4 Bedroom homes for sale & real estate in Chester, VT

4 Bedroom Homes for Sale in Chester, VT

Welcome to an extraordinary property where Vermont living meets year-round recreation and relaxation. Located a mile from the center of Londonderry and within 20 minutes of three ski resorts. This spacious 4-bedroom, 3-bath home offers a truly uncommon amenity: your very own private indoor pool. Imagine having a private wellness retreat with recreation spaces, and gathering spots under the stars without leaving home. There's room for family, overnight guests, entertaining, and creating flexible spaces for work or relaxation. This house has easy access to skiing at Magic, Bromley, Stratton and Okemo. In the warmer months enjoy hiking, biking, area lakes and rivers. Slow down, gather, and enj

4 Bedroom Homes for Sale in Chester, VT

Historic Rowen Farm is an extraordinary Vermont country property, where 87.92 private acres across 2 separately deeded parcels of reclaimed meadow, woodland, brooks and mountain views surround an exceptionally restored circa-1812 Federal farmhouse. Restored stone walls trace the land, woodland trails invite exploration, and open meadows extend toward the ridgeline, creating a setting that feels both expansive and intimate. Inside, exceptional historic preservation meets refined modern comfort. Original wide-plank floors, exposed beams, doors, period details and 4 wood-burning fireplaces are complemented by updated kitchen, baths and lighting by Teaselwood Designs. The home unfolds with a we

4 Bedroom Homes for Sale in Chester, VT

Experience the ultimate mountain lifestyle in this turnkey, beautifully remodeled three-level townhome. Located just steps from the Lower Sachem Slope, this property offers a seamless blend of winter convenience and summer relaxation. Step inside through the practical air-lock mudroom, designed to keep the winter chill out and ski gear organized. The main living level boasts an open-concept dining and living area framed by soaring cathedral ceilings, rich wood flooring, a classic wood-burning fireplace, and walls of windows that flood the space with natural light. The brand-new kitchen is fully updated and ready for entertaining. From the living room, step out onto a spacious, private deck

4 Bedroom Homes for Sale in Chester, VT

Quintessential 1880s Vermont farmhouse in bucolic Weston. Nestled on 7 private acres, this 4 bedroom, 3 bath retreat offers authentic pine floors, historical charm throughout with a tranquil pond greeting you upon arrival. It is the perfect blend or timeless character and rural serenity. BRAND NEW DRILLED WELL & MOUND SEPTIC SYSTEM just installed in August 2026. Updated electric makes this house ready for the next steward. The kitchen is authentic and you may choose to update. Situated in the picturesque town of Weston, one of Southern Vermont's most coveted historic villages. The village is home to the iconic Vermont Country Store and the renowned Weston Theater Company. The large sw

4 Bedroom Homes for Sale in Chester, VT

Welcome to a truly special Vermont property where craftsmanship, comfort, and the beauty of the outdoors come together. Offering over 3,000 square feet of beautifully renovated living space, this distinctive home is filled with custom features and exceptional woodworking throughout. The heart of the home is the custom kitchen, featuring rich cherry cabinetry and timeless soapstone countertops, complemented by numerous thoughtful updates. With four bedrooms, there is plenty of space for family and guests. The beautifully renovated primary bath offers a luxurious retreat with a stone and tile walk-in shower and a Jacuzzi soaking tub. Set on two picturesque acres, the property offers a peacefu

4 Bedroom Homes for Sale in Chester, VT

This spacious Londonderry contemporary house sits on a sunny, level one-acre lot and is conveniently located at the base of Glebe Mountain and mere minutes from Magic Mountain for snow sports and Lowell Lake for summer hikes, kayaking and keeping an eye on the native loons that nest there. The layout offers three levels of bright and roomy living spaces with a comfortable floorplan and lots of room for gathering or finding private quiet time. The main level features a large kitchen and dining area, living room with fireplace and vaulted ceilings, and two bedrooms including an expansive primary suite with a fireplace, walk-in closet and private bathroom. Above is large loft, partially open t