Oak Bluffs got its start as a resort community when the Martha’s Vineyard Camp Meeting Association began constructing permanent summer cottages in 1860 in the area known as Wesleyan Grove. Due to this success, a couple wealthy men in Edgartown formed the Oak Bluffs Land and Wharf Company, who purchased land adjacent to the Grove, between the Campground and Nantucket Sound. The 75-acre parcel was laid out by Robert Morris Copeland, a Boston landscape architect, who created a system of curvilinear streets and parks, with house lots surrounding each park, in much the same manner as the Campground itself. A few parcels were established for places of worship, but the development wanted to appeal to other religions as the Methodists already had an entire development, from this the 1870 Union Chapel, designed by Samuel Freeman Pratt, was the first built. Another anchor of the development was to be a large luxury resort.

At the head of the Steamship Wharf, the Company built one of the most spacious and luxurious resort hotels of its time, the Sea View House. When it was completed in 1872, the Sea View House was the symbol of the Company’s success. The Sea View was built at a cost of $102,000 with a further cost of $30,000 in furnishings; five stories high on the waterside and four on the inland elevation, it measured 225 feet in length and 40 feet in depth. It contained 125 rooms, office, parlor, spacious dining salons and reception suites. Speaking tubes connected every room with the office; the whole hotel was lit by gas, and warmed by steam heat. The hotel was the first thing seen by new visitors disembarking from the steamers onto the island. The hotel was designed by the same architect as the Union Chapel, Samuel Freeman Pratt. He continued his use of the Stick style for the hotel with elaborate wood framing, trim and Victorian flair. Sadly, on September 24, 1892, the Sea View House caught fire and burned to the ground in less than 40 minutes after the alarm was sounded. The fire originated in the basement near the kitchen, and it was thought resulted from a stray spark getting into the cotton waste that was near the engine.