Windsor, VT Homes in ZIP Code 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
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• 

  

  

  /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
• 

  

  

  /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
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  /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
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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

  $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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

  $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
• 

  

  /8

  $110,000 Sold Mar 21, 2025

  • Land
  • 0.97 Acre
  • $113,402 per Acre

  • 162 Days On Market

  1028 Fairbanks Turn, Woodstock, VT 05091

  Nestled within the prestigious Quechee Lakes Landowners Association, this lot offers a serene escape while providing easy access to the community's world-class amenities. Located in the highly desirable Section 1 and just a short golf cart ride to the Quechee Club, this is a rare opportunity to build your dream home in a prime location where no other lots are currently available on Fairbanks

  Heather Ashline BHHS Verani Upper Valley

  1028 Fairbanks Turn, 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
• 

  

  /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
• 

  

  /36

  $1,535,000 Sold Mar 07, 2025

  • 4,681 Sq Ft
  • $328/SF
  • 32 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1993

  10 Fairbanks Turn, Hartford, VT 05059

  10 FAIRBANKS TURN- Elegant and spacious home in ideal central Quechee location with easy access to downtown Woodstock and Hanover. Sited on a large 1.4-acre beautifully landscaped lot with flat lawns and a variety of plantings and garden beds, the property is just minutes from the Quechee Club and its two championship 18-hole golf courses. The house features an open floor plan with high ceilings

  David Donegan Snyder Donegan Real Estate Group

  10 Fairbanks Turn, Hartford, VT 05059
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /38

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,390 Sq Ft

  702 Route 12, Hartland, VT 05048

  702 Route 12, Hartland, VT 05048
• 

  

  /32

  $729,000

  • 4 Beds
  • 4 Baths
  • 2,436 Sq Ft

  168 Thorn Apple Ln, Hartford, VT 05047

  Sweet 4 bedroom / 4 bath home nestled between Hillside and High Pastures Road. Accessed by a private road, you will find this property to be located in a great setting that’s quiet and has views of the Woodstock hillside. This home offers nice generous size rooms throughout and a wonderful floor plan. On the main floor, there is a nice size kitchen open to a large living room with a wood burning

  Lisa Baldwin Coldwell Banker LIFESTYLES - Hanover

  168 Thorn Apple Ln, Hartford, VT 05047
• 

  

  /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
• 

  

  /40

  Est $1,164,310 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  8 Garvin Hill Rd, Woodstock, VT 05091

  8 Garvin Hill 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
• 

  

  /14

  $245,000 Sold Jan 21, 2025

  • 550 Sq Ft
  • $445/SF
  • 24 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2017

  1340 Oxbow Rd, Woodstock, VT 05091

  If you are looking for a private, secluded getaway with a view that is off the grid but with all the comforts of home. You just found it. This little cozy home could be year round or a weekend retreat, with a deck that has a spectacular view. There is a fenced in small garden and a deeded short walk to a waterfall that comes deeded with the property. Recently installed solar panels and generator

  Ara Cardew BHG Masiello Keene

  1340 Oxbow Rd, Woodstock, VT 05091
• 

  

  /40

  Est $551,305 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,472 Sq Ft

  140 Cream Pot Rd, Hartland, VT 05048

  140 Cream Pot Rd, Hartland, VT 05048
• 

  

  /34

  $2,199,000

  • 4 Beds
  • 3.5 Baths
  • 3,564 Sq Ft

  15 Hathorn Hill Street Extension, Woodstock, VT 05091

  An incredibly rare combination of in-Village and country living. 4+ acres and privacy with a pond and heated in-ground pool, yet walk-to-the Green. The residence, designed and built by the well-respected design-build firm Ambrose Construction, offers modern amenities, appliances and construction with a “Vermont Farmhouse” aesthetic. The vaulted ceiling timber frame great-gathering room has

  John Snyder Snyder Donegan Real Estate Group

  15 Hathorn Hill Street Extension, 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
• 

  

  /39

  Est $806,403 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,263 Sq Ft

  200 Garvin Hill Rd, Woodstock, VT 05091

  200 Garvin Hill Rd, Woodstock, VT 05091
• 

  

  /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
• 

  

  /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
• 

  

  /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

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