Two units came onto the Bay Colony market this summer a few weeks apart. One sat in Trieste, the community's newest beachfront tower, finished in 2002. The other was several buildings south in Contessa, completed in 1991. A buyer working from the age on the listing sheet alone would reach for the newer tower without much thought. That instinct is the one worth setting aside.
In Bay Colony right now, a tower's birth year tells you less about your risk than where that tower sits on Florida's post-Surfside inspection calendar. The buildings that have already closed out that process are, on paper, the more transparent purchase. The ones still working through it are asking a buyer to underwrite a number nobody has finished calculating yet.
The Three-Mile Rule Bay Colony Can't Opt Out Of
Florida's Milestone Inspection law applies to any condominium or cooperative building three habitable stories or taller. Statewide, the first inspection comes due at 30 years. But the City of Naples building department applies a shorter clock to anything within three miles of the coastline: 25 years, then every 10 years after that. Bay Colony sits directly on the Gulf, which means every tower in the community, from beachfront Contessa to the inland Marquesa and Salerno buildings, falls inside that accelerated window regardless of how far back from the sand it stands.
That detail matters because it means age doesn't buy a Bay Colony tower much extra runway. A building doesn't get to wait until 30 just because it's set back from the water.
Five Towers, Four Decades, One Set of Deadlines
Line up the community's named high-rises by completion date and the spread is wider than it looks from the beach:
- Contessa, completed 1991, 20 floors, 76 residences including two penthouses
- Carlysle, delivered 1992 by WCI Communities, 20 stories, 75 residences
- Remington, completed 1996, 22 stories, 75 residences
- Toscana, completed 1999, 19 floors, 65 units
- Trieste, built 2002 by WCI and designed by architect Robert Wedroe AIA, 20 stories, 106 units, the newest of the group
Run each completion year through the 25-year coastal formula and the milestones land in different years entirely: Contessa's first trigger arrives around 2016, Carlysle's around 2017, Remington's around 2021, Toscana's around 2024, and Trieste's not until 2027. Compared by age alone, these five towers would rank in a straight line from oldest to newest. Compared by their place on the inspection calendar, they scatter across more than a decade.
None of that arithmetic ends up mattering as much as what already happened statewide over the past year.
The Deadline That Already Passed
The Milestone Inspection's 25-year trigger is tied to a building's own age. The Structural Integrity Reserve Study, the financial companion to that inspection, is not. Under Florida's Division of Condominiums guidance, any unit-owner-controlled association operating a qualifying building had to complete its first SIRS by December 31, 2025, regardless of the building's individual milestone year. Full reserve funding for the eight structural components a SIRS covers, roofs, load-bearing elements, waterproofing, plumbing, electrical, fire protection, windows and exterior doors, and anything else over the statutory threshold, was required to begin January 1, 2026.
Both dates are already behind us. As of this month, every Bay Colony association, whether it governs a tower built in 1991 or one built in 2002, should already have a completed SIRS on file and should already be funding those reserves on schedule. The building's own age no longer buys extra time on this part of the requirement. If an association can't produce that document today, the gap itself is the finding.
What a Completed File Actually Buys a Buyer
A completed Milestone Inspection and SIRS convert an open question into a set of numbers: a reserve balance, a funding schedule, and if Phase 2 testing was triggered, a defined repair scope with a cost attached. A building still working through the process is offering a buyer a promise instead.
That gap hasn't closed everywhere. Naples Press reported in July 2026 that of the 245 buildings identified by the city's building department, 83 percent had completed their required reports as of mid-2025, according to figures from the Gulf Shore Association of Condominiums. That leaves roughly one in six Naples buildings that hadn't finished as of that count, a gap that has likely narrowed in the year since but hasn't necessarily closed to zero.
The same reporting tied a broader rebound in Naples condo activity directly to buildings clearing that hurdle. Buyers who sat out the last several years while associations worked through SIRS and milestone requirements are returning now that the process is settled for most towers, often finding properties that have been fully vetted and improved at prices still below where they sat a few years ago. Among the recent Bay Colony transactions the paper cited was a $3.4 million residence in the Carlysle, the kind of sale that reflects returning confidence in a building whose paperwork is already closed rather than still open.
A tower that finished its Milestone Inspection and Structural Integrity Reserve Study hands a buyer a number. A tower that hasn't finished yet hands a buyer a question.
The File to Request Before Writing an Offer
Before comparing two Bay Colony units on price per square foot or floor height, ask the listing agent for:
- The completed Milestone Inspection report, including the completion date and whether Phase 2 testing was triggered
- The most recent Structural Integrity Reserve Study, with the funding schedule and current reserve balance measured against the target
- The past two years of board meeting minutes, to check whether reserves for structural components were waived before the practice became illegal for budgets adopted after December 31, 2024
- Current insurance declarations, wind and flood, since coverage terms have shifted alongside the new inspection rules
- Confirmation of whether the building appears on a lender's non-warrantable list, since Fannie Mae has tightened its condo project review standards around exactly this kind of open compliance gap
None of this replaces walking the building or reading the floor plan. It just means the comparison between two Bay Colony towers should start with the file, not the facade.
FAQ
Does this apply to Bay Colony's single-family homes or the community's low-rise villas? No. Both the Milestone Inspection and SIRS requirements apply only to condominium and cooperative buildings three or more habitable stories tall. Single-family homes and shorter structures in Bay Colony fall outside the law entirely.
If a tower already completed one round of inspections, is it done for good? No. Under the city's coastal rule, the cycle repeats every 10 years after the first inspection. A clean file today doesn't remove a building from the schedule going forward.
Can a seller simply decline to share the SIRS during a sale? Not easily. Associations with 25 or more units are now required to make governing documents, budgets, and reserve studies available through an online account, and as of 2026, buyers have a seven-day window to review financial and inspection records before being bound to a purchase agreement.
Comparing Bay Colony towers on view or floor plan alone leaves out the part of the deal that's currently doing the most to set price and risk. If you're weighing two addresses in the community this season, Earls & Lappin can pull the inspection history and reserve position on both before you write an offer. Contact Us.