Oak Bluffs Classified Ad Listings

20 Hyannis Point Rd Unit 20. Make sure to ask about Seller's incentive if closing happens in 2026!! Sunny Nantucket-inspired villa with charm in abundance-from its cheerful coastal character and relaxed village setting to the inviting outdoor spaces that make it feel like a true seaside retreat. You will feel like you are always on vacation in Maushop Village! Enjoy a welcoming front patio and ...

179 Sheaffer Rd. A meticulously maintained property built in 1972, offering 1500+ square feet of living space. This inviting home, is currently in ready-to-move-in condition, embodies a lifestyle of comfort and refined ease. The ranch-style architecture provides a seamless flow throughout the interior. The residence encompasses three well-proportioned bedrooms, offering versatile living arrange...

16 Cove Point Ln. Situated on a bluff overlooking Prince Cove, this exceptional waterfront estate presents a rare combination of natural beauty, modern luxury, and total privacy in an unmatched setting. Meticulously designed and cared for, the property delivers Cape Cod living at its finest with a private dock, resort-style swimming pool, and extensive outdoor living spaces surrounded by water ...

19 Maple St. Welcome to 19 Maple Street, a beautifully renovated 3-bedroom, 3-bath home offering comfortable living with deeded rights to Mashpee Wakeby Pond. The bright, inviting interior features a light-filled renovated sunroom, a cozy fireplace, and thoughtful updates throughout. The finished lower level provides additional living space with a spacious recreation room, perfect for entertain...

451 County Rd. NEW PRICE! Motivated seller welcomes offers. Welcome to 451 County Road, a beautifully updated Gambrel offering 2,952 sq. ft. of finished living space in desirable Pocasset, just a short distance from Monument Beach. Set on a fenced, nearly half-acre lot, this 3-bedroom, 2-bath home offers an impressive combination of space, location, and thoughtful improvements. The main level f...

39 Tower Hill Unit Bldg 1 Rd Unit 1A. FIRST FLOOR RENOVATED CONDO in the heart of Osterville Village! Enjoy the best of village living with an easy walk to Osterville's shops, restaurants, and local amenities. This tastefully renovated condo with new floors, kitchen and baths offers two generously sized bedrooms and two full bathrooms. The spacious living room features a cozy fireplace and flow...

16 Witchwood Ln. Situated down a long private driveway, this renovated 3.5-acre Katama estate offers a rare opportunity to acquire a turnkey property with a deep-water dock slip on Katama Bay. Impeccably executed throughout, the estate showcases exceptional craftsmanship, distinctive materials, top-of-the-line appliances, and an impressive array of amenities. Highlights include a finished lower...

18 Bonwood Dr Unit 402. Welcome to Southport, the area's best 55+ community. Enjoy an active life playing golf, tennis, or pickleball, walking trails, hitting one of the clubhouses, the fitness center or one of two pools. This home overlooks the 6th fairway with a pond and fountain. Beautifully maintained and professionally managed, this townhouse offers the best comfort and ease-of-maintenance...

181 Daniels Island Rd. A Place Where Dreams Are Made! Elevated coastal living awaits in this extraordinary waterfront residence nestled within the exclusive enclave of Daniels Island. Perfectly positioned to capture sweeping views of Popponesset Bay and Nantucket Sound, this exceptional home offers an unparalleled blend of elegance, comfort, and the timeless beauty. With impeccable attention to...

5 Bayview Rd. Welcome to Seconsett Island! A truly unique area where water views and stunning sunsets surround you. Beautifully updated home throughout with gleaming hardwood floors. The kitchen features polished granite countertops, stainless steel appliances, plenty of cabinets including a pantry and large breakfast bar. Open to your cozy living room for gatherings or your dining area with ad...

744 Old Barnstable Rd. Fantastic Find ESTATE SALE: 3-Bedroom 2-Bath Colonial Home with a 4-Bedroom Septic set on a Spacious 41,000+sf Lot leaving plenty of room for outside Enjoyment, Home Expansion, or Pool. Front-to-back Living room with Fireplace, Wainscoting, Hardwood Floors, and Built-ins. Open Dining room. Kitchen with Solid Surface Counters, Oversized Island work center, Stainless Steel ...

78 Gold Leaf Ln. Tucked at the quiet end of Gold Leaf Lane in Windchime, this light-filled townhome offers true privacy, backing to conservation land so the woods-not neighbors-are your view. Easy first-floor living starts with a primary suite featuring a vaulted ceiling, skylight, and ensuite bath. The open living room has a gas fireplace, hardwood floors, skylights, and a slider to the deck. ...

52 Packet Landing Way. 4.2 Acres - West Barnstable, Cape Cod. Rare opportunity to own 4.2 private acres in one of Cape Cod's most desirable villages. Tucked away off Packet Landing Way, this exceptional parcel offers the perfect blend of privacy, natural beauty, and convenience. The property has already passed a perc test, providing a significant advantage for future development. Access is prov...

9 Elaine Rd. This attractive, move-in ready home offers the perfect blend of comfort and convenience. Located just 1.6 miles from Craigville Beach and minutes from Hyannis shops, dining, and the marina, it's an ideal Cape escape. Inside, you'll find central AC, gleaming hardwood floors, and a finished lower level for flexible living. The second-floor family room provides excellent potential for...

14 Thayer St. 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, an...

39 Ryder Ln. Ideally situated in Marion Village, moments from the harbor, beaches, and Tabor Academy, this beautifully updated residence offers more than 4,345 square feet of refined coastal living on a spacious, professionally landscaped lot. Timeless character and thoughtful improvements create an inviting home for elegant entertaining, multigenerational living, and relaxed everyday enjoyment...

40 Sweet William Wt Way # 155. THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with t...

2 Old Farms Trl. 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 ...

2 Fieldstone Ln. New construction! 7002 sq ft lot available in Sippican Woods, Marion s newest subdivision! Turnkey home packages available starting at $339,900. We have several models available on spec or can build to suit client s needs. Contact listing agent for details.. 3 Bedrooms. 2 Bathroom. 1660 ft

52 Willimantic Dr. From the moment you arrive, the classic white picket fence and welcoming curb appeal make a wonderful first impression. Inside, the bright and inviting living room features beautiful hardwood floors, abundant natural light, and a stunning fireplace that creates the perfect gathering space. The open layout flows effortlessly into the dining area and updated kitchen, making eve...