Pool Homes for Sale in Osprey, FL
Buyers who want a pool search for the pool first. This page tracks every Osprey 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.
35 homes with a private pool are for sale or pending in Osprey, FL today across 22 communities. The median asking price is $1,399,000, from $529,000 to $9,750,000. Listings in Osprey without that feature have a median of $540,000. Most listings right now: Southbay Yacht & Racquet Club (7), Casey Key (3), Park Trace Estates (3). Updated September 27, 2026 from the MLS.
Live pool homes in Osprey: the listings
23 active listings carry the flag today (33% of Osprey inventory), median asking $1,165,000, $376/sq ft, median 111 days on market. Photo cards link to the listing; refreshed nightly.
Newest pool homes in Osprey
The most expensive pool homes in Osprey
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 1216 N Casey Key Road | $9,750,000 | 8,050 | Casey Key |
| 121 N Casey Key Road | $6,475,000 | 4,096 | Casey Key |
| 313 Lookout Point Drive | $5,999,999 | 5,337 | Southbay Yacht & Racquet Club |
| 236 Saint James Park | $2,700,000 | 6,246 | Oaks 2 Ph 2 |
| 852 Macewen Drive | $2,395,000 | 4,519 | Oaks 2 Ph 2 |
| 154 Lookout Point Drive | $2,095,000 | 4,578 | Southbay Yacht & Racquet Club |
| 18 N Casey Key Road | $1,750,000 | 1,977 | Casey Key |
| 141 Sugar Mill Drive | $1,700,000 | 3,118 | — |
| 206 Four Knot Lane | $1,690,000 | 2,411 | Southbay Yacht & Racquet Club |
| 909 Macewen Drive | $1,595,000 | 4,241 | Oaks 2 Ph 2 |
Pool Homes by price
| Band | For sale | Share |
|---|---|---|
| $500K–$750K | 6 | 26% |
| $750K–$1M | 3 | 13% |
| $1M+ | 14 | 61% |
Osprey 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 |
|---|---|---|---|---|
| Southbay Yacht & Racquet Club | 7 | 0 | $1,690,000 | $760,000 |
| Casey Key | 3 | 0 | $6,475,000 | $1,750,000 |
| Park Trace Estates | 3 | 0 | $824,900 | $669,900 |
| Oaks 2 Ph 1 | 2 | 0 | $2,250,000 | $1,800,000 |
| Oaks 2 Ph 2 | 2 | 0 | $2,147,500 | $1,900,000 |
| Bay Oaks Estates | 2 | 0 | $672,000 | $529,000 |
| Bayside | 1 | 0 | $2,850,000 | $2,850,000 |
| Oaks 2 Ph 4 | 1 | 0 | $2,750,000 | $2,750,000 |
| Oaks 2 Ph 4C Part 1 | 1 | 0 | $2,600,000 | $2,600,000 |
| Oaks 2 Ph 4-C Pt 3 | 1 | 0 | $1,950,000 | $1,950,000 |
| The Oaks | 1 | 0 | $1,700,000 | $1,700,000 |
| Oaks 2 Phase 2 | 1 | 0 | $1,595,000 | $1,595,000 |
| Pine Ranch East | 1 | 0 | $1,100,000 | $1,100,000 |
| Rivendell The Woodlands | 1 | 0 | $1,100,000 | $1,100,000 |
| Emerald Woods At Oaks 03 Ph 02 | 1 | 0 | $1,050,000 | $1,050,000 |
| Bishopscourt At The Oaks Preserve | 1 | 0 | $789,000 | $789,000 |
| Willowbend Ph 1 | 1 | 0 | $749,900 | $749,900 |
| Trinity Acres | 1 | 0 | $749,000 | $749,000 |
| Edgewater/Hidden Bay Ph 3 | 1 | 1 | $719,000 | $719,000 |
| Rivendell Woodlands | 1 | 0 | $700,000 | $700,000 |
| Rivendell | 1 | 0 | $655,000 | $655,000 |
| Saunders V A Resub | 1 | 0 | $649,000 | $649,000 |
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 Osprey?
What do pool homes cost in Osprey?
Which Osprey community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
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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 Osprey, 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.