Properties Near 489 Main Street Chester, VT

Nestled on a serene, quiet town maintained dirt road, this spacious home offers the perfect blend of tranquility and comfort. As you approach, you'll be captivated by the stunning long-range views that greet you from the expansive deck, a haven for relaxation and outdoor enjoyment. The deck overlooks a picturesque pond, not on the property but offering a beautiful, calming view that enhances the natural charm of the setting all the same. Step inside to discover a thoughtfully designed interior where ample space meets cozy. The large, finished basement is a true bonus, featuring a cozy and convientent propane stove and serving as an ideal games room or entertainment space for family and friends. Featureing 4 large bedrooms, 3.5 bathrooms, with large primary ensuite, large living room with views and that all enticing party or craft space in the below. This is equally a perfect vacation retreat or spacious family home. Conveniently located close to the popular ski areas of Okemo, Stratton, and Magic this home is perfect for winter sports enthusiasts. Whether you're seeking a peaceful year-round residence or a seasonal getaway, this property promises a lifestyle of serene beauty and endless recreational opportunities. Welcome home to your personal oasis.

A classic, easy maintenance four bedroom, two bath home in Chester village on .12 acres +/-, within walking distance to the Village Green for summer concerts, restaurants and shopping. The front porch is a focal point and a great way to meet your neighbors and passersby on the walking loop. The first floor features a large foyer, spacious living room, large dining room with corner built-in and elegant lighting, a country kitchen with marble tile flooring, first floor bath with tiled shower and an adjoining bedroom with a lovely reading/entertainment nook that connects with the dining room. The second floor has a large landing with two adjoining bedrooms, a full bath with radiant heat in the floor and a cool, private back bedroom. The basement has foam insulation and the windows, water heater and oil tank have been replaced. Ready for your enjoyment as primary, secondary or investment property. Close to Magic, Okemo, Bromley and Stratton Resorts, and year year-round recreational activities.

Unique Chester property on 10.08+/- acres with home business potential! This 3 bedroom, 1.5 bath Contemporary has lovely grounds that feature a pond, landscaped rock gardens, a vegetable garden and ample open space for more gardening endeavors. The detached 3-bay garage offers multiple large spaces and oversized doors. Whether you are an artist, contractor, carpenter or mechanic, the high ceilings and huge amount of work space will be appreciated. Set back from the road with plenty of parking area, there is room to add more outbuildings for business needs. The efficient house features a cozy living room, first floor bedroom, full bath and kitchen/dining that opens to the back deck overlooking the private pond. The second floor has a large common area adjoined by two bedrooms and a half bath with laundry. The whole house generator and Fiber Optic internet service will keep your systems and business running during power outages. Commutable to the Upper Valley, convenient to Springfield, skiing, shopping, Chester Village and all the area has to offer.

The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a delightful three season sunroom and formal dining room with woodstove insert, chandelier and an array of full light doors which open to the large, bright kitchen and first floor full bath. A sitting room with a double-sided fireplace connects to the spacious living room. The inviting foyer leads to the second floor which features 3 bedrooms, 2 baths and a sitting room. An addition added by the author and named the Queen's Room during the current owners bnb tenure features built-ins, a partition wall with transom window and a wood stove insert flanked by cozy built-in seats. The primary bath features gold-plated fixtures, a skylight and soaking tub. The first floor also has a heated, retail space for a home business with a separate entrance and office above that has served as an antique shop. The two-car attached, garage has unfinished, overhead space. The exterior needs some sprucing up and a new owner will want to add cosmetic upgrades. The property on .70 acres has a lovely yard with a hydrangea bush, charming bridge, small pond and stone bench overlooking the picturesque village.

This beautifully renovated farmhouse offers a perfect mix of classic charm and modern updates, located just a short distance from the historic town green, shopping, and dining. The home features a spacious living room and cozy family room, providing plenty of space for both relaxation and entertainment. A dining area off the modern kitchen is perfect for family meals or hosting guests. The wood stove in the kitchen provides warmth and ambience The main floor also includes a convenient first-floor bedroom, while the second level features three additional bedrooms, one of which is an excellent option for a home office. You'll also find a large laundry room and a second floor back porch providing access down. Recent updates include new hardwood floors, fresh interior paint, and updated bathrooms. Mini-split systems on both floors provide efficient air conditioning and additional heating for year-round comfort. Enjoy outdoor living with a private fenced in back courtyard, a back porch entry, and a fenced-in backyard. A 1-car garage barn adds extra storage. This home is a dream for outdoor enthusiasts, with major ski resorts including Okemo, Magic, Bromley, and Stratton just a short drive away. The town Recreation Center, pool, and VAST snowmobile trails offer year-round fun, with plenty of biking and hiking trails only a half mile away. Vermont living at its finest—right in town!

Escape to this charming log cabin, tucked away on a quiet dead-end road. With an attached two-car garage and a small horse barn, this property is perfect for those seeking a blend of rustic charm and practicality. Inside, you’ll find a thoughtfully designed two-bedroom, one-bathroom layout with an airy open floor plan. The kitchen and living room flow seamlessly together, centered around a wood stove that creates a warm and inviting atmosphere during the winter months. The main living area features classic wide board pine flooring, while the bedrooms boast updated vinyl plank floors for a modern touch. A spacious entryway doubles as a den, providing versatility to suit your lifestyle. The full basement includes a finished bonus room for additional living space and offers potential for further expansion. Step outside to enjoy summer evenings on the covered front porch. This peaceful retreat is just minutes from Chester’s charming village center, where you’ll find dining and shopping options. Plus, it’s a short drive to Okemo Mountain for year-round recreation. Whether you’re looking for a cozy home or a weekend getaway, this property has it all! Don’t miss your chance to own this log cabin in an ideal location within close proximity to ski mountains, lakes, shopping, and dining! Visit the Okemo real estate community today. Taxes are based on current town assessment.

This beautiful privately located 3 bedroom, 2 bathroom manufactured home is move in ready and just waiting for your finishing touches! It has a wonderful level yard with plenty of space for gardens, room to play, or put in a camp fire to sit around on a lovely Vermont evening. There is an additional gravel pad in place that you could put a tiny home as a rental opportunity or a guest house when company comes to visit. You can use the drilled well for both house and the tiny house you add. There is also an approved septic design in place if you choose to add a tiny house there. Other great features are a 30 x 60 hoop building with lots of storage space and another shed with even more storage potential! Would make a great first home, family home, home for someone looking to downsize, or so many other options! Call to schedule your appointment today! Agent is a relative of seller.