Bayshore Drive redevelopment signals new era in Naples area

After seeing a steady transformation over recent years, Bayshore Drive just east of Naples is poised for some of its biggest changes yet. Folks who think they have already witnessed a lot of changes on Bayshore may be surprised at what is yet to come.

A variety of plans are in the works for the local road stretching a few miles south from U.S. 41 East. Starting with the likely redevelopment of the 56-year-old Gulf Gate Plaza at the entrance to Bayshore Drive, expect more than a dozen projects culminating with a 90-home community proposed near the road’s southern terminus, near state-owned conservation land directly east of Keewaydin Island.

Calling it “the next wave,” local developer Mike Whalen is optimistic about the changes happening within the Bayshore Gateway Triangle Community Redevelopment Area on Bayshore Drive. 

“I’m all in. We are all in on the Bayshore corridor. I don’t know if there’s anybody else that has more invested on that street than my partners and I,” he says.

Whalen and his New Era Construction are behind a boutique hotel, a small community of single-family homes, a townhome project and more coming to Bayshore.

“It’s prime for redevelopment, and the county’s done a really good job of incentivizing us to do more in that area,” he says. 

Recent changes follow efforts by local residents such as Rebecca Maddox. She was one of the local entrepreneurs who helped jumpstart redevelopment of Bayshore Drive decades ago in an effort to distance it from its seedy reputation as Kelly Road, commonly known as a local red-light district before its name and trajectory were changed in 1984.

With an eventual goal to create an artsy, walkable SoHo-type district, Maddox converted an old, dilapidated waterfront bar and boat docks into Three60 Market, a vibrant restaurant and wine shop on Haldeman Creek, which flows under Bayshore Drive. She then bought a vacant lot across the creek to create Celebration Park, a waterfront destination with food trucks and a bar. Then, Maddox turned it up a notch with her self-named Rebecca’s and The Maddox, a public wine bar and a members-only club, respectively.

These successes especially brought new attention to a street that already was home to the renowned Naples Botanical Garden and longtime local restaurants, such as The Real Macaw and Taqueria San Julian. “In another year, there won’t even be anything left to buy here,” Maddox says.

In 2025, Maddox leased her former Three60 Market spot to young restaurateurs who successfully launched Seventh South Waterfront there. Bayshore Bodega, Bean To Cup and Twisted Gallery/Art Space also opened nearby. Expect more new projects targeted for development in 2026 and 2027 to be game-changers.

Grand entrance

Talk of redeveloping Gulf Gate Plaza on the southwest corner of U.S. 41 East and Bayshore Drive is becoming more than just talk now, but formal plans have yet to be presented by Isram Realty Group, owner of the 55-year-old shopping center with vacant anchor spots.

Doing business as Gulf Gate Plaza LLC, Isram has had discussions with Collier County officials about redeveloping the more than 200,000-square-foot retail center on at least 13 acres at the entrance to Bayshore Drive. Local officials had the opportunity recently to tour a similar redevelopment project that Isram orchestrated in Boynton Beach on Florida’s east coast, said Shirley Garcia, program manager of the Bayshore Gateway Triangle CRA.

Garcia, Collier County Commissioner Dan Kowal and some members of the Bayshore Gateway Triangle Local Redevelopment Advisory Board were impressed with what Isram was able to do at its Riverwalk Plaza, where Isram razed a vacated Winn-Dixie supermarket and built the 10-story Avion Riverwalk with 319 luxury apartments above five new retail suites and covered parking. The more than $85 million, resort-inspired development near the Intracoastal Waterway broke ground in 2021 and was completed in 2023.

“It was a beautiful mixed-use, absolutely beautiful,” Garcia says. “We loved it and we asked them if they would do the same on this coast for Gulf Gate Plaza.”

Garcia has been anticipating redevelopment of that aging center for years. “They’ve been great partners with us, working with the CRA over the course of 20 years that I’ve been here,” she says. “They’ve been a great asset. They’re willing to work with us to get that corner revitalized. I told them, ‘You’re the gateway into Bayshore.’ They should be the anchor into Bayshore Drive and do a project. They so badly want to be involved in the revitalization of this area, and that would be a great promotional opportunity for them to do something grandiose like that. We would just love to see that happen here on the corner. It would just be fabulous.”

After touring Isram’s Avion Riverwalk, Kowal compared the development to a self-contained campus-like setting with restaurants and stores to serve the high-end residences in the integrated community created. “It’s kind of like you don’t really have to leave campus if you don’t want to,” he says. “It’s a unique setting with restaurants and a mixed-type design.”

Doing something similar here, converting at least part of the inline commercial center at Gulf Gate Plaza to a mixed-use project, could be a good return on investment for Isram. 

“I think that’s on the lines of where they probably want to go,” Kowal says. “Now, that would have to be a rezone and a PUD down the road. They would have to create their own planned unit development, what they call a mixed planned unit development, an MPUD. That would go through zoning and everything.”

Nevertheless, Kowal sees the redevelopment of Gulf Gate Plaza as a viable opportunity.

“The CRA was created just for that reason. These people pay a few cents on their tax to have redevelopment or to have blighted properties brought up to a modern, better-looking product than what’s been there in the past. You look at Rebecca’s place and you look at all these things that are popping up around there, and then you’ve got Gulf Gate Plaza that looks run-down; you’ve got empty stores; you don’t have an anchor store there anymore. That’s the whole idea of community redevelopment. The extra tax you pay to be part of that is the whole idea to put a facelift on the community, so that’s the whole concept of creating it.”

Maddox loves the idea of beautiful condos at the entrance to Bayshore. “It’s just fantastic, I think,” she says. “I know we’re talking three years, five years away, but it would just become then the gateway to the Bayshore area. It’s just so exciting.”

Maddox said her early accomplishments on Bayshore will pale in comparison to what is coming when the street is built out. “We’re at that tipping point now,” she says. “And I’m happy, believe me. I’m thrilled about it. Thrilled, thrilled, thrilled!”

Maddox has long been a proponent of Bayshore Drive’s walkability, so she sees the new boardwalk to Sugden Regional Park and the eventual redevelopment of Gulf Gate Plaza as catalysts to connect the community by giving people more destinations and opportunities.

“I think if we created a Mercato-like thing on the corner it would help everybody walk,” she says. “So, I think it’s mostly good news.”

Ryan Hayoun, a leasing agent for Isram Realty Group, said he didn’t know how far along plans are for a mixed-use redevelopment of the center, but Isram wants to redevelop the center that includes the space vacated by Big Lots. 

“We’re in talks right now,” he says. “Yes, we plan on doing that, but nothing is signed yet.”

While there is not a timeline yet for plans there, an agreement is expected in 2026. Isram President Matthew Rikman could not be reached for comment.

“It needs a facelift. It truly does,” Garcia says. “To bring new economic opportunities into that plaza there are grants from the [Collier County] Growth Management Division that really could greatly assist with that, with the economic development aspect of it. There’s a lot of impact fee credits, grants, opportunities. There are some financial opportunities that the county could assist with the revitalization of that corner, as well. And, they’re committed to investing. It’s just a wonderful contribution to this district.”

Looming luxury 

Directly behind Gulf Gate Plaza, plans have been proposed to redevelop the 18-unit Gulf Gate South retail strip into 5th Avenue Car Club, promoted as “a sanctuary for extraordinary cars.” Two blocks south on the other side of Bayshore, Elevation Naples is planned with five stories of condos in a mixed-use development that includes restaurant, retail and parking garage spaces. 

Both of these projects, with renderings designed by MHK Architecture, propose to elevate Bayshore in terms of both height and luxury. 

The physical height for 5th Avenue Car Club comes with its 56-foot “sky gallery” planned for the corner of Bayshore and Weeks Avenue. Luxury vehicles will be placed on its seven levels with a state-of-the-art automated storage retrieval system set to accommodate 466 cars. More than 30 individual car condos also are planned on the 3.3 acres at 2740 Bayshore Drive that Fort Myers-based GCM Contracting Solutions acquired in a $4 million transaction Nov. 20. 

“To the west of the automated storage, we are building luxury car condominiums with flexible floor plans up to and including entire buildings as one entity. We have an expression of interest already for building three as one clear-span unit,” says Paul O’Callaghan, project executive for GCM, a full-service design-build general contractor.

The car condominiums will have their own bathrooms, mezzanines, outdoor balconies and other amenities for the luxury car community, O’Callaghan said.

“The owners will have the first right of refusal to take space in the automated car storage facility,” he says. “This is a first-of-its-kind, unique offering that allows a connoisseur to store their entire collection of tens to hundreds of vehicles in one luxury motor storage facility.”

On the other side of Bayshore Drive, vacant commercial property immediately south of Rebecca’s and The Maddox is proposed as the site for Elevation Naples, a major mixed-use development that also plans to raise the bar on Bayshore by integrating luxury living with convenience, wellness and lifestyle-focused amenities. The development would be directly across Bayshore Drive from Celebration Park on property owned by Thomas Burgess, CEO and founder of Burgess Commercial Real Estate.

“In addition to building a 45-room condominium hotel, we’re also supplying 300 parking spaces to the neighborhood there, which desperately needs additional parking. Elevation Naples will be the first drive-up condo building in the area,” Burgess says. “I’m excited to deliver this product type, as well as the building with a long list of amenities.”

Elevation Naples’ first floor would include a 4,200-square-foot restaurant; about 6,000 square feet of retail space; and shared amenity areas with a total of 45 transient units on the second through fifth floors, primarily two-bedroom/two-bathroom units each with private garages allowing direct vehicle access to units. The fifth floor would feature premium resident amenities, including a swimming pool, a landscaped pond with a pedestrian bridge, a bar and dining areas, a fitness center and an Indonesian-inspired spa with multiple wellness and treatment rooms. A private marina with a waterfront deck is proposed along the property’s frontage on Haldeman Creek.

Burgess thinks his project will be a great fit for the neighborhood and the community.

“I think it will be a great addition — something a little bit different from the rest of the offerings in Naples,” he says. “We’re talking with just a phenomenal hotel management company that I think is perfectly suited for Naples.”

The mixed-use development would share the entrance drive for Rebecca’s and The Maddox, conceptual plans show. Maddox looks forward to these additional collaborative opportunities with more high-end clientele coming to Bayshore.

“It’s hard to make a living in Naples in the hospitality industry because you have so few months to make it,” she says. “So, there’s lots of reasons to say, ‘Hey, let me see if we can’t do something together.’ I’m very excited about it.” 

The next wave

Three model homes are under construction at The Grove at Bayshore, a community of 32 single-family homes being built on a higher grade with high-end finishes.

“We are the next step in really elevating Bayshore with fine architecture, fine homes and fine interior furnishings,” says Jerry Maxson, who is co-developing the residential development with Mike Whalen. “It looks great. The colors are cool. Super excited.”

The team is seeking permits now for three more homes, said Maxson, noting that the road infrastructure is already in. “The site work is coming along quite well. It’s looking spectacular,” he says.

Depending on sales, the 10-acre community on the east side of Bayshore is projected to be completed in about two years. The Serhant real estate team is handling sales of the homes, promoted as “worry-free living” because of their amenities. 

The Grove will be fronted on Bayshore by a mixed-use development. “We have 16 units of condos on 1 acre of commercial property in front of The Grove,” says Whalen, who hopes to break ground on that commercial project in 2026. 

Nearby, work on Whalen’s boutique hotel temporarily stalled at 3467 Bayshore Drive, but his team is regrouping for a restart.

“All is going forward and we are in the process of changing plan revisions and submitting them to the county,” says Whalen, who is hoping his new plans are approved this spring. “We look to be done within 12 months from when we get the revisions approved.”

The four-story building will have eight suites with a rooftop bar and swimming pool. The suites will be above ground-floor commercial tenants that will include a public restaurant, two retail units and two office spaces.

As of earlier this year, a restaurant tenant had not been confirmed. “We’ve had a few people reach out to us locally and it’s still a little too early to sign someone up yet,” Whalen says.

The hotel also will have an adjacent cluster of cottages behind it at 3000 Areca Ave. that gives it a total of 20 overnight accommodations.

“Last year, we acquired the property to the east of us that includes 12 bungalow units,” Whalen says. “We’re currently remodeling them for the first occupants.” 

Palisociety, a hospitality operating company, is projected to be the hotel operator, Whalen said, “but the name of the hotel is still up in the air.”

Cultural connection 

Elsewhere in the Bayshore Arts District, a new boardwalk completed in February does more than bridge the street with Sugden Regional Park and other adjacent amenities in East Naples. It expands the horizon for additional cultural opportunities at its Bayshore base — 17 acres that have been considered for years as a possible home for a performing arts center.

Earlier this year, Opera Naples, Theater in the Garden and the Luciano Pavarotti Foundation announced that an anonymous seven-figure gift was obtained to purchase this property to build an international center for the arts in Naples. A multipurpose space would be designed to fill a local cultural need and honor the legacy of globally celebrated tenor Pavarotti. 

“The property will embrace a 900-seat state-of-the-art indoor theater, an outdoor amphitheater in a landscaped garden setting, an opera museum, The Luciano Pavarotti Foundation Opera Naples International Voice Competition and an opera-themed restaurant,” according to a mid-January news release from Opera Naples. 

End of the road

National homebuilder Toll Brothers plans to build Windward Landing, a proposed community of 90 single-family homes on a 71.5-acre site on the west side of Bayshore Drive, south of Naples Botanical Garden. Because it’s actually at the end of the road, the developer plans to build a road extension from the southern end of Bayshore Drive at Holly Avenue to the entrance to Windward Landing. Before the development can proceed, though, the property would need to be approved for rezoning from rural agricultural and residential single-family zoning districts to a residential planned unit development.

Other projects

Huey Magoo’s Chicken Tenders 

The fast-food chain plans its first Collier County location, a 2,650-square-foot restaurant with a drive-thru on the spot of the former Circle K store on the southeast corner of U.S. 41 East and Bayshore Drive. 

Lakeview homes 

A four-unit multifamily development is proposed in two two-story buildings at Lakeview Drive and Bayshore Drive.

Cielo Azul 

A small residential community is proposed for three single-family homes and one access drive off Bayshore Drive abutting the vacated Kelly Court. The homes would abut an existing lake near the new boardwalk to Sugden Park.

Del’s Corner 

Although not in the permitting pipeline yet, future redevelopment eventually is expected on the county-owned vacant lot where Del’s 24-Hour Store operated for more than 50 years on the southeast quadrant of Bayshore and Thomasson drives.

Bayview Boatyard 

A redeveloped marina and boat storage building is proposed on 2.5 acres along Haldeman Creek on the north side of Bayview Drive west of Seventh South Waterfront.

Van Buren Apartments 

Thirteen apartment units are proposed on 1.87 acres at the eastern end of Van Buren Avenue off Bayshore.

Camden Landings 

Eight five-story condo buildings with a total of 127 units are proposed on the northeast corner of Bayshore and Thomasson drives.