Windsor, VT Homes

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  /42

  $985,000

  • 5 Beds
  • 4 Baths
  • 3,625 Sq Ft

  1166 Rte 100, Weston, VT 05161

  Nearly 5,000 sq ft of flexible living space in one of Vermont’s most desirable towns—perfect for second-home buyers or investors. This unique property offers two distinct living areas under one roof: a beautifully designed walk-out lower level apartment ideal for rental income, in-law suite, or guest quarters, and an updated main level with style and comfort. The main level features a modern

  Carrie Mathews Winhall Real Estate

  1166 Rte 100, Weston, VT 05161
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  /32

  $159,000 Sold Aug 01, 2025

  • Land
  • 4.00 Acres
  • $39,750 per Acre

  • 0 Days On Market

  11 and 12 Boynton Rd, Weston, VT 05161

  Discover two beautiful building lots nestled along a quiet, scenic country road - ideal for you dream home or country retreat. These prime lots boasts a perfect blend of privacy, charm and beauty. A well was installed in 2013 on Lot 11. An adjacent 5.8 parcel known as the Woodcock Farm Common Land is available for your enjoyment. A 50' wide Right A Way travels between the two lots to

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  11 and 12 Boynton Rd, Weston, VT 05161
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  /32

  Est $509,223 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft

  15 Markham Ln, Weston, VT 05161

  15 Markham Ln, Weston, VT 05161
• 

  

  

  /51

  $1,400,000

  • 7 Beds
  • 5.5 Baths
  • 4,914 Sq Ft

  49 Burton Rd, Weston, VT 05161

  Location, Views, and Room for Everyone – It’s All Here and Waiting for You! Offering maximum warmth, comfort, and charm, this beautifully-built and well-maintained home features traditional New England architecture on 7+ picturesque and tranquil acres just outside the delightful village of Weston. The inviting layout features classic design and rich architectural details with formal and informal

  Claudia Harris Mary Mitchell Miller Real Estate

  49 Burton Rd, Weston, VT 05161
• 

  

  

  /55

  $722,000 Sold Jul 22, 2025

  • 2,110 Sq Ft
  • $342/SF
  • 229 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  45 Casper Ln, Weston, VT 05161

  This gorgeous high quality three-bedroom house with over 2100 of finished living space is situated on two beautifully landscaped acres in the special town of Weston. Located in the heart of ski country with four ski areas close by, this home has much to offer. The house has a wonderful feel of relaxation and welcoming. As a four-season destination, Weston and the surrounding area has much

  Chuck Sweetman Mary Mitchell Miller Real Estate

  45 Casper Ln, Weston, VT 05161
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  /35

  Est $294,898 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,576 Sq Ft

  650 Main St, Weston, VT 05161

  650 Main St, Weston, VT 05161
• 

  

  /49

  $849,000

  • 7 Beds
  • 6 Baths
  • 4,642 Sq Ft

  41 Lawrence Hill Rd, Weston, VT 05161

  This charming historic home, nestled on a hillside in the heart of Weston Village, offers a unique blend of old-world character and modern comfort. Built in the 1800s, the house is rich with architectural details, including aged barn wood accents, warm pine floors, and sunlit rooms that create a welcoming atmosphere for family and friends.The spacious living area is perfect for

  Jessica Citera Cummings & Co

  41 Lawrence Hill Rd, Weston, VT 05161
• 

  

  /34

  $565,000 Sold Jul 18, 2025

  • 1,471 Sq Ft
  • $384/SF
  • 56 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1989

  31 Highland View Rd, Weston, VT 05161

  Welcome to your Vermont log home retreat, nestled on 3 serene, flat acres, this beautifully crafted log home with post-and-beam interior offers timeless charm and spacious living just minutes from downtown Weston and Londonderry.inside you are welcomed into a warm, open-concept layout where the living room, dining area, and kitchen flow effortlessly under wood-beamed ceilings. The main floor

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  31 Highland View Rd, Weston, VT 05161
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  /13

  Est $334,185 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,128 Sq Ft

  749 Main St, Weston, VT 05161

  749 Main St, Weston, VT 05161
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  /30

  $1,200,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,118 Sq Ft

  124 Turner Rd, Weston, VT 05161

  A mountain retreat surrounded on three sides by the Green Mountain National Forest and yet only a few miles from the village green in Weston and the Weston Playhouse. Big views to breathe in. Turner Farm is located on a dead end road above the trout club. The 134 acre parcel covers the eastern slope of Peabody Hill; the land climbs to an elevation of 2,770 feet and is threaded with trails for

  Dia Jenks LandVest, Inc/Woodstock

  124 Turner Rd, Weston, VT 05161
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  /24

  $379,000 Sold Jul 14, 2025

  • 360 Sq Ft
  • $1053/SF
  • 60 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2023

  173 Piper Hill Rd, Weston, VT 05161

  Nestled on over 9 picturesque acres along desirable Piper Hill Road, this property offers the perfect blend of privacy and convenience—located less than a mile from the heart of historic Weston village, and 15-30 minutes from 4 major ski areas in southern VT. With sweeping views, mature trees, and open meadows, it's an ideal setting for a full-time residence, vacation getaway, or future dream

  Christopher Cummings Cummings & Co

  173 Piper Hill Rd, Weston, VT 05161
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  /28

  Est $439,572 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft

  700 Main St, Weston, VT 05161

  700 Main St, Weston, VT 05161
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  /55

  $1,195,000 Under Contract

  • 3 Beds
  • 5 Baths
  • 4,075 Sq Ft

  134 Lawrence Hill Rd, Weston, VT 05161

  Nestled on 10.2 acres of rolling woods, stone walls and beautiful gardens and attractive stone patio. This updated modern farmhouse was lovingly constructed by its owner, a lifelong home builder. With plenty of space to entertain guests, it features a bright newly remodeled kitchen, wide plank oak floors and a stone fireplace. Possibilities are endless with a bevy of bedrooms, spacious

  Kathy Snyder Mary Mitchell Miller Real Estate

  134 Lawrence Hill Rd, Weston, VT 05161
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  /29

  $543,000 Sold Jul 08, 2025

  • 2,185 Sq Ft
  • $249/SF
  • 38 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1969

  35 Markham Ln, Weston, VT 05161

  Tucked above the historic village of Weston, this charming Cape-style home offers a serene retreat on 3.5 private acres. Wood beams bring authentic charm to the newly renovated kitchen. The residence features a spacious Great Room with vaulted ceilings and a Jotul wood stove, perfect for entertaining or quiet nights at home. The main level includes two bedrooms and a full bath, while the upper

  Christiane Carroccio TPW Real Estate

  35 Markham Ln, Weston, VT 05161
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  /27

  Est $851,121 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,048 Sq Ft

  520 Piper Hill Rd, Weston, VT 05161

  520 Piper Hill Rd, Weston, VT 05161
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  /59

  $740,000 Under Contract

  • 6 Beds
  • 7 Baths
  • 3,380 Sq Ft

  815 Vermont Route 100, Weston, VT 05161

  Escape to this enchanting circa 1830 Colonial, a quintessential Vermont country retreat perfectly positioned at the edge of Weston Village with breathtaking Green Mountain views. Embrace the beauty of nature with nearby XC ski trails, snowmobiling, and snowshoeing, plus five renowned ski mountains just a short drive away. In summer, Weston comes alive with concerts on the village green, summer

  Lee Brown Four Seasons Sotheby's Int'l Realty

  815 Vermont Route 100, Weston, VT 05161
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  /31

  $375,000 Sold Jun 30, 2025

  • 1,573 Sq Ft
  • $238/SF
  • 58 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1955

  905 Vermont Route 100, Weston, VT 05161

  This adorable, well-maintained raised ranch will welcome you to Weston with open arms and an open heart! The property include 11 beautiful wooded acres, ripe for exploration and adventure, with a large backyard, and the sunny lot will be a gardener’s delight. The house has been lovingly cared for and features what feels like a surprisingly large floor plan with the entry, living, dining, and

  Claudia Harris Mary Mitchell Miller Real Estate

  905 Vermont Route 100, Weston, VT 05161
• 

  

  /35

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  392 Piper Hill Rd, Weston, VT 05161

  392 Piper Hill Rd, Weston, VT 05161
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  /37

  $549,000

  • 4 Beds
  • 2 Baths
  • 2,541 Sq Ft

  106 Vermont Route 100, Weston, VT 05161

  This historic property located on Weston Island, the original settlement of the village of Weston, was once home to the area's beloved country doctor. Rich in antique farmhouse allure, it has been thoughtfully updated for modern living. The first floor features a generous mudroom, a living room with wide plank floors and wood stove, and a den with built ins and a wood burning fireplace that could

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  106 Vermont Route 100, Weston, VT 05161
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  /24

  $300,000 Sold Jun 24, 2025

  • Land
  • 33 Acres
  • $9,091 per Acre

  • 0 Days On Market

  122 Jaquith Rd, Weston, VT 05161

  Discover an extraordinary 33-acre parcel in Weston, Vermont, offering a rare combination of privacy, panoramic mountain views, and abutting thousands of acres of protected National Forest. This breathtaking property features open meadows, a spring-fed pond, and a peaceful blend of hardwoods and evergreens, creating a tranquil setting for your future home or retreat. With long-range views across

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  122 Jaquith Rd, Weston, VT 05161
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  /40

  Est $794,889 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,604 Sq Ft

  128 Dale Rd, Weston, VT 05161

  128 Dale Rd, Weston, VT 05161
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  /33

  $325,000

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  85 Slawson Rd, Weston, VT 05161

  This adorable Weston home offers more than meets the eye – come check it out! The house sits on just shy of 2.5 acres and is adjacent to thousands of conserved acres in the Okemo State Forest and the Mount Holly Conservation Trust. Slawson Road is a quiet neighborhood with a nice mix of primary and vacation homes, offering true peace and quiet, and is located almost equidistant to Weston and

  Claudia Harris Mary Mitchell Miller Real Estate

  85 Slawson Rd, Weston, VT 05161
• 

  

  /40

  $575,000 Sold Jun 13, 2025

  • 2,209 Sq Ft
  • $260/SF
  • 51 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1997

  26 Summit Trails Rd, Weston, VT 05161

  Perched above the mountain village of Weston in a private, wooded 3+ acre lot, this light and spacious 3 bed/3 bath contemporary features multiple indoor and outdoor spaces that capture classic Vermont living. Redesigned and rebuilt in 1997 by a top area architect and contractor, it sports updated appliances and fixtures and a new roof installed in 2021. The first floor includes a welcoming

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  26 Summit Trails Rd, Weston, VT 05161
• 

  

  /23

  Est $841,935 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  95 Summit Trails Rd, Weston, VT 05161

  95 Summit Trails Rd, Weston, VT 05161
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  /18

  $199,000

  • Land
  • 19 Acres
  • $10,596 per Acre

  00 Boynton Rd, Londonderry, VT 05148

  Located off quiet, town-maintained Boynton Road in Londonderry, this nearly 20-acre wooded parcel offers the perfect opportunity to build your dream home in the heart of southern Vermont. With power and fiber optic internet available at the street and a state-issued wastewater permit in place for a five-bedroom residence, this raw land is ready for your vision. A small stream runs parallel to the

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  00 Boynton Rd, Londonderry, VT 05148
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  /28

  $195,000 Sold May 22, 2025

  • 1,568 Sq Ft
  • $124/SF
  • 34 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  119 Old Tavern Rd, Weston, VT 05161

  Tucked back on a peaceful 3.5 acres surrounded by trees, just .5 miles from the Weston Fields.This unit offers great space with a high ceilings, a laundry room, separate dining area, two bedrooms with large closets and a primary bedroom with a large closet and private bath. A gas stove warms the living area on the cooler days. A slider walk out to the back deck where you can enjoy the quiet

  Jessica Citera Cummings & Co

  119 Old Tavern Rd, Weston, VT 05161
• 

  

  /29

  Est $615,257 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,788 Sq Ft

  81 Summit Trails Rd, Weston, VT 05161

  81 Summit Trails Rd, Weston, VT 05161
• 

  

  /31

  $475,000

  • 4 Beds
  • 2 Baths
  • 1,715 Sq Ft

  151 Burton Rd, Weston, VT 05161

  This beautifully updated 4-bedroom chalet-style home is nestled on a serene 1.4-acre lot, just minutes from the heart of Weston, the iconic Vermont Country Store, and the renowned Weston Playhouse. Featuring a freshly painted interior, newly finished walkout basement, and a new Harman pellet stove that efficiently heats the main level and upper loft, this home is move-in ready and perfect for

  Gary Coger Four Seasons Sotheby's Int'l Realty

  151 Burton Rd, Weston, VT 05161
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  /52

  $450,000 Sold Dec 17, 2024

  • 1,950 Sq Ft
  • $231/SF
  • 61 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1950

  225 Old County Rd, Weston, VT 05161

  Welcome to Weston! One of the most desirable towns in Vermont known for its picturesque village, world class theatre and the Vermont Country Store. You will find restaurants, shops, and galleries in this amazing community. Close to hiking and skiing, near the Green Mountain National Forest and just down the road from the Priory, this property could be yours! In the same family for 65 years, first

  Tyleen Murray Kelley Real Estate, Inc.

  225 Old County Rd, Weston, VT 05161
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  /38

  Est $577,569 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft

  198 Highland View Rd, Weston, VT 05161

  198 Highland View Rd, Weston, VT 05161
• 

  

  /31

  $300,000

  • 2 Beds
  • 1.5 Baths
  • 1,070 Sq Ft

  27 Lawrence Hill Rd Unit 5, Weston, VT 05161

  Tuttle Barn Unit 5 enjoys one of Weston's best views overlooking the West River waterfalls and historic Mill with lovely meadows and mountains beyond! The handsome c. 1907 barn was converted to condos in 1983 and, with just five units “the barn” offers the best of in-town living with a small footprint and low-to-no maintenance demands. This charming unit offers two bedrooms (plus a loft) and

  Claudia Harris Mary Mitchell Miller Real Estate

  27 Lawrence Hill Rd Unit 5, Weston, VT 05161
• 

  

  /40

  $810,000 Sold Nov 15, 2024

  • 2,974 Sq Ft
  • $272/SF
  • 519 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1850

  209 Holden Hill Rd, Weston, VT 05161

  Beautifully situated on 27.90 acres in both Landgrove and Weston, this beautifully maintained Vintage residence is loaded with historical charm. The setting is quintessential Vermont w/ meadow, woodlands, stonewalls, a pond & wonderful views of the surrounding mountain ridge lines. All of which combine to make this a very special offering. Just 20 minutes to Bromley, Okemo, & Stratton skiing &

  Kim Morgan-Wohler Wohler Realty Group

  209 Holden Hill Rd, Weston, VT 05161
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  /40

  Est $637,795 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  40 Holden Hill Rd, Weston, VT 05161

  40 Holden Hill Rd, Weston, VT 05161
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  /32

  $300,000

  • 2 Beds
  • 1.5 Baths
  • 1,070 Sq Ft

  27 Lawrence Hill Rd Unit 5, Weston, VT 05161

  Tuttle Barn Unit 5 enjoys one of Weston's best views overlooking the West River waterfalls and historic Mill with lovely meadows and mountains beyond! The handsome c. 1907 barn was converted to condos in 1983 and, with just five units “the barn” offers the best of in-town living with a small footprint and low-to-no maintenance demands. This charming unit offers two bedrooms (plus a loft) and

  Claudia Harris Mary Mitchell Miller Real Estate

  27 Lawrence Hill Rd Unit 5, Weston, VT 05161
• 

  

  /24

  $260,000 Sold Nov 05, 2024

  • 660 Sq Ft
  • $394/SF
  • 9 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  920 Vermont Route 100, Weston, VT 05161

  This sweet cottage is small but mighty and as cute as a bug! The house is just north of the charming village of Weston with summer theater and music concerts nearby and close proximity to four-season recreation, cultural events and everything that makes Southern Vermont such a special place to call “Home.” There are two bedrooms and one bathroom, full kitchen, living room, and a small deck at the

  Claudia Harris Mary Mitchell Miller Real Estate

  920 Vermont Route 100, Weston, VT 05161
• 

  

  /40

  Est $544,757 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,208 Sq Ft

  79 Obed Moore Rd, Weston, VT 05161

  79 Obed Moore Rd, Weston, VT 05161
• 

  

  /10

  $189,000

  • Land
  • 34 Acres
  • $5,642 per Acre

  00 Vermont Route 100, Weston, VT 05161

  If you have been keeping your eye on this property, now is the time to make a move as the price has been reduced! Purchase your land now and get your permits in place to work on your plan! Are you ready for a lifestyle change or a project to get you enjoying the outdoors? This Weston parcel borders Okemo State Forest - 33.5 Acres of Vermont is waiting for your cabin...or perhaps you have a tiny

  Tyleen Murray Kelley Real Estate, Inc.

  00 Vermont Route 100, Weston, VT 05161
• 

  

  /40

  $489,000 Sold Nov 04, 2024

  • 2,145 Sq Ft
  • $228/SF
  • 63 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1945

  87 Lawrence Hill Rd, Weston, VT 05161

  ENJOY THIS IS VERMONT!! Location-Location!! 3/10 of a mile from the Weston Green, the playhouse, country stores, town hall, post office, and restaurants, this 5-bedroom 2145 finished sq ft cape built in 1945 has been enjoyed and cared for by the seller for 40 years. The 3-acre property provides privacy and includes a wonderful spring fed pond and relaxing mountain views. A beautiful large

  Chuck Sweetman Mary Mitchell Miller Real Estate

  87 Lawrence Hill Rd, Weston, VT 05161
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  /34

  Est $595,248 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,879 Sq Ft

  50 Burton Rd, Weston, VT 05161

  50 Burton Rd, Weston, VT 05161
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  /33

  $164,500

  • Land
  • 5.00 Acres
  • $32,900 per Acre

  0 Route 155 Unit 4905774, Weston, VT 05161

  OWNER TERMS POSSIBLE FOR THE RIGHT BUYER! Driveway has been improved to drive up to a cleared potential house site!Two parcels with two installed septic systems being sold as one offering. These parcels are private, yet convenient to to the Village of Weston, Okemo for skiing, and near the Priory.The land behind these lots is a large parcel owned by the neighbor.There is access

  Tyleen Murray Kelley Real Estate, Inc.

  0 Route 155 Unit 4905774, Weston, VT 05161

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