Pool Homes for Sale in Longboat Key, FL
Buyers who want a pool search for the pool first. This page tracks every Longboat Key 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.
75 homes with a private pool are for sale or pending in Longboat Key, FL today across 46 communities. The median asking price is $2,500,000, from $369,000 to $38,450,000. Listings in Longboat Key without that feature have a median of $799,000. Most listings right now: Sleepy Lagoon Park (6), Bay Isles (5), Country Club Shores (5). Updated September 8, 2026 from the MLS.
Longboat Key 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 |
|---|---|---|---|---|
| Sleepy Lagoon Park | 6 | 1 | $2,947,500 | $975,000 |
| Bay Isles | 5 | 1 | $3,950,000 | $1,250,000 |
| Country Club Shores | 5 | 0 | $2,999,000 | $1,999,000 |
| Longboat Key | 5 | 2 | $2,900,000 | $999,000 |
| Sleepy Lagoon Park 2 | 4 | 1 | $2,675,000 | $1,175,000 |
| Water Club 01 At Longboat Key | 4 | 0 | $1,772,500 | $950,000 |
| Queens Harbour | 3 | 0 | $2,650,000 | $2,550,000 |
| Sleepy Lagoon | 2 | 2 | $14,497,500 | $13,995,000 |
| Longboat Shores Rev | 2 | 1 | $2,885,000 | $1,375,000 |
| Emerald Pointe South | 2 | 0 | $1,697,500 | $1,445,000 |
| Westchester Apts | 2 | 0 | $712,500 | $700,000 |
| T J Oxford | 1 | 0 | $15,550,000 | $15,550,000 |
| Rauch | 1 | 0 | $12,900,000 | $12,900,000 |
| Country Club Shores, Unit 5, Sec 3 | 1 | 0 | $9,400,000 | $9,400,000 |
| Bonaire At Longboat Key | 1 | 0 | $7,495,000 | $7,495,000 |
| Lighthouse Point | 1 | 0 | $6,995,000 | $6,995,000 |
| Longbeach On Longboat Key | 1 | 1 | $6,995,000 | $6,995,000 |
| Emerald Harbor | 1 | 1 | $6,495,000 | $6,495,000 |
| Hideaway Bay Sub | 1 | 0 | $6,295,000 | $6,295,000 |
| Pierre | 1 | 0 | $5,295,000 | $5,295,000 |
| Buttonwood Harbor | 1 | 1 | $4,000,000 | $4,000,000 |
| Country Club Shores Sec 02 | 1 | 0 | $3,999,990 | $3,999,990 |
| Weston Pointe | 1 | 0 | $3,100,000 | $3,100,000 |
| Country Club Shores Sec 2 | 1 | 0 | $2,900,000 | $2,900,000 |
| Shipmans Add | 1 | 0 | $2,795,000 | $2,795,000 |
| The Grande At Longboat Key | 1 | 0 | $2,750,000 | $2,750,000 |
| The Preserve/Longbeach | 1 | 1 | $2,650,000 | $2,650,000 |
| Tangerine Bay Club | 1 | 0 | $2,345,000 | $2,345,000 |
| Longboat Key Estates | 1 | 0 | $2,150,000 | $2,150,000 |
| Country Club Shores Sec 1 | 1 | 0 | $1,950,000 | $1,950,000 |
| Triton Cove | 1 | 0 | $1,899,000 | $1,899,000 |
| Grand Bay 1 | 1 | 0 | $1,798,000 | $1,798,000 |
| Longbeach Village | 1 | 0 | $1,575,000 | $1,575,000 |
| Sands Point | 1 | 0 | $980,000 | $980,000 |
| Privateer South | 1 | 0 | $949,000 | $949,000 |
| Harbour Villa Club At The Buccaneer | 1 | 0 | $949,000 | $949,000 |
| Inn On The Beach Ph Ii | 1 | 0 | $899,900 | $899,900 |
| Beachplace I | 1 | 0 | $875,000 | $875,000 |
| Fractional Sub | 1 | 0 | $849,500 | $849,500 |
| Harbour Oaks 2 | 1 | 0 | $835,000 | $835,000 |
| Windward Bay Amd | 1 | 0 | $769,000 | $769,000 |
| Longboat Arms | 1 | 0 | $675,000 | $675,000 |
| Whitney Beach Iii | 1 | 0 | $649,000 | $649,000 |
| Seaplace Vi | 1 | 0 | $569,000 | $569,000 |
| Silver Sands | 1 | 0 | $505,000 | $505,000 |
| Beach Harbor Club | 1 | 0 | $369,000 | $369,000 |
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 Longboat Key?
What do pool homes cost in Longboat Key?
Which Longboat Key community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
Keep exploring Longboat Key
Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Longboat Key, 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.