Pool Homes for Sale in Oldsmar, FL
Buyers who want a pool search for the pool first. This page tracks every Oldsmar 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.
29 homes with a private pool are for sale or pending in Oldsmar, FL today across 21 communities. The median asking price is $695,000, from $158,990 to $2,300,000. Listings in Oldsmar without that feature have a median of $293,950. Most listings right now: East Lake Woodlands (6), Cross Pointe (2), Oldsmar Rev Map (2). Updated September 27, 2026 from the MLS.
Live pool homes in Oldsmar: the listings
19 active listings carry the flag today (12% of Oldsmar inventory), median asking $698,000, $265/sq ft, median 56 days on market. Photo cards link to the listing; refreshed nightly.
Newest pool homes in Oldsmar
The most expensive pool homes in Oldsmar
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 1330 Preservation Way | $2,300,000 | 6,460 | — |
| 50 Willowood Lane | $1,499,900 | 4,475 | Deerpath |
| 1404 East Lake Woodlands Parkway | $1,100,000 | 4,312 | Greenhaven |
| 35 Greenhaven Trail | $1,099,000 | 3,098 | Greenhaven |
| 2328 Warwick Drive | $829,000 | 3,294 | — |
| 1723 Captiva Drive | $825,700 | 2,736 | Cross Pointe |
| 743 Wellington Court | $775,000 | 3,058 | Wellington Estates |
| 470 Hickorynut Avenue | $739,000 | 2,922 | east lake woodlands |
| 402 Shore Drive | $725,000 | 1,711 | west oldsmar |
| 80 Foxfire Lane | $698,000 | 2,584 | east lake woodlands |
Pool Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 1 | 5% |
| $300K–$500K | 2 | 11% |
| $500K–$750K | 9 | 47% |
| $750K–$1M | 3 | 16% |
| $1M+ | 4 | 21% |
Oldsmar 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 |
|---|---|---|---|---|
| East Lake Woodlands | 6 | 0 | $683,500 | $189,999 |
| Cross Pointe | 2 | 0 | $785,350 | $745,000 |
| Oldsmar Rev Map | 2 | 0 | $637,500 | $550,000 |
| Worthington | 2 | 0 | $606,950 | $584,900 |
| Preserve The | 1 | 0 | $2,300,000 | $2,300,000 |
| Deerpath Unit One | 1 | 0 | $1,499,900 | $1,499,900 |
| Greenhaven Unit Three | 1 | 0 | $1,100,000 | $1,100,000 |
| Greenhaven Unit Two | 1 | 0 | $1,099,000 | $1,099,000 |
| Aberdeen Unit Two | 1 | 0 | $1,025,000 | $1,025,000 |
| Warwick Hills | 1 | 0 | $829,000 | $829,000 |
| Wellington Estates | 1 | 0 | $775,000 | $775,000 |
| Stonebriar | 1 | 0 | $729,900 | $729,900 |
| Country Club Add To Oldsmar Rev | 1 | 0 | $695,000 | $695,000 |
| Eastlake Oaks Ph 4 | 1 | 0 | $589,000 | $589,000 |
| Kingsmill | 1 | 0 | $585,000 | $585,000 |
| Bay Arbor Unit 1A | 1 | 0 | $584,900 | $584,900 |
| Fountains At Cypress Lakes Ii-B | 1 | 0 | $558,900 | $558,900 |
| Bays End | 1 | 0 | $499,000 | $499,000 |
| Shoreview Ph 2 | 1 | 0 | $375,000 | $375,000 |
| Harbor Palms-Unit Two | 1 | 0 | $329,000 | $329,000 |
| Tampashores Bay Sec | 1 | 0 | $158,990 | $158,990 |
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 Oldsmar?
What do pool homes cost in Oldsmar?
Which Oldsmar community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
Keep exploring Oldsmar
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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 Oldsmar, 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.