Pool Homes for Sale in Winter Haven, FL
Buyers who want a pool search for the pool first. This page tracks every Winter Haven 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.
110 homes with a private pool are for sale or pending in Winter Haven, FL today across 84 communities. The median asking price is $399,000, from $79,000 to $1,399,900. Listings in Winter Haven without that feature have a median of $275,000. Most listings right now: Waterford Oaks (4), Eloise Woods Lake Mariam Unit (3), Lake Mariam Hills Rep (3). Updated September 27, 2026 from the MLS.
Winter Haven pool homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale. The 60 communities with the most pool homes listed are tabled; the rest follow.
| Community | Pool Homes | New build | Median list | From |
|---|---|---|---|---|
| Waterford Oaks | 4 | 0 | $769,950 | $725,000 |
| Eloise Woods Lake Mariam Unit | 3 | 0 | $495,500 | $299,900 |
| Lake Mariam Hills Rep | 3 | 0 | $399,999 | $389,000 |
| Eloise Woods East Lake Mariam Unit | 3 | 0 | $290,000 | $250,000 |
| Magnolia Shores | 2 | 0 | $1,024,900 | $649,900 |
| Lesnick Park | 2 | 0 | $749,950 | $349,900 |
| Hamilton Pointe | 2 | 0 | $649,000 | $533,000 |
| Southeast Terrace | 2 | 0 | $439,500 | $400,000 |
| Buckeye Pointe | 2 | 0 | $399,950 | $369,900 |
| Overlook Estates | 2 | 0 | $367,450 | $304,900 |
| Berryhill | 2 | 0 | $287,500 | $260,000 |
| Jan Phyl Village | 2 | 0 | $264,450 | $219,000 |
| Mirro Mac | 1 | 0 | $899,000 | $899,000 |
| Lake Eloise Sub | 1 | 0 | $880,000 | $880,000 |
| Gaines Cove | 1 | 0 | $765,000 | $765,000 |
| Waters Lake Mariam | 1 | 0 | $750,000 | $750,000 |
| Orchid Springs Unrecorded | 1 | 0 | $750,000 | $750,000 |
| Cypresswood Palma Ceia | 1 | 0 | $749,000 | $749,000 |
| Hamilton Ridge | 1 | 0 | $699,900 | $699,900 |
| Hart Lake Hills Ph 01 | 1 | 0 | $699,000 | $699,000 |
| Eloise Pointe Ests Phase Two | 1 | 0 | $655,000 | $655,000 |
| Lake Ashton West Ph 01 | 1 | 0 | $599,900 | $599,900 |
| Sand Hill Lane | 1 | 0 | $574,900 | $574,900 |
| Lake Ashton West Ph Ii North | 1 | 0 | $565,000 | $565,000 |
| Cypresswood Plantation | 1 | 0 | $563,900 | $563,900 |
| Estates/Lk Florence | 1 | 1 | $549,500 | $549,500 |
| Orleans | 1 | 0 | $525,000 | $525,000 |
| Harbour Estates | 1 | 0 | $524,900 | $524,900 |
| Tuscany At Winterset | 1 | 0 | $519,990 | $519,990 |
| Pinnacle Point | 1 | 0 | $475,900 | $475,900 |
| Village/Spirit Lake Ph 01 | 1 | 0 | $469,000 | $469,000 |
| Ruby Lake Sub Ph Ii | 1 | 0 | $465,999 | $465,999 |
| Lake Mariam Hills | 1 | 0 | $465,000 | $465,000 |
| Lake Thomas Woods Eighth Add | 1 | 0 | $440,000 | $440,000 |
| Overlook Ests Ph 3 | 1 | 0 | $439,000 | $439,000 |
| Island Lakes | 1 | 0 | $434,900 | $434,900 |
| Lake Winterset Acres Unit #2 | 1 | 0 | $430,000 | $430,000 |
| Sun Rdg Village East | 1 | 0 | $425,000 | $425,000 |
| Lake Ashton West Ph Ii South | 1 | 0 | $422,999 | $422,999 |
| Lake Lucerne Ph 1 | 1 | 0 | $419,000 | $419,000 |
| Lake Eloise Place | 1 | 0 | $415,000 | $415,000 |
| Cypress Grove Ph 02 Stage 01 | 1 | 0 | $410,000 | $410,000 |
| Winterset Gardens | 1 | 0 | $399,000 | $399,000 |
| Pine Terrace Rep | 1 | 0 | $399,000 | $399,000 |
| Summer Haven Shores | 1 | 0 | $389,900 | $389,900 |
| Eloise Woods Lake Roy Un | 1 | 0 | $389,000 | $389,000 |
| Terranova Ph 01 | 1 | 0 | $385,000 | $385,000 |
| Lakewood Community Association | 1 | 0 | $385,000 | $385,000 |
| Lake Thomas Woods Sixth Add | 1 | 0 | $385,000 | $385,000 |
| College Estates | 1 | 0 | $379,900 | $379,900 |
| Eloise Cove | 1 | 0 | $363,500 | $363,500 |
| Cypresswood | 1 | 0 | $355,000 | $355,000 |
| Homewood Sub | 1 | 0 | $350,000 | $350,000 |
| Terranova Ph Iv | 1 | 0 | $350,000 | $350,000 |
| Summit East Ph 02 | 1 | 0 | $340,000 | $340,000 |
| Cypresswood Fairway Patio Homes | 1 | 0 | $337,000 | $337,000 |
| Almeda Park | 1 | 0 | $330,000 | $330,000 |
| Lake Elbert Heights Unit 01 02 Rep | 1 | 0 | $329,900 | $329,900 |
| Mandolin | 1 | 0 | $320,000 | $320,000 |
| Haven Place | 1 | 0 | $314,999 | $314,999 |
Also with pool homes for sale
- Haven Homes Sub (1)
- Plaza Sub (1)
- Jan Phyl Village Un #16 (1)
- Gardens Ph 01 (1)
- Waterside Village (1)
- Inwood (1)
- Saxon Myers Rep Ph 2 (1)
- Hutchinson Add (1)
- Carefree Cove (1)
- Shadow Wood (1)
- Country Walk/Winter Haven (1)
- Elbert Acres (1)
- Leisure Shores (1)
- Planters Walk (1)
- Fla Highlands Co Sub (1)
- Timber Wood (1)
- Lake View Sub (1)
- Dugger Rep (1)
- Deer Lake Terrace Sub (1)
- Cinnamon Ridge Ph 03 (1)
- Royal Crescent Condo (1)
- The Haven (1)
- Imperial Harboursphases 01 & 02 (1)
- Lakeside Ranch For Mobile Homes (1)
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 Winter Haven?
What do pool homes cost in Winter Haven?
Which Winter Haven community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
Keep exploring Winter Haven
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- Winter Haven homes under $300K
- Winter Haven homes $300Kâ$500K
- Pool Homes in every city
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 Winter Haven, 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.