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.

Seeking a blissful location. Look no further!! Lot 1: This wooded 3.5+/- acre lot is ready for your building plan. The country location has lots of wildlife and possible views to the North with clearing. A great spot for your family home or vacation home. This property is surveyed and permitted with a septic design for a 3 bdrm home. *It is adjacent to Lot 2 which is 6.3 acres, surveyed and permitted with a septic design for a 3 bdrm home, as well. See MLS# 5057246

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.

Rural Dream! Lot 2: Build your home on this country location just outside of Chester village. The land is a quiet wooded lot with potential southerly views upon clearing. This 6.3+/- acre lot is ready for your building plan. A great spot for your family home or vacation home. This property is surveyed and permitted with a septic design for a 3 bdrm home. *It is adjacent to Lot 1 which is 3.5 acres , surveyed and permitted with a septic design for a 3 bdrm home as well. See MLS# 5057241

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

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.

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.

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.

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!

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.

Discover this exceptional 27.8± acre hillside parcel in picturesque Chester, Vermont, offering sweeping mountain views and endless possibilities. With an approved VT state wastewater permit for a 4-bedroom home, you can begin planning your dream family retreat right away. An easily accessed preliminary building site is already cleared, and a logging trail leads to stunning plateau atop the ridge- the perfect location for an off-the-grid cabin or studio, complete with breathtaking vistas. The property borders Chester Town forest, adding privacy and protected surroundings. Outdoor enthusiasts will appreciate the chance to enroll in Vermont’s Current Use Program, ideal for timber management and potential tax savings. With over 1,000 ft of frontage, future subdivision is also an option. There is granite stone throughout the property for your landscaping projects. Enjoy Vermont’s renowned four-season recreation: hike, snowshoe, or mountain bike right from your doorstep, cross-country ski in nearby Grafton, or head to Magic, Okemo, Stratton, and Bromley Mountains for world-class downhill skiing. Located minutes from Chester Village and convenient to I-91—just 3 hours to Boston and 4.5 hours to NYC—this property blends natural beauty, accessibility, and investment potential.

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.

Escape to southern Vermont with this expansive 75-acre parcel offering the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded mountain retreat, starting a hobby farm, or preserving pristine land for recreation and conservation, this property is your blank canvas. Improvements include a septic system, dug well, electricity and a cleared lot. Conveniently located 15 minutes to I-91, Under 30 minutes to Okemo, Bromley and Magic Mountain and under an hour to Stratton and Killington.