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.
140 homes with a private pool are for sale or pending in Winter Park, FL today across 93 communities. The median asking price is $1,600,000, from $182,900 to $6,995,000. Listings in Winter Park without that feature have a median of $479,000. Most listings right now: Winter Park Pines (6), The Enclave Winter Park (5), Winter Park Village (5). Updated September 27, 2026 from the MLS.
Live pool homes in Winter Park: the listings
92 active listings carry the flag today (39% of Winter Park inventory), median asking $1,674,000, $577/sq ft, median 43 days on market. Photo cards link to the listing; refreshed nightly.
Newest pool homes in Winter Park
The most expensive pool homes in Winter Park
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 1260 Alabama Drive | $6,900,000 | 6,396 | J Kronenberger |
| 1571 Woodland Avenue | $6,000,000 | 7,397 | Comstock Park |
| 2661 Via Tuscany | $5,999,990 | 3,880 | Maitland Shores |
| 2228 Azalea Place | $5,600,000 | 5,152 | Maitland Shores |
| 313 Sylvan Drive | $5,500,000 | 4,775 | Sylvan Park |
| 1166 Palmer Avenue | $5,500,000 | 5,181 | Palmer Ave Lakeside Prop |
| 825 Palmer Avenue | $5,195,900 | 5,122 | J Kronenberger |
| 231 Chelton Circle | $4,700,000 | 5,550 | Forest Hills |
| 857 Brock Street | $4,650,000 | 4,827 | Park Grove |
| 702 Via Bella | $4,400,000 | 3,720 | Palmer Ave Lakeside Prop |
Pool Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 4 | 4% |
| $300K–$500K | 5 | 5% |
| $500K–$750K | 10 | 11% |
| $750K–$1M | 6 | 7% |
| $1M+ | 67 | 73% |
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 |
|---|---|---|---|---|
| Winter Park Pines | 6 | 0 | $682,450 | $619,500 |
| The Enclave Winter Park | 5 | 5 | $2,300,000 | $2,070,000 |
| Winter Park Village | 5 | 5 | $1,749,000 | $1,579,000 |
| Charmont | 4 | 2 | $2,194,000 | $1,525,000 |
| Maitland Shores First Add | 3 | 1 | $5,600,000 | $1,319,950 |
| J Kronenberger Sub | 3 | 1 | $5,195,900 | $2,195,000 |
| Forest Hills | 3 | 1 | $3,395,000 | $3,075,000 |
| Kenilworth Shores Sec 06 | 3 | 3 | $2,800,000 | $2,700,000 |
| Lake Knowles Terrace Add 02 | 3 | 2 | $2,549,000 | $1,690,000 |
| Lawndale | 3 | 3 | $1,419,900 | $1,399,000 |
| Palmer Ave Lakeside Prop | 2 | 1 | $4,950,000 | $4,400,000 |
| Park Grove | 2 | 1 | $4,072,500 | $3,495,000 |
| Comstock Park | 2 | 0 | $3,797,500 | $1,595,000 |
| Kenilworth Shores Sec 01 | 2 | 2 | $2,494,995 | $1,999,990 |
| Conwill Estates | 2 | 2 | $2,312,500 | $1,900,000 |
| Lake Forest Park | 2 | 2 | $2,079,500 | $1,699,000 |
| Sylvan Heights | 2 | 2 | $1,900,000 | $1,750,000 |
| Fontainebleau | 2 | 0 | $1,687,500 | $1,625,000 |
| Waters Edge At Hawks Crest | 2 | 0 | $1,462,500 | $1,325,000 |
| Lake Waunatta Woods | 2 | 0 | $654,388 | $569,000 |
| Winter Park Estates | 2 | 0 | $562,500 | $550,000 |
| Woodcrest Unit 5 | 2 | 0 | $487,450 | $479,900 |
| Tanglewood Sec 3 Rep | 2 | 0 | $458,500 | $355,000 |
| Garden Lake Estates Unit 1 | 2 | 0 | $442,495 | $435,000 |
| Winter Woods Unit 01 | 2 | 0 | $430,000 | $375,000 |
| Eastbrook Sub | 2 | 0 | $379,000 | $368,000 |
| Golfview Terrace | 1 | 0 | $6,995,000 | $6,995,000 |
| Greens/Pk | 1 | 1 | $6,195,000 | $6,195,000 |
| Sylvan Park | 1 | 1 | $5,500,000 | $5,500,000 |
| 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 |
| Orange Grove Sub | 1 | 1 | $2,569,999 | $2,569,999 |
| Winter Park | 1 | 1 | $2,495,000 | $2,495,000 |
| Northwood Terrace | 1 | 1 | $2,495,000 | $2,495,000 |
| Villa View Park | 1 | 0 | $2,390,000 | $2,390,000 |
| Lugano Terrace | 1 | 0 | $2,195,000 | $2,195,000 |
| Lake Virgina Shores | 1 | 0 | $2,095,000 | $2,095,000 |
| Parklando 03 | 1 | 0 | $1,890,000 | $1,890,000 |
| 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 |
| Temple Estates | 1 | 0 | $1,795,000 | $1,795,000 |
| Winter Park Rev | 1 | 0 | $1,770,000 | $1,770,000 |
| Sharon Place | 1 | 0 | $1,749,000 | $1,749,000 |
| Lakeview Terrace | 1 | 0 | $1,725,000 | $1,725,000 |
| Twin Acres | 1 | 0 | $1,649,000 | $1,649,000 |
| Killarney Estates | 1 | 0 | $1,600,000 | $1,600,000 |
| Lake Killarney Shores | 1 | 0 | $1,599,000 | $1,599,000 |
| Fremar | 1 | 0 | $1,599,000 | $1,599,000 |
| Winter Park Oasis | 1 | 0 | $1,499,000 | $1,499,000 |
| Bear Gully Pointe | 1 | 0 | $1,395,000 | $1,395,000 |
| Orwin Manor Westminster Sec | 1 | 1 | $1,369,000 | $1,369,000 |
| Eastgate Sub | 1 | 1 | $1,299,000 | $1,299,000 |
Also with pool homes for sale
- Kenilworth Shores Sec 07 (1)
- Quail Hollow (1)
- Banks Colonial Estates (1)
- Edgewood Sub (1)
- Lords Sub (1)
- Kenilworth Shores Sec 04 (1)
- Village Winterset Inc (1)
- Park Pointe Rep (1)
- Temple Terrace (1)
- Brookshire Heights 4Th Add (1)
- Lake Ann Estates Unit 3 (1)
- Flamingo Shores (1)
- Golfside Sec 02 (1)
- Lake Ann Estates Unit 2 (1)
- Kenilworth Estates 1St Add (1)
- Seville Park (1)
- Sanctuary At Aloma (1)
- Glencoe Sub (1)
- Winter Park Pines Rep (1)
- Lake Waunatta Wods (1)
- Glencoe Subdivision (1)
- Arrowhead Cove (1)
- Winter Woods Unit 03 (1)
- Fairshores Place (1)
- Wrenwood Unit 3 3Rd Add (1)
- Bel Aire Pines (1)
- Village Green (1)
- Georgetown Estates (1)
- Suburban Homes First Add (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
- All homes for sale in Winter Park
- Winter Park ZIP codes with prices
- Winter Park waterfront homes
- Winter Park gated community homes
- Winter Park 4-bedroom homes
- Winter Park homes under $300K
- Winter Park homes $300K–$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 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.