Windsor, VT Homes

/22
$165,000 Sold May 28, 2025
- Land
- 50 Acres
- $3,300 per Acre
- 0 Days On Market
674 Vermont 12, Hartland, VT 05048

50 wooded Acres available for your dreams to materialize. Lovely and substantial rolling brook with an internal trail system. Majority of property would be accessible by a new bridge which would need to be built. Extensive road frontage and good parking. Great deer hunting grounds and big timber with old growth forest. Older structures are not salvageable and would need to be removed. Excellent

John Bassette Bassette Real Estate Group

674 Vermont 12, Hartland, VT 05048
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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
$459,000
- 3 Beds
- 2 Baths
- 2,314 Sq Ft
7265 U S 4, Bridgewater, VT 05034

This captivating historic cape has been tastefully updated while retaining its unique architectural charm. The spacious floor plan is centered around the lovely eat-in kitchen with its butcher block covered center island all of which is detailed by a striking exposed beamed ceiling. Located off one side of the kitchen is the mudroom entryway with built-ins that introduces you to an inviting

Mary Mayhew Snyder Donegan Real Estate Group

7265 U S 4, Bridgewater, VT 05034
/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
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

/28
$249,000
- 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
/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

/39
Est $3,387,678 Not Listed For Sale
- 10 Beds
- 15 Baths
- 10,206 Sq Ft
3 Church St, Woodstock, VT 05091

3 Church St, Woodstock, VT 05091

/18
$239,500
- 1 Bed
- 1 Bath
- 856 Sq Ft
56 Heritage Condo Way Unit 9, Woodstock, VT 05091

Lots of upgrades to this quiet, two level condo, with lovely views off back baloney. Bonus- new mini split heat pump providing both air conditioning and heat. Kitchen has some upgraded as well with a new dishwasher. This open floor concept condo provides lots of natural sunlight. Cozy up in the living room/dining room and read a book during the winter months overlooking the spacious

Gretchjen Smith Williamson Group Sothebys Intl. Realty

56 Heritage Condo Way Unit 9, 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
Est $1,580,609 Not Listed For Sale
- 6 Beds
- 4 Baths
- 3,719 Sq Ft
26 River St, Woodstock, VT 05091

26 River St, Woodstock, VT 05091

/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
/20
$2,900,000 Sold May 05, 2025
- 3,550 Sq Ft
- $817/SF
- 0 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1986
3086 South Rd, Woodstock, VT 05091

Beautifully and extensively renovated residence, newer construction barn-garage with five overhead doors and an attached one-bedroom apartment (ADU). The land component offers over a mile of private trails perfect for walking, horseback, snowshoeing and biking, including a coursing stream with waterfalls, open meadows, a sledding hill and beautiful landscaping. Detached screened porch and stone

John Snyder Snyder Donegan Real Estate Group

3086 South Rd, Woodstock, VT 05091

/29
Est $705,187 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,930 Sq Ft
42 River St, Woodstock, VT 05091

42 River St, Woodstock, VT 05091

/30
$480,000
- 2 Beds
- 1 Bath
- 768 Sq Ft
37 Atwood Ave, Woodstock, VT 05091

Charming, updated, and perfectly located—this turnkey gem is your ticket to easy living in one of the area’s most adorable neighborhoods! With all the major systems recently upgraded - including a new furnace, hot water heater, Tesla Powerwall, and water purification system - this efficient home is move-in ready.Inside, you’ll love the fresh renovations: a modern kitchen with

Keri Cole Williamson Group Sothebys Intl. Realty

37 Atwood Ave, 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 $876,301 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,632 Sq Ft
25 Slayton Terrace, Woodstock, VT 05091

25 Slayton Terrace, 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
/36
$460,000 Sold Apr 18, 2025
- 2,996 Sq Ft
- $154/SF
- 325 Days On Market
- 5 Beds
- 2 Baths
- Built 1840
24 High St, Woodstock, VT 05091

Constructed in 1840, this post & beam home is situated in the heart of Woodstock Village. A short stroll across the Kedron Brook footbridge to shopping and restaurants, the property is just steps away from all of the amenities this renowned Vermont town has to offer. Woodstock Elementary School, Vail Field and the Woodstock Inn are also just around the corner. Historic High Street, once home to

Danny Kogut Williamson Group Sothebys Intl. Realty

24 High St, Woodstock, VT 05091

/40
Est $1,022,699 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 2,136 Sq Ft
77 Central St, Woodstock, VT 05091

77 Central St, 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
/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

/40
Est $2,888,623 Not Listed For Sale
- 7 Beds
- 4.5 Baths
- 5,306 Sq Ft
4 Bond St, Woodstock, VT 05091

4 Bond St, Woodstock, VT 05091

/40
$465,000
- 3 Beds
- 3 Baths
- 1,600 Sq Ft
2 High St, Woodstock, VT 05091

FLASH OPPORTUNITY AWAITS – Historic c. 1890 1,600 sq/ft. unfinished home in the center of downtown Woodstock. In the heart of everything! LOOKING FOR A FAST SALE - AND A CASH BUYER. The home has been stripped back to framing and is ready for a builder or future investment. It is not currently habitable and will not be able to be sold or shown to someone looking for financing or construction loan

John Bassette Bassette Real Estate Group

2 High St, Woodstock, VT 05091
/39
$410,000 Sold Apr 01, 2025
- 1,052 Sq Ft
- $390/SF
- 97 Days On Market
- 1 Bed
- 1 Bath
- Built 1930
6 Highland Ave, Woodstock, VT 05091

A rare opportunity for Woodstock! An affordable Woodstock Village cottage! The advantage of contemporary solar powered energy efficiency, with connection to an energy storing Tesla battery! The property further benefits from valuable infrastructure components of the municipal sewer system and the Woodstock Aqueduct Water Company! An attractive interior features wood flooring throughout! A large

John Wetmore Wetmore Real Estate

6 Highland Ave, Woodstock, VT 05091

/35
Not Listed For Sale
- 7 Beds
- 5.5 Baths
- 6,472 Sq Ft
3 Bond St, Woodstock, VT 05091

3 Bond St, 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
/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
- 5 Beds
- 3.5 Baths
- 3,488 Sq Ft
28 Pleasant St, Woodstock, VT 05091

28 Pleasant St, Woodstock, VT 05091

/27
$950,000
- 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
/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

/40
Est $525,894 Not Listed For Sale
- 2 Beds
- 2 Baths
- 2,012 Sq Ft
3052 Brownsville Hartland Rd, West Windsor, VT 05089

3052 Brownsville Hartland Rd, West Windsor, VT 05089

/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
/30
$405,000 Sold Mar 14, 2025
- 1,248 Sq Ft
- $325/SF
- 5 Days On Market
- 2 Beds
- 2 Baths
- Built 1989
6293 Route 106, Reading, VT 05062

Welcome to Reading Overlook. This country home has some great views, 10 acres of trails, and the neighbor is one of the most photographed farms in the world. What a beautiful neighborhood to live in. There are 2 bedrooms plus a bonus room, 2 baths, and an open-concept living space. The primary bedroom is en suite and has hardwood floors like the living and dining areas. The kitchen has plenty of

Kevin Barnes William Raveis Real Estate Vermont Properties

6293 Route 106, Reading, VT 05062

/40
Est $300,736 Not Listed For Sale
- 3 Beds
- 1 Bath
- 835 Sq Ft
4157 Route 106, Reading, VT 05062

4157 Route 106, Reading, VT 05062

/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
/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

/21
Est $574,155 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,048 Sq Ft
193 Hartland Hill Rd, Woodstock, VT 05091

193 Hartland Hill 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
$3,700,000 Sold Feb 14, 2025
- 4,286 Sq Ft
- $863/SF
- 283 Days On Market
- 4 Beds
- 5.5 Baths
- Built 1784
322 Weed Rd, Hartland, VT 05048

Ferguson Farm is a restored, classic brick Federal home dating back to 1784, embraced by sugar maples and stone walls. Located just outside the village of Woodstock on a quiet gravel road, the property also features a four-level Shaker barn and offers views across 83 acres of undulating fields, woodlands, and a 4 acre swimming pond. What sets this place apart are those intangible qualities: a

Story Jenks LandVest, Inc/Woodstock

322 Weed Rd, Hartland, VT 05048

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