Windsor, VT Homes

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  /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
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• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
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  /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 $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
• 

  

  /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
• 

  

  /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 $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
• 

  

  /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
• 

  

  /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 $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
• 

  

  /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
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  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /21

  Est $561,735 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
• 

  

  /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
• 

  /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 $1,247,521 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
• 

  

  /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
• 

  

  /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
• 

  

  /39

  Est $744,958 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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 $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
• 

  

  /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
• 

  

  /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
• 

  

  /60

  $1,995,000

  • 3 Beds
  • 2.5 Baths
  • 5,422 Sq Ft

  2334 South Rd, Woodstock, VT 05091

  Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire

  Danny Kogut Williamson Group Sothebys Intl. Realty

  2334 South Rd, Woodstock, VT 05091
• 

  

  /42

  $1,580,000 Sold Dec 30, 2024

  • 4,378 Sq Ft
  • $361/SF
  • 79 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1886

  33 River St, Woodstock, VT 05091

  BEAUTIFULLY renovated rare antique residence in the heart of historic Woodstock! Located in a premiere neighborhood within walking distance to all of towns amenities, hiking on Mtn Tom in your backyard. Situated on a very large lot featuring an in-ground pool accented with arbor and pool house. Lovely perennial gardens and large backyard for those seeking a vegetable garden or room for

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  33 River St, Woodstock, VT 05091
• 

  

  /30

  Est $1,388,485 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,218 Sq Ft

  2409 South Rd, Woodstock, VT 05091

  2409 South 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

Showing Results 41 - 80, Page 2 of 18