Chatham Homes with Shingle Style

Welcome to Chatham, Massachusetts, a picturesque coastal town nestled in Barnstable County on Cape Cod. Renowned for its stunning beaches, charming downtown, and vibrant maritime culture, Chatham is the quintessential New England getaway. With its rich history and breathtaking landscapes, it offers a unique blend of small-town charm and coastal allure that attracts visitors and residents alike.

One of the most captivating aspects of Chatham’s architectural landscape is the prevalence of Shingle Style homes. This distinctive design, characterized by its use of wooden shingles and an informal, asymmetrical appearance, perfectly complements the town's natural beauty. These homes often feature expansive porches, large windows, and open floor plans, allowing residents to embrace the coastal lifestyle while enjoying panoramic views of the surrounding scenery.

Living in a Shingle Style home in Chatham means immersing yourself in a community that values both tradition and innovation. The architecture reflects the town's heritage while providing modern comforts, making it a perfect fit for families, retirees, and anyone looking to enjoy the Cape Cod experience.

With its vibrant arts scene, delicious seafood dining, and a plethora of outdoor activities—from boating to hiking—the Chatham lifestyle is truly unparalleled. Whether you’re strolling along the picturesque Main Street or soaking up the sun on a pristine beach, Chatham offers an idyllic setting for those seeking a serene yet active lifestyle. Explore the enchanting Shingle Style homes that grace this charming town and discover your dream home in Chatham today!

Newest Chatham Homes with Shingle Style

$12,000,000

4 Beds ⋅ 3 Baths ⋅ 22603612 MLS

The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering landscaping leads to a bluestone patio and entertaining spaces over the beach, with a private trail to the water's edge -- one of the first points on the Eastern Seaboard to greet the sunrise each morning. Inside, a shiplap-clad great room opens the home for gathering, flowing into dining and kitchen areas with water views from every angle. The primary suite is a private retreat framed by its own bay window, while well-appointed guest spaces offer comfort for family and friends. Extensively renovated, the home retains the craftsmanship of its original build - true, enduring Cape Cod character. This is where summers are made. Shore Road beachfront grows more coveted with time, and opportunities like this rarely surface - a chance to secure one of the most aspirational addresses on the entire East Coast.

166 Shore Road, Chatham

$5,900,000

4 Beds ⋅ 5 Baths ⋅ 22603274 MLS

Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and additions in several directions in this very private location of North Chatham...Choice of 3 primary bedrooms with attached baths... Views over Chatham Harbor and beyond.......Beach and boating just an easy walk away. Or swim and relax in your own backyard in the recently retiled heated Gunite pool....House has been very well maintained by the current owner who has been here for over 36 years and completed a new roof, many new windows, new bedroom addition, newer family room addition and more......All information here has not been independently verified and buyer should do his/her own due diligence by checking with their attorney, and zoning and building rules and by laws, etc.. Assessment numbers subject to change with new Fiscal Year.

95 Cotchpinicut Road, Chatham

$4,995,000

5 Beds ⋅ 5 Baths ⋅ 22601118 MLS

LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort. The open floor plan showcases oversized windows and soaring ceilings, allowing natural light to pour in and illuminating the stunning views of the swimming pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated fenced-in lawn. Ownership includes deeded neighborhood access to Lighthouse Beach. The gourmet kitchen and oversized island seamlessly integrate with the dining room, custom bar, pantry, and wine storage. The inviting living room features a cozy gas fireplace. The fifth bedroom has been thoughtfully transformed into an inspiring study. Ascending to the second floor, you'll discover four wonderfully proportioned bedrooms, each offering distant Atlantic Ocean views, and three stylish full baths. The primary suite is a true retreat, boasting glorious views, a spacious walk-in closet, a dressing room, and an exquisite bathroom and shower. Around the corner is the Outermost Harbor Marina, and the nearby Old Village is the gateway to the start of Chatham's Main Street.

101 Morris Island Road, Chatham

$5,850,000

5 Beds ⋅ 6 Baths ⋅ 22601111 MLS

This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

15 Windy Hill Way, Chatham

$2,700,000

3 Beds ⋅ 2 Baths ⋅ 22505704 MLS

Discover the charm of coastal living just moments from Hardings Beach. This inviting 3-bedroom, 2-bath home enjoys beautiful water views over Bucks Creek and spectacular west-facing sunsets. Private stairs lead directly to the water's edge, making it easy to launch a kayak, explore the creek, or simply relax by the shore. The light-filled sunroom provides the perfect place to unwind while taking in the ever-changing coastal scenery throughout the seasons. Residents enjoy access to the Hardings Beach Hills Association dock, kayak storage, and waterfront picnic area, offering exceptional opportunities to enjoy life on the water. Whether you're seeking a year-round residence, seasonal retreat, or investment opportunity, this home offers an exceptional Chatham location surrounded by natural beauty. Abutting property at 92 Indian Trail is also available for $3,200,000.

78 Indian Trail, Chatham

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