The Island Cottages In A Naples Bay Village

Who is developing those beautiful new in-town cottages on Jeepers Drive in The Bayshore Arts District? And, why are they so different from the blasé big production homes being built at so many communities around Naples?

Well, Michael Sherman is the developer! But let me tell you his story.

Michael Sherman or Mike as he likes to be called, is from a small town in Massachusetts called Marblehead. It was founded as a cod fishing village in 1629. As there were no cars then, the rocky little town developed in a way that was convenient for its residents to walk to everywhere they went from the harbor to the shops to their homes. The good news is that it has been preserved that way and it still is a lovely place by the water to live, work and play today. Mike attributes much of his design inspiration from his quaint home town and also from the many other seaside “walking” villages that he has visited and enjoyed.

Mike had a forty year career in the commercial real estate business, being involved in the design, development, management and marketing of literally hundreds of office buildings, shopping centers and industrial buildings. Eventually his successful career culminated in his retirement from CB Richard Ellis NE after twenty years as CEO and Managing Partner.

Along the way, he and his wife Bonnie found a seaside village in Florida called Naples. 17 years ago, they became Bayshore Arts District residents and Mike became a longtime member of the Bayshore Gateway Triangle CRA Advisory Board. With his love for great seaside villages, Mike quickly bought in to the CRA’s redevelopment vision. With its proximity to Old Naples exciting downtown and being right on Naples Bay, this was a vision that he liked well enough to decide in 2005 to “put his money where his mouth was”! You see, Mike is a rare breed of person, an urban pioneer if you will. He doesn’t shy from being first in an area where he can pursue an exciting vision to help to create a new reality…in this case, The Bayshore Arts District.

This vision is not completely new to the city planning scene. It is well documented in a philosophy called “New Urbanism”. It is a movement that seeks to design neighborhoods around people’s societal needs and desires for “community” rather than being subjugated to the de-personalizing impacts of the automobile. These are “walkable “ towns, with urban charm and uniqueness not boring uniformity. They want to be friendly towns where neighbors take the time to get to know each other offering smiles and waves and conversation from their front porches as they go about their day. Towns not unlike a little fishing village called Marblehead!

In 2005, Mike started working on his retirement dream, buying a few lots off Bayshore on Jeepers Drive, to begin building an infill “New Urbanist” neighborhood called “The Island Cottages in a Naples Bay Village”. This would be his contribution to the Bayshore Arts District renewal. His concept includes “contemporary Old Florida” architecture, white picket fences, friendly front porches, parking (and unsightly garage doors) relegated to the rear to enhance the beauty and the “walkable” charm of the quiet street. To evoke the feeling of seaside villages around the world, each cottage is named for a favorite island and memorialized with a “Quarterboard” sign reminiscent of the whaling ships and unique homes in places like the island of Nantucket.

Today, with the ups and downs of the Great Recession in the rear view mirror, four homes are close to complete with “Key West House”, “Tuckernuck Island Cottage” and “Gasparilla Island House” already sold. “Bahama Cottage” is for sale and ready for move in now. Mike is readying plans for at least six more Island cottages. Some will be designed for speculation and some will be fully “custom designed” to discerning tastes and desires by the future home owner(s) and Mike’s team. It just has to be unique and friendly and named for a favorite island and… a good addition to the Bayshore Arts District!

So, if you like seaside villages, and have a pioneering spirit and want to live in a walk-able, bike-able and boat-able neighborhood with a friendly front porch, call David Goebel at 239-285,2038 for a tour of the village and the exciting vision. And if you see Mike, give him a wave as we walk by!


Why should you consider moving into The Island Cottages in a Naples Bay Village?

You should check out this unique urban in-fill community,

because today, you can be involved in custom-designing your own contemporary “Island Cottage” single family home for:
The Island Cottages in a Naples Bay Villagea fraction of the cost of one in a nearby gated community
or, less than a third of a similar home in Old Naples, just a short distance away,

because “downtown Naples” is expanding rapidly to the south making big changes to the Bayshore /Gateway CRA area. It is now much better and closer to “downtown”!,

because all these amazing changes and improvements are raising the value of property in The Bayshore Arts District, which will mean $$$ in your pocket someday,

because the street pattern of the District is perfect for developing a “New Urbanist” neighborhood where streets like Jeepers Drive are becoming home to fascinating, “Island-style” architecture, with friendly front porches and picket fences where neighbors can socialize with their friends without hiding behind unsightly garage doors,

because your cottage, which you can name for your own favorite island (and have identified as such with a beautiful Nantucket style “Quarterboard” sign), can be designed to offer you whatever you want in the beautifully landscaped main house (as many bedrooms as you want, whatever dream kitchen you can dream up and afford and all the rest). All homes will have the friendly front porch, of course as well as a generous screened lanai. Then, you can add other amenities either when completing the original construction or later. You might consider things such as a pool, spa, carriage house, garden, garden shed, boat storage, etc.,

because in the District, you can walk, bike or boat (or drive…) to an amazing array of attractions within only a few minutes:
Old Naples Downtown Shopping & Restaurants
Naples spectacular beach
Naples Bay
The Gulf of Mexico
Sugden Park & Lake Avalon Beach
Bayview Boat Ramp & Park
East Naples Community Athletic Park (think Pickleball!)
Naples Botanical Garden
The great and growing eclectic group of shops and restaurants right here in The Bayshore Arts District
The nearby join-able Golf and Yacht Clubs & Communities: Windstar on Naples Bay, Southpointe Yacht Club, The Isles of Colliers Preserve and Hamilton Harbor Yacht Club
Local marinas and boat service facilities.

And lastly, because you won’t have to join a condominium or home owners association… saving you thousands of dollars over the years!

Today is the time to get in on the ground floor!

Take a hard look at The Bayshore Arts District and a new custom-designed home in

The Island Cottages in a Naples Bay Village


The Goal of our Development Team at

The Island Cottages in a Naples Bay Village

is to bring interesting architecture and New Urbanist design to a unique waterfront neighborhood in the form of ”Island Contemporary” single family homes….and, to do this at a reasonable cost!

We have found the opportunity to achieve this goal in


the rapidly changing and improving, diverse community where the location on Naples Bay and the many public and commercial amenities combine to offer an in-town, walk-able, bike-able, boat-able and most importantly, an affordable lifestyle.