Every once in a while, we find a hidden gem in Naples. In this case, it’s the Island Cottages, a cluster of contemporary Old Florida-style cottages tucked away in East Naples’ Bayshore Arts District on Jeepers Drive. With its white picket fences and wide front porches, the street exudes an old-school neighborhood feel—where residents get to know each other, hold friendly block parties, and walk or bike to nearby restaurants and attractions.

This sense of community didn’t happen by accident—the developer, Michael Sherman, cites his hometown in seaside New England as inspiration for the Island Cottages, each of which is named for a favorite island and memorialized with a carved quarterboard sign, reminiscent of those on whaling ships and unique homes in places like Nantucket.

The style of homes is similar to those that have gained popularity in nearby downtown Naples, but their pricepoint falls short of the often exorbitant home prices in Old Naples. (The Island Cottages range from $399,000-700,000, compared to the homes in Old Naples, which are frequently in the millions.)

Curious to check out the Island Cottages in the Bayshore Arts District? A model home is available for touring, with a handful of other lots available for design and development. (Each home is custom-built to buyer specifications.) Contact Michael Sherman at (617) 240-9578 for information.

The interiors are just what you’d expect from a coastal contemporary cottage: light, bright and airy.




The Bayshore Arts District has earned a fresh reputation as an up-and-coming area, thanks to the addition of new restaurants, a brewery and a burgeoning arts scene.



4820 Bayshore Drive
Comprised of nine named gardens and a 90-acre nature sanctuary that’s home to hundreds of animal species, Naples Botanical Garden represents plants and cultures from around the world, including Southwest Asia, Brazil and the Caribbean. A range of art, gardening, wellness and birding educational programs for children and adults is also available.


2891 Bayview Drive
This cute little spot serves breakfast and lunch in its restaurant and to-go meals, pastries, pasta and snacks on its market side. There’s a shaded waterfront patio for dining (dog friendly—yay!), and many menu items are made from scratch daily. But perhaps the coolest thing about Three60? Its wine program.


2880 Becca Ave.
This waterfront food truck park and open-air tiki bar is a favorite hangout for all ages. You’ll find something for every taste, from barbecue to lobster rolls—and there’s usually live music on weekends, too.


3555 Bayshore Drive
This microbrewery features plenty of craft beers on tap, as well an outdoor, pet-friendly beer garden, perfect for sipping their homemade brews on a nice day. They also host regular trivia nights and outdoor yoga classes.

3 Comments on The Island Cottages: A Naples Hidden Gem

  1. We love the community of old style homes, is there a neighborhood being started closer to the Fort Myers area? Or any other area available?

    • Hi Kristine! Horse Creek is a new development in Fort Myers with large lots and Old Florida-style homes. Caloosa Creek and Coconut Creek (both established neighborhoods) are further south and also beautiful. All have the same builder, Daniel Wayne.

  2. We would like to come by to take a look at the model home. We are here in Naples this week and could stop by on Friday if that works.

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