Introducing a landmark property in Edgartown’s Starbuck Neck enclave, just one tenth of a mile to Fuller Street Beach. Included in this sale is an adjoining vacant buildable lot. 14 STARBUCK NECK features a 7-bedroom house with 5 full bathrooms, garage, and plunge pool. Known as the Tower House, this home offers delightful views of the harbor from the first and second floors. The views from the bedroom and office located in the tower are stunning. 23 THAYER STREET is an extremely rare vacant lot in the heart of the Starbuck Neck neighborhood. With well over a third of an acre of land, the lot will comfortably accommodate a 5-bedroom house with guesthouse and pool.

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Unique opportunity to purchase two adjoining lots at 211 Upper Main Street and 26 Curtis Lane in Downtown Edgartown. 211 Upper Main St., Edgartown is a 15 bedrooms, 18 full baths, 2 half baths building with two large artist/fitness studios attached. It is in the B1 Commercial zoning district. Each bedroom includes an en-suite bathroom. Spacious kitchen and dining area. The kitchen/dining area includes: 2 refrigerators and 4 freezer drawers, A 5-burner gas stove and oven, 2 dishwashers, 1 microwave. Spacious living room: including 2 sofas and 1 coffee table, finished basement (2,000 square feet), Basement includes: 10 washer/dryers, 1 television and DVD player, 2 small rehearsal rooms, Complimentary Wi-Fi, Outdoor deck with picnic tables. 26 Curtis Lane is an exceptional 8 bedroom home with attached artist/fitness barn studios. Each bedroom includes a en-suite bathroom. The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill. Two more adjacent lots with parking and a yard are also available for purchase upon request.

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Set within the prestigious Cow Bay Association, one of the island’s most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of private shoreline, beach cabanas, Trapps Pond and potential mooring. Despite its remarkable seclusion, the property remains just minutes from the charm and sophistication of downtown Edgartown. The six-bedroom main residence is a masterclass in timeless design and effortless elegance. Grand yet inviting, the home offers beautifully proportioned living and dining spaces, a thoughtfully designed chef’s kitchen and a sweeping screened porch, all oriented to capture wonderful views across the pool and out to Vineyard Sound. Every room is infused with natural light and a sense of understated luxury. The grounds are nothing short of spectacular, a curated landscape of mature plantings, expansive stone terraces, and romantic pergolas draped in cascading wisteria. At the heart of the property, a stunning pool and lounge area create a private resort-like setting, ideal for both intimate relaxation and sophisticated, large-scale entertaining. A separate carriage/guest house with full amenities offers flexible accommodations for guests or staff. This is more than a home; it is a rare and irreplaceable offering, a legacy property in one of the island’s most coveted coastal settings.

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Thirty-eight (38 acres) of available land in Edgartown! This is a truly extraordinary and increasingly rare opportunity to own thirty-eight (38) acres of contiguous land in Edgartown. Come create a landmark estate or private compound in one of Edgartown’s most sought-after locations. Perfectly positioned between the charm of Edgartown Historic Village and the sweeping sands of South Beach and moments from Edgartown Great Pond. This premier parcel offers an unparalleled setting for a world-class residential retreat. The property’s scale and configuration present exceptional development potential, the creation of a substantial main residence complemented by guest accommodations, recreational amenities, and expansive outdoor living spaces. Whether envisioned as a generational compound or a singular statement estate, the land provides the flexibility to bring a sophisticated vision to life. Surrounded by prestigious homes and natural Vineyard beauty, the setting offers both privacy and proximity, close to harbor access, Edgartown Great Pond, fine dining, boutiques, and some of the island’s most celebrated beaches. Opportunities of this caliber, combining estate-scale potential with such a coveted location, are exceedingly rare and highly prized. An offering of this distinction is seldom available. This is an exceptional canvas for the discerning buyer seeking to establish a lasting presence in Edgartown.

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You truly can have it all—just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village yet set along one of the most spectacular stretches of beach, with a 190' private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartown Lighthouse. A gentle slope leads to the sandy shore, where days unfold along the pristine waters of the harbor. Inside, casual elegance defines the home, with a seamless blend of gracious formal spaces and inviting areas for relaxed gatherings. The grounds are equally captivating, made even more exceptional by the inclusion of 75 Landing Place Road, with the availability of an additional conforming lot further elevating this offering — providing the opportunity to create a one-of-a-kind family compound and enduring legacy estate. Cherished by the same family for generations, this extraordinary waterfront compound is a truly special place.

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An exceptional offering in the heart of Edgartown Village, 14 Thayer Street presents the rare combination of estate-scale grounds, privacy, and an in-town location. Set across an extraordinary 0.62-acre double lot, the property unfolds as a private retreat just moments from the harbor, shops, galleries, and restaurants of downtown Edgartown. Expansive lawns, mature landscaping, and a substantial swimming pool create a setting more often associated with properties well beyond the Village center, offering remarkable space for outdoor living, entertaining, and generations of summer gatherings. At the heart of the property is a distinguished five-bedroom, five-bath residence encompassing more than 3,100 square feet. Rich in authentic Vineyard character, the home is attributed to Frederick Baylies Jr., builder of Edgartown’s iconic Old Whaling Church, lending architectural significance to an already exceptional property. Yet it is the combination of land, location, and lifestyle that truly distinguishes 14 Thayer Street. Opportunities to own this level of acreage and privacy within Edgartown Village are exceedingly limited, making this a compelling chance to acquire a true in-town estate in one of Martha’s Vineyard’s most coveted settings.

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Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. This is one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in a Vineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming in from the oversized windows, wonderful craftsmanship throughout and the home that offers 7 bedrooms, all with private baths. The 2-story living room features a massive stone fireplace, balconies that look down from the second floor and a grand 20 ft. diameter circular staircase. There is a huge gourmet kitchen, dining room, lower-level gym, media room and recreation area, are nicely arranged on the over 8,000 sq. ft. of living space. There is a large parking courtyard, a 3-car garage and swimming pool, all amidst a lush backdrop of manicured landscaping and mature perimeter vegetation. This incredible newly offered neighborhood is located less than a mile to town in one direction and same distance to the white sandy beach at the bend-in-the-road in the other. A very special property due for completion this fall and ready to enjoy.

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YOUR OWN PRIVATE WATERFRONT OASIS: CAPTIVATING ESTATE LIVING. This extraordinary Katama Bay waterfront retreat blends timeless coastal architecture, refined interiors, and the natural beauty of Chappaquiddick in unforgettable fashion. Designed by noted architect Patrick Ahearn, this magnificent residence is privately sited at the end of a winding drive on 16.4 acres, offering more than 7,200 square feet of beautifully appointed living space created for the ultimate luxury: treasured time with family and friends. Inside, the home exudes warmth and sophistication with four wood-burning fireplaces, handsome hardwood and painted floors, custom millwork, built-ins, inviting gathering spaces, and sweeping views of Katama Bay from nearly every room. A rooftop widow’s walk crowns the home, offering breathtaking 360-degree vistas across the bay, dunes, tidal ponds, and surrounding grasslands. One of the home’s most captivating features is the expansive screened and covered porch, extending nearly the full length of the house and overlooking the sparkling waters of Katama Bay. It is an idyllic setting for relaxed summer dinners, quiet afternoons with a book, lively games, or simply taking in the brilliant evening sunsets. With more than 320 feet of Katama Bay frontage, the property invites a true waterfront lifestyle, with exceptional opportunities for sailing, boating, paddleboarding, fishing, and clamming. Beyond the shoreline, Chappaquiddick offers a rare sense of peace and privacy, with miles of unspoiled beaches, nature trails, sand dunes, tidal ponds, and protected habitats to explore. An attached three-bay garage provides ample storage for an island car, watercraft, bicycles, beach gear, fishing equipment, and every essential for life by the water. Offered turnkey, the home includes hand-selected furnishings and accessories by interior designer Jon Hattaway of MJ Berries Design in Boston, whose vibrant colors, curated objects, and artful details bring character and delight to every room. Enjoy the property exactly as it is, or make it your own and create a signature coastal haven. At once elegant, welcoming, and deeply connected to its extraordinary setting, this private Katama Bay retreat is designed for effortless waterfront living.

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A winding approach through 9.8 acres sets the tone for 12 Boldwater Road: a private Edgartown estate of uncommon scale and distinction. At its heart stands a seven-bedroom, ten-bath residence designed by Robert A.M. Stern. A gracious foyer introduces light-filled interiors, a dramatic post-and-beam living room, multiple fireplaces, and a gourmet kitchen equally suited to intimate dinners and large gatherings. The grounds offer the ease of a private resort. Spend the day beside the heated 20' x 60' pool, or retreat to the pool house with an exterior hot tub, complete with a fully equipped gym, sauna, massage room, and screened porch with fireplace. Every element of the property invites a slower, more considered way of living on the Vineyard. The Boldwater Association membership adds access to a private ocean beach, boat landing, tennis, and pickleball courts. Together with the estate’s remarkable privacy, these amenities offer a compelling balance of seclusion and coastal recreation. Architectural heritage, expansive land, and a setting designed to be enjoyed across generations make 12 Boldwater Road an extraordinary Vineyard offering.

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TIMELESS ARCHITECT-DESIGNED KATAMA RETREAT MADE FOR SUMMER LIVING. At the end of a long private drive, tucked into a quiet 1.5-acre setting near South Beach, this Patrick Ahearn-designed Katama estate feels like a true Vineyard retreat . . . elegant, relaxed, and made for gathering. The home brings Ahearn’s award-winning coastal architecture to life with style, sophistication, and luxury throughout this jewel-box designed property. Vaulted ceilings, custom shiplap paneling, custom millwork, antique rough-hewn beams, Rubio Monocoat floors, plus high-end fixtures, and luxurious finishes create a home that feels both newly built and instantly timeless. The spacious Great Room is anchored by a floor-to-ceiling gas stone fireplace, perfect for cozy nights during the island's shoulder seasons and for holiday gatherings. At the heart of the home is the Gourmet Cook’s Kitchen, designed not just for cooking, but for connection. Open on three sides to the Living Room, Dining Room, and Family Room, it naturally draws everyone together — for morning coffee around the island, long dinners after the beach, or easy summer evenings that move seamlessly from indoors to out. A Butler’s Pantry off the Dining Room adds both function and polish for entertaining. French doors open to the screened porch, offering a quiet, shaded retreat for morning coffee, an afternoon break from the sun, or a breezy lunch between swims. The outdoor living area carries the home’s sense of ease into the evening, with a PebbleTec-finished gunite pool, built-in whirlpool spa, bluestone patio, outdoor shower, and a pergola-covered lounge with a wood-burning fireplace. It is the kind of setting that naturally draws everyone back together after dinner — fireside, relaxed, and lingering under the Vineyard sky. The home offers four en suite bedrooms, including a serene Primary Suite with vaulted ceilings, a walk-in closet, spa-inspired bath, and direct access to the pool area. An attached two-bay garage adds ease, while the full unfinished basement offers exceptional future potential for a Media Room, Game Room, in-house gym, Wine Cellar, or additional lifestyle space. Private, beautifully crafted, and deeply connected to its Katama setting, this is a rare Martha’s Vineyard home designed for true island living: beach days, shared meals, quiet mornings, and effortless summer nights.

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Great Potential with Pond & Beach Access ~ Set on ten private wooded acres in the Boldwater community, this unique property combines privacy, flexibility, and exceptional potential. It includes a beautifully appointed guest house ready to enjoy, plus an approximately 5,400 sq. ft. structure offering the opportunity to create a custom main residence with a swimming pool. Owners enjoy deeded access to Edgartown Great Pond and a private Atlantic Ocean beach, all while being ideally located only 13 minutes to Edgartown Village or Martha's Vineyard Airport. The property may also be purchased with a waterfront residence in Boldwater, creating a rare opportunity for a private family compound. Whether purchased on its own or as part of a larger estate, this is an increasingly rare Martha's Vineyard offering with outstanding space, privacy, and long-term potential. FYI: First photo shows deeded pond access close-by to access the barrier beach on the south shore.

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This truly remarkable Chappaquiddick property offers a rare opportunity to step back in time and experience the quintessential character of Martha’s Vineyard. The original historic home, built in 1892, is distinguished by its signature four-story tower with 270-degree water views and gracious wraparound porch. The main house features a spacious open living room with fireplace, dining room, kitchen with pantry, and comfortable TV room. A ground-floor bedroom and bath provide convenient access to a generous outdoor shower and jacuzzi. The 2nd, 3rd, and 4th floors feature six additional bedrooms, 2.5 baths, and office. The feeling throughout the home is wonderfully timeless, combining historic charm and architectural character with fresh surfaces and updated mechanical systems. Two charming guest cottages provide 3 additional bedrooms and a shared bath. A newly built, traditionally styled barn adds further versatility, while a private clay (Har-Tru) tennis court and storage shed create an exceptional setting for summer recreation. Set on 4.73 acres of beautiful lawns and wildflower-filled pastures, the property is framed by mature trees and enjoys spectacular water views in multiple directions. Every element, from the historic main house and charming cottages to the barn, tennis court, and expansive grounds, contributes to an extraordinary sense of place. Complimenting the entire property is deeded private beach access to Katama Bay as well as a mooring. This is a truly special and one-of-a-kind Chappaquiddick property, where history, natural beauty, and timeless Martha’s Vineyard living come together in a remarkable way.

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