Chester VT Real Estate & Homes for Sale

This wonderfully well-maintained home sits back nestled off of route 12 between the village of Chester and town of Springfield. This property features 2 bedrooms and 1 1/2 bathrooms, a standing seam roof, an oversized two car garage and a nice open lot.

Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential! The first being the business store front, second is a space in the back which could easily be turned into a rental with a kitchen and separate bathroom, the third is a second floor 2bedroom 1 bathroom which has recently been updated with a freshly painted interior as well as new flooring and other updates. Along with the many benefits of this property's location comes parking right on the Green. Some recent updates are the back portion on the building has a new roof and solar was added to the whole building recently as well.

Looking for the perfect ready to move in home in Vermont? This beautiful home is centrally located in the quiet town of Chester, Vermont on Route 103. Close to many ski mountains, within 10 minutes to Okemo mountain. House features a beautiful indoor and outdoor fireplace, outside hot tub, beautiful stone patio, large private deck, 2 car garage, 4 bedrooms (but lots of room for more people), 2 bathrooms, a bonus bunk room, 2 extra lofts for an office or library, extra recreation room, and paved driveway. The house is a short distance to several beautiful lakes, mountains to hike, near the VAST trails, and interstate 91. Very spacious and also currently a great short term rental income property. And if you happen to lose power there is a 20kw stand-by propane generator ready to go. Call for a showing today!

With it's stone fireplace, exposed beams, and textured logs, this home offers an authentic connection to the great outdoors. For nature enthusiasts, the property's proximity to Okemo Mountain, hiking trails, VAST trails, golf courses, and swimming spots is unbeatable, all within 8 miles. Tucked away on Whitmore Road just up off of 103, this home offers privacy in a serene setting, yet still very close to all amenities. Though the house itself requires some tender loving care, it presents an exciting opportunity for those with vision and ambition. Picture transforming the spacious living area with its impressive stone fireplace to match your unique style. Cathedral ceilings create an expansive and airy ambiance. A designated area with a bar offers the potential to create a remarkable entertainment space. Adjacent to the house, a poured foundation awaits your creative touch, approved for a barn or additional structure. Whether you choose to complete the vision or let your imagination run wild, this property offers endless possibilities for customization and personalization. Escape the hustle and bustle of modern life and envision your own Vermont retreat in this charming log home. Schedule a showing today and take the first step toward turning your vision into reality.

Located in the neighborhood of Putnam Hill in Chester, this newly constructed dormered 2.5 story 5 bedroom, 4 bath home on 3.2+/- acres has been framed and is utility ready with septic, well, electric in place. The first floor space features a Great Room with 16' ceilings at its highest points, large kitchen with work area and plenty of cabinet space, a separate dining room for large gatherings, a formal living room and full bath which could also function as a first floor bedroom. The second floor is designed for 4 bedrooms and 2 full baths and the third floor has flex space with four large dormers and beautiful views. This thoughtfully designed home includes a walkout basement with 9' ceilings and intentional framing to include large windows. Solid wood doors are on site along with 10" wide plank pine flooring, furnace and misc. materials. This home was built by a Master tradesman with years of experience. The architectural framing is quite remarkable as is the desirable location of Chester VT with short drives to various ski mountains.

Opportunity awaits! This three-unit property has been very well maintained and is fully rented with long term tenants. This investment features an in-town location within walking distance to shopping, restaurants and local conveniences. This property also includes additional unfinished square footage in the barn, currently used for storage, with great potential for new ideas. Even the basement is impressive. The outside of this home has been freshly painted as of 6/6/2023. All apartments are in good shape and fully applianced.

Classic 1852 brick colonial home located on the corner of Grafton and Main Streets in beautiful downtown Chester. A short stroll to the town green, library, shops and antique shops. Currently a 2 unit apartment, it's top floor consists of a two bedroom one bath unit while the downstairs is set up as a one bedroom cozy apartment. The house can very easily be converted back to a single family home by simply removing a wall on the lower level which was installed only a few years ago. The whole house has electric and plumbing updates. Two recent hybrid water heaters and furnace. A new roof was just installed. Priced to sell, please note current tenants are occupying both units. Appointments with at least 48 hours notice are needed. Showings will be scheduled in blocks of time. This is an excellent opportunity to either convert the home back to a single family or live in one and rent the other. Visit the Okemo real estate community today. Taxes are based on town assessment.

Classic 1852 brick colonial home located on the corner of Grafton and Main Streets in beautiful downtown Chester. A short stroll to the town green, library, shops and antique shops. Currently a 2 unit apartment, it's top floor consists of a two bedroom one bath unit while the downstairs is set up as a one bedroom cozy apartment. The house can very easily be converted back to a single family home by simply removing a wall on the lower level which was installed only a few years ago. The whole house has electric and plumbing updates. Two recent hybrid water heaters and furnace. A new roof was just installed. Priced to sell, please note current tenants are occupying both units. Appointments with at least 48 hours notice are needed. Showings will be scheduled in blocks of time. This is an excellent opportunity to either convert the home back to a single family or live in one and rent the other. Visit the Okemo real estate community today Taxes are based on town assessment.