One of the best reasons to live in Old Naples is that dinner is a walk away. The neighborhood holds three of the densest dining areas in Naples, Florida: 3rd Street South, 5th Avenue South and Crayton Cove on Naples Bay. Here is a local's starting list. Menus, hours and even owners change, so call ahead or check each restaurant's website, and reserve in season (January through April).
The historic village center is known for courtyard and patio dining on the blocks between Broad Avenue South and 14th Avenue South.
5th Avenue South is the main street of Old Naples, with sidewalk seating at most restaurants and live music during Evening on Fifth on select Thursday nights. Favorites include Osteria Tulia for rustic Italian, Del Mar for coastal Mediterranean in the former Cafe Lurcat space, and Truluck's just off the avenue on 4th Avenue South for seafood and steaks.
At the west edge of Naples Bay, Crayton Cove has a relaxed Old Florida feel, with waterfront tables at The Dock at Crayton Cove overlooking the city docks. It is a favorite for boaters and a short golf-cart ride from most of Old Naples.
On Saturday mornings, the Third Street South Farmers Market runs from 7:30 to 11:30 a.m. with coffee, baked goods and prepared foods. Bad Ass Coffee on Third Street South and Tony's Off Third are easy weekday stops.
Many Old Naples condos are within a few blocks of 3rd Street South or 5th Avenue South. Get new listings sent to you first.
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Walkability is priced in, but there is a range. In mid-November 2026, Old Naples condos were listed from about $275,000 for a 1-bedroom in an older building to about $7.7 million for a new luxury residence, and single-family homes from about $3 million.
3rd Street South and 5th Avenue South have the highest concentration, with more waterfront options at Crayton Cove on Naples Bay.
From January through April, reservations are recommended at most sit-down restaurants, especially for dinner and outdoor seating.
Glen Bigness, REALTOR®
Bigness Group LLC with Premiere Plus Realty
Serving Southwest Florida buyers and sellers since 1986
Call or text 239-272-4663 or email glenbigness@gmail.com. Learn more about Glen.
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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.
Old Naples buyers and sellers since 1986. Call or text 239-272-4663 or glenbigness@gmail.com
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