Chester, MA homes for sale & real estate

Chester, MA Homes for Sale

Bring your vision and make this Berkshire property your own! This property offers a unique renovation opportunity with plenty of space and potential for a year-round home, weekend getaway, or investment. Located in Becket Estates, enjoy the relaxed Berkshire lifestyle with the pond just a short walk away. Set in a peaceful 2-acre wooded setting and conveniently located near Jacob's Pillow, area lakes, hiking, and all the Berkshires have to offer. With updates, some TLC, and imagination, this property could become an amazing home or country retreat once again.

Chester, MA Homes for Sale

Attention investors, cash buyers, and those ready to bring their vision to life—this charming 1837 Colonial-style farmhouse offers a unique opportunity in the heart of beautiful Middlefield. With approximately 3,576 square feet of bright, sun-filled living space, the home features generously sized rooms, a flexible floor plan, up to 5+ possible bedrooms, and 3 full bathrooms. The attached red carriage barn/workshop adds valuable versatility, providing ample space for hobbies, storage, a workshop, or creative pursuits. Set on a full acre, the property features mature landscaping, pear trees, blueberry bushes, and a spacious lawn that creates a peaceful country retreat. Enjoy the best o

Chester, MA Homes for Sale

Step back in time at this remarkable 1768 antique Colonial set on approximately 7 acres in scenic Blandford. Formerly the Baird Tavern, was the home for the family for many years and more recently it was used as a bed and breakfast. Rich with character and historic charm, this 4-bedroom, 2.5-bath home offers approximately 2,920 square feet of living space, featuring original post-and-beam construction, wood and pine flooring, and three fireplaces. The property offers an exceptional opportunity for those seeking space, privacy, and the potential for a hobby farm or equestrian use, with a barn/stable, storage shed, and horses permitted. A new septic system with Certificate of Compliance to be

Chester, MA Homes for Sale

Tucked well back from the road on 3.5 private acres, this modern, lightly used home offers an effortless blend of low-maintenance living, single-story convenience, and quintessential Berkshires charm. Designed with an open, light-filled layout, the main level features gleaming hardwood floors and an seamless flow throughout the common living areas. At the heart of the main floor is a inviting living room with a gas fireplace framed by a stone surround and hearth, an updated kitchen, and a generous primary suite complete with a large walk-in closet. Enjoy indoor-outdoor living with a covered front porch, a spacious screened porch, and an expansive wrap-around deck perfect for entertaining or

Chester, MA Homes for Sale

Welcome to a custom-designed architectural haven where clean, modern design meets inviting warmth. Meticulously maintained and lightly lived-in, this spotless, move-in ready retreat offers the ultimate in effortless, single-floor living set against a backdrop of mature perennial gardens, custom walking paths, and complete privacy. Step through the inviting front porch into a bright, open-airy floor plan anchored by soaring ceilings, oversized windows, and rich bamboo floors that seamlessly bring the outdoors in. The heart of the home features a cozy gas fireplace and radiant-heated floors for year-round comfort. The chef's kitchen and main living spaces flow effortlessly onto an expansive w

Chester, MA Homes for Sale

Welcome to 177 Fred Snow Road! This 3-bedroom, 2-bath home sits on approximately 14 acres, offering plenty of space and privacy in a peaceful, wooded setting. The property features a new roof, new windows and a new water heater along with a two-car garage, spacious back deck, storage shed, large yard and trails to explore throughout the property. Located in the beautiful town of Beckett and just minutes from Center Pond and Becket Town Beach. A great opportunity to enjoy your own private piece of the Berkshires!