- Chester VT Land / Acres $0 to $30000000
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$74,000 | Price Per Acre $0 | Total Lots 26 | Acres 15.5 CHESTER VT
View Details & 14 images
Description:Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.
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$74,500 | Price Per Acre $0 | Total Lots 26 | Acres 16.24 CHESTER VT
View Details & 18 images
Description:Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots. Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!
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Price Change! reduced by $6,000 down 7% on November 9th 2025
$89,000 | Price Per Acre $0 | Total Lots 26 | Acres 10.4 CHESTER VT
View Details & 28 images
Description:Rolling, wooded 10.4+/- acre surveyed parcel in Chester offering 244 feet of road frontage and a mix of hardwoods and pine. A lovely stream meanders through the property which is also dotted with interesting large boulders and old stone walls. If you are looking for privacy, there is potential for a secluded home site set back from the road. Atop the plateau further into the lot there are nice ridgeline views. Utility pole is at the road and the location is just 20 minutes from Okemo and centrally located to conveniences. Explore this acreage for your cabin in the woods, primary home setting or recreational fun.
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$115,000 | Price Per Acre $0 | Total Lots 26 | Acres 3.28 CHESTER VT
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Description:Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether you're dreaming of a cozy cabin, a modern hideaway, or a base for four-season adventure, this property has the flexibility and setting to make it happen. Just minutes to Chester Village, and an easy drive to Okemo Mountain, local trails, and swimming holes, this location strikes the perfect balance between convenience and tranquility.
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$115,000 | Price Per Acre $0 | Total Lots 26 | Acres 3.35 CHESTER VT
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Description:Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether you're dreaming of a cozy cabin, a modern hideaway, or a base for four-season adventure, this property has the flexibility and setting to make it happen. Just minutes to Chester Village, and an easy drive to Okemo Mountain, local trails, and swimming holes, this location strikes the perfect balance between convenience and tranquility.
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$120,000 | Price Per Acre $0 | Total Lots 1 | Acres 3.24 CHESTER VT
View Details & 12 images
Description:This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn—ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out beautifully—creating a prime site to build your dream home. State wastewater permit WW-2-4040-1 approved for a 5-bedroom home.
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$129,000 | Price Per Acre $0 | Total Lots 1 | Acres 7.95 CHESTER VT
View Details & 9 images
Description:Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and village below an ideal backdrop for your dream home or getaway retreat. Whether you’re looking to build, relax, or invest this property is sure to impress. Quiet, scenic, and full of Vermont character, this is a special piece of land where you can truly slow down and enjoy the surroundings—yet still be just a short drive from the heart of Chester.
- Under Contract
$145,000 | Price Per Acre $0 | Total Lots 1 | Acres 22.23 CHESTER VT
View Details & 21 images
Description:Located only 2 miles from the picturesque Chester Green you will encounter this newly created 22 acre building parcel on scenic Lover's Lane. This property consists of a 2 acre meadow ideal for building and a 20 acre woodlot consisting of pine, hemlock, oak and maple for sugaring. Beautiful fieldstone walls border most of the boundary lines. The surveyed parcel has an approved 4 bedroom State Wastewater Permit and Town Subdivision Permit. This property is located within a mile from Pinnacle Recreation Facility and only 12 miles to Okemo Mt. Ski area.
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$153,000 | Price Per Acre $0 | Total Lots 1 | Acres 4.7 Waterfront Owned 1400 Ft. of shoreline | CHESTER VT
View Details & 29 images
Description:Welcome to a place where the sound of the river becomes part of your daily rhythm. This 4.7-acre parcel with an end-of-road location offers an extraordinary 1,400 feet of frontage on the Williams River, creating a private and tranquil retreat just five minutes from the quintessential Vermont charm of Chester Village. The land unfolds beautifully: wide, flat, sun-filled fields stretch toward the river, softened by a scattering of mature trees that add shade, character, and seasonal color. Set along gentle bends in the river, the property feels open yet intimate—an ideal setting for gardens, gatherings, or simply relaxing under the sky. Wildlife is abundant here: deer grazing at dusk, fox weaving through the meadow, and birdsong drifting from the forest edge. A 33-foot camper is already positioned on the designated house site outside the floodplain, allowing you to enjoy the property from day one. Powered by a solar-supported electric generator and a gas generator, it serves as the perfect basecamp while you plan your future build—or as a ready-made retreat just as it is. An 8' x 8' storage unit provides convenient space for kayaks, fishing gear, a mower, or all the toys that come with Vermont living. The house site—where the camper is located—sits entirely outside the floodplain and comes with an approved 4-bedroom wastewater permit and power at the road. While a portion of the land does lie within the floodplain, the property as a whole saw very little impact during the 2023 flood. This land offers a peacefulness that’s hard to find and impossible to replicate.
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$159,000 | Price Per Acre $0 | Total Lots 1 | Acres 5 CHESTER VT
View Details & 3 images
Description:There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town maintained road is easy access and power near by. It is the perfect time to escape, start a new beginning, or just take a weekend to breathe. Please call GMP and communications for availability and cost.
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Data last updated June 2nd, 2026
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