Chester Vermont Real Estate

If you're dreaming of open skies, peaceful surroundings, and your own slice of Vermont, this property delivers. Just minutes from the charming Chester village green, this land offers the best of both worlds—seclusion and convenience. Step onto the property and take in the wide-open space surrounded by mature trees, offering privacy and natural beauty in every season. Whether you're envisioning gardens, outdoor entertaining space, or simply a quiet retreat to unwind, there's room here to bring your ideas to life - this is the kind of setting that makes you want to stay awhile. The lot is bright and sunny with a gently sloping landscape, ideal for enjoying long afternoons outside. With a VT WW permit in place for a 3-bedroom septic system, you can move forward with confidence. Located in the heart of southern Vermont, with easy access to skiing, hiking, local dining, and year-round events, this property is a rare find.

Building lot with driveway and culverts in place, lot has preliminary site work complete including level grass land area, electrical transformer and 100 amp electrical power plus VTel fiber internet on lot for your new Vermont home. Home must be a minimun of 1,800 square feet of finished living space. Wastewater design and permits in place. A 16' x 25' garage/shed on lot for storage while building your new home. Two miles to Chester Green, plus six ski areas within 25 to 60 minute drive, including Okemo and Stratton. Building lot is located on a dead-end cul-de-sac close to hiking trails and swimming holes. Build here and enjoy all the year-round activities that Vermont has to offer.

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.

This rolling, wooded 10.4+/- acre surveyed parcel in Chester offers 244 feet of road frontage and gently rolling land with 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. 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.

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. Whether you're envisioning a year-round residence or a private getaway, this lot has the natural character and infrastructure to bring your vision to life. State wastewater permit WW-2-4040-1 approved for a 5-bedroom home

Looking for an opportunity in an ideal location? This property offers unbeatable potential in the sought-after town of Chester. Located on a quiet country road, but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property offers both open and wooded acreage with fruit trees to enjoy! Featuring two generously sized garages, this home is ideal for buyers looking to create their dream space. Whether you're a car enthusiast, need extra room for tools, toys, and equipment, or just want the flexibility of additional secure space, these garages add both value and versatility to the home. If you're an investor or a homeowner with vision, this is your chance to transform a fixer-upper into something truly special. This property is an ideal location to Okemo Mountain Resort (under 10 miles) as well as Magic Mountain (11 miles), Bromley Mountain (20 miles) and Stratton Mountain Resort (24 miles) where you can enjoy skiing and all of Vermonts seasonal activities alternating year round. Schedule your private showing today!

Explore this 27.8 acre+/- hillside parcel with mountain views and an approved VT state permit for a 4 bedroom family residence, close to the Village of Chester and adjoining Chester Town land. An easily accessed preliminary site has already been cleared. At the top of the ridge, a nice cleared plateau would be a fabulous spot for an off-the-grid bonus cabin retreat with amazing views! This parcel would qualify for the VT Current Use Program for timber management and tax savings. 1 acre (R-40) zoning and 1478' of frontage along Quarry Road makes further subdivision a possibility. Enjoy the year-round recreation the area offers. Close to Grafton for x-country skiing and mountain biking. Convenient to Magic, Okemo, Stratton and Bromley Mountains for downhill enthusiasts. Convenient to I-91, 3 hours to Boston and 4.5 hours to NYC.

91± Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking 91± acre 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.