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.

167 homes with a private pool are for sale or pending in Key West, FL today across 59 communities. The median asking price is $1,500,000, from $330,000 to $12,500,000. Most listings right now: Old Town - Unrecord (1.0) (20), Key West Golf Club Dev (4.0) (19), Old Town - Unlisted (1.0) (16). Updated September 8, 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	1	$2,990,000	$779,000
Key West Golf Club Dev (4.0)	19	0	$669,000	$585,000
Old Town - Unlisted (1.0)	16	3	$2,322,000	$575,000
New Town - Unlisted (2.0)	6	0	$1,012,492	$749,000
Santa Clara (3.0)	6	0	$355,000	$330,000
Riviera Shores (3.0)	5	0	$2,475,000	$1,079,000
Sunrise Shores (4.0)	5	0	$2,165,000	$1,875,000
Webb Realty Co Sub (1.0)	4	1	$3,075,000	$1,299,000
Monroe Investement Co Sub (2.0)	4	0	$1,944,382	$1,350,000
Key West Realty Cos Sub (3.0)	4	0	$1,849,000	$1,385,000
Seaside Key West Residences	4	0	$1,224,000	$1,099,000
Key West By The Sea (3.0)	4	0	$844,000	$615,000
Las Salinas (3.0)	4	0	$529,000	$475,000
Sunset Key (Tank) Island Unrcd (0.0)	3	0	$9,495,000	$7,000,000
Moffats Sub (2.0)	3	0	$1,899,000	$539,000
Gwynn Sub (1.0)	3	0	$1,575,000	$995,000
Solana Village (3.0)	3	0	$675,000	$392,000
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
Land Buyers Assn (3.0)	2	1	$2,187,000	$1,474,000
Roosevelt Annex (2.0)	2	0	$1,974,500	$1,549,000
Coconut Mallory Resort & Marina (4.0)	2	0	$1,074,000	$1,074,000
La Brisa North (2.0)	2	0	$737,450	$625,000
Vista Del Mar (4.0)	1	0	$7,500,000	$7,500,000
The Foundry (1.0)	1	0	$6,850,000	$6,850,000
Martello Towers (1.0)	1	0	$5,500,000	$5,500,000
Casa Caselles (2.0)	1	0	$4,995,000	$4,995,000
Key West Beach Club 2 (2.0)	1	0	$4,499,999	$4,499,999
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	$2,445,000	$2,445,000
Riviera Shr Amd Plat (3.0)	1	0	$1,995,000	$1,995,000
Lime Grove (3.0)	1	1	$1,949,000	$1,949,000
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
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
New Town - Unrecord (3.0)	1	0	$1,249,000	$1,249,000
Kamien Plat #2 (2.0)	1	0	$1,225,000	$1,225,000
Campbell Courtyard (1.0)	1	0	$1,175,000	$1,175,000
Knights Sub (2.0)	1	0	$992,000	$992,000
La Brisa South (2.0)	1	0	$890,000	$890,000
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?

As of September 8, 2026, 167 Key West, FL listings whose MLS record reports a private pool are active or pending, across 59 communities. The count updates with every MLS refresh.

What do pool homes cost in Key West?

The median asking price today is $1,500,000, with listings from $330,000 to $12,500,000.

Which Key West community has the most pool homes for sale?

Old Town - Unrecord (1.0) has the most right now (20), followed by Key West Golf Club Dev (4.0) (19), Old Town - Unlisted (1.0) (16), New Town - Unlisted (2.0) (6).

Does a pool raise homeowners insurance in Florida?

Usually modestly on premium but meaningfully on requirements: most carriers want a barrier, self-latching gate or approved alarm, and a screen enclosure is often excluded or sub-limited for wind. Get the quote before you offer and ask specifically how the enclosure is covered.

Keep exploring Key West

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.

Listing data provided by Florida Keys MLS, Inc. Information is deemed reliable but is not guaranteed by the MLS to be accurate.