Windsor, VT Homes

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  /8

  $300,000

  • Land
  • 55 Acres
  • $5,415 per Acre

  452 Morse Rd, Bethel, VT 05032

  Seldom does a parcel of this quality come onto the open market. Hay fields offering south facing views, 1/2 mile of gravel Town road frontage, and bounded by the Second Branch of the White River. About half of the land is open with the balance being mixed woodland. Truly a spectacular property located on the Bethel/Royalton Town line, convenient to I-89, exit 3.

  Dean Goulet Dunrovin Real Estate

  452 Morse Rd, Bethel, VT 05032
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  /15

  $83,500 Sold Jul 25, 2025

  • Land
  • 1.87 Acres
  • $44,652 per Acre

  • 377 Days On Market

  Lot 1-25 Madison Brook Ln, Stockbridge, VT 05772

  Build your dream home and enjoy amazing views and spectacular sunsets on this elevated building lot in the desirable Highwood community. This cleared home site with roughed-in driveway and sewer rights in the Our World/Highwood community sewer system is approved for a three-bedroom residence. Architectural review and protective covenants ensure that the quality of life in this small community is

  Kyle Kershner Killington Pico Realty

  Lot 1-25 Madison Brook Ln, Stockbridge, VT 05772
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  /40

  Est $248,214 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  4149 Vt Route 107, Stockbridge, VT 05772

  4149 Vt Route 107, Stockbridge, VT 05772
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  /29

  $185,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1514 Blackmer Blvd, Stockbridge, VT 05772

  Don’t miss this opportunity to own a charming country home with great potential. Set on a quiet road in a sunny, open setting, this livable fixer-upper offers a solid foundation for your vision. The main level is fully functional and move-in ready, while the full walkout basement is framed and prepped for finishing—sheetrock is already on site, just waiting for installation. With a little effort,

  Kyle Kershner Killington Pico Realty

  1514 Blackmer Blvd, Stockbridge, VT 05772
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  /17

  $120,000 Sold Jul 16, 2025

  • Land
  • 5.00 Acres
  • $24,000 per Acre

  • 176 Days On Market

  0 Blackmer Blvd, Stockbridge, VT 05772

  1500 feet of frontage on the beautiful White River! This private water frontage along a level shoreline affords easy access to the river, for casual wading in the mesmerizing water! The property has a history of providing anglers with excellent fishing! There is an elevated area on the property that could provide the opportunity of a building site, in an area of minimal flood hazard. Access is

  John Wetmore Wetmore Real Estate

  0 Blackmer Blvd, Stockbridge, VT 05772
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  /37

  Est $248,913 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  2074 Stony Brook Rd, Stockbridge, VT 05772

  2074 Stony Brook Rd, Stockbridge, VT 05772
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  /43

  $679,000

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  108 Heritage Heights, Stockbridge, VT 05772

  Welcome to your dream home in the heart of Vermont! ONLY MINUTES TO KILLINGTON MOUNTAIN RESORT. This stunning 3 bedroom, 2 bath home offers breathtaking views from many of the rooms of the house and the expansive deck allowing you to soak up the beauty of every season. The bright and airy open floor plan is perfect for both relaxing and entertaining. Walk into the spacious tiled mudroom, ideal

  Katie McFadden RE/MAX North Professionals

  108 Heritage Heights, Stockbridge, VT 05772
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  /45

  $370,000 Sold May 30, 2025

  • 1,248 Sq Ft
  • $296/SF
  • 109 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2005

  4189 Stony Brook Rd, Stockbridge, VT 05772

  Private Vermont Retreat for Outdoor Enthusiasts! Escape to your own wonderful haven nestled against the Vermont Wildlife Management Area to ensure lasting privacy and unspoiled natural beauty. Step off your porch and onto a VAST network of snowmobiling, VASA for ATV’s, and mountain biking trails, offering year-round recreation right from your doorstep. Just a short walk to the A-T trails. Whether

  Will Spanos KW Vermont-Killington

  4189 Stony Brook Rd, Stockbridge, VT 05772
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  /3

  Est $238,630 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,410 Sq Ft

  5612 Vt Route 107, Stockbridge, VT 05772

  5612 Vt Route 107, Stockbridge, VT 05772
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  /9

  $99,000

  • Land
  • 3.80 Acres
  • $26,053 per Acre

  20,31,32 Pitt Rd, Stockbridge, VT 05722

  Nestled in the Green Mountain National Forest, this 3-lot offering in the Timber Hawk community spans nearly 4 wooded acres with approx. 600 ft of frontage along Pit Road, bordering the scenic White River. This package offers a unique opportunity for homeowners, builders, or investors: build one private home or explore the potential to develop up to three single-family homes. Three individual

  Tucker Adirondack Lange Vermont Real Estate Company

  20,31,32 Pitt Rd, Stockbridge, VT 05722
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  /55

  $491,976 Sold May 23, 2025

  • 2,088 Sq Ft
  • $236/SF
  • 50 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1988

  166 Tweed River Dr, Stockbridge, VT 05772

  Nicely maintained home with strong rental history. Open floor plan on first floor. Upstairs there are 2 bedrooms with an additional permitted sleeping loft that an owner could turn into a fully enclosed bedroom. This house has 3 bathrooms, a walkout basement, large deck, hot tub, and a custom, double sided fireplace. Near the VAST trail network and a short drive to Killington and Pico. Multi-zone

  Laura Derderian Killington Valley Real Estate

  166 Tweed River Dr, Stockbridge, VT 05772
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  /15

  Not Listed For Sale

  Lot 10 S Hill Rd, Stockbridge, VT 05772

  Lot 10 S Hill Rd, Stockbridge, VT 05772
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  /9

  $49,000

  • Land
  • 1.70 Acres
  • $28,824 per Acre

  LOT #23 Westwind Rd, Stockbridge, VT 05772

  Perched above the White River and a 5 minute walk to the Peavine Day Use Area river swim spot, this raw land is perfect to build your Vermont dream home. Enjoy breathtaking views and take in the Vermont countryside located in the Timber Hawk neighborhood.

  Tucker Adirondack Lange Vermont Real Estate Company

  LOT #23 Westwind Rd, Stockbridge, VT 05772
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  /10

  $13,500 Sold May 20, 2025

  • Land
  • 2.10 Acres
  • $6,429 per Acre

  • 41 Days On Market

  0 Route 107 Unit 5032274, Stockbridge, VT 05772

  An affordable 2 acre parcel of land with 248 foot frontage on a paved State of Vermont maintained year round road. The topography of the parcel makes it best suited for recreational use or for camping. The Town of Stockbridge is home to numerous vacation homes oriented towards skiing at well known Killington. Shopping, casual dining, recreation opportunities and scenic Vermont Route 100 are all

  John Wetmore Wetmore Real Estate

  0 Route 107 Unit 5032274, Stockbridge, VT 05772
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  /39

  Est $622,333 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,770 Sq Ft

  59 Cedarwood Rd, Stockbridge, VT 05772

  59 Cedarwood Rd, Stockbridge, VT 05772
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  /51

  $450,000

  • Land
  • 264 Acres
  • $1,708 per Acre

  0 Peavine Blvd Unit 5046570, Bethel, VT 05032

  First time being offered, a 263-acre parcel of wooded and open land, with local and long-distance views. The topography is level too steep with new and old logging trails that crisscross the property. Multiple house sites have been identified from the recent logging, along with destination locations to admire the views and tranquility that nature offers. For the wildlife enthusiast or hunter,

  Terry Davis Williamson Group Sothebys Intl. Realty

  0 Peavine Blvd Unit 5046570, Bethel, VT 05032
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  /7

  $145,000 Sold May 02, 2025

  • 768 Sq Ft
  • $189/SF
  • 163 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1978

  2195 Music Mountain Rd, Stockbridge, VT 05772

  Located in the picturesque town of Stockbridge on beautiful Music Mountain Rd, this property is ideal for a vacation home or a starter home. Three bedrooms, open concept living room, kitchen with a very large deck the abundance of nature surrounding it. Minutes to Killington and all the local recreation found in that valley.

  Hurley Cavacas New England Lakeside Realty

  2195 Music Mountain Rd, Stockbridge, VT 05772
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  /31

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  2223 River Rd, Stockbridge, VT 05772

  2223 River Rd, Stockbridge, VT 05772
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  /42

  $345,000

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  2903 Vermont 107, Stockbridge, VT 05772

  Come take a look at this 3 bedroom, 1 3/4 bath, well cared for and tastefully updated "Country Charmer". This home has a little bit of everything for everyone. Sited on an amazing well-manicured level lot. There is an additional 2 bay garage w/ample workshop area, a sugar house, and a pony/animal run-in. The first floor has a primary bedroom, 3/4 bath and laundry. Enjoy the sunny, open flow from

  Rose Wright Vermont Heritage Real Estate

  2903 Vermont 107, Stockbridge, VT 05772
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  /41

  $432,523 Sold Apr 14, 2025

  • 2,116 Sq Ft
  • $204/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1956

  192 Stockbridge Common, Stockbridge, VT 05772

  Located on the scenic Stockbridge Common, this expanded ranch-style home offers modern updates and timeless charm. Features include a renovated kitchen and bathrooms, an expansive great room with vaulted ceilings and a cozy woodstove for apres-ski relaxation, a gas fireplace for dining ambiance, a heated mudroom, full basement, and two-car garage. The main home retains beautiful refinished

  Kyle Kershner Killington Pico Realty

  192 Stockbridge Common, Stockbridge, VT 05772
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  /5

  Not Listed For Sale

  1-26 Madison Brook Ln Unit 1-26, Stockbridge, VT 05772

  1-26 Madison Brook Ln Unit 1-26, Stockbridge, VT 05772
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  /2

  $149,999

  • Land
  • 56 Acres
  • $2,655 per Acre

  00 Blackmer Blvd, Stockbridge, VT 05772

  An affordable 56.5 acres of desirable woodland! Pathways heading towards elevated destinations meander up through this tranquil hillside of trees. While some marketable timber has been identified, for many people these classic Vermont woods could be the setting for the construction of a rustic cabin. At the dramatic height of the land the property abuts extensive acreage of conserved land owned

  John Wetmore Wetmore Real Estate

  00 Blackmer Blvd, Stockbridge, VT 05772
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  /57

  $327,000 Sold Mar 31, 2025

  • 3,136 Sq Ft
  • $104/SF
  • 48 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  6230 Vt Route 107, Stockbridge, VT 05772

  Impeccably maintained home in prime location! Welcome to this beautifully cared-for residence, where spaciousness and quality abound. Step into a home featuring stunning Brazilian hardwood floors in the dining and living rooms, adding a touch of elegance to every gathering. The three generously sized bedrooms are comfortably carpeted, while the remaining areas boast durable vinyl plank and tile

  Linda Winter KW Vermont - Barre

  6230 Vt Route 107, Stockbridge, VT 05772
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  /40

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,740 Sq Ft

  3628 Vermont Route 100, Stockbridge, VT 05772

  3628 Vermont Route 100, Stockbridge, VT 05772
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  /12

  $39,000

  • Land
  • 1.58 Acres
  • $24,684 per Acre

  Lot 1-26 Madison Brook Ln, Stockbridge, VT 05772

  Attractive building lot in the desirable Highwood community. This lot offers potential long range views and includes sewer rights in the Our World/Highwood community sewer system, sufficient for a three-bedroom residence. Architectural review and protective covenants ensure that the quality of life in this small community is always preserved. Adjacent to the Green Mountain Trail network for

  Kyle Kershner Killington Pico Realty

  Lot 1-26 Madison Brook Ln, Stockbridge, VT 05772
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  /40

  $315,000 Sold Mar 26, 2025

  • 2,448 Sq Ft
  • $129/SF
  • 75 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1930

  27 Kelly Rd, Stockbridge, VT 05772

  Look no further, this newly renovated home brings classic architecture into the 21st Century, offering both comfort and functionality. Upon entering the home, you are greeted by an open-concept that seamlessly connects the dining area and kitchen. The floorplan encourages interaction and flow, making it perfect for family gatherings and entertaining guests. This ideal home, perched above the

  Christopher Atencio Atencio Real Estate

  27 Kelly Rd, Stockbridge, VT 05772
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  /13

  Not Listed For Sale

  0 New Boston Rd, Stockbridge, VT 05772

  0 New Boston Rd, Stockbridge, VT 05772
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  /8

  $169,000

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  3052 Vermont 107, Stockbridge, VT 05772

  Small home in need of rehab. House has been vacant for several years and is in need of an interior floor system. Located on Rt 107 for easy access to ski areas and I89 exit 3. Commercially zones area. Property goes up the hillside for further development and views. Should be purchased with cash or construction loan and should be verified with town as an approved homestead. Comes with a

  Patricia Harvey Xsell Realty LLC

  3052 Vermont 107, Stockbridge, VT 05772
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  /16

  $60,000 Sold Mar 14, 2025

  • Land
  • 4.24 Acres
  • $14,151 per Acre

  • 7 Days On Market

  TBD Lilliesville Brook Rd, Stockbridge, VT 05746

  This 4.24 acre lot with a barn and river frontage on a quiet rural public maintained road is ready for you to make your own!

  Leslie Drown Leslie Drown Real Estate LLC

  TBD Lilliesville Brook Rd, Stockbridge, VT 05746
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  /24

  Not Listed For Sale

  0 Timber Hawk Rd Unit 68, Stockbridge, VT 05772

  0 Timber Hawk Rd Unit 68, Stockbridge, VT 05772
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  /36

  $183,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,376 Sq Ft

  127 Fort Morrow Knoll, Stockbridge, VT 05772

  LOST VILLAGE LODGE – Exceptional property, location and privacy in central VT – with easy access from I 89 and Rte.100. Adirondack style log cabin with spectacular view that can be recovered. Situated in private development with private drive. Open, light and airy layout.; 2-bedroom cabin w/10 ft. tall Heatilator stone fireplace. Central heating, 2 woodstoves, skylights. 2 porches, deck, gardens.

  Patricia Harvey Xsell Realty LLC

  127 Fort Morrow Knoll, Stockbridge, VT 05772
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  /2

  $20,000 Sold Mar 10, 2025

  • Land
  • 1.00 Acre
  • $20,000 per Acre

  • 0 Days On Market

  0 Whitcomb Hill Rd, Stockbridge, VT 05772

  An affordable one acre parcel of open land with good level access, on a year round town maintained road. Perhaps a good site for a camper trailer or a tiny home! A peaceful stream meanders along one edge of the property. Whitcomb Hill Road is a quiet country road with extensive wooded parcels on either side. The scenic White River is just a short distance away. The Town of Stockbridge currently

  John Wetmore Wetmore Real Estate

  0 Whitcomb Hill Rd, Stockbridge, VT 05772
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  /14

  Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 4,548 Sq Ft

  220 Spring St, Stockbridge, VT 05772

  220 Spring St, Stockbridge, VT 05772
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  /43

  $349,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft

  247 Vulture Mountain Rd, Stockbridge, VT 05772

  This delightful mountain chalet in a private wooded setting offers a perfect blend of comfort and convenience. A gently sloping stone walkway, framed by terraced stone walls, leads to a welcoming entry porch. The garden-level entry opens to a cozy family room with a woodstove, three guest bedrooms, a full bathroom, and a laundry area with a utility sink. Upstairs, the living room shines with

  Kyle Kershner Killington Pico Realty

  247 Vulture Mountain Rd, Stockbridge, VT 05772
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  /3

  $11,000 Sold Mar 10, 2025

  • Land
  • 2.10 Acres
  • $5,238 per Acre

  • 23 Days On Market

  0 Route 107 Unit 5027257, Stockbridge, VT 05772

  An affordable 2 acre parcel of land with 248 foot frontage on a paved State of Vermont maintained year round road. The Town of Stockbridge is home to numerous vacation homes oriented towards skiing at well known Killington. Shopping, casual dining, recreation opportunities and scenic Vermont Route 100 are all within a short drive away!

  John Wetmore Wetmore Real Estate

  0 Route 107 Unit 5027257, Stockbridge, VT 05772
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  /40

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /40

  $672,000 Sold Feb 13, 2025

  • 2,433 Sq Ft
  • $276/SF
  • 139 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1979

  188 Vermont Route 100, Stockbridge, VT 05772

  Nestled along one of Vermont’s most scenic byways, this beautifully updated post and beam home sits majestically on 3.4 acres of pastoral land with frontage on the picturesque Tweed River. The property features mature landscaping, perennial beds bursting with seasonal color, a charming greenhouse for gardening endeavors, and a burgeoning Christmas tree farm that adds a festive touch year round.

  Kyle Kershner Killington Pico Realty

  188 Vermont Route 100, Stockbridge, VT 05772
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  /32

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 856 Sq Ft

  441 Lilliesville Brook Rd, Bethel, VT 05032

  441 Lilliesville Brook Rd, Bethel, VT 05032
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  /33

  $125,000 Sold Feb 07, 2025

  • Land
  • 38 Acres
  • $3,264 per Acre

  • 5 Days On Market

  0 Labadie Rd, Stockbridge, VT 05772

  Beautiful drive in along Fletcher Brook and Taggart Brook to this end of road secluded 38.3 acre parcel. Cleared lot with existing septic design. Selective cutting has provided many trails and clearings. Numerous alternative house sites further into this sloping wooded parcel. Great winter mountain views that could be opened up for year round enjoyment! An unmaintained portion of Labadie Rd

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  0 Labadie Rd, Stockbridge, VT 05772
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  /32

  Est $324,283 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,552 Sq Ft

  77 Music Mountain Rd, Stockbridge, VT 05772

  77 Music Mountain Rd, Stockbridge, VT 05772

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