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106 Hall Rd, Chester
$210,000
1 Beds ⋅ 1 Baths ⋅ 5059814 MLS
Welcome to your Vermont retreat, an inviting one bedroom, one bath home sat on 2.5 acres at the end of a dead end road in Chester. This 528 square-foot cottage has been thoughtfully updated for four season, comfort, featuring full insulation, a woodstove for cozy evenings, and efficient mini-splits providing both heating and air-conditioning. Recent upgrades include a brand new three bedroom septic system, making expansion a future option and a detached two car garage that offers excellent storage for vehicles, ski gear, or workshop space, along with an electric car charging station hookup. The property is dotted with mature sugar maples, already tapped, bringing an authentic Vermont sugaring tradition right to your doorstep. Just minutes from Chester‘s, charming Village center, and Springfield amenities, and a short drive to Okemo Mountain resort, this location is ideal for year-round, living, a ski getaway, or a weekend retreat. Whether you’re seeking a low maintenance primary residence or a charming, second home, this property blends, rustic appeal with modern convenience in quintessential Vermont setting.

106 Hall Rd, Chester

1372 Potash Brook Rd, Chester
$190,000
2 Beds ⋅ 1 Baths ⋅ 5098053 MLS
Set on 18 forested acres along quiet, dead-end Potash Brook Road in Chester, this peaceful cabin offers a simple and inviting Vermont retreat with no through traffic and a true sense of calm. Well suited for a hunting camp, recreational getaway, or quiet place to unwind, the property provides privacy, natural surroundings, and easy access to the outdoor lifestyle Southern Vermont is known for. The cabin includes propane heat, a spring well, septic, and an inviting and cozy living space for weekends, seasonal use, or time away from the noise of everyday life. The structure will require new footings and is being sold as is, offering an opportunity for the next owner to make needed improvements while enjoying the land, setting, and existing cabin. The property is wooded and rustic in feel, with room to explore, observe wildlife, and enjoy the changing seasons. A brook runs through the land, adding natural character to the setting. Whether used as a base for hunting, hiking, snowmobiling, skiing, or simply relaxing in the woods, this property offers a practical and appealing Vermont escape. Ski areas, trail networks, fishing, and year-round recreation are all within reach, while the setting itself remains quiet, private, and refreshingly simple. If you are looking for land, privacy, and a modest cabin with key systems already in place, this Chester retreat is well worth a look.

1372 Potash Brook Rd, Chester

641 Depot St, Chester
$180,000
3 Beds ⋅ 2 Baths ⋅ 5100719 MLS
Opportunity awaits with this charming home nestled in the heart of Chester, Vermont. Just steps from the village's quaint shops, restaurants, galleries, and local amenities, this property offers a great location and endless potential. In need of some updating, this home is the perfect project for investors, contractors, or buyers looking to restore its character and create something truly special. Whether you're envisioning a primary residence, vacation getaway, or investment property, the possibilities are wide open. With solid bones, classic Vermont charm, and a highly desirable village setting, this is your chance to bring your take to one of Southern Vermont's most beloved communities. Enjoy easy access to skiing, hiking, snowmobiling, and year round recreation all while being part of Chester's vibrant small town atmosphere.

641 Depot St, Chester

469 Williams Rd, Chester
$129,000
5074309 MLS
Beautiful, secluded lot tucked away on the quintessential back roads of Chester, VT. This 10.88± acre parcel offers privacy and serenity while remaining conveniently located near shops and restaurants in Chester, the quaint village of Grafton and within 30 minutes of Okemo, Bromley, and Magic Mountains, and less than an hour to Stratton Mountain. The current owners have completed key improvements, including a cleared homesite, driveway installation, completed septic plan, and 200-amp electric service brought to the lot. Lumber for a Vermont Cottage Shop 20’x30’ cabin is included; it has been stored on-site for over three years, and most (though likely not all) remains usable. A wonderful opportunity to build your dream home or create a peaceful Vermont getaway.

469 Williams Rd, Chester

250 Fenton Rd, Chester
$120,000
5090458 MLS
PRICE DROP!!!! 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, sleeps multiple people with a queen bed in the bedroom, 3 bunks in the bunkroom, and a couch and dining booth that convert to beds as well, and there is an inside and an OUTSIDE kitchen! 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. All measurements approximate

250 Fenton Rd, Chester

Green Mountain Tpke, Chester
$100,000
5081034 MLS
Nestled in the picturesque hills of Chester, this inviting 7.95 +\ minus 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.

Green Mountain Tpke, Chester

Remington Rd, Chester
$80,000
5049898 MLS
Bring your plans and build your own piece of paradise! Just minutes from the iconic Chester town green, this scenic parcel offers the perfect blend of privacy, mountain views, and convenience. With a cleared, gently sloping build site already in place, this lot is ready for your imagination. Underground power is on site, and a well-crafted stone retaining wall, drilled well and septic components are already installed—saving you time and money. Surrounded by a mix of open space and mature forest, the property provides a peaceful, natural setting with long-range views. Enjoy easy access to all that makes Chester special, including the beloved Southern Pie Company, charming shops, and community events like the Chester Fall Festival. Whether you're looking to build now or invest for the future, this is a rare opportunity to own a piece of Vermont close to skiing, hiking, and all-season adventure.

Remington Rd, Chester

1673 Dean Brook Rd, Chester
$28,500
5108359 MLS
This 3.2-acre lot is ideal for anyone seeking a piece of Vermont to enjoy the outdoors. With Great Brook running through the property, you can catch brook trout, pick elderberries, or explore the terrain right at home. A flat, cleared half-acre area is ready for use. Bring your camping gear or RV to relax in a quiet setting that remains close to local conveniences. Just six miles away, quaint downtown Chester offers antique shops, bookstores, the historic Stone Village, local dining, and community events like the annual Chester Fall Festival. Use this location as a central starting point to explore nearby attractions all within 12 miles, including Okemo Mountain Resort, Ludlow, Grafton Village Cheese, and the Vermont Country Store in Rockingham, plus all the everyday conveniences of Springfield. Outdoor enthusiasts can also head to Williams River State Park for fishing and hiking, or enjoy hiking, snowshoeing, and Nordic skiing along the Lost Mine Trail while taking in views of Mount Ascutney. No permitting or perc testing has been completed. Buyers must do their own due dillegence.

1673 Dean Brook Rd, Chester

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