Properties Near 332 Hidden Heights Road Chester, VT

Experience the warmth of history with the ease of modern living at 663 Depot Street. This fully renovated 3-bedroom, 2-bath home offers historic charm with today’s updates. Since 2022, insulation, drywall, electrical, plumbing, HVAC, furnace, water heater, fixtures, countertops, cabinets, and appliances have all been replaced. The home's original wood flooring has been carefully refinished to honor its roots. Period-appropriate paint colors and thoughtful details like exposed beams and original woodwork add to the timeless feel. The attached 2-story post-and-beam barn—larger than the house—offers incredible potential to expand your living space or create a dream workshop. Set on 1 acre with a sprawling lawn, fire pit, and 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.

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!

This charming multi-level home provides 4 bedrooms and a variety of places to find private space for quiet. Also a large open recreation room which includes a full size pool table/table tennis table and dry bar. Located just 3 miles from the charming Town of Chester. An easy drive to Bromley Mt, Magic Mt and Okemo, this makes a great home for an active family. Beautiful views from the deck provide a great place for morning coffee and an evening watching the stars. There is plenty of space for gardens and outdoor activities as well as wooded land to spend relaxing time in. House has automatic whole house propane generator. There are two firemen that live on the road, so it is always well plowed and maintained.

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.

Come find your own peaceful piece of the Vermont countryside in the beautiful town of Andover. Look no further than this move in ready homestead on 51.2 rolling acres with two large paddocks fenced and ready waiting for your animals, complete with two spacious sheds, and a chicken coop ready to house them. Established asparagus patch, blueberry bushes, apple trees, and even your own cranberry bog meticulously maintained by the current owners await you. Live in the updated home or build the home of your dreams up on the hill overlooking the farm. Make hay for your animals in the fields up on top of the hill, dig gravel from your own private gravel pit, or sit next to the beautiful pond! Plenty of land to hike, hunt, or just relax away from the hustle and bustle of the world. Soak up the sun in the attached sunroom or have plenty of room to have all the indoor plants you can dream of. Close to VAST snowmobile trail and within 10-45 minutes of Bromley, Okemo, Stratton, and Magic Mountains! The current owners have done so much to improve and clear the land and are ready to retire to a smaller lot. Their loss is your gain, come take a look today.

Tucked away on 31 beautiful acres in Andover is this lovely camp, cottage ready to be finished and enjoyed. The current owners have provided a great start with electric service, forced hot air heat and a finished living room to relax in. The land is a nature lover's dream with a year round stream in back of the camp, open area with a firepit and surrounded by a vast variety of trees on the mostly wooded acreage. The long driveway approach gives you a true sense of a cabin in the woods retreat. A recently done septic Design and Wastewater permit make this a year round home possibility. Fantastic location on Middletown Rd. Just minutes to center of Weston where you'll find the Vermont Country Store, excellent dining and the historic Weston Playhouse. Near several major ski resorts, Okemo, Magic, Stratton and Bromley Mountain. This is truly a find that offers the best of the Vermont experience. State approved WW permit available

Prepare for an exhilarating mountain getaway at this enchanting four-bedroom chalet, nestled on a lush 2.1-acre estate in the heart of Andover. 2025 Ski season has been epic so far! Envision yourself minutes away from four renowned ski resorts, making this the perfect launchpad for your winter adventures. Immerse yourself in the local charm with easy access to the VAST trail network, offering a plethora of entry points nearby. This alpine retreat has been a cherished sanctuary for over 40 years, lovingly maintained by its owners and their dedicated local caretakers. Offering a seamless blend of comfort and convenience, this home is sold fully furnished, ready for you to step in and relish its homely charm "as is." The layout features two cozy bedrooms on each floor, ensuring ample space for family and guests alike. Step inside to discover a welcoming front porch at the entry level, and ascend to the top floor to unwind on the deck with south-eastern views. The heart of the chalet hosts the kitchen and dining areas on the first floor, while the main living and family rooms upstairs provide a spacious haven for relaxation and entertainment. Enhanced by high-speed fiber optics internet from VTel, stay connected and productive in your serene mountain escape. Positioned ideally for those passionate about skiing and outdoor activities, choose from Magic, Stratton, Okemo, and Bromley ski areas, or indulge in hiking, fishing, biking, golfing, and swimming in the vibrant surroundings.