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.
121 homes with a private pool are for sale or pending in Winter Haven, FL today across 93 communities. The median asking price is $390,000, from $74,900 to $1,799,900. Listings in Winter Haven without that feature have a median of $280,000. Most listings right now: Eloise Woods East Lake Mariam Unit (4), Lake Mariam Hills Rep (3), Jan Phyl Village (3). Updated September 8, 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 |
|---|---|---|---|---|
| Eloise Woods East Lake Mariam Unit | 4 | 0 | $334,250 | $250,000 |
| Lake Mariam Hills Rep | 3 | 0 | $420,000 | $389,000 |
| Jan Phyl Village | 3 | 0 | $315,000 | $240,000 |
| Magnolia Shores | 2 | 0 | $1,049,925 | $699,950 |
| Waterford Oaks | 2 | 0 | $894,950 | $799,900 |
| Waters Lake Mariam | 2 | 0 | $789,500 | $760,000 |
| Lesnick Park | 2 | 0 | $764,950 | $379,900 |
| Hamilton Pointe | 2 | 0 | $657,000 | $549,000 |
| Hart Lake Hills Ph 01 | 2 | 0 | $597,000 | $495,000 |
| Southeast Terrace | 2 | 0 | $450,000 | $400,000 |
| Eloise Woods Lake Mariam Unit | 2 | 0 | $417,450 | $319,900 |
| Buckeye Pointe | 2 | 0 | $399,950 | $369,900 |
| Overlook Estates | 2 | 0 | $374,950 | $319,900 |
| Terranova Ph Iv | 2 | 0 | $362,500 | $360,000 |
| Berryhill | 2 | 0 | $287,500 | $260,000 |
| Lake Eloise Sub | 1 | 0 | $900,000 | $900,000 |
| Mirro Mac | 1 | 0 | $899,000 | $899,000 |
| Gaines Cove | 1 | 0 | $765,000 | $765,000 |
| 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 |
| Renaissance | 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 | $585,000 | $585,000 |
| Heron Cay | 1 | 0 | $579,900 | $579,900 |
| 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 | $549,900 | $549,900 |
| Orleans | 1 | 0 | $525,000 | $525,000 |
| Harbour Estates | 1 | 0 | $524,900 | $524,900 |
| Tuscany At Winterset | 1 | 0 | $519,990 | $519,990 |
| Lake Mariam Hills | 1 | 0 | $480,000 | $480,000 |
| Pinnacle Point | 1 | 0 | $475,900 | $475,900 |
| Valencia Wood Hills | 1 | 0 | $475,000 | $475,000 |
| Village/Spirit Lake Ph 01 | 1 | 0 | $469,000 | $469,000 |
| Ruby Lake Sub Ph Ii | 1 | 0 | $465,999 | $465,999 |
| Country Club Estates | 1 | 0 | $459,990 | $459,990 |
| Lakewood | 1 | 0 | $451,000 | $451,000 |
| Lake Thomas Woods Eighth Add | 1 | 0 | $450,000 | $450,000 |
| Lakewood Tr 173 | 1 | 0 | $450,000 | $450,000 |
| Island Lakes | 1 | 0 | $439,999 | $439,999 |
| Overlook Ests Ph 3 | 1 | 0 | $439,000 | $439,000 |
| Sun Rdg Village East | 1 | 0 | $425,000 | $425,000 |
| Winterset Gardens | 1 | 0 | $425,000 | $425,000 |
| Lake Ashton West Ph Ii South | 1 | 0 | $422,999 | $422,999 |
| Lake Eloise Place | 1 | 0 | $415,000 | $415,000 |
| Cypress Grove Ph 02 Stage 01 | 1 | 0 | $410,000 | $410,000 |
| Summer Haven Shores | 1 | 0 | $399,900 | $399,900 |
| Pine Terrace Rep | 1 | 0 | $399,000 | $399,000 |
| Eloise Woods Lake Roy Un | 1 | 0 | $389,000 | $389,000 |
| Terranova Ph 01 | 1 | 0 | $385,000 | $385,000 |
| Lake Thomas Woods Sixth Add | 1 | 0 | $385,000 | $385,000 |
| Lakewood Community Association | 1 | 0 | $385,000 | $385,000 |
| College Grove Rep | 1 | 0 | $365,000 | $365,000 |
| Eloise Cove | 1 | 0 | $363,500 | $363,500 |
| Cypresswood | 1 | 0 | $360,000 | $360,000 |
| Revised Map Of Fernwood Add | 1 | 0 | $345,000 | $345,000 |
| Cypresswood Fairway Patio Homes | 1 | 0 | $337,000 | $337,000 |
| Garden Grove | 1 | 0 | $335,000 | $335,000 |
Also with pool homes for sale: Almeda Park (1), Lake Elbert Heights Unit 01 02 Rep (1), Mandolin (1), Haven Place (1), Lake Link Estates (1), Haven Homes Sub (1), Plaza Sub (1), Queens Cove Ph 02 (1), Waterside Village (1), Jan Phyl Village Un #16 (1), Vienna Square Ph 01 (1), Gardens Ph 01 (1), Shadow Wood (1), Saxon Myers Rep Ph 2 (1), Inwood (1), Carefree Cove (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), Biltmore Shores (1), Tranquil Oaks (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), Orchid Spgs Vill 100 Condo (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
- All homes for sale in Winter Haven
- Winter Haven ZIP codes with prices
- Winter Haven waterfront homes
- 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.