Bay Isles Parkway Might Soon Belong to the Town: What Changes for Residents

Disclosure: Danielle Gladding's husband, Nick Gladding, serves as Longboat Key's District 3 Town Commissioner. They speak for themselves and not for each other, and nothing here represents the Town of Longboat Key or its Town Commission. He does not review this content before it is published. This post discusses Town of Longboat Key matters.

Danielle Gladding lives in Queens Harbour inside Bay Isles and drives this road most days. She has been a licensed Florida Realtor since 1981 and a broker since 1987, and runs Danielle Gladding & Co. Realty with her daughter Alison Kanter.

“We’re not looking for shortcuts. We want this to be credible, defensible and realistic.”

That’s H. Joseph Reiser, president of the Bay Isles Association, talking to Longboat Key town staff about a stretch of road most of us drive without thinking twice. I’ve lived inside these gates in Queens Harbour long enough to know that half-mile by feel: past the gatehouse, past the Longboat Key Club entrance, straight to the Publix parking lot when the fridge runs low. What I didn’t know until this year is that the Association itself doesn’t want to keep owning it.

A disclosure before we go further. My husband, Nick Gladding, is the District 3 Commissioner on the Longboat Key Town Commission, the body that will decide whether the town accepts this road. He had no hand in this piece, and nothing here reflects his position or the Commission’s. What follows is the public record and reporting from Your Observer, nothing more. I am not arguing for an outcome here, and I would say the same if the answer turns out to be no.

Bay Isles Parkway is short. It connects Gulf of Mexico Drive to Harbourside Drive, and it is the way in and out for the hundreds of homes past the gatehouse. It is also the way in and out for the Town Shoppes of Bay Isles, the commercial strip anchored by Publix and CVS. Those two facts sitting next to each other turn out to be the whole story.

What the traffic count found

In March 2025 the Bay Isles Association ran its own traffic count over three days. The results, reported by Your Observer, showed 53% of cars entering the road turned into the Publix parking lot, 8% continued to Bay Isles Road, and 39% passed through to the Bay Isles gatehouse. A follow-up engineering study by Stantec put the annual figure at 5.3 million cars using the Parkway.

This is a private road, owned, insured and maintained by a homeowners association, and by that count the majority of the people driving on it are not going home. They are going grocery shopping. The Association has been carrying liability for a road that substantially serves the general public, and that is the mismatch the transfer discussion is built on.

According to town records, the Association and the Town of Longboat Key have been discussing a transfer since 2023, with a formal proposal submitted in April 2025.

The tunnel transfer came first

On June 29, 2026, the Longboat Key Town Commission unanimously approved a donation agreement transferring the Association’s Arvida-era pedestrian tunnel under Gulf of Mexico Drive, connecting Seaplace and Bay Isles, to the town. The tunnel dates to the late 1970s. It was originally built for golf cart crossings that never materialized, because the two courses ended up a mile apart, so it functions today as a walking underpass. Commissioner Penny Gold, who lives at Seaplace, told the commission her neighbors use it constantly.

The Association had been paying to maintain it — pressure washing, repainting on a five-year cycle, landscaping and electrical. Because title records showing Bay Isles’ ownership were missing, the tunnel changed hands through a quit-claim deed rather than a standard sale, and the town’s existing liability coverage absorbed it at no added cost.

That transfer is the nearest precedent for the Parkway discussion. Same developer-era infrastructure, same question about who insures an asset that serves more than one community.

What the framework would change, and what it would not

As of the August 2026 reporting, the framework both sides describe as understood looks like this:

The Association keeps paying for needed maintenance, including resurfacing.
The Association keeps funding landscaping along the road.
The town takes ownership and handles insurance.
Stormwater runoff keeps draining to the Longboat Key Club golf course, unchanged.

The operational shift worth noting is enforcement. Longboat Key Police Chief Russ Mager confirmed that running speed enforcement on a private road currently requires a memorandum of understanding between the department and the Association. Town ownership removes that step. If Bay Isles Parkway has felt like a cut-through for drivers in a hurry to reach the Publix lot, this is the mechanism that would let the town patrol it the way it patrols Gulf of Mexico Drive.

On cost, a Bay Isles representative identified in reporting as Deming addressed what residents should expect:

“The current Board of Directors’ objective is to address any costs associated with this initiative through the Association’s established budgeting procedures and long-term financial planning, without the need to impose a special assessment upon the membership.”

The road’s eventual resurfacing and replacement are already line items in the Association’s 2024 Reserve Study, the document that governs long-range capital planning for the community.

Where it stands now

Nothing has closed. As of the most recent reporting, the town and the Association have not set final terms, though both sides describe the framework as understood. An earlier round of discussions in 2025 stalled over a Stantec estimate for bringing the road to municipal standard, and over the Association’s position that it had already brought the road to standard once, in 2012, when Publix opened. The current framework is structured differently, and the matter has not yet come to a vote.

If you drive this road daily — to the Longboat Key Club, to the Moorings, or for milk and prescriptions at the Town Shoppes — what is realistic to expect over the coming months is landscaping exactly as it looks now, a resurfacing cycle funded the way it always has been, and possibly speed enforcement near the Publix entrance if the transfer goes through.

Frequently asked questions

Who owns Bay Isles Parkway today?

The Bay Isles Association. It is a private road, owned, insured and maintained by the association, notwithstanding that it also serves as the access road for a Publix-anchored shopping center open to the public.

Would a transfer raise assessments for Bay Isles owners?

The Association’s stated objective is to handle any associated costs through established budgeting and long-range planning rather than a special assessment. Resurfacing and replacement are already carried in the 2024 Reserve Study. Nothing has been finalized, so treat this as the Association’s stated position rather than a settled outcome.

What would actually change for residents day to day?

Under the framework as described, very little on the surface. Landscaping and maintenance funding stay with the Association. Ownership and insurance move to the town. The visible difference would be enforcement — the town could patrol speed on the road without a separate agreement.

Has the Town Commission voted on this?

No. As of this writing the matter has not come to a vote and final terms have not been set. The Commission did unanimously approve a separate transfer, of the pedestrian tunnel under Gulf of Mexico Drive, on June 29, 2026.

Does this affect Bay Isles Beach Club access?

No. Beach Club membership conveys with every home inside Bay Isles and is governed separately from the Parkway. You can read more about how that works in our guide to the Bay Isles Beach Club.

Where can I read more about how Bay Isles is governed?

Our buyer’s guide to Bay Isles covers how the master association and its sub-associations divide responsibility for shared infrastructure, and which governing documents are worth reading before you buy.

About the authors

We are Danielle Gladding and Alison Kanter of Danielle Gladding & Co. Realty. Danielle Gladding holds the Luxury Homes Certification, ABR, CWS and CRLS designations. Alison was born and raised in Sarasota, has been licensed since May 2023, and holds the CWS, RENE and CRLS designations. We work together across Sarasota and Manatee County.

For more on the community itself, see our Bay Isles neighborhood guide, which covers all sixteen residential neighborhoods inside the gates.

If you are thinking about buying or selling in Sarasota, Longboat Key, or the surrounding areas in the next year or two, we would be glad to hear from you.

More on the Area

Longboat Key — the island end to end

Danielle Gladding lives in Queens Harbour inside Bay Isles and walks the neighborhood most mornings. She has been a licensed Florida Realtor since 1981 and a broker since 1987, and runs Danielle Gladding & Co. Realty with her daughter and Sales Partner Alison Kanter, who was born and raised in Sarasota and has been licensed since May 2023. Danielle: (941) 539-8535 · Alison: (941) 306-9786

This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.