Nestled in the heart of the picturesque town of Stockbridge, Massachusetts, the property at 2 Cherry Street offers a rare blend of historic charm and modern conveniences. With its rich history, quaint setting, and beautiful design, this home represents the quintessential New England experience. Whether you are a history enthusiast, an architecture aficionado, or someone simply looking for a cozy and well-maintained residence, 2 Cherry Street provides a unique opportunity to own a piece of Stockbridge’s storied past.
A Piece of Stockbridge History
Stockbridge, known for its historic homes and scenic beauty, is the ideal setting for this charming house built in 1900. The home’s classic design reflects the style of that time, offering a glimpse into the past while providing modern comforts. It sits on a 0.91-acre lot, surrounded by the natural beauty of Berkshire County.
Stockbridge is also famous for its history as the home of American artist Norman Rockwell, who often featured the town in his paintings. This peaceful, small-town vibe is reflected on Cherry Street, where this lovely home blends perfectly with its surroundings.
Welcoming Exterior
The exterior of 2 Cherry Street reflects classic New England charm. The house has white clapboard siding and traditional shuttered windows. These details give it a timeless and elegant look. A welcoming front porch invites you to sit and relax. It’s a great spot to enjoy the peaceful surroundings. The quiet neighborhood adds to the calm atmosphere. The well-kept garden brings color to the property and makes it even more inviting.
The home sits on a large 0.91-acre lot. The outdoor space is designed for easy use and relaxation. The backyard offers a peaceful escape from daily life. There’s plenty of room for a small garden or outdoor dining area. It’s perfect for summer barbecues or quiet family meals. The backyard also features a pool, providing a refreshing spot to cool off during warm days. With its large lot and pool, the outdoor space is a private retreat where you can relax and enjoy the outdoors.

Elegant Interior
When you enter, you immediately feel the warmth and history of the home. The 1,012-square-foot interior is both cozy and spacious. It has 6 bedrooms and 4.5 bathrooms, making it perfect for families. Original details, like hardwood floors, trim work, and vintage fixtures, have been carefully preserved. These features honor the home’s 19th-century roots while providing a great base for modern updates.
Living Spaces
The living room is a standout feature of the home, filled with natural light from large windows. This creates a warm and inviting atmosphere. It’s a great space for entertaining guests, spending time with family, or relaxing with a good book. The neutral colors make the room feel even more open and spacious.
Next to the living room is the dining area. There’s plenty of room for a dining table, perfect for hosting dinners or casual get-togethers. The open flow between the two spaces adds to the home’s functionality, making it ideal for everyday living.

Updated Kitchen
While the home maintains its historic charm, the kitchen has been thoughtfully updated to meet modern standards. Featuring white cabinets, stainless steel appliances, and stone countertops, this space strikes the perfect balance between classic style and modern functionality. The kitchen is compact yet efficient, providing everything you need for meal preparation while seamlessly blending with the home’s overall aesthetic.
A small breakfast nook adjacent to the kitchen is the perfect spot for enjoying morning coffee or a casual meal while overlooking the backyard. The windows in this area offer lovely views of the outdoor space, adding to the home’s overall charm.

Comfortable Bedrooms
The home boasts six bedrooms and four and a half bathrooms, thoughtfully spread across two floors to maximize comfort and privacy. Each bedroom is generously sized, with large windows that allow for abundant natural light. The neutral color scheme throughout creates a calming atmosphere, allowing for easy customization to suit any style or preference. Whether you need a master suite, guest rooms, or home offices, the layout provides flexibility to accommodate any homeowner’s needs.
The bathrooms have been updated with modern fixtures, while still retaining a timeless elegance. On the upper floor, the full bathrooms feature a bathtub/shower combination, storage vanities, and elegant tile work, blending style with practicality to create a functional yet sophisticated space.

Ideal Location
One of the most appealing aspects of this home is its location. Situated just a short walk from downtown Stockbridge, residents of 2 Cherry Street can enjoy easy access to the town’s many amenities. Whether you’re looking to explore local shops, dine at one of the town’s charming restaurants, or take a stroll through the famous Stockbridge Bowl, you’ll find that everything is within reach.
The home’s proximity to Tanglewood, the summer home of the Boston Symphony Orchestra, as well as the Norman Rockwell Museum, further enhances its appeal. Outdoor enthusiasts will appreciate the nearby opportunities for hiking, skiing, and enjoying the natural beauty of the Berkshires.

A Perfect Blend of History and Modern Comfort
Owning a historic home like 2 Cherry Street offers a unique opportunity to be part of Stockbridge’s rich heritage while enjoying the comforts of modern living. The careful preservation of its original features, combined with thoughtful updates, makes this property truly special. Whether you are looking for a full-time residence, a vacation home, or a rental property, this home provides endless possibilities.
Its manageable size and prime location make it an excellent choice for those seeking a low-maintenance lifestyle without sacrificing charm or convenience. The serene neighborhood, combined with the vibrant culture of Stockbridge and the greater Berkshire area, ensures that residents will have plenty to enjoy year-round.

Conclusion
For those looking to invest in a piece of New England history, 2 Cherry Street in Stockbridge, MA, offers the perfect opportunity. With its blend of historic charm, modern amenities, and an ideal location, this home is a true gem. Whether you’re drawn to its cozy interior, its connection to Stockbridge’s artistic and cultural legacy, or its peaceful surroundings, this property is a must-see for anyone seeking a unique and special place to call home.
For more information or to schedule a viewing, contact Stone House Properties today!
