Windsor, VT Homes

/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
/51
$1,300,000 Sold Jul 02, 2025
- 4,228 Sq Ft
- $307/SF
- 91 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1980
608 Fletcher Hill Rd, Woodstock, VT 05091

Open House Sunday, April 13, 12:00 to 2:00 - Tucked away in the serene forests of Woodstock, Vermont, this beautifully remodeled 11-room home offers 4 bedrooms, 4 bathrooms, and 4,225 sq. ft. of luxurious living space on 5.4 private acres. The open-concept design is flooded with natural light, featuring a stunning chef’s kitchen with high-end stainless steel appliances, Vermont soapstone

Sandy Reavill Real Broker LLC

608 Fletcher Hill Rd, Woodstock, VT 05091

/39
Est $3,408,450 Not Listed For Sale
- 10 Beds
- 15 Baths
- 10,206 Sq Ft
3 Church St, Woodstock, VT 05091

3 Church St, 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
/28
$882,500 Sold Jun 18, 2025
- 1,616 Sq Ft
- $546/SF
- 111 Days On Market
- 3 Beds
- 2 Baths
- Built 1989
46 Stewart Ln Unit P-304, Ludlow, VT 05149

Winterplace on Okemo Mountain – A One-of-a-Kind Opportunity! Discover the ultimate mountain retreat at Winterplace, one of Okemo's most sought-after condominium complexes. This exceptional top-floor, 3-bedroom plus loft condominium has been beautifully remodeled, blending modern comfort with classic alpine charm. The expanded loft has been transformed into a spacious second living area, perfect

Katherine Burns William Raveis Real Estate Vermont Properties

46 Stewart Ln Unit P-304, Ludlow, VT 05149

/40
Est $1,534,685 Not Listed For Sale
- 6 Beds
- 4 Baths
- 3,719 Sq Ft
26 River St, Woodstock, VT 05091

26 River St, Woodstock, VT 05091

/39
$610,000
- 2 Beds
- 2 Baths
- 2,248 Sq Ft
2456 Cox District Rd Unit 250.32.02.01, Woodstock, VT 05091

This is a beautiful spacious Ranch. NEW Bosch furnace. New floors in basement. Basement has family room, and 2 large rooms with large windows and separate doors.Living room looks out to beautiful country settings. Large deck off living room.Dining room, eat in kitchen and BRAND NEW large custom bathroom on main floor, just finished yesterday!! This property has a pond and plush lawns.

Dorothea Mongulla High End Realty

2456 Cox District Rd Unit 250.32.02.01, Woodstock, VT 05091
/31
$475,000 Sold Jun 16, 2025
- 2,091 Sq Ft
- $227/SF
- 29 Days On Market
- 2 Beds
- 3 Baths
- Built 1978
85 Townhouse Way Unit 18, Woodstock, VT 05091

Fully furnished and equipped condo nestled in a small quiet community just 5 minutes from historic Woodstock. This is an end unit in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. New windows throughout. Spacious living room anchored by a wood burning fireplace with hardwood floors. A couple of steps down takes you

Gretchjen Smith Williamson Group Sothebys Intl. Realty

85 Townhouse Way Unit 18, Woodstock, VT 05091

/29
Est $700,981 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

/35
$549,000
- 4 Beds
- 3 Baths
- 2,470 Sq Ft
3364 W Woodstock Rd, Woodstock, VT 05091

Welcome to this lovingly updated antique Cape, set on two open, level acres across from the sparkling Ottauquechee River. Just five minutes from Woodstock Village and perfectly positioned on the west side for quick trips to Killington and Pico, this home makes the ideal Vermont getaway.Inside, you’ll find four comfortable bedrooms and a warm, inviting layout designed for making memories.

Keri Cole Williamson Group Sothebys Intl. Realty

3364 W Woodstock Rd, Woodstock, VT 05091
/49
$390,000 Sold Jun 05, 2025
- 2,534 Sq Ft
- $154/SF
- 216 Days On Market
- 4 Beds
- 4 Baths
- Built 1980
732 Bridgewater Center Rd, Bridgewater Corners, VT 05035

Nestled in the scenic town of Bridgewater, Vermont, just 9 minutes from Killington Ski Resort and 25 minutes from Okemo, this charming 2-unit single-family home on 1 acre is a unique mountain retreat and a proven rental success. One of the standout features is the thoroughly renovated first-floor kitchen, which boasts elegant marble countertops and ample counter space, perfect for cooking family

Jeremy Collins Ridgeline Real Estate

732 Bridgewater Center Rd, Bridgewater Corners, VT 05035

/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

/42
$3,500,000
- 6 Beds
- 8 Baths
- 5,142 Sq Ft
18 The Green, Woodstock, VT 05091

Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort

Danny Kogut Williamson Group Sothebys Intl. Realty

18 The Green, Woodstock, VT 05091
/32
$700,000 Sold May 30, 2025
- 1,520 Sq Ft
- $461/SF
- 0 Days On Market
- 2 Beds
- 2 Baths
- Built 1880
13 Golf Ave, Woodstock, VT 05091

Charming circa 1880 cape in Woodstock Village! Located on a quiet dead-end street across from Mt Peg trail head... Walk to all of towns amenities, shops, restaurants and events on Historic Woodstock Green. Championship golf, fly fishing and skiing near by. This lovely antique cottage has hardwood floors through out, open kitchen with first floor laundry. Adjacent is sitting area and dining.

Gretchjen Smith Williamson Group Sothebys Intl. Realty

13 Golf Ave, 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

/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
Est $2,575,692 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

/34
$475,000
- 3 Beds
- 2 Baths
- 1,489 Sq Ft
6852 Us Route 4, Bridgewater, VT 05034

This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

Laird Bradley Williamson Group Sothebys Intl. Realty

6852 Us Route 4, Bridgewater, VT 05034
/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

/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

/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
/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
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

/30
$465,000
- 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
/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

/37
Est $540,030 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,550 Sq Ft
18 Town Line Rd, Plymouth, VT 05056

18 Town Line Rd, Plymouth, VT 05056

/44
$795,000
- 4 Beds
- 2 Baths
- 2,496 Sq Ft
410 Upper Rd, Bridgewater Corners, VT 05035

This 1892 Farmhouse offers two fully furnished and equipped 2-bedroom residences and is superbly located midway between historic Woodstock Vermont and the Killington and Okemo Mt. ski areas, just 15- and 30-minutes' drive away, respectively. The current owners work from home but travel frequently and very successfully (see attached income statement) leased both units on a short-term basis. The

Laird Bradley Williamson Group Sothebys Intl. Realty

410 Upper Rd, Bridgewater Corners, VT 05035
/40
$2,500,000 Sold May 02, 2025
- 3,562 Sq Ft
- $702/SF
- 646 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1979
2051 Goldcoast Rd, Bridgewater, VT 05091

Peace. Tranquility. Big views. Located in the Chateauguay No Town Conservation Area near Woodstock, Wolfstar offers a haven with breathtaking views of the Green Mountains. Meticulously reenvisioned in 2008 by Vermont architect David Beilman, this 15-acre property, cherished as a second home for 35 years, provides complete privacy and understated luxury.The 3,562 sq ft shingle-style home

Story Jenks LandVest, Inc/Woodstock

2051 Goldcoast Rd, Bridgewater, VT 05091

/40
Est $300,297 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,350 Sq Ft
140 Hale Hollow Rd, Bridgewater Corners, VT 05035

140 Hale Hollow Rd, Bridgewater Corners, VT 05035

/49
$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
/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

/35
Est $631,488 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,920 Sq Ft
139 Jennes Rd, Bridgewater Corners, VT 05035

139 Jennes Rd, Bridgewater Corners, VT 05035

/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
/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

/12
Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,673 Sq Ft
391 Phelps Rd, Woodstock, VT 05091

391 Phelps Rd, 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
/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 $914,902 Not Listed For Sale
- 5 Beds
- 5 Baths
- 2,555 Sq Ft
3090 South Rd, Woodstock, VT 05091

3090 South Rd, Woodstock, VT 05091

/60
$859,000
- 7 Beds
- 7 Baths
- 4,581 Sq Ft
7137 Us Route 4, Bridgewater, VT 05034

The historic Bridgewater Inn consists of a 3-bedroom, 3-bath spacious home excellent for families or groups. The home has two covered porches, a large eat-in kitchen, living room with gas fireplace and two game rooms. The house has new furniture, paint and floors along with new flush mounted mini splits.Attached are 4 turnkey suites with entrances separate form the home. The property is

Laura Derderian Killington Valley Real Estate

7137 Us Route 4, Bridgewater, VT 05034

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