In Old Naples, the beach is at best a few steps away and at worst a short bike ride. Residents can opt out of cooking for the evening and walk to dinner or stock up at Tony’s Off Third, an upscale market that offers supplies and staples, wines and cheese, and gourmet dinners to go. Close to beach clubs and marinas, Old Naples gives even landlocked homeowners the chance to own a boat and offers tree-lined green space at Cambier and Rodgers parks. Old-growth trees create a canopy overhead, and blooms and gardens add punches of color to this anything-but-urban scene.

PINE RIDGE
Sandwiched between some of Naples’ busiest roadways (Tamiami Trail and Goodlette-Frank Road), Pine Ridge’s neighborhood often surprises first-time visitors with the size and number of its homes, seven large lakes and the presence of horse stables and riding arenas.

The neighborhood offers large private lots, often boasting tennis courts, miniature soccer fields, guesthouses and either brand-new or 1970s-era homes. It’s on the east side of Tamiami Trail, just south of Pine Ridge Road, and the sprawl of commercial development and shopping centers eventually gives way to gracious homes fronting Trail Boulevard. Condos, found in Emerald Woods to the north of the neighborhood boundaries, start in the high $200,000s. Single-family homes, even those sold "as is," start just below $1 million and top out around $4.5 million.

PORT ROYAL
Perhaps Naples’ most recognizable address, Port Royal was developed more than 50 years ago by John Glen Sample, who built his personal fortune as an advertising executive in Chicago. So smitten was Sample with Naples, he purchased the city’s southernmost two miles along the Gulf and began taming swamplands, hammocks and beachfront into roughly 560 mostly waterfront lots.

His ambition was simple: He wanted to "make this the finest place to live in the United States." Today, Sample’s prophecy holds true. Large shade trees create a canopy above the neighborhood’s streets; manmade peninsulas, coves and bays bring water into most back yards; and manicured hedges and enviable landscaping provide privacy. Many beachfront property owners have added to their land holdings, acquiring bayfront real estate to dock a boat.

Sprawling mansions five times the size of the original 2,000-square-foot homes have replaced those first homes, and property values reach beyond the million-dollar mark. It’s a secluded neighborhood whose fate was determined by the arrival of the Ritz-Carlton, says long-time Naples builder Gary Carlson. "The Ritz brought in a whole new clientele to Naples," he says. Today prices fluctuate from $2.25 million for a non-waterfront likely teardown to nearly $25 million.