Pool Homes for Sale in Winter Park, FL
Buyers who want a pool search for the pool first. This page tracks every Winter Park 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.
125 homes with a private pool are for sale or pending in Winter Park, FL today across 85 communities. The median asking price is $1,640,000, from $182,900 to $7,250,000. Listings in Winter Park without that feature have a median of $1,250,000. Most listings right now: The Enclave Winter Park (5), Kenilworth Shores Sec 06 (4), Charmont (4). Updated September 8, 2026 from the MLS.
Winter Park 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 |
|---|---|---|---|---|
| The Enclave Winter Park | 5 | 5 | $2,300,000 | $2,070,000 |
| Kenilworth Shores Sec 06 | 4 | 3 | $2,750,000 | $1,590,000 |
| Charmont | 4 | 3 | $2,749,000 | $1,565,000 |
| Winter Park Village | 4 | 4 | $1,772,000 | $1,598,000 |
| Winter Park Pines | 4 | 0 | $682,450 | $639,500 |
| Park Grove | 3 | 3 | $4,595,000 | $3,999,000 |
| Comstock Park | 3 | 0 | $2,699,000 | $1,640,000 |
| Lawndale | 3 | 3 | $1,419,900 | $1,400,000 |
| Winter Park Estates | 3 | 0 | $575,000 | $460,000 |
| Garden Lake Estates Unit 1 | 3 | 0 | $435,000 | $399,800 |
| Maitland Shores First Add | 2 | 0 | $4,175,000 | $2,750,000 |
| Forest Hills | 2 | 1 | $4,012,500 | $3,075,000 |
| Villa View Park | 2 | 0 | $2,120,000 | $1,850,000 |
| Lake Knowles Terrace Add 02 | 2 | 1 | $2,119,500 | $1,690,000 |
| Temple Estates | 2 | 1 | $2,090,000 | $1,795,000 |
| Lake Forest Park | 2 | 2 | $2,079,500 | $1,699,000 |
| Sylvan Heights | 2 | 2 | $1,900,000 | $1,750,000 |
| Fontainebleau | 2 | 0 | $1,745,000 | $1,625,000 |
| Eastgate Sub | 2 | 1 | $899,500 | $500,000 |
| Lake Waunatta Woods | 2 | 0 | $654,388 | $569,000 |
| Woodcrest Unit 5 | 2 | 0 | $487,450 | $479,900 |
| Eastbrook Sub | 2 | 0 | $383,500 | $368,000 |
| Robert Dhu Macdonald Park | 1 | 1 | $7,250,000 | $7,250,000 |
| J Kronenberger Sub | 1 | 0 | $6,900,000 | $6,900,000 |
| Sylvan Park | 1 | 1 | $5,500,000 | $5,500,000 |
| Woodmere Terrace Rep | 1 | 0 | $4,900,000 | $4,900,000 |
| Lake Maitland | 1 | 0 | $4,750,000 | $4,750,000 |
| Alexander Place | 1 | 0 | $4,250,000 | $4,250,000 |
| Winflor Court Pt Rep | 1 | 0 | $3,995,000 | $3,995,000 |
| Timberlane Shores | 1 | 1 | $3,890,000 | $3,890,000 |
| Cloister Grove Sub | 1 | 1 | $3,750,000 | $3,750,000 |
| Detmar Terrace Winter Park | 1 | 0 | $3,600,000 | $3,600,000 |
| Maitland Shores 1St Add | 1 | 0 | $3,500,000 | $3,500,000 |
| Sylvan Lake Shores | 1 | 1 | $3,300,000 | $3,300,000 |
| Ellno Willo | 1 | 0 | $3,275,000 | $3,275,000 |
| Green Oaks Rep 02 | 1 | 0 | $3,265,000 | $3,265,000 |
| Winter Park | 1 | 1 | $2,650,000 | $2,650,000 |
| Orange Grove Sub | 1 | 1 | $2,569,999 | $2,569,999 |
| Northwood Terrace | 1 | 1 | $2,495,000 | $2,495,000 |
| Lugano Terrace | 1 | 0 | $2,195,000 | $2,195,000 |
| Kenilworth Shores Sec 01 | 1 | 1 | $1,999,990 | $1,999,990 |
| Conwill Estates | 1 | 1 | $1,900,000 | $1,900,000 |
| Parklando 03 | 1 | 0 | $1,899,000 | $1,899,000 |
| Lake Knowles Terrace 2Nd Add | 1 | 1 | $1,829,000 | $1,829,000 |
| Kenilworth Shores Sec 03 | 1 | 0 | $1,800,000 | $1,800,000 |
| Osceola Or Lakeview Deed | 1 | 0 | $1,775,000 | $1,775,000 |
| Winter Park Rev | 1 | 0 | $1,770,000 | $1,770,000 |
| Lakeview Terrace | 1 | 0 | $1,725,000 | $1,725,000 |
| Twin Acres | 1 | 0 | $1,675,000 | $1,675,000 |
| Killarney Estates | 1 | 0 | $1,600,000 | $1,600,000 |
| Winter Park Oasis | 1 | 0 | $1,599,000 | $1,599,000 |
| Fremar | 1 | 0 | $1,599,000 | $1,599,000 |
| Orwin Manor Westminster Sec | 1 | 1 | $1,399,000 | $1,399,000 |
| Lake Killarney Shores | 1 | 1 | $1,389,500 | $1,389,500 |
| Waters Edge At Hawks Crest | 1 | 0 | $1,350,000 | $1,350,000 |
| Edgewood Sub | 1 | 0 | $1,300,000 | $1,300,000 |
| Kenilworth Shores Sec 07 | 1 | 0 | $1,262,500 | $1,262,500 |
| Quail Hollow | 1 | 0 | $1,199,000 | $1,199,000 |
| Banks Colonial Estates | 1 | 0 | $1,150,000 | $1,150,000 |
| Lords Sub | 1 | 0 | $1,050,000 | $1,050,000 |
Also with pool homes for sale: Park Pointe Rep (1), Kenilworth Shores Sec 04 (1), Village Winterset Inc (1), Temple Terrace (1), Lake Ann Estates Unit 3 (1), Flamingo Shores (1), Greenview At Winter Pines (1), Lake Ann Estates Unit 2 (1), Glencoe Sub (1), Seville Park (1), Winter Park Pines Rep (1), Arrowhead Cove (1), Lake Waunatta Wods (1), Glencoe Subdivision (1), Tanglewood Sec 3 Rep (1), Fairshores Place (1), Winter Woods Unit 03 (1), Winter Park Pines Merrie Oaks (1), Georgetown Estates (1), Autumn Glen Ph 3 (1), Winter Woods Unit 01 (1), Lake Killarney Condo (1), Mead Garden Condominium (1), Lake Killarney Condominium Assn Inc. (1), Stratford A Winter Park 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 Park?
What do pool homes cost in Winter Park?
Which Winter Park community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
Keep exploring Winter Park
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 Park, 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.