Time to break the bank. These ultra-luxurious properties, from an 1,800-acre beachfront ranch in Santa Barbara to a private island in Florida, come with price tags to match.

You could drop a cool $250 million on the highest-priced home in America on the market right now. But you wouldn’t be on the beach. And what’s the point of spending all that money if you can’t have your morning coffee with your toes in the sand and sea? With an eye on the ultimate real estate prize—being on the water—here are four gloriously luxurious estates that are among the top 25 most expensive offerings on the market. Check them out, and call your banker.

1. Great Island, Darien, Connecticut: $175 million

Protected from the outside world by acres of conservation land and the water of the Long Island Sound, Great Island—connected to the mainland by narrow isthmuses—has 63 acres of New England greenery and views of the Sound from the stone main house. Outbuildings include a stable, beach cottages, a caretaker’s house with a greenhouse, and a cow barn. Only 55 minutes from Manhattan, this estate also has a polo field and a workout track for the equestrians in the family. Great Island is listed by David Ogilvy and Kathleen Coumou of David Ogilvy & Associates Realtors/Christie’s International Real Estate.

2. Las Varas Ranch, Goleta, California: $108 million

In the rolling hills of Goleta, not far from Santa Barbara, this working ranch is a rare piece of California property—1,800 acres, to be exact. Las Varas Ranch has flat pastures, forests, orchards, creeks, a private reservoir, and two miles of beachfront. It also has a large owner’s residence, a guest house, and various outbuildings (some of which are from the 1880s); you can see all its offerings on the property website. Las Varas Ranch is listed by Anthony Punnett of Douglas Elliman Real Estate.

3. Pumpkin Key, Key Largo, Florida: $95 million

A private island in the Florida Keys is hard to come by; a private island you can make your own is even more rare. But Pumpkin Key is just that: a 26-acre island with one main home, two caretakers’ cottages, and a dock master’s apartment—leaving plenty of room for customization. It currently has 12 large bay-front lots, a central tennis court (which can also serve as a helipad), and a 20-slip marina, but with an island like this, anything is possible. Pumpkin Key is listed by Russell Post Sotheby’s International Realty.

4. Thimble Islands Portfolio, Branford, Connecticut: $78 million

With this once-in-a-lifetime property, you get eight private islands for one (sizable) price. Scattered across the Thimble Islands of the Long Island Sound, offshore of Branford, Connecticut, this groomed collection has multiple residences, guest houses, and outbuildings—see inside some of these storied properties here. At the center of it all is Rogers Island (pictured) and its 10-bedroom estate. With accommodations scattered across the islands and docks and piers that allow boating among them all, it’s difficult to imagine what this property is lacking. This Thimble Islands collection is listed by Shelly Tretter Lynch of Sotheby International Realty’s Greenwich Brokerage.

Photos, from top: Stanley Jesudowich; courtesy of Douglas Elliman Real Estate (2); courtesy of Russell Post Sotheby’s International Realty (2); Devin Groody (2)