Pool Homes for Sale in Key West, FL
Buyers who want a pool search for the pool first. This page tracks every Key West 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.
168 homes with a private pool are for sale or pending in Key West, FL today across 60 communities. The median asking price is $1,412,500, from $330,000 to $12,500,000. Listings in Key West without that feature have a median of $999,000. Most listings right now: Old Town - Unrecord (1.0) (20), Key West Golf Club Dev (4.0) (20), Old Town - Unlisted (1.0) (18). Updated September 27, 2026 from the MLS.
Key West 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 |
|---|---|---|---|---|
| Old Town - Unrecord (1.0) | 20 | 0 | $2,699,500 | $779,000 |
| Key West Golf Club Dev (4.0) | 20 | 0 | $734,000 | $585,000 |
| Old Town - Unlisted (1.0) | 18 | 4 | $2,122,000 | $575,000 |
| Santa Clara (3.0) | 7 | 0 | $365,000 | $330,000 |
| New Town - Unlisted (2.0) | 6 | 0 | $1,009,995 | $749,000 |
| Riviera Shores (3.0) | 5 | 0 | $2,399,000 | $1,079,000 |
| Sunrise Shores (4.0) | 5 | 0 | $2,100,000 | $1,875,000 |
| Key West Realty Cos Sub (3.0) | 5 | 0 | $1,799,000 | $1,385,000 |
| Seaside Key West Residences | 4 | 0 | $1,219,000 | $1,099,000 |
| Key West By The Sea (3.0) | 4 | 0 | $844,000 | $599,000 |
| Las Salinas (3.0) | 4 | 0 | $529,000 | $475,000 |
| Monroe Investement Co Sub (2.0) | 3 | 0 | $1,799,765 | $1,350,000 |
| Solana Village (3.0) | 3 | 0 | $675,000 | $392,000 |
| Sunset Key (Tank) Island Unrcd (0.0) | 2 | 0 | $10,997,500 | $9,495,000 |
| Key West Beach Club 2 (2.0) | 2 | 0 | $3,574,999 | $2,650,000 |
| Webb Realty Co Sub (1.0) | 2 | 0 | $2,997,500 | $2,500,000 |
| Key West Investment Co Sub (1.0) | 2 | 0 | $2,745,000 | $2,595,000 |
| Tropical Bldt & Investment Co Sub (2.0) | 2 | 0 | $2,387,500 | $2,250,000 |
| Moffats Sub (2.0) | 2 | 0 | $2,344,500 | $1,899,000 |
| Land Buyers Assn (3.0) | 2 | 1 | $2,187,000 | $1,474,000 |
| New Town - Unrecord (3.0) | 2 | 0 | $2,084,000 | $1,249,000 |
| Roosevelt Annex (2.0) | 2 | 0 | $1,974,500 | $1,549,000 |
| Riviera Shr Amd Plat (3.0) | 2 | 0 | $1,630,000 | $1,285,000 |
| Gwynn Sub (1.0) | 2 | 0 | $1,285,000 | $995,000 |
| Coconut Mallory Resort & Marina (4.0) | 2 | 0 | $1,070,000 | $1,070,000 |
| La Brisa North (2.0) | 2 | 0 | $737,450 | $625,000 |
| The Foundry (1.0) | 1 | 0 | $6,850,000 | $6,850,000 |
| Vista Del Mar (4.0) | 1 | 0 | $6,200,000 | $6,200,000 |
| Martello Towers (1.0) | 1 | 0 | $5,500,000 | $5,500,000 |
| Casa Caselles (2.0) | 1 | 0 | $4,995,000 | $4,995,000 |
| Prog Land Imp Co Diag (2.0) | 1 | 0 | $3,599,000 | $3,599,000 |
| Sunset Marina (4.0) | 1 | 0 | $3,100,000 | $3,100,000 |
| Gardens of Key West (1.0) | 1 | 0 | $3,100,000 | $3,100,000 |
| East Martello Towers (2.0) | 1 | 0 | $2,999,999 | $2,999,999 |
| Mills Place (1.0) | 1 | 0 | $2,999,500 | $2,999,500 |
| Investment Co Sub (1.0) | 1 | 1 | $2,550,000 | $2,550,000 |
| White & Pierce Diagram (1.0) | 1 | 1 | $2,499,000 | $2,499,000 |
| Wm. Fleming House (1.0) | 1 | 0 | $2,399,000 | $2,399,000 |
| Benj Alburys Subd (2.0) | 1 | 0 | $1,899,000 | $1,899,000 |
| Pearlmans Subd (2.0) | 1 | 0 | $1,850,000 | $1,850,000 |
| George W Nichols Sub (1.0) | 1 | 0 | $1,825,000 | $1,825,000 |
| Waddells Subdivision (2.0) | 1 | 0 | $1,750,000 | $1,750,000 |
| La Brisa East (2.0) | 1 | 0 | $1,425,000 | $1,425,000 |
| Pearlman Heights (4.0) | 1 | 0 | $1,400,000 | $1,400,000 |
| GG Watson Sub (1.0) | 1 | 0 | $1,375,000 | $1,375,000 |
| Flaglers Landing (2.0) | 1 | 0 | $1,375,000 | $1,375,000 |
| Filer Boyle Sub (1.0) | 1 | 0 | $1,250,000 | $1,250,000 |
| Kamien Plat #2 (2.0) | 1 | 0 | $1,225,000 | $1,225,000 |
| La Brisa West (2.0) | 1 | 0 | $1,190,000 | $1,190,000 |
| Campbell Courtyard (1.0) | 1 | 0 | $1,175,000 | $1,175,000 |
| La Brisa South (2.0) | 1 | 0 | $890,000 | $890,000 |
| Shipyard PH 2 (1.0) | 1 | 0 | $869,000 | $869,000 |
| Sunrise At Seaside (3.0) | 1 | 0 | $868,000 | $868,000 |
| Shipyard PH 1 (1.0) | 1 | 0 | $865,000 | $865,000 |
| Lionsgate Key West A Condo (1.0) | 1 | 0 | $839,000 | $839,000 |
| Newton Park (2.0) | 1 | 0 | $699,000 | $699,000 |
| Key Cove (2.0) | 1 | 0 | $679,500 | $679,500 |
| Key West Estates (4.0) | 1 | 0 | $665,000 | $665,000 |
| Southpark (1.0) | 1 | 0 | $599,000 | $599,000 |
| Salt Pond (3.0) | 1 | 0 | $599,000 | $599,000 |
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
How many homes with a private pool are for sale in Key West?
What do pool homes cost in Key West?
Which Key West community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
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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 Key West, 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.