Waterfront For Sale on Martha's Vineyard - What's New for Spring 2025?

https://www.tealaneassociates.com/for-sale/34-edys-island-way-chilmark

Legacy Waterfront Estate on Menemsha Pond

Nestled in the heart of Menemsha, this exceptional waterfront compound includes both a main house and guest house, complete with a private dock extending into a serene estuary cove. Surrounded by water on three sides, the property offers a rare combination of privacy and convenience, with the vibrant Menemsha Harbor, beach, boutique galleries, and renowned seafood restaurants just a short walk away.

Cherished by the same Island family for over four generations, this property embodies timeless Vineyard charm. To the southeast, enjoy 120 degrees of unobstructed views as Menemsha Pond ebbs and flows around sandy islands. To the northwest, elevated rooms capture breathtaking sunsets over the harbor.

The grounds feature a secluded, partially shaded lawn bordered by a historic stone wall and mature blue spruce. A southern orientation ensures full sun throughout the day for both the main residence and guest house. From the dock, venture into a private cove that opens to the main pond and ocean beyond—offering a truly unique and secure waterfront experience.

The estate is equipped for year-round living, with water access and a new five-bedroom, Title 5-compliant septic system. The existing structure offers significant opportunities for thoughtful expansion and remodeling, including a spacious attic with panoramic views and a sunlit lower level ideal for additional living space.

Opportunities like this are rare—a property rich in history, enveloped in natural beauty, and offering unmatched potential. You are invited to continue the legacy of this extraordinary Menemsha estate.

34 Edys Island Way, Chilmark is listed exclusively for $8,750,000

Waterfront Elegance on 5.6 Acres with Sweeping Vineyard Sound Views

Set on 5.6 acres of pristine, landscaped grounds, this custom-built waterfront estate offers a rare blend of seclusion, craftsmanship, and timeless Vineyard character. The 4-bedroom, 2.5-bath main residence is complemented by a detached 1-bedroom, 1-bath guest studio—ideal for hosting or private retreat.

Nearly every room in the main home frames panoramic views of Vineyard Sound, with unforgettable sunsets showcased from the expansive stone terrace, screened porch, or the private balcony off the primary suite. Inside, thoughtful design meets fine craftsmanship, featuring salvaged heart pine floors, reclaimed beams, and hand-selected architectural elements that tell a story of care and tradition.

The home's generous building envelope offers ample room for future expansion—whether adding additional living space, amenities, or outbuildings—making it as much a sound investment as a sanctuary.

Surrounded by mature trees, vibrant gardens, and open lawn, this property radiates quiet elegance. A short, scenic stroll through the grounds leads to 340 feet of private waterfront—perfect for peaceful swims, kayaking, or simply taking in the natural serenity of the shoreline.

Located just a leisurely walk from the charm of Menemsha Village, with its harbor, shops, and fresh seafood offerings, this unique property is the ideal convergence of natural beauty, refined living, and Vineyard legacy.

94 Menemsha Inn Road, Chilmark is listed for $8,450,000

Dramatic North Shore Waterfront with Sweeping Views and Beach Access

Perched high on 3.8 acres of secure, elevated land in Chilmark's coveted Spring Point community, this extraordinary waterfront property offers panoramic, year-round sunset views over Vineyard Sound—stretching from the iconic Gay Head Lighthouse to the Elizabeth Islands.

Designed by renowned architect Heikki Soikkeli and featuring a signature Lew French fireplace and chimney, the 5-bedroom, 3.5-bath, 4,050 sq. ft. home is thoughtfully laid out with three separate bedroom wings for privacy and comfort. Move-in ready, the home combines architectural integrity with modern convenience, making it equally suited for year-round living or a seasonal retreat.

Positioned on a 48-foot elevation with a 425-foot setback, the property ensures ultimate privacy and unobstructed views of the ocean’s tranquil sailing, fishing, and boating activity. The expansive living room, primary suite, and kitchen all showcase stunning water vistas, seamlessly integrating the natural surroundings into the home's design.

Located in the exclusive 330-acre Spring Point community—home to just 48 property owners—residents enjoy access to 90 acres of preserved land, two tennis courts, and five miles of scenic trails and country roads. A private north shore bluff path leads to over a mile of pristine sandy beach, with direct access to the serene Great Rock Bight Beach Cove and neighboring 200-acre Menemsha Hills Reservation.

A short stroll down a grassy, canopied path leads you to the water’s edge, where you can enjoy peaceful moments on the beach or explore the shoreline. Rarely does a property offer such an ideal blend of architectural distinction, community, and natural beauty.

78 Hammett Road, Chilmark is exclusively listed for sale for $6,750,000

Rare Waterfront Retreat on Tisbury Great Pond – South Shore of Chilmark

Tucked along the serene shoreline of Tisbury Great Pond, this extraordinary five-bedroom waterfront estate offers an unmatched south shore beach house experience. Surrounded by sweeping views of water, sand, and sky, and bordered by conservation land on two sides, this rare offering presents the ultimate in tranquility, natural beauty, and coastal living.

The residence is thoughtfully designed as a connected compound, with a three-bedroom main house linked by charming walkways to a two-bedroom guest wing—complete with a spacious studio above. From nearly every room, including the ground floor, enjoy panoramic vistas of the pond and its ever-changing light.

Step outside into a meadow-like yard that gently transitions into a sandy shoreline along the pond. A grassy path leads directly to the water’s edge, perfect for launching paddleboards, kayaks, and small boats. Cross the pond for quick access to the unspoiled south shore ocean beach, or linger along your own calm, swimmable shoreline—ideal for children and quiet afternoons.

With a six-bedroom septic system already in place, the property offers exciting potential for renovation, reimagining, or expansion in harmony with its breathtaking surroundings.

This is a unique opportunity to create a private family sanctuary on one of Chilmark’s most coveted waterfront settings—where the quiet beauty of the pond meets the power and allure of the ocean, all within a protected natural environment and with deeded access to Chilmark’s famed beaches.

146 Quansoo Road, Chilmark is exclusively listed for sale for $5,475,000

An exceptional Waterfront Compound on Tisbury Great Pond.
Located across the Tisbury Great Pond from the exclusive Blue Heron Farm, this remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond.

Both the main house and guest house boast unobstructed water views, creating a tranquil and picturesque setting perfect for birdwatching, relaxation, and year-round enjoyment.
The main house features 4 bedrooms, 2.5 bathrooms, central air conditioning, screened porch for stunning sunset views, den/sunroom with wet bar plus a spacious unfinished basement for additional potential
The guest house provides an additional 2 bedrooms, 2 bathrooms and has its own separate three-bedroom septic system. The guest house has been recently updated with new roof, windows, and cedar shingle siding.
Additional highlights for this property include a permitted dock for direct pond access and a generator.
There is no waiting period to add a pool, barn, or expand on the 3 acre property—unlike in nearby Chilmark.
This central location with close proximity to both West Tisbury village and all island towns, offers a perfect blend of up-island privacy with down-island convenience.
This is a rare opportunity to move in immediately, renovate to your taste, or rebuild over time—all while enjoying the best of Martha’s Vineyard living in an exceptional natural setting.

104 Pond View Farm Road, West Tisbury is exclusively listed for sale for $4,800,000

Contemporary Beach House on Dogfish Bar – Private Waterfront in Aquinnah

Set along one of the most exclusive stretches of preserved beachfront in Aquinnah, this rare waterfront gem offers an unparalleled connection to the Island’s natural beauty. Nestled among rolling dunes with 198 feet of pristine shoreline, this contemporary beach house captures sweeping views, immersive sunsets, and direct access to one of Martha’s Vineyard’s most secluded sandy beaches.

Built in 2009 with a modern reverse floor plan, the upper level is devoted entirely to open-concept living, dining, and kitchen areas—all framed by expansive windows that invite the outdoors in. Cherry floors, a cozy fireplace, and abundant natural light create a warm and elegant space ideal for entertaining or relaxing in full view of the ocean.

The lower level features an en suite primary bedroom, plus two guest bedrooms sharing a full bath, offering comfort and privacy for family and visitors alike. A newly expanded deck off the main living area provides the perfect vantage point for taking in the sea breeze, stargazing, or gathering for evening sunsets.

Additional features include a detached shed that houses the water filtration system and provides ample storage for bikes, beach gear, and fishing equipment. A private path winds through the dunes, leading directly to the sandy beach—where some of the Island’s best swimming, boating, fishing, and beachcombing await.

This is more than a beach house—it’s a secluded sanctuary on Dogfish Bar, where the rhythm of the tides sets the pace of life, and nature provides a breathtaking backdrop for every moment.

29 Oxcart Road, Aquinnah is exclusively listed for sale for $3,950,000

Exceptional Waterfront Land Offering off Lambert’s Cove Road – Build Your Dream Home

A rare and extraordinary opportunity awaits just off coveted Lambert’s Cove Road—a chance to design and build your dream home in one of Martha’s Vineyard’s most desirable and exclusive locations. This exceptional parcel offers year-round waterfront living with a unique blend of privacy, beach access, and long-term investment value, free from the typical concerns of coastal erosion.

Architectural plans by the renowned Moskow Linn Architects have already been approved for a thoughtfully designed estate featuring a four-bedroom main residence, a two-bedroom carriage house, and a pool—streamlining the path to your ideal Vineyard retreat. The land easily supports a home of this scale and quality, with partial views of Vineyard Sound and unforgettable west-facing sunsets.

Included in the offering is 50% ownership of an adjacent waterfront parcel, providing private access to a serene sandy beach and calm, swimmable waters—ideal for a morning swim, paddle, or evening stroll by the shore. This rare amenity enhances both the lifestyle and long-term value of the property.

While existing structures remain on-site, they are in disrepair and do not contribute to the property's value. The true opportunity lies in the land, the location, and the potential to create something extraordinary.

Tired of compromising in your home search? This is your chance to bring your vision to life in a setting that exceeds expectations—where sunsets, serenity, and design potential meet in perfect harmony.

26 Chappaquiddick Ave & Passamaquoddy Ave, West Tisbury, is exclusively offered for sale for $2,650,000

Blackpoint Beach rights!

Blackpoint Beach is an exquisite destination for beach walking, swimming, and access to Blackpoint Pond, which leads to the Tisbury Great Pond. Miles of sandy beach east and west with easy access via a boardwalk to the beach. Grassy parking, private gated beach access on the south shore of Chilmark. Blackpoint is a less common offering. This is a great time of year to include this in your summer or year-round living. This is not a buildable property, strictly beach and pond access only

A key for Blackpoint Beach is listed exclusively for $415,000