Pull up listings for Strattons on Upper Matecumbe Key right now and you will see a 358 square foot condotel unit at Cheeca Lodge priced at $549,500 sitting in the same subdivision code as a fully renovated oceanfront estate asking $24,995,000. Scroll further and there is an 8-bedroom single-family home at $8,490,000. Same subdivision. Same mile marker. A roughly 45x difference in total price depending on which listing you happen to click.
That is not a typo and it is not a market anomaly waiting to correct itself. It is how the Florida Keys MLS has always coded this stretch of downtown Islamorada, and understanding why matters more than any median price you will find on a portal, because in Strattons, the median describes a blend of two products that have almost nothing in common.
One Subdivision Code, Two Businesses
Strattons (82.5) covers the ground around mile marker 82.5 on Upper Matecumbe Key, which puts it at the center of downtown Islamorada rather than on its own quiet lane. That single subdivision boundary happens to wrap around two very different kinds of real estate. On one side sits Cheeca Lodge & Spa, a 27-acre oceanfront resort that has operated for more than 70 years and drew celebrities, athletes, and U.S. presidents through its doors long before condotel ownership existed as a category. On the other side, spreading out from the resort toward the water, are privately owned, site-built homes on their own oceanfront and bayfront lots, ranging from modest fishing cottages to some of the largest estates in the Upper Keys.
Both fall under Strattons because both sit on the same historic parcel of land at mile marker 82.5. Neither product resembles the other once you look past the address.
What Roughly $550,000 to $735,000 Buys at Cheeca Lodge
A meaningful share of Cheeca Lodge's guest rooms were converted years ago into individually owned condotel units, and a handful are on the market right now. A 358 square foot unit is currently listed at $549,500. A similar unit sits at $585,000. Larger 550 square foot suites are listed between $699,000 and $735,000. What buyers own is a hotel room with a deed attached to it, not a standalone residence.
The tradeoff is built into the ownership structure. Owners of these units typically use their room up to 28 days a year and collect a monthly check the rest of the time, with the resort's professional management team handling bookings, housekeeping, and guest turnover. In exchange, owners get access to the full resort: a Jack Nicklaus-designed 9-hole par-3 golf course, a 525-foot pier that is the longest in the Florida Keys, multiple pools, tiki bars, and the fine dining rooms on property. It is a real estate purchase built around income and hands-off convenience, not square footage or privacy.
What $8 Million to $25 Million Buys 50 Feet Away
Walk a few hundred feet from the resort gate and the product changes completely. The current listing at 82719 Old Highway, marketed as an oceanfront estate that was completely renovated in 2022, spans 10,182 square feet with 7 bedrooms and 9.5 baths on nearly an acre, with a 100-foot private dock and a rooftop terrace facing the Atlantic. It was listed in December 2025 at $24,995,000.
A second listing at 1101 Mastic Street offers 8 bedrooms and 6 baths across 3,649 square feet at $8,490,000. Neither of these homes shares a rental program, a resort HOA, or a management company with the condotel units a short walk away. Site-built homes in Strattons typically carry no mandatory homeowners association at all, according to MLS records on comparable listings in the subdivision. What you are buying here is privacy, dockage, and land, priced the way waterfront land in the middle of downtown Islamorada gets priced when there is essentially none of it left to build on.
Strattons, Side by Side
| Product | Typical Size | Current Price Range | Ownership Structure | Built-In Income |
|---|---|---|---|---|
| Cheeca Lodge condotel unit | 350 to 550 sq ft | $549,500 to $735,000 | Deeded hotel room, resort-managed | Rental pool, ~28 owner-use days per year |
| Site-built estate or single-family home | 3,600 to 10,000+ sq ft | $8,490,000 to $24,995,000 | Standalone lot, typically no mandatory HOA | None built in; owner-controlled |
Why the Median Doesn't Mean Anything Here
If you averaged every active Strattons listing right now, from the $549,500 hotel room to the $24,995,000 estate, you would land on a number that describes neither property. It would overstate what a condotel buyer is actually spending and dramatically understate what an estate buyer needs. This is the trap of pulling a single median or average price for a subdivision without first asking what kind of ownership is being sold inside it.
A neighborhood's median only means something when the properties inside it are close enough in kind to be compared. Strattons fails that test on purpose, because the MLS subdivision boundary was drawn around a piece of land, not around a type of home.
The One Thing Both Tiers Are Paying For
What condotel owners and estate owners in Strattons do share is location. This is downtown Islamorada, walkable to the mermaid sign at Lorelei Restaurant & Cabana Bar on the bayside at mile marker 82, to the breakfast counter at Mangrove Mike's Cafe at mile marker 82.2, to the tasting room at Islamorada Beer Company, and to the exhibits at the Florida Keys History & Discovery Center near mile marker 82.1. Cheeca Lodge itself was rebuilt after Hurricane Irma and still hosts the annual George H.W. Bush-Cheeca Lodge Bonefish Tournament, a charity fishing event the late president helped found in 1994.
Whether you are buying a hotel room or a ten-thousand-square-foot compound, you are paying for that same short walk to dinner, that same stretch of Overseas Highway that put Islamorada on the map long before either product existed. The walkability is the constant. Everything else about price is a function of which product you picked.
How to Actually Search Strattons Listings
If a portal search is showing you a Strattons result that seems oddly cheap or oddly expensive compared to everything around it, check the property type before you check the price. A condotel or condo-hotel unit filed under Strattons is not a discount on Islamorada real estate. It is a completely different asset, with a completely different cost structure once you factor in resort fees and management splits against a rental income stream. A site-built single-family home filed under the same code is closer to what most buyers picture when they search for a Keys home, and it should be evaluated on dockage, lot size, and flood elevation the way any waterfront property would be.
The fix is simple: filter by property type first, then compare within that type. Comparing a condotel to a private estate because they share a subdivision name will only produce confusion, not insight.
Strattons rewards the buyer who understands which market they are actually shopping in. If you are trying to figure out whether a hands-off condotel investment or a private waterfront estate makes more sense for how you want to use the Keys, The Florida Keys Sold Sisters can walk you through both sides of this subdivision and what each one actually costs to own. Start Your Island Home Search — Schedule a Personal Consultation.
