Wayside Inn District Real Estate

Welcome to the Wayside Inn District, a charming and historic subdivision nestled in the heart of Sudbury, Massachusetts. Known for its scenic beauty and rich heritage, this area is a delightful blend of quaint New England charm and modern convenience.

The Wayside Inn District is famously home to the iconic Wayside Inn, one of the oldest operating inns in the United States, which dates back to 1716. This picturesque landmark not only serves as a reminder of Sudbury's storied past but also offers a cozy dining experience and a glimpse into the area’s history. The surrounding streets are lined with beautiful colonial-style homes, each exuding character and warmth, making it a perfect place for families and individuals seeking a peaceful retreat.

Residents of the Wayside Inn District enjoy a tight-knit community atmosphere, with access to lush parks, walking trails, and recreational facilities. The nearby Sudbury River provides opportunities for kayaking and fishing, while the local conservation areas offer miles of trails for hiking and nature walks.

Conveniently located, the Wayside Inn District offers easy access to major highways and is just a short drive from Boston, allowing residents to enjoy the tranquility of suburban living while being close to the vibrant city life. Excellent schools, shopping centers, and dining options are just around the corner, ensuring that everything you need is within reach.

Whether you’re drawn by the historical significance, the beautiful landscapes, or the welcoming community, the Wayside Inn District is a place where you can truly feel at home. Discover the charm of Sudbury and make the Wayside Inn District your next destination!

Newest Listings in Wayside Inn District

$1,425,000

4 Beds ⋅ 4 Baths ⋅ 73574088 MLS

Impeccable condition, thoughtful design, and a floor plan that truly works for today’s lifestyle define this graciously appointed home. Lovingly maintained by its original owners, it offers a wonderful balance of comfortable everyday living, inviting spaces for gathering, and exceptional versatility for work, family, and guests. The well-appointed kitchen is designed for both everyday living and entertaining, with generous workspace, quality finishes, and an easy connection to the bright family room, where a fireplace creates a warm and inviting gathering space. Equally suited to a quiet morning or a lively gathering with friends, this welcoming space is complemented by an elegant dining room where hosting feels effortless. A private home office and a study provide ideal flexibility for today’s work-from-home lifestyle. Upstairs, the luxurious primary suite features a spa-like bath, walk-in closet, and comfortable reading area. A generous playroom, ensuite bedroom, a full bath, and two additional bedrooms offer wonderful options for family, guests, hobbies, or a teen suite. Throughout, the home has been exceptionally cared for, with spaces designed to be both comfortable and stylish. Set in Sudbury’s historic Wayside Inn District and tucked privately off the road on 5 acres, the established grounds create a peaceful and picturesque setting for everyday enjoyment. Whole Foods, Starbucks, and an array of shops are nearby, while the Rail Trail and conservation lands offer opportunities for walking and biking just minutes away. Conveniently positioned for commuters, the location provides easy access to Routes 20 and 117, with connections to Routes 9, 128, and 495 for Boston and destinations throughout MetroWest. Quality, exceptional versatility, and an enviable setting come together in this special home.

111 Dutton Road, Sudbury

Listing courtesy of Listing Agent: Sharon Mendosa from Listing Office: Compass.

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