Pool Homes for Sale in Upper Matecumbe Key Islamorada, FL
Buyers who want a pool search for the pool first. This page tracks every Upper Matecumbe Key Islamorada listing whose MLS record reports a private pool, by community, with live counts and asking prices, and what the pool adds to the cost of ownership.
26 homes with a private pool are for sale or pending in Upper Matecumbe Key Islamorada, FL today across 12 communities. The median asking price is $3,345,000, from $549,500 to $29,500,000. Most listings right now: Strattons (82.5) (8), Russell Estates (83.2) (5), Misc Upper Matacumbe (82.0) (3). Updated September 8, 2026 from the MLS.
Upper Matecumbe Key Islamorada pool homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Pool Homes | New build | Median list | From |
|---|---|---|---|---|
| Strattons (82.5) | 8 | 1 | $674,000 | $549,500 |
| Russell Estates (83.2) | 5 | 5 | $4,000,000 | $3,800,000 |
| Misc Upper Matacumbe (82.0) | 3 | 2 | $15,950,000 | $13,750,000 |
| Sand Pebbles (80.5) | 2 | 0 | $572,500 | $550,000 |
| Tea Table (79.5) | 1 | 0 | $29,500,000 | $29,500,000 |
| Caribee Beach (80.0) | 1 | 0 | $7,400,000 | $7,400,000 |
| Venetian Shores (86.0) | 1 | 1 | $4,500,000 | $4,500,000 |
| Maison Matecumbe (81.0) | 1 | 0 | $3,495,000 | $3,495,000 |
| Misc Condo Upper Mat (82.0) | 1 | 1 | $3,195,000 | $3,195,000 |
| Bay Colony Villas (81.5) | 1 | 0 | $2,485,000 | $2,485,000 |
| Penn Key Club (83.0) | 1 | 0 | $2,195,000 | $2,195,000 |
| Hammock (83.5) | 1 | 1 | $1,550,000 | $1,550,000 |
What a private pool actually costs to own
Budget three things beyond the price: the pool itself (chemicals, pump electricity and a service if you do not want to do it yourself typically run $150 to $300 a month), the screen enclosure where there is one (a full re-screen every 8 to 12 years; a replacement enclosure is a five-figure job after a storm), and insurance, where a pool adds liability exposure and many carriers require a fence, self-latching gate or approved alarm. Florida’s Residential Swimming Pool Safety Act requires at least one safety feature on a new pool, and lenders and insurers ask about it on older ones. Have the pool inspected separately from the house: the pump, heater, surface finish and deck are the expensive items. Our true cost of ownership calculator puts insurance, taxes and upkeep into one monthly number.
Questions to ask about any pool listing
How old are the pump, filter and heater, and is there a warranty? When was the surface last refinished? Is the enclosure permitted and when was it last re-screened? Is there a barrier or alarm that satisfies the insurer? What did the seller pay for homeowners insurance last year, and did the carrier require anything for the pool? A local agent who works the area will know which enclosures came through the last storm.
Common questions
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Live data: floridakeys, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Upper Matecumbe Key Islamorada, FL whose MLS record reports a private pool. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.