Properties Near 525 Route 103 N Chester, VT

The Stone Cottage began its long history as a schoolhouse built as the Civil War was nearing its conclusion in 1864. Scottish craftsmen from the Aberdeen region constructed the sturdy structure using a technique referred to as 'snecked ashlar' with hewn ashlar stones laid in horizontal and vertical courses with spaces filled with smaller 'snecks joined with mortar. The random patchwork yields a strong and handsome bond that endures the harsh climates of Scotland and Vermont. Comprehensively renovated 25 years ago the home centers around great room featuring a substantial stone fireplace with vaulted wood paneled ceiling and a wall of windows overlooking the Williams River below. The gracious country kitchen is accented with custom cherry cabinets, built-in dish hutch, granite topped island and expansive bay windows next to the kitchen table and a sliding glass doors opening out to a wide stone paved patio. The light and airy primary bedroom and ensuite bath is located on the second floor, and the private guest quarter bedroom is sited on the lower level with walk-out access to a sitting area above the scenic waterfront. The detached 3 level gambrel barn-garage offers potential for a variety of uses including a workshop and additional residential accommodation. Chester's famous 'Stone Village' is nearby and the Okemo Ski is a 20 minute drive away.

The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some love, and this property is looking for that person who can bring it back to its former glory days. As they say, the buildings have good bones, so consider this a blank canvas to do whatever you please for renovations. Since it's very original, you can update without having to tear out former "improvements" that might have taken away the antique charm. Since it was a working farm at one time, it still has the old silo. Years ago, this was made into a 4-level living unit. You can bring this back to life and use it as a very unique vacation rental or keep it as a very cool place for your kids and grandkids - much cooler than a treehouse! The attached barn is huge and for years it was used as a barn antique store. You could do that again, or you could use it for animals. With the open land which supplies a big supply of hay each year, this property would be great for horses, cows, and other large animals. There is also a sugar house, plus a separate building out front that was also used for the antique business. Several apple trees, a huge rhubarb patch, and more! Don't wait on this one!

Nestled in peaceful seclusion on 21.4 acres, this inviting split-level home is ready to welcome its next owners. While privately situated and out of view from the road, the property remains conveniently close to VT Routes 106 and 10, offering the perfect blend of privacy and accessibility. Step inside from the charming covered porch into a spacious mudroom with Vermont slate flooring, providing interior access to the one-car garage with additional storage space. The lower level also features a large workshop with laundry, a generous family room, and an interior staircase leading to the main living area. Upstairs, enjoy a bright and functional kitchen with ample counter space and cabinetry, opening to the dining area and living room—both highlighted by hardwood floors. Down the hall, you'll find a full bathroom, two well-sized bedrooms, and a primary suite complete with its own private bath, all with new paint and flooring! Outdoor living is a dream with two decks accessible from the dining room, a professionally installed fenced yard—perfect for safe play or pets—and a charming log cabin-style shed for storage. The expansive grounds provide level, open space for a camper, boat, or future recreational projects. An added bonus: the property has subdivision potential. Preliminary plans have been made, including a utility easement already in place for a possible second lot. Don’t miss this opportunity to own a versatile and serene piece of Vermont!

This delightful home is sure to please. Set in a lovely wooded cul-de-sac, surround yourself with lovely, terraced landscaping, stone walls and a peaceful wooded setting to while away the hours. This beautiful well cared home features many delightful settings. The living room features a cathedral ceiling and stone fireplace, with a wood stove insert, along with many windows to bring in the outdoors. The kitchen is a cook's dream with lots of cabinets, counters with room for the family while making dinner. The adjacent dining room offers another option for a gas insert in the second stone fireplace. Enjoy your dessert in the 4-season room or perhaps the deck to as you enjoy the late afternoon peace. Additionally, there are 4 bedrooms and an additional room than can be used as an office or a study and 2 baths. The full basement has a room for a workout or hobby room. The 2 car garage and additional wood shed are added features This is a well-cared for home with many improvements in a great setting.

Historically known as the Frank Harris House, this distinguished circa 1880 Queen Anne style Victorian commercial building on .75+/- acres has long been a landmark presence in the village of Chester. With its welcoming veranda and timeless charm, the property has served as a thriving office for many years and has many period architectural details throughout such as, a unique, colored transom window in the first floor meeting room, a white brick decorative fireplace with accent mirror in the large office/reception area, graceful bay windows, a mix of hardwood and softwood floors and a slate roof with diamond patterned bands. The heating system has recently been upgraded with a new direct vent boiler and efficient hydronic wall units to ensure comfort throughout the seasons. Additional features include a spacious kitchen area, 1.5 baths, a handicap access ramp and public water and sewer. The attached rustic two-story barn offers additional storage space and there is a large, second story three-season porch! Whether your vision involves refreshing the property for use as office space, transforming it to a multi-unit investment property or restoring it to a grand, single family home, the Harris House presents a rare opportunity—centrally located in the heart of Chester and within walking distance to the town green, shops, elementary school and recreation area. Also listed as under MLS #5058558.

Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a beautifully curated vintage Martini pedestal sink. Original wide plank wood floors have been lovingly refinished, preserving a sense of warmth and history. The standing seam metal roof offers long-term durability, and outside, the expansive level lawn and massive post-and-beam barn are overflowing with potential—whether for gardening, recreation, storage, or transforming into additional living space. A standout opportunity for anyone seeking a move-in-ready home with timeless charm and room to grow. This home is in a prime location near Chester’s Stone Village, Grist Mill, Smitty’s Market, and more. Just 15 min to Okemo and the lakes, 30 min to Bromley, and under an hour to Killington, Stratton, and Mount Snow, it’s ideal for year-round fun. Currently enjoyed as both a family getaway and a successful Airbnb, it offers strong income potential. Whether you’re looking for a primary home or investment, this timeless property is not to be missed.

Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep. Inside, the home is open and inviting, with plenty of room to relax or entertain. The large finished basement provides valuable living space, ideal for a game room, media area, or accommodating guests. Recent improvements include a brand-new roof and a high-efficiency propane furnace, both installed just last year, offering modern comfort and peace of mind. Ideally located close to Okemo, plus Stratton, and Magic Mountain are just a short hop away; this property offers the perfect balance of privacy and accessibility. With Vast trails, dirt roads to roam on this is a heavenly location. Whether you're seeking a full-time residence or a weekend escape, this home welcomes you to experience the best of Vermont living.