111 North Water Street

HISTORIC CAPTAIN'S HOME WITH GUEST COTTAGE AND DEEP WATER DOCK. Step into the heritage and heart of Edgartown Village with this iconic historic captain’s home, dating to circa 1850 and thoughtfully reimagined in 2002 under the vision of renowned architect Patrick Ahearn. Perfectly positioned on a rare double-wide lot along highly-coveted North Water Street, this extraordinary property seamlessly blends classic Vineyard character with luxurious modern amenities. Sweeping harbor views greet you from nearly every angle of the bright, sun-washed living spaces, wrapped in windows that frame an awe-inspiring 180-degree panorama of Edgartown Harbor and its iconic lighthouse. The open-concept first floor creates an effortless flow between the living room, dining area, and an inviting eat-in kitchen, all finished with beautiful heart pine flooring, custom millwork, timeless paneling and a handpainted wall mural by well-known island artist, Margot Datz. French doors lead outside to an expansive 18x29-foot mahogany deck — a picture-perfect stage for al fresco dining, summer entertaining, or simply soaking in the serene waterside setting. There are a total of six bedrooms, including a spacious Owner's Suite on the second floor with exceptional views and an en suite bathroom with double vanity and walk-in glass shower. The detached, charming guest house provides private accommodations for visitors, maintaining the same timeless coastal appeal. The lawn gently slopes to the water’s edge, complemented by perennial gardens, an arbor, and a deep-water pier for convenient boating access. Set among lush gardens and surrounded by Edgartown’s most storied residences, this is a truly rare waterfront opportunity — where legacy, lifestyle, and location converge.