Islamorada's Real Neighborhoods: Six Communities, One Village

Six Communities, One Incorporation: The 1997 Merger

Islamorada, Village of Islands was incorporated in 1997, merging six previously separate communities into a single municipal government: Upper Matecumbe Key, Lower Matecumbe Key, Windley Key, Plantation Key, Tea Table Key, and part of Long Key. The Village's own site hosts an official document, "Why Islamorada Matters," laying out the incorporation rationale -- confirming this wasn't an informal grouping but a real, documented municipal merger. Together, these six areas span roughly mile markers 72 to 90 along the Overseas Highway, a range this site's Florida Keys hub page also cites.

What this research could not confirm is any specific vote count, referendum margin, or contested detail of how that 1997 merger actually happened -- so no such figure is stated here. What is clear across the source material is the basic shape of the story: six keys, each with its own name and history predating 1997, now governed as one village. That's worth taking seriously as the real neighborhood structure here, rather than treating "Islamorada" as a single undifferentiated place the way a newer planned community might be.

The Six Keys, By Name

Upper Matecumbe Key, Lower Matecumbe Key, Windley Key, Plantation Key, Tea Table Key, and part of Long Key are the six areas that make up Islamorada. Each retains its own name and identity in everyday local use -- an address, a marina, or a landmark on any of the six is still commonly described by its specific key, not simply as "Islamorada," even though all six now fall under one village government, one set of village ordinances, and one village building department.

This page is not going to invent a distinct real-estate character, price tier, or lifestyle description for each of the six -- that specific, sub-area-by-sub-area detail was not confirmed anywhere in this research, and manufacturing it would be worse than leaving the gap open. If you're comparing, say, a Plantation Key address against a Lower Matecumbe address, the honest answer is that this page cannot tell you how their pricing, lot character, or resale patterns actually differ. A Florida Keys-licensed real-estate agent working specifically in Islamorada is the right source for that comparison -- they'll know current inventory and recent comparable sales key by key in a way no general research pass can responsibly substitute for.

Bayside and Oceanside: One Village, Two Shorelines

Because Islamorada's six constituent keys run along a stretch of the Overseas Highway between Florida Bay and the Atlantic, the village has direct frontage on both sides: bayside addresses face Florida Bay (and, further out, the Everglades National Park backcountry), while oceanside addresses face the open Atlantic and its reef line. That bayside/oceanside distinction is a real, practical geography fact that cuts across all six of the merged communities -- it isn't specific to any one of the six keys, since each of them, depending on the exact address, can have a bayside or an oceanside orientation.

As with the six keys themselves, this page does not have sourced, Islamorada-specific data comparing bayside and oceanside property characteristics, flood risk, or pricing patterns. That's a real, disclosed gap rather than a filled-in guess -- ask a local agent which side of a specific address in Islamorada faces which body of water, and what that has actually meant for recent comparable sales, before assuming either side commands a premium.

BPAS: One Permitting System Covering All Six Areas

One thing that genuinely is uniform across all six of Islamorada's merged communities: the Village's own Building Permit Allocation System (BPAS), the local permit-allocation mechanism the Village Council runs on top of -- and distinct from -- Monroe County's countywide Rate of Growth Ordinance (ROGO), which governs unincorporated parts of the Keys instead. Because Islamorada is a single incorporated municipality, BPAS applies the same way whether a property sits on Upper Matecumbe, Windley Key, Tea Table Key, or any of the other four areas -- there is no separate permitting regime for one of the six keys versus another.

The Village Council passed Ordinance 23-10 in 2023, establishing a moratorium on new residential building-permit applications, and extended it with Ordinance 24-12 in 2024 -- both real, currently-documented ordinances covered by Keys Weekly's ongoing local reporting. Separately, Florida Senate Bill 180 (2025) restricts local governments' ability to impose building moratoria, and legal-industry analysis (Bilzin Sumberg) has flagged real tension between that state law and Islamorada's own moratorium ordinances. Whether the moratorium remains in effect as of today, and how that state-versus-local tension has actually been resolved, are exactly the kind of fast-moving local-government facts this page cannot responsibly freeze in place -- confirm current BPAS and moratorium status directly with the Village of Islamorada's Building Department before assuming any specific lot, on any of the six keys, is buildable on a given timeline.

What This Page Doesn't Have

No neighborhood-specific, currently verified median home price, lot-size pattern, or price-per-square-foot figure appears anywhere on this page -- not for Upper Matecumbe Key, Lower Matecumbe Key, Windley Key, Plantation Key, Tea Table Key, or the part of Long Key inside the village. This research also could not confirm specific vote-count or contested-election detail from the 1997 incorporation, a boundary map showing exactly where one of the six keys ends and the next begins, or any current data comparing bayside versus oceanside pricing. Those are open questions a follow-up research pass, or a conversation with a Florida Keys-licensed agent working in Islamorada, should close -- not gaps this page fills with an invented number.

A Professional-Consult Disclaimer

Islamorada's 1997 incorporation from six previously separate communities, the resulting village-wide BPAS permit system, and the current residential-permit moratorium under Ordinances 23-10 and 24-12 are confirmed via the Village of Islamorada's own site and Keys Weekly's ongoing local coverage, with the SB 180 state-preemption tension sourced to legal-industry analysis (Bilzin Sumberg). No specific vote count, sub-area price or character comparison, or bayside-versus-oceanside pricing data is confirmed here, and none is stated. Confirm current BPAS/moratorium status directly with the Village of Islamorada's Building Department, and get current listings, comparable sales, and any key-specific guidance from a Florida Keys-licensed real estate agent working in Islamorada before making a purchase decision. Nothing on this page is legal, tax, or financial advice.