Chappaquiddick Homes with Shingle Style

Welcome to Chappaquiddick, a hidden gem nestled off the coast of Edgartown in Dukes County, Massachusetts. This enchanting island, accessible via a short ferry ride, offers a serene escape from the hustle and bustle of mainland life. Known for its stunning natural beauty, Chappaquiddick boasts pristine beaches, lush landscapes, and a rich tapestry of history that beckons you to explore.

One of the most captivating features of Chappaquiddick is its architectural charm, particularly the iconic Shingle Style homes that grace the landscape. These distinctive residences, characterized by their weathered wood shingles and elegant lines, blend seamlessly with the island’s coastal environment. The Shingle Style emerged in the late 19th century, and here in Chappaquiddick, it flourishes, showcasing the artistry and craftsmanship that define this unique architectural genre.

Imagine waking up to the gentle sounds of waves lapping against the shore, with the scent of salt air wafting through your windows. The homes here offer a perfect balance of rustic charm and modern amenities, making them ideal for both year-round living and seasonal retreats. With spacious porches that invite you to sip your morning coffee while watching the sunrise, and expansive yards perfect for summer gatherings, these homes embody the essence of coastal living.

Whether you’re drawn to the island for its natural beauty, its rich history, or the allure of Shingle Style architecture, Chappaquiddick promises a lifestyle that is both enchanting and serene. Come discover your piece of paradise in this idyllic corner of Massachusetts!

Newest Chappaquiddick Homes with Shingle Style

$4,725,000

3 Beds ⋅ 5 Baths ⋅ 73564664 MLS

Set amongst beautifully landscaped grounds and vibrant gardens, this inviting Chappaquiddick retreat offers a wonderful sense of privacy and tranquility. Stunning hydrangeas frame the property, also complemented by mature trees, colorful blooms, and established gardens, creating a beautiful setting throughout the seasons. Multiple outdoor spaces invite relaxing and entertaining, with a heated saltwater pool, completed in 2025, serving as the centerpiece. Inside, warm and inviting living spaces are filled with natural light, while shiplap details and a relaxed coastal aesthetic give the home a classic island feel. Vaulted ceilings and thoughtful attention to detail enhance the home’s comfortable, refined character, while a thoughtfully designed single-level layout offers the ease and convenience of true first-floor living, with a private primary suite and separate guest wing providing an ideal sense of space and privacy. The detached studio with workshop is a hobbyist’s dream, overlooking the pool and offering a versatile space for creative pursuits, hobbies, or use as a pool cabana.

149 Litchfield Road, Edgartown

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