Oak Bluffs Classified Ad Listings

New Brokerage Listing: Check out this 2006 Holby Marine 17 Bristol Skiff, which is in excellent condition and powered by a reliable Tohatsu 40HP engine. This classic 17-foot skiff features comfortable bench seating and a center console with rod holders, giving it a timeless appeal. The elegant wood rub rail adds a touch of sophistication, and the overall condition of the skiff is impressive. It...

6 Wakeman Rd. Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist's studio, and a detached garage with an additional bedroom above - creating the ideal retreat fo...

11 Manor Dr. This beautiful Cape, located in a well-established neighborhood, boasts many custom features. The open kitchen and family room with fireplace and built in bookcases has ample space for entertaining family and friends. There is a formal dining room, a den/office, and a spacious primary suite with a gas fireplace and large walk-in closet. Also on the first floor is a half bath, laund...

27 Sachem Dr. This beautiful Year-Round Colonial home is in a quiet neighborhood within a short distance to Sagamore Beaches, the Cape Cod Canal and conveniently nearby to the commuter bus stop. First floor has front to back living room and dining area with sliding glass doors that step out to a large deck overlooking the private back yard. Small storage/garden shed. There is new Luxury Vinyl f...

11 Hammett Ln. BOOKING SUMMER 2027 AND FALL/SPRING '26 SPRING '27 Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower wi...

396 Baxters Neck Road. Single Family Home for sale in Marstons Mills, MA for $6,950,000 with 4 bedrooms and 6 full baths, 1 half bath. This 9,886 square foot home was built in 1989 on a lot size of 1.61.. Set within the coveted Baxters Neck enclave, this exceptional waterfront estate home has been reimagined by architects and leading designers, with a thoughtful floorplan suited to both family ...

9 HI River Rd. Casa Blanca Farm - An Iconic Cape Cod Estate. Beyond the stately columned entrance and winding cobblestone drive, this extraordinary estate unfolds across nearly five breathtaking acres. Masterfully renovated and meticulously redesigned, the residence blends timeless architecture with exceptional craftsmanship and sophisticated design. Sun-filled interiors showcase custom millwor...

43 N Slope Ln. Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, fea...

18 Point Inner Way. A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a ...

26 Vineyard View Ln Unit 639. Don't miss out on a rare opportunity to own a scenic ocean-view, Nantucket style cottage being sold ''Turn Key'' just steps to your own private deeded sandy beach with views of Martha's Vineyard. Panoramic views from almost every room surround this stunning recently renovated end unit. This gorgeous cottage offers an open design with high ceilings, beautiful pine f...

25 Ripple Cove Rd. Hyannis Harbor views from your deck!! Just steps to boat launch for your kayak, canoe or larger boat! Private way to water and Veterans Beach is just 1/4 mile away! Main Street shops and restaurants are less than 1/2 mile away! Enjoy summer concerts at the Village Green or Aselton Park! This 5BR, 3BA home has a nicely appointed kitchen with granite counters, hardwood floors o...

224 North Rd # CH248. THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with th...

12 Foxcroft Ln. 12 Foxcroft Lane | East Sandwich A once-in-a-generation waterfront estate, 12 Foxcroft Lane represents the pinnacle of Cape Cod coastal luxury. Set on beautifully manicured grounds with sweeping lawns, a pristine private sandy beach, and panoramic views of Cape Cod Bay from Plymouth to Provincetown, this extraordinary 16,000+/- sq. ft. residence offers six bedrooms and ten baths...

16 Alder Ln. Experience the perfect blend of modern luxury and coastal living in this exceptional 3 br, 3 1/2 bath contemporary home. Located in the highly desired WILD HARBOR ESTATES, this property offers a lifestyle complete with access to a private sandy beach and tennis courts overlooking the harbor.Step inside to an expansive open-concept main level designed for relaxed living and entertai...

174 Middle Rd. Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. T...

2 Kendall Rae Pl Unit 1202. Introducing Residence 1202, an exceptional 1,574 sq. ft. corner residence at Cape Crossings, a new construction resort-style condominium community located directly on the Cape Cod Canal. Positioned on the building's desirable corner footprint, this home maximizes privacy, natural sunlight, and architectural sophistication. Designed for seamless living, the open-conce...

9 Winchester Dr. Enjoy effortless single-level living in this beautifully updated home nestled within a desirable waterfront community offering an association beach and rights-of-way to the water. Thoughtfully refreshed throughout, this inviting three-bedroom residence offers the perfect blend of comfort, style, and relaxed Cape Cod living. The bright, open living area flows seamlessly into a w...

68 Mid Iron Way Unit 7525. Set along the 3rd fairway of New Seabury's Dunes Course, this beautifully situated two-bedroom, two-bath end-unit Patio Villa offers privacy, comfort and an exceptional golf-course setting. The home features an updated kitchen with quartz countertops, a new heating system and is being offered furnished. Ideal for year-round living, a Cape Cod retreat or an easy getawa...

66 Osprey Ln. Charming 3-Bedroom, 2-Bath Home in a Desirable Neighborhood! Welcome to this inviting 3-bedroom, 2-bathroom home, conveniently located in a residential neighborhood with easy access to the highway, shopping, and local amenities. The first floor features a spacious bedroom with easy-care flooring, a full bathroom, and convenient first-floor laundry, offering the comfort and flexibi...

14 Sea Knoll Ct Unit 14. Nestled within the Brookside community, this Cranberry end-unit offers a lifestyle defined by understated elegance, comfort and style. Positioned to capture the soft glow of the morning sun, the residence overlooks the 10th hole, providing a tranquil backdrop with custom hardscape and beautiful plantings.Thoughtfully reimagined with a sophisticated, neutral palette, the...