Billy Joel’s roughly 26-acre, waterfront estate on the North Shore of Long Island is coming on the market for $49 million.

The Grammy winner paid $22.5 million for the first roughly 14 acres of the Oyster Bay, N.Y., estate in 2002, public records show. More recently, he acquired several adjacent parcels of land, restoring much of an original estate that was broken up in the 1950s, according to listing agent Bonnie Williamson of Daniel Gale Sotheby’s International Realty.

Known as Middlesea, the property was briefly listed for sale in 2006 asking $37.5 million, but was taken off the market soon after, Ms. Williamson said. She said the Piano Man is looking to sell now because he and his wife, Alexis Roderick, with whom he shares two young children, are spending more time in Florida.

Located on Centre Island, a small island roughly 40 miles east of Midtown Manhattan, the estate is close to Mr. Joel’s hometown of Hicksville, a hamlet also located in the town of Oyster Bay. The centerpiece of the estate is a roughly 20,000-square-foot mansion. The property also has a floating dock, a beach house with guest rooms, a gate house, two outdoor pools and a helipad, Ms. Williamson said.

Currently under renovation, the five-bedroom main house has covered porches, brick columns and archways, and a two-story entry hall with black-and-white marble tiled floors. Other amenities at the estate include an under-construction playroom, a room designed to be a spa and hair salon, a bowling alley and a wine cellar. Mr. Joel covered up an indoor pool so he could use the space, which has excellent acoustics, as a music room, Ms. Williamson said.

The renovation of the house is expected to be complete by the late summer or fall, she said. Mr. Joel decided to put the house on the market in the midst of the renovation, Ms. Williamson said, because “whoever buys will want to do their own selections of how to paint and decorate and perhaps style the kitchen.”

Mr. Joel, known for songs like “Piano Man,” “We Didn’t Start the Fire” and “Uptown Girl,” is in the midst of residency at Madison Square Garden in New York.

Records show a company tied to Mr. Joel purchased an estate in the Lantana, Fla., area, for about $22 million in 2015. Another company tied to Mr. Joel also owns property in Sag Harbor, N.Y., records show.

Middlesea will be the most expensive home for sale in Oyster Bay, where the next priciest listing is asking $8.5 million, according to Zillow. In the first quarter, Long Island luxury sales were down by about 34% from the same period of last year, according to a recent report by Douglas Elliman.