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OAK BLUFFS
Single Family Residence

99 Ocean Avenue, Oak Bluffs, MA 02557

$3,975,000.00
Listed 1st August, 2026 for $3,975,000
LINK ID: 44771
STATUS: AVAILABLE
Bedrooms: 4
Baths: 2
Half Baths: 1
Rooms: 9
Living Space: 2600
Acreage: 0.1000
Water Frontage: None
1st Floor Bedrooms 1

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Outdoor Spaces: Water Views, Porch, C/Tennis, Beach Access - Public, Deck
Features: MiniSplit, Outdoor Shower
Year Built: 1885
Year Renovated: 2018
Second Dwelling: None
Zoning: R1
Water: Town
Sewer: Septic Tank
Lead Paint: Unknown
Foundation : Crawlspace
Heat: Heat Pump
Fireplaces: 1
Flooring: Mix of wood and carpeting
Stove: Yes
Washer: Yes
TV: Cable

DESCRIPTION

A Victorian Grand Dame overlooking Ocean Park -- in a truly spectacular setting with sweeping water views from two stories of verandas. Located in Oak Bluffs most popular and exciting neighborhood and just steps from the beaches of Nantucket Sound, fine restaurants, art galleries, shopping, harbor, ferries, the Campground and the Tabernacle. This treasured property has been home to family and guests that have enjoyed dramatic sunsets, spectacular August fireworks and evening strolls to town for generations. This historic home retains its Victorian character while having been carefully maintained and updated over the years. Recent improvements include a Title V septic, all new windows, ducted mini-splits for heat/AC throughout the house plus two propane monitors and outdoor shower. Lastly, there is parking for three cars in the parking area behind the house -- a big plus in the heart of downtown.

FIRST FLOOR DESCRIPTION
Entertain family and friends on the large wrap around porch over looking historic Ocean Park and the ocean. The 1st floor includes a large living room with beach stone fireplace, water views and front door access from the wrap around front porch. Completing the main floor is a family room with piano, dining area, bedroom, half bath, kitchen with large pantry, washer/dryer and access to rear patio, backyard, two sheds for yard and garden equipment and parking. Mature perennial backyard garden.

SECOND FLOOR DESCRIPTION
The 2nd floor includes the primary bedroom with water views and balcony access, two additional bedrooms, two full bathrooms and a bonus room for overflow family and guests.

THIRD FLOOR DESCRIPTION
The ceiling height attic running the length of the house currently used for duct work and storage has potential areas for expansion.

BASEMENT DESCRIPTION
Crawlspace

SECOND DWELLING
None

PARKING
For several cars in driveway
Martha's Vineyard - Island Wide Listings - Updated September 20, 2026
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ALISAN LOHAN-CONWAY PROPERTIES MARTHA'S VINEYARD
Martha's Vineyard Real Estate Sales and Rentals
PO Box 2670, Edgartown, MA 02539
Phone: 508.627.1858 Fax: 508.696.7648

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