4 Bedroom Homes for Sale in Upper Matecumbe Key Islamorada, FL
Four bedrooms is the most-searched size in most Florida and Georgia markets. This page tracks every Upper Matecumbe Key Islamorada listing whose MLS record reports four or more bedrooms, by community, with live counts and asking prices, and how the price compares with smaller homes in the same city.
13 homes with four or more bedrooms are for sale or pending in Upper Matecumbe Key Islamorada, FL today across 7 communities. The median asking price is $4,000,000, from $1,550,000 to $29,500,000. Listings in Upper Matecumbe Key Islamorada without that feature have a median of $789,000. Most listings right now: Russell Estates (83.2) (5), Misc Upper Matacumbe (82.0) (3), Tea Table (79.5) (1). Updated September 13, 2026 from the MLS.
Upper Matecumbe Key Islamorada 4-bedroom homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | 4-Bedroom Homes | New build | Median list | From |
|---|---|---|---|---|
| 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 |
| Tea Table (79.5) | 1 | 0 | $29,500,000 | $29,500,000 |
| Strattons (82.5) | 1 | 0 | $6,999,000 | $6,999,000 |
| 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 |
| Hammock (83.5) | 1 | 1 | $1,550,000 | $1,550,000 |
What the fourth bedroom costs
The answer block above compares the median asking price of four-plus-bedroom homes with the median of everything else listed in the city; the gap is what the extra room, and usually the extra square footage and lot, is priced at today. Compare on price per square foot, not price alone: a four-bedroom home at 2,000 square feet and one at 2,800 are different purchases, and the MLS square footage on each listing page makes that comparison in seconds. Newer subdivisions tend to deliver four bedrooms in less square footage than older ones; the community pages show year-built ranges so you can see which is which.
Questions to ask about any four-bedroom listing
Is the fourth bedroom a true bedroom with a closet and window, or a converted den, garage bay or bonus room? Are the bedrooms split (owner’s suite away from the others) or all on one side? Is there a second full bath near the secondary bedrooms? What does the seller pay for insurance and, in an HOA community, what do the dues cover? A local agent who works the area will know which builders’ four-bedroom plans hold their value.
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 four or more bedrooms. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.