Oak Bluffs Massachusetts homes for sale starting at Fifty Thousand Dollars

$2,285,000 - Oak Bluffs, MA

4 Dempster Park Oak Bluffs, MA - East Chop -- This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. The 1st floor includes large living room with dining area and Rumford wood burning fireplace that opens out to a front porch and deck running the length of the house and which wraps around to the rear patio. Completing the 1st floor is a kitchen and bedroom with half bath. 2nd floor includes three additional bedrooms, one ensuite plus another full bathroom. The second floor also has plumbing, electrical and venting in large hall closet for another washer and dryer. In addition, the second floor has additional storage that runs the length of the front of the house that is accessible from the two front bedrooms. Unfinished basement includes two large storage areas, washer/dryer and a large additional room that could be a family room or studio/workshop. Property includes spacious rear patio, outdoor shower, and parking for several cars on the front of the property. Yard is been nicely landscaped. Rental income approx. $7,000/wk in season. Available for showings with 24-hr notice.

$2,150,000 - Oak Bluffs, MA

30 Franklin Avenue Oak Bluffs, MA - Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5 baths, including a spa room, this residence offers both comfort and relaxation. The bright living room offers a gas fireplace with built-in shelving, and access to a wrap around porch and stone patio. The 2-car garage provides ample storage space. Located just minutes from downtown Oak Bluffs, this home offers convenience and charm. Don't miss the opportunity to own this fantastic property.

$1,995,000 - Oak Bluffs, MA

47 E Chop Drive Unit: #3 Oak Bluffs, MA - East Chop Water Front Luxury Condominiums -- This 2BR, waterfront condominium, the ''Highlands'', features outstanding water views of the harbor, the sound and the Cape beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 2nd floor unit includes new kitchen with Bosch appliances, living and dining areas and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include a private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40' T at the end for a 9th boat. Each unit includes a designated parking space for one vehicle. The property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Laundry service and house keeping available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condo documents. Available for showing with 24-hr notice until June 15th, thereafter Satruday's 10-12.

$1,995,000 - Oak Bluffs, MA

47 E Chop Drive Unit: #4 Oak Bluffs, MA - East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condominium, the ''Tivoli'', features outstanding water views of the harbor and the sound beyond all the way to Chappaquiddick. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living and dining areas and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include a private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40' T at the end for a 9th boat. Each unit includes a designated parking space for one vehicle. The property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Features include crown molding and attention to detail, as well as beautifully landscaped grounds. Laundry service available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condo docs.

$1,850,000 - Oak Bluffs, MA

34 Tower Ridge Road Oak Bluffs, MA - Nestled on a beautifully landscaped lot with lush gardens and mature trees, 34 Tower Ridge offers the perfect blend of privacy and convenience. Ideally located just minutes from downtown Oak Bluffs and the Farm Neck Golf Course, this well-maintained property is suited for comfortable year-round living or as a serene Island retreat. Inside, the bright and open layout features an updated kitchen and generous living spaces that flow seamlessly-ideal for both entertaining and everyday life. With two spacious primary suites, including one on the first floor, the home provides flexible accommodations for family and guests alike. The third level adds even more versatility with a large bonus space perfect for a home office, den, or fifth bedroom-supported by a five-bedroom septic system. Outdoors, enjoy thoughtfully manicured grounds with ample space for entertaining, gardening, or simply relaxing in your own private oasis. Tower Ridge residents also benefit from association tennis courts, adding to the appeal of this sought-after neighborhood.

$1,575,000 - Oak Bluffs, MA

8 School House Village Oak Bluffs, MA - Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attractive colorful landscaping, this property offers a pleasantly appointed 3-bedroom, 2.5-bath home and a recently renovated 1-bedroom, 1-bath apartment above the 2-car garage. The first floor features a spacious living room with a pellet stove and a fabulous great room with a wood-burning stove. French doors lead to a large deck, perfect for outdoor entertaining. The open kitchen and dining room are at the back of the house and enjoy direct deck access. There is a half bath off the living room. The primary suite with a full bath, and 2 additional bedrooms that share a full bath, complete the second floor. An exceptional feature of this property is the apartment with comfortable living space and a private entrance and deck. The location is ideal with easy access to the bike path, YMCA, high school, and state forest, and centrally located to all the down-island towns! Easy to show and being sold mostly furnished, this property is ready for immediate use. FIRST FLOOR: The spacious living room with a wood-burning stove and half bath are at the front of the home. The kitchen and dining room are at the back of the house with direct access to the deck. Completing this floor is the outstanding great room with French doors to the deck. SECOND FLOOR: The primary suite with a full bath is on the left and 2 additional bedrooms which share a large full bath occupy the right side of this floor. BASEMENT: Full unfinished basement with plenty of room for storage with interior and bulkhead access. The laundry for the house is in the basement. APARTMENT: Above the 2-car garage is a wonderful fully renovated 1-bedroom, 1 full bath apartment with great natural light, a full kitchen, and an open living area. This space offers many options with excellent rental potential and is perfect for overflow guests!

$1,495,000 - Oak Bluffs, MA

47 E Chop Drive Unit: #1 Oak Bluffs, MA - East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condominium, ''Oak Bluffs'', features outstanding water views of the harbor and sound beyond. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock with water/electric for 8 slips and a 40' T at the end for a 9th boat; Each condo unit includes a designated parking space for one vehicle. The property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Laundry service available. Sold with furniture depending on price. Occupancy available beginning Nov. 1st, 2025. Available for showing with 24-hr notice until June 15th, thereafter Saturday's 10-12.

$1,495,000 - Oak Bluffs, MA

47 E Chop Drive Unit: #2 Oak Bluffs, MA - East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, ''Cottage City'', features outstanding water views of the harbor and sound beyond, a cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 1st-floor unit includes new kitchen with Bosch appliances, living room with fireplace, dining area and a private covered front porch over-looking the water (see floor plans). The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40' T at the end for a 9th boat. The property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Laundry service and house keeping available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval. Available for showings with 24-hr notice until June 15th, thereafter Saturday's 10-12.

$1,495,000 - Oak Bluffs, MA

47 E Chop Drive Unit: #5 Oak Bluffs, MA - East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Captain's Quarters'', features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch over-looking the water (see floor plans). The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40' T at the end for a 9th boat. Each condo unit includes a designated parking space for one vehicle. The property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, and dredged dockage. Features include crown molding, new kitchen and bathroom (with handicap accessible shower) both with Italian Carrara subway tile. Occupancy beginning Nov. 1st, 2025. New condominium pending buyer approval of condo docs.

$1,450,000 - Oak Bluffs, MA

35 Vineyard Avenue Extension Oak Bluffs, MA - Charming Home Steps from Lagoon Pond - This three bedroom, two bath home is just 550 feet from the sandy shores and calm waters of Lagoon Pond, perfect for swimming, boating and shell fishing. Ideal for both year-round living or vacationing, the home offers an open floor plan, a private primary suite with a walk-in closet and en-suite bath, two guest bedrooms plus a den/office. The finished basement area adds extra space for a gym or game room and there is lots of room for storage. While outside, enjoy the brick patio with a wood-burning fireplace, front and side decks, an outdoor shower, flower and vegetable gardens and potting/tool shed. A must-see home for those who love the water and want convenience to all Oak Bluffs has to offer!

Oak Bluffs, Massachusetts listings for sale

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