Waterfront homes for sale & real estate in Oak Bluffs, MA

Waterfront Home for sale in Oak Bluffs, MA:

The Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to a peaceful and private deck. Living room offers a comfortable space for TV and relaxing. There is also nice size first floor primary with walk-in closet and spacious en-suite bathroom. The grand entryway takes you to the second floor which offers a second primary bedroom with walk-in closet and en-

Waterfront Home for sale in Oak Bluffs, MA:

Classic Style Meets Timeless Charm - Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this residence provides a modern and spacious environment for comfortable island living. The home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen is a chef's delight that seamlessly connects with the living and dining areas. A cozy Family Room/Den is also located on the main floor. The second-floor primary bedroom is a private sanctuary, complete with a walk-in closet and a spa-like en suite bathroom. Outside, the meticulously landscaped yard provides a serene escape for o

Waterfront Home for sale in Oak Bluffs, MA:

27 SEVENTH STREET NORTH, EDGARTOWN offers NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2026; just in time to bring in the 2026 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers an island with seating for four. The kitchen sports Bosch appliances, an island with a built in drawer microwave, quartz countertops and an easy layout for cooking and entertaining. The kitchen then opens to a separate dining room. A half bath off the living room and a first floor primary bedroom with a luxurious p

Waterfront Home for sale in Oak Bluffs, MA:

For the very first time, the historic Ben Luce Homestead (circa 1850) is being offered on the open market. This charming farmhouse blends rich Island history with timeless appeal. Once home to Benjamin Norton Luce (1840–1912) — Civil War veteran, blacksmith, and town constable — the property sits on 1.5 acres of pastoral land and offers 5 bedrooms, 2 full baths, solar panels, barn, and a newly updated septic system meeting current standards. Thoughtfully restored for year-round living, the home provides comfort, character, and sustainability. Just minutes from Vineyard Haven’s harbor, shops, and ferry, this rare offering combines privacy with exceptional convenience.

Waterfront Home for sale in Oak Bluffs, MA:

STUNNING WATERFRONT HOME IN WEST CHOPThis elegant six-bedroom home with 200 feet of private sandy beach overlooks Vineyard Haven's outer harbor, the East Chop lighthouse and Nantucket Sound on 1.75 acres of land. Built in 1945, it was renovated in 2002 to include an attached three-car garage with a two-bedroom guest apartment above. A small entry hall leads to the great room with hardwood floors, the sweeping water views and French doors to the large deck. Built-in bookcases and a woodburning fireplace in the great room offer a gathering spot to chase the off-season chill. On the right are three bedrooms, one with ensuite bath. A shared bath and hallway with ample storage including a cedar

Waterfront Home for sale in Oak Bluffs, MA:

Nestled at 5 Pinetree Lane, Vineyard Haven, MA, this single-family residence in Dukes County presents a unique opportunity to own a piece of classic American architecture. Built in 1927, this home offers a blend of vintage charm and comfortable living. The residence features three full bathrooms, providing convenience and privacy for all occupants. Imagine mornings where everyone can prepare for the day without the rush, and evenings where relaxation is never compromised. The thoughtful design ensures that personal space is always readily available. With four bedrooms, this home provides ample space for rest and rejuvenation. Envision each room becoming a personalized sanctuary, tailored to