Chappaquiddick Real Estate

Welcome to Chappaquiddick, a hidden gem nestled off the southeastern coast of Martha’s Vineyard, in Dukes County, Massachusetts. This enchanting island, accessible by a short ferry ride from Edgartown, offers a unique blend of natural beauty, rich history, and tranquil living that captivates residents and visitors alike.

Chappaquiddick is renowned for its picturesque landscapes, featuring pristine beaches, lush woodlands, and breathtaking coastal views. The island is home to the famous Wasque Point, where the Atlantic Ocean meets the calm waters of Katama Bay, providing a stunning backdrop for outdoor enthusiasts and nature lovers. Here, you can explore miles of scenic trails, indulge in birdwatching, or simply soak in the sun on the soft sands of South Beach.

Rich in history, Chappaquiddick is perhaps best known for its role in the Kennedy family legacy. The island is steeped in stories that echo through its charming streets, from the iconic Dyke Bridge to the serene, secluded spots that have become synonymous with summer retreats and family gatherings.

For those seeking a peaceful escape, Chappaquiddick offers a tight-knit community atmosphere, with quaint cottages and luxurious homes that blend seamlessly into the island’s natural surroundings. Whether you’re looking for a seasonal getaway or a permanent residence, this enchanting island promises a lifestyle filled with relaxation, adventure, and a deep connection to nature.

Discover the allure of Chappaquiddick, where every day feels like a vacation and the beauty of the landscape is matched only by the warmth of its community. Experience the magic of island living and make your mark in this idyllic paradise.

Newest Listings in Chappaquiddick

$2,875,000

4 Beds ⋅ 5 Baths ⋅ 73594795 MLS

Set on 4.9 acres surrounded by the natural beauty of Chappaquiddick, this residence offers approximately 2,900 square feet of living space, quality craftsmanship, and a private setting. The home features three bedrooms, including a first-floor primary suite with a private bath. Upstairs, two additional bedrooms each have ensuite baths. The living room features soaring cathedral ceilings finished in tongue-and-groove wood and a wood-burning fireplace. Custom interior doors and detailed woodwork are found throughout, while the kitchen is appointed with high-end appliances and custom Neff cabinetry.The enclosed, year-round porch features tongue-and-groove ceilings, slate flooring, and a wood-burning fireplace, providing additional living space in every season. A mahogany deck overlooks the surrounding property. Above the detached garage is an additional bedroom and full bath, offering flexibility for guests, a home office, or studio. A new Mitsubishi inverter-technology heating and cooling system, installed in 2026, features six independently controlled zones, with heating and cooling extending to the basement and enclosed porch. Owned solar panels provide a net $100.00 per month positive utility bill. There is an 8 bedroom septic system and so expansion opportunities are plenty. Approximately one acre of the property is located across Litchfield Road, offering potential for a future guest house or accessory dwelling unit (ADU), subject to applicable approvals. Located on Chappaquiddick, the property offers convenient access to beaches, conservation trails, and the natural surroundings that define Chappy, all just a short ferry ride from downtown Edgartown.

91 Litchfield Rd, Edgartown

$3,995,000

4 Beds ⋅ 6 Baths ⋅ 73588921 MLS

Tucked into a quiet corner of Chappaquiddick, with protected views of Nantucket Sound and abutting the Pocha Pond Reservation and miles of endless hiking trails, this beautifully crafted custom home offers a rare combination of privacy, natural beauty, and effortless island living. The home is defined by a sense of casual elegance, with dramatic soaring ceilings and a striking prism skylight that fills the interior with warmth and natural light. An expansive, open living area is anchored by a floor-to-ceiling, double-sided fieldstone fireplace, creating a welcoming gathering space with a strong connection to the surrounding landscape. A remarkable two-story screened porch captures the water views and extends the living space outdoors, with a comfortable gathering area on the first level and a charming sleeping porch above. Four generously sized bedrooms, each with its own ensuite bath, offer privacy and comfort, with two enjoying water views. A finished lower level and oversized attached garage provide ample space for beach, boating, and fishing gear. Close to the ocean beaches of Wasque, yet within easy reach of downtown Edgartown, the property offers the best of Chappaquiddick, quiet, natural, and wonderfully removed, while still connected to everything the island has to offer. A cherished home in a truly special setting, ready for its next chapter.

4 Garrett Way, Edgartown

$2,950,000

8 Beds ⋅ 7 Baths ⋅ 73586117 MLS

Perched atop the highest point on Chappaquiddick, this private compound truly has it all, while still being a short distance from Chappy favorites including the Community Center, Beach Club, Ferry, and Slip Away Farm. Designed for both relaxation and recreation, the property offers endless ways to enjoy time with family and friends. Spend the afternoon on the sports courts, cool off at the pool, or relax on one of the expansive porches or patios. The guest house provides additional space and privacy. The pool house, complete with a half bath and kitchenette, makes entertaining effortless, with everything you need close at hand. A separate gym and game room offer even more ways to stay active or unwind, whatever the weather. With a strong rental history, the property also presents an excellent investment opportunity, while its generous amenities and multiple living spaces make it an ideal generational home to be enjoyed for years to come.

72 Chappaquiddick, Edgartown

$10,750,000

7 Beds ⋅ 4 Baths ⋅ 73563263 MLS

Overlooking the active waters of the outer harbor and set just off the paved road, this remarkable waterfront estate occupies one of Chappaquiddick’s most spectacular stretches of beach, just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village. A rare and truly exceptional family compound, the property offers an extraordinary combination of scale, privacy, waterfront, and amenities. Expansive grounds unfold toward sweeping water views, with a gentle slope leading to a protected stretch of sandy beach and access to a 190-foot private dock with mooring. The stately main residence offers beautifully proportioned spaces updated with today’s comforts, with a thoughtful layout well suited to both intimate family living and multigenerational gatherings. The estate extends beyond the main residence to include 75 Landing Place, an additional waterfront parcel that seamlessly expands the property, offering beautiful vistas, greater privacy, and a sense of scale rarely found on Chappaquiddick. An additional three-acre parcel is also available, creating a singular opportunity to assemble a one-of-a-kind family compound of exceptional size and privacy, with the flexibility to shape the property for generations to come. Cherished by the same family for generations, this remarkable waterfront estate represents a rare opportunity to create something truly enduring—a private family retreat with the space, setting, and flexibility to become a legacy for generations to come.

139 Chappaquiddick Road, Edgartown

$1,500,000

3 Beds ⋅ 2 Baths ⋅ 73559452 MLS

CHAPPAQUIDDICK – Opportunity awaits on this conforming 3-acre parcel, featuring a year-round home with a 5-bedroom septic system, offering exceptional potential for future expansion, including a guest house. Privately tucked away off the main road, yet conveniently located just minutes from the Chappaquiddick Community Center, the Ferry, Wasque Beach, and Quammox Preserve with its public access to Katama Bay, this property is perfectly positioned to enjoy the best of Chappy. Abutting conservation land, with the Cross Chappy Trail and Pocha Pond Reservation just outside your door, it offers direct access to some of the island's most treasured natural landscapes. The home's efficient floor plan features a first-floor bedroom, open living spaces, and a cozy sunroom, creating the perfect retreat to enjoy all that Chappaquiddick has to offer today, while providing outstanding opportunities for future expansion.

8 Pip'n Circle, Edgartown

$2,195,000

5 Beds ⋅ 4 Baths ⋅ 73520213 MLS

Life on Chappaquiddick has a rhythm all its own — and this exceptional compound is designed to savor every moment of it.Set on three park-like acres of meadows and woodland, two freshly painted log cabin-style homes offer a private world apart. The three-bedroom main house is open and generous, with living spaces that flow seamlessly from inside to out. The two-bedroom guest house is its own considered retreat, complete with covered porch, back deck, and outdoor shower. An oversized garage with loft provides additional space to gather and unwind.A circular drive and pea stone pathways connect the buildings across beautifully layered grounds. Adirondack chairs ring a custom firepit for late nights under the stars; a sauna and cold plunge pool on a bluestone patio create your own personal spa. An enclosed garden, garden shed, and multiple outbuildings complete the setting — your own private park among Martha’s Vineyard most beautiful natural setting.

7 Pip'n Circle, Edgartown

$550,000

73495792 MLS

CHAPPAQUIDDICK — Just over one acre in the desirable Calebs Common neighborhood, ideally located near the ferry, beach, and Community Center. Enjoy easy access to beaches, miles of walking trails, and the surrounding conservation land that makes Chappy so special. A wonderful opportunity to create your own island retreat. Per the Board of Health, the lot may support a three-bedroom home with an enhanced system and proper approvals. Also included in the sale is the owner's share of the Calebs Beach Corporation, giving you access to the sandy beach on the outer harbor.

23 Calebs Common Lane, Edgartown

$3,495,000

73473022 MLS

CHAPPAQUIDDICK -Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to ½ mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding and everything in between. Sheltered amongst 200 acres of conservation land, enjoy and explore the wonders of the natural habitat right in your backyard. An exceptional opportunity to create more than just a home, but cherished memories for generations to come.Directions: Please call the listing agent to accompany you on showings.

Pocha Rd Ext, Edgartown

$2,299,000

4 Beds ⋅ 3 Baths ⋅ 73472929 MLS

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shellfishing. Nearby, the Wasque Preserve offers over 200 acres. of pristine conservation land, with scenic trails, abundant wildlife, and direct ocean access. Whether you're seeking a serene coastal retreat, a multi-generational family home, or a proven investment property, 76 Washque has it all. With

76 Washque Ave, Edgartown

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Chappaquiddick Real Estate

Newest Listings in Chappaquiddick

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