Windsor, VT Homes

• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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 $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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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 $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
• 

  

  /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 $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
• 

  

  /42

  $435,000 Sold Apr 01, 2025

  • 1,514 Sq Ft
  • $287/SF
  • 10 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  773 Hale Hollow Rd, Plymouth, VT 05056

  If you are looking for a home out in the country yet convenient to world class ski resorts, golf, lakes and quintessential villages...this home is for you! Situated on a quiet road with beautiful views the house has two spacious living areas with many windows letting in the natural light. There's a stone hearth and woodstove making it warm and cozy for chilly VT evenings. The dine-in kitchen

  Lorien Kelly Kelley Real Estate, Inc.

  773 Hale Hollow Rd, Plymouth, VT 05056
• 

  

  /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
• 

  

  /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 located midway between historic Woodstock Vermont and the Killington and Okemo Mt. ski areas, just 15- and 30-minutes' drive away, respectively. The property is privately sited above the Ottauquechee (an Abenaki name translated as 'Bright Water') River and directly across from Long Trial Brewing where a main

  Laird Bradley Williamson Group Sothebys Intl. Realty

  410 Upper Rd, Bridgewater Corners, VT 05035
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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 $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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /55

  $975,000 Open Sun 1PM - 3PM

  • 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
• 

  /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

  Est $1,012,803 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 2,555 Sq Ft

  3090 South Rd, Woodstock, VT 05091

  3090 South Rd, Woodstock, VT 05091
• 

  

  /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

  $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
• 

  

  /37

  Est $1,177,591 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,949 Sq Ft

  326 Hall Cir, Woodstock, VT 05091

  326 Hall Cir, 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
• 

  

  /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

Showing Results 41 - 80, Page 2 of 18