Properties Near 196 North Street Chester, VT

Step into the charm of yesteryear with all the comforts of today at 663 Depot Street. This completely renovated 3-bedroom, 2-bathroom home combines historic character with modern convenience. Since 2022, everything from the insulation, drywall, electrical, plumbing, & HVAC has been updated, including a new furnace, water heater, fixtures, countertops, cabinets & appliances. The only original feature left untouched is the flooring- beautifully refinished original wood. The owners thoughtfully chose period-appropriate paint colors & preserved unique touches like exposed beams & original woodwork. You'll love the Victorian martini pedestal sink in the upper bathroom! There is also a 2-story attached post-and-beam barn—larger than the house itself—with a powered overhead door. Keep it as a garage or workshop, or explore the incredible potential to double your livable space by finishing it. Sited on 1 acre, the property has a sprawling lawn, fire pit for evenings under the stars & an unbeatable location near Chester's Stone Village, Grist Mill, Smitty's Market, & other local amenities. Just 15 min to Okemo Mtn & the lakes, 30 min to Bromley, & under an hr to Killington, Stratton, & Mt Snow—a prime spot for skiing, hiking, & year-round fun. Currently used as both a family getaway & a successful Airbnb, this property has serious income potential for those looking to maximize its use. Whether you’re searching for a primary home or an investment, this timeless home is not one to miss.

Exciting Red Brick Ranch in a Beautiful Serene Setting! This delightful red brick ranch combines the charm of one-level living with incredible potential! Nestled on a private lot, surrounded by breathtaking woods and offering a glimpse of Ascutney Mountain in the winter, this inviting residence features spacious bedrooms, a luxurious primary suite with large tub for soaking in after a long day. With an additional ensuite and a third full bathroom, comfort and convenience are at your fingertips for family and guests alike. Step inside and be captivated by the open-plan kitchen, living, and dining area that flows effortlessly into a stunning solarium, perfect for basking in natural light. The cozy rec room and games room in the basement are ideal for family fun or creating a vibrant play space for kids. Unwind in the sauna, and enjoy the added convenience of a dedicated laundry area off the kitchen. And dont forget the extra workshop space in the main house! Outdoor living truly shines here, with a sparkling in-ground pool and a pool house, surrounded by fruit trees and mature plantings. The three-bay heated garage offers ample storage, another workshop along with dedicated RV parking and a lean-to for extra space. With a separate one-bedroom rental or in-law apartment option, this is a versatile property. Recently painted and ready for your personal touch, this cute ranch invites you to create lasting memories. 30 Minutes to Okemo & Magic mountains and VAST access nearby!

This spacious 1800's home is filled with Vermont charm and located in the heart of Chester. Filled with natural light from newly installed windows, the home boasts beautiful wood floors throughout and antique door handles that capture the essence of the era. Spacious bedrooms provide ample comfort, while smart thermostats ensure modern convenience. A newly built, covered front porch welcomes you into the home, and a deck off the kitchen leads to an open, level backyard—perfect for gardening or outdoor activities. One of the standout features of this property is the versatile studio space. Accessible via its own entrance from Main Street, this expansive area features vaulted ceilings and two half baths, offering endless possibilities. Whether you're looking to create a storefront, set up an at-home business, or convert the space into a private apartment, the potential is limitless. This property offers a unique opportunity to live in a quintessential Vermont town while having the flexibility to tailor the space to your needs. It's a must-see for anyone seeking a charming, functional home with potential for growth!

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.

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.

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 nice short range view and a small seasonal stream.

Welcome to this beautifully maintained 3-bedroom, 2-bathroom ranch-style home nestled in the serene town of Chester, Vermont. This property combines comfort, convenience, and a unique connection to the great outdoors, making it a great retreat or year-round residence. Step inside to discover a bright and inviting living space with a large, combined living room, dining area, and kitchen. The home's layout offers both functionality and warmth, with ample natural light and high ceilings. The three bedrooms provide plenty of room for family, guests, or a home office, while the two full bathrooms offer modern comfort and convenience as well as one of those being attached to the primary bedroom. This home has been lovingly cared for and is in excellent condition, ready for you to move in and make it your own. Outdoor enthusiasts will adore the location! You'll find yourself just steps away from the renowned Vast snowmobile trails, offering endless adventures in every season. Additionally, a short stroll up the class IV portion of Wyman falls road takes you to the wonderful Wyman Falls, where you can enjoy the calming sounds of cascading water and the beauty of nature. Located in charming Chester, this home offers the perfect blend of small-town charm and easy access to Vermont’s outdoor treasures. This is your opportunity to own a slice of Vermont paradise.