- Chester VT Land / Acres $0 to $30000000
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$129,000 | Price Per Acre $0 | Acres 7.95 CHESTER VT
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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.
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$145,000 | Price Per Acre $0 | Acres 22.23 CHESTER VT
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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 | Acres 4.7 Waterfront Owned 1400 Ft. of shoreline | CHESTER VT
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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
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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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$175,000 | Price Per Acre $0 | Total Lots 1 | Acres 12.51 CHESTER VT
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Description:Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home. Located in an area identified for development, it offers both a wonderful building site and long-term investment potential. The septic design is complete, and a 50-foot right-of-way is shown on the survey and is ready to be roughed-in. Bring in electricity, water, and septic, then start building your Vermont dream. Properties like this are increasingly hard to find: private, scenic and close to the heart of the village.
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$200,000 | Price Per Acre $0 | Total Lots 1 | Acres 6.63 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 aproposed 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 offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether you're dreaming of a cozy cabin, amodern 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. There is also an option to purchase 1 of the two lots. This option is for two combined lots.
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Price Change! reduced by $20,000 down 9% on December 19th 2025
$229,000 | Price Per Acre $0 | Total Lots 1 | Acres 27.8 CHESTER VT
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Description:Discover your perfect Vermont getaway on this exceptional 27.8± acre hillside parcel in picturesque Chester, Vermont. Offering sweeping mountain views, privacy, and endless possibilities, this property is ready for your vision. With an approved Vermont state wastewater permit for a 4-bedroom home, you can begin designing your dream family retreat or vacation home right away. A cleared preliminary building site makes for easy access and immediate potential. A logging trail winds to a stunning ridge-top plateau, ideal for an off-the-grid cabin, artist studio, or peaceful sanctuary surrounded by breathtaking vistas. The land borders the Chester Town Forest, ensuring lasting privacy and a connection to nature. Outdoor enthusiasts will love the opportunity to hike, snowshoe, or mountain bike directly from the property. You can also cross-country ski in nearby Grafton or enjoy downhill skiing at Okemo, Magic, Stratton, or Bromley Mountains, all within easy reach. Conveniently located just minutes from Chester Village and close to I-91, this unique property combines natural beauty, accessibility, and investment potential—only 3 hours from Boston and 4.5 hours from New York City. Embrace the best of Vermont’s four-season lifestyle and make this remarkable Chester VT property your own mountain retreat.
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Price Change! reduced by $50,000 down 20% on May 7th 2026
$249,000 | Price Per Acre $0 | Total Lots 1 | Acres 84 CHESTER VT
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Description:84+/- Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property embodies the best of quintessential Vermont countryside living. A perfect horse property with an outdoor arena and lots of dirt roads for trail riding. The land includes several open meadows, perfect for future development, homesteading, or recreation. Enrolled in Vermont’s Current Use Program, the property is both environmentally and financially sustainable. A section of the land was selectively logged, creating a network of trails and plateaus, ideal for hiking, wildlife exploration, or building opportunities. This property offers unparalleled potential for dream homes, private retreats, or as an investment in Vermont real estate. Don’t miss the chance to own this unique Vermont land with its stunning mountain views and incredible development possibilities.
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Price Change! reduced by $10,000 down 3% on December 19th 2025
$290,000 | Price Per Acre $0 | Total Lots 1 | Acres 75 CHESTER VT
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Description:Discover the true meaning of "getting away from it all" at 1175 Quarry Road. This expansive 75 acre parcel is tucked away a full mile up a quiet, dead end dirt road in the desirable town of Chester. Mostly wooded with rising topography. It’s an ideal canvas for a private homestead, a hunting camp, or a seasonal getaway. You get the peace of a dead end road with the convenience of being near four local ski mountains. Land of this scale and privacy is increasingly rare. Come explore and see the potential for yourself. Conveniently located 15 minutes to I-91, Under 30 minutes to Okemo, Bromley and Magic Mountain and under an hour to Stratton and Killington.
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Data last updated June 9th, 2026
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