $334/SF
- 144 Days On Market
- 4 Beds
- 1 Bath
- Built 1971
378 Fletcher Hill Rd, South Woodstock, VT 05071

Privately located, in desirable South Woodstock! A comfortable home with the benefit of great outside spaces providing the opportunity for recreation, gardening or entertaining! South Woodstock is well known for the potential of having wonderful access to miles of trails enjoyed by equestrians, hikers and snowmobilers. The numerous amenities of historic Woodstock Village are just minutes away!

John Wetmore Wetmore Real Estate

378 Fletcher Hill Rd, South Woodstock, VT 05071

/40
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 3,135 Sq Ft
418 Fletcher Hill Rd, South Woodstock, VT 05071

418 Fletcher Hill Rd, South Woodstock, VT 05071

/32
$899,500
- 4 Beds
- 3 Baths
- 3,190 Sq Ft
598 E Woodstock Rd, Woodstock, VT 05091

This stately, rambling gambrel home offers privacy, convenience, antique charm, and room for everyone. Walking distance to the east end of Woodstock village, on 2.9 lush acres including a fenced backyard, a fenced vegetable garden, and extensive perennial beds. The home is a stunning mixture of antique touches and modern functionality, with beautiful built-ins and closet spaces at every turn. The

Geoff Eckler Real Broker LLC

598 E Woodstock Rd, Woodstock, VT 05091
/24
$230,000 Sold Mar 26, 2025
- 856 Sq Ft
- $269/SF
- 3 Days On Market
- 1 Bed
- 1 Bath
- Built 1984
29 Heritage Condos Unit 29D, Woodstock, VT 05091

OPEN HOUSE CANCELLED.A desirable 1 bedroom condo in Woodstock! Just a short distance from the high school, Farmer's Market, and Thompson Senior Center and only a 3 minute drive from the Woodstock town green and less than 12 minutes to Saskadena Six for skiing. The condo association takes care of all the exterior maintenance (minus clearing off the balcony), and provides interior lockable storage

Franchesca Collins Hall Collins Real Estate Group

29 Heritage Condos Unit 29D, Woodstock, VT 05091

/37
Est $3,079,598 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

/37
$845,000
- 2 Beds
- 1.5 Baths
- 1,714 Sq Ft
403 Horse Shoe Way, Woodstock, VT 05071

Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

Danny Kogut Williamson Group Sothebys Intl. Realty

403 Horse Shoe Way, Woodstock, VT 05071
/43
$700,000 Sold Feb 14, 2025
- 2,616 Sq Ft
- $268/SF
- 15 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1988
944 College Hill Rd, Woodstock, VT 05091

PRIVATE- Cape Cod Home less than a mile to Historic Woodstock Village! This generous sized home consisting of 2616 squ ft. sits on 3.62 secluded acres. Built in 1988 and first time on the market- this home has been well maintained with an abundance of light, generous proportioned rooms with handsome hardwood floors. First floor consists of kitchen with quartz counters and soft neutral toned

Gretchjen Smith Williamson Group Sothebys Intl. Realty

944 College Hill Rd, Woodstock, VT 05091

/39
Est $833,733 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,460 Sq Ft
46 Stewart Ln Unit P305, Ludlow, VT 05149

46 Stewart Ln Unit P305, Ludlow, VT 05149

/50
$945,000
- 4 Beds
- 2.5 Baths
- 2,044 Sq Ft
100 Pomfret Rd, Woodstock, VT 05091

Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting.Inside, you’ll find a sun-drenched home featuring four

Keri Cole Williamson Group Sothebys Intl. Realty

100 Pomfret Rd, Woodstock, VT 05091
/40
$2,750,000 Sold Feb 13, 2025
- 6,443 Sq Ft
- $427/SF
- 495 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1970
318 Ebbin Lockwood Way, Woodstock, VT 05071

Serene, private, contemporary: Sited on a ridge above South Woodstock village, the 54 acre property offers complete seclusion in an elegant setting with an extensive network of trails. The three bedroom main dwelling is sleek and elegant, with an open floor plan crafted to take in the beauty of the site with abundant use of organic material designed to integrate the design with the surrounding

Story Jenks LandVest, Inc/Woodstock

318 Ebbin Lockwood Way, Woodstock, VT 05071

/40
Est $887,987 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,844 Sq Ft
917 Carlton Hill Rd, Woodstock, VT 05091

917 Carlton Hill Rd, Woodstock, VT 05091

/19
$695,000
- Land
- 61 Acres
- $11,474 per Acre
0 Noah Wood Rd, Woodstock, VT 05071

Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

Dan Noble Snyder Donegan Real Estate Group

0 Noah Wood Rd, Woodstock, VT 05071
/2
$1,175,000 Sold Jan 29, 2025
- 2,660 Sq Ft
- $442/SF
- 186 Days On Market
- 3 Beds
- 3 Baths
- Built 2014
6453 South Rd, Woodstock, VT 05071

Round Top Cottage is sited on a knoll just outside the village of South Woodstock on 20 acres, offering complete privacy and views of the rolling hills framing the Kedron Valley. This three-bedroom lodge, fully renovated in 2024, blends modern amenities with rustic elegance. The open floor plan features cathedral ceilings in the main living and dining area, creating an inviting space to gather

Story Jenks LandVest, Inc/Woodstock

6453 South Rd, Woodstock, VT 05071

/40
Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 6,799 Sq Ft
587 Old River Rd, Woodstock, VT 05091

587 Old River Rd, 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
/40
$4,205,000 Sold Jan 27, 2025
- 5,939 Sq Ft
- $708/SF
- 121 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1797
327 Fletcher Schoolhouse Rd, Woodstock, VT 05071

ByBrook Farm: Reimagined, turnkey 1790s farmhouse set in one of Vermont's most loved valleys, perennial gardens, stone walls, a spring fed pond, a brook, and rolling meadows. Quiet luxury. Just outside the hamlet of South Woodstock on 25 acres, the 2-bedroom 4,667 sf farmhouse and the 2-bedroom 1,273 sf guest cottage are connected by a stone pathway through the gardens. In the recent renovations

Story Jenks LandVest, Inc/Woodstock

327 Fletcher Schoolhouse Rd, Woodstock, VT 05071

/38
Est $1,181,000 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,492 Sq Ft
506 Westerdale Rd, Woodstock, VT 05091

506 Westerdale Rd, Woodstock, VT 05091

/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
/37
$975,000 Sold Jan 10, 2025
- 2,944 Sq Ft
- $331/SF
- 28 Days On Market
- 4 Beds
- 3 Baths
- Built 1994
828 Deerbrook Way, Woodstock, VT 05091

A gem of a property on 12 spectacular, mostly wooded, acres in the desirable Deerbrook Way area of Woodstock. Four+ miles to all the amenities of Woodstock Village and 8 miles to the Skyship Gondola at Killington. Built in 1994, this custom designed red oak Post and Beam Contemporary provides everything you would want in a primary residence or a get away vacation retreat. Situated on a 12+ acre

Stan Butler Four Seasons Sotheby's Int'l Realty

828 Deerbrook Way, Woodstock, VT 05091

/40
Est $684,050 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,888 Sq Ft
3256 South Rd, Woodstock, VT 05091

3256 South 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
/60
$1,499,000 Sold Jan 06, 2025
- 3,001 Sq Ft
- $500/SF
- 181 Days On Market
- 3 Beds
- 3 Baths
- Built 1985
1133 Atwood Ln, Woodstock, VT 05091

**Price Improvement**Beautiful country contemporary home offers the best of Vermont living.Private yet convenient,just 6 miles from Woodstock Village and within 30 min. drive to DHMC,Dartmouth College,& Upper Valley shopping, dining, arts and amenities.Set on 28.6 acres,the property feels like a private sanctuary w/ stunning views and southern exposure.Inside,warm wood floors & finishes flow

Tambrey Vutech KW Vermont Woodstock

1133 Atwood Ln, Woodstock, VT 05091

/29
Est $620,172 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,350 Sq Ft
64 Fowler Rd Unit Q103, Ludlow, VT 05149

64 Fowler Rd Unit Q103, Ludlow, VT 05149

/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
/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 $719,162 Not Listed For Sale
- 5 Beds
- 2 Baths
- 2,904 Sq Ft
588 Kendall Rd, Woodstock, VT 05091

588 Kendall Rd, Woodstock, VT 05091

/58
$549,000
- Land
- 20 Acres
- $27,178 per Acre
00 Long Hill Rd, Woodstock, VT 05071

Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west.Located just minutes from

Eric Johnston Four Seasons Sotheby's Int'l Realty

00 Long Hill Rd, Woodstock, VT 05071
/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

/24
Est $524,042 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,034 Sq Ft
708 E Woodstock Rd, Woodstock, VT 05091

708 E Woodstock 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
/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 $1,505,107 Not Listed For Sale
- 5 Beds
- 4 Baths
- 3,042 Sq Ft
612 Church Hill Rd, Woodstock, VT 05091

612 Church Hill Rd, Woodstock, VT 05091

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