Properties Near 26 Main Street Chester, VT

Welcome to Silver Birches — a serene Vermont retreat nestled on 27 acres along a quiet country road, perfectly situated Grafton and Chester villages. Sprawling ranch-style home offers a fantastic floor plan with generously sized rooms and a natural flow, making it ideal as a year-round homestead or a peaceful getaway. The open-concept kitchen and dining area, complete with a cozy fireplace and access to the screened porch, is ready for your dream renovation and connects seamlessly to the spacious living room. Enjoy relaxing by the propane-insert hearth in the living room while taking in sweeping views of the acreage stretching out behind the home. At the opposite end of the house, you'll find three large bedrooms, a full bathroom, and a sweet office just off the formal front entryway-perfect for remote work or creative pursuits. Beautiful hardwood floors run throughout, and the walls offer a canvas for your personal style. Whether you choose to keep some of the tasteful vintage wallpaper or start fresh, the potential is here! Full, dry basement with finished living space and a bathroom. Convenient mudroom/laundry area with a half bath connecting the attached two-car garage. Fresh exterior paint and clean results from recent water, radon, and septic inspections are available. 15 minutes from both Grafton and Chester villages, offering access to the best of Vermont: outdoor recreation, quaint shops, dining and more. A truly lovely home among the trees, come experience it!

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!

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.

HUGE PRICE REDUCTION! OWNER HAS MOVED SO THE PROPERTY MUST BE SOLD. POSSIBLE OWNER FINANCING!! This Hilltop Homestead/Mini farm boasts 5 acres of mostly open land and a sprawling 4,000 plus sq. ft. ranch style home with a full finished walkout basement with attached 2 car garage and numerous barns and outbuildings. Easy access to Springfield or Chester and I-91. The home features a huge primary bedroom suite, two other bedrooms and another full bath on the main level, modern kitchen that flows into a living/dining open concept area with access to the back decks and views of the private back yard and mountain tops beyond. There is a combination of Bamboo, vinyl plank, slate and tile floors throughout the main level, two fireplaces, a second living/family room and 1st floor laundry with breezeway to the attached garage. The basement offers a small kitchenette, the 3rd bath, an additional bedroom, recreation/exercise room, workshop and much more. Outside you'll find plenty of outdoor space for gardening, animals, family time, cookouts/events or outdoor recreation. The back and side yards are completely fenced with gates to allow mowers and other equipment but also creates an ideal situation for animals and pets. The current owners have cleared additional forested land to add to the open/level land and also have trails through the remaining wooded acreage. There is an old gambrel timber frame barn plus a new heated Jamaica Cottage barn for animals. This is a DEAL!

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.

Welcome to 34 Fox Chair Terrace, a peaceful, private three-bedroom, two-bath home set on a full acre just minutes from downtown Springfield and charming Chester, Vermont. Tucked away in a quiet rural setting, this spacious property offers the best of both worlds: privacy and nature, with easy access to shopping, schools, the local hospital, and other area amenities. Step inside to find a bright and comfortable layout. The partially finished basement adds valuable flexible space perfect for a home office, workout area, or playroom. The detached two-car garage keeps your vehicles and gear protected year-round. Whether looking for your forever home or a peaceful retreat, this property delivers comfort, space, and convenience in a beautiful Vermont setting.

This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also features a newly built timber frame sugar style shack perfect for many different uses. There is the possibility for single level living with the downstairs bedroom being right across from the full bathroom as well as the laundry hook up's being on the first floor. In a great location just a few minutes from the quaint town of Chester 13 minutes from Magic Mountain and just 25 minutes from Okemo Mountain where there are shops, restaurants, Skiing and so much more!

Beautiful New Englander on two picturesque acres between Chester and Springfield, 5 minutes from local shopping and the hospital. The house sits on a quiet, paved and town-maintained road, with breathtaking views and wonderful privacy. Lots of flowers and berry bushes pepper an expansive and lovely lawn. Park your vehicles in a spacious 2-car electrified garage with an overhead storage area, and a new EV Charger! There's also a storage shed for lawn tools. Feel the charm as soon as you enter the enclosed sunroom, with a wall of windows overlooking scenic mountain vistas and wildlife. From here, step up into a cozy dining room, which flows into a quaint den looking out over the deck and onto an expansive and deep backyard. The dining room, den and kitchen ALL have heated floors, so feet stay warm on those winter night trips to the kitchen! A cozy living room sports new carpet (ALL carpeted surfaces have new carpet!). The kitchen boasts plenty of cabinet space and a small butler panty, as well as a brand new induction oven, safe for kids, as the stovetop does not get hot during cooking! Also on the first floor is a full bath, a laundry room, and an office. There are built-ins throughout the house. On the second level are 3 nice-sized bedrooms, a large, wide hallway, and another full bath, as well as a small area that has been used as another office. Recent electrical and exterior upgrades have brought this house to the next level. Bring your dreams to this well-loved home!