Pool Homes for Sale in Winter Garden, FL
Buyers who want a pool search for the pool first. This page tracks every Winter Garden 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.
114 homes with a private pool are for sale or pending in Winter Garden, FL today across 83 communities. The median asking price is $964,500, from $289,000 to $5,995,000. Listings in Winter Garden without that feature have a median of $554,490. Most listings right now: Lakeshore Preserve Ph 4 (4), Avalon Cove (3), Lakeshore Preserve Ph 2 (3). Updated September 27, 2026 from the MLS.
Live pool homes in Winter Garden: the listings
66 active listings carry the flag today (13% of Winter Garden inventory), median asking $994,500, $310/sq ft, median 59 days on market. Photo cards link to the listing; refreshed nightly.
Newest pool homes in Winter Garden
The most expensive pool homes in Winter Garden
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 13542 Sunset Lakes Circle | $3,799,000 | 5,450 | Sunset Lakes |
| 15522 Shorebird Lane | $2,700,000 | 6,400 | Lakeshore Preserve |
| 7693 Green Mountain Way | $2,600,000 | 5,115 | Summerlake Pd |
| 15505 Shorebird Lane | $2,500,000 | 5,287 | Lakeshore Preserve |
| 15675 Panther Lake Drive | $2,399,000 | 4,213 | Lakeshore Preserve |
| 16870 Sanctuary Drive | $2,250,000 | 4,132 | Sanctuary Twin Waters |
| 15475 Shorebird Lane | $2,125,000 | 4,253 | Lakeshore Preserve |
| 16038 Johns Lake Overlook Drive | $2,099,000 | 4,139 | hickory hammock |
| 9056 Morgana Court | $2,050,000 | 4,832 | Avalon Cove |
| 9110 Morgana Court | $1,999,000 | 4,661 | Avalon Cove |
Pool Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 1 | 2% |
| $300K–$500K | 1 | 2% |
| $500K–$750K | 9 | 14% |
| $750K–$1M | 22 | 33% |
| $1M+ | 33 | 50% |
Winter Garden 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 |
|---|---|---|---|---|
| Lakeshore Preserve Ph 4 | 4 | 0 | $2,312,500 | $1,450,000 |
| Avalon Cove | 3 | 0 | $1,999,000 | $1,339,000 |
| Lakeshore Preserve Ph 2 | 3 | 0 | $1,950,000 | $1,190,000 |
| Lakeshore Preserve Ph 1 | 3 | 0 | $1,085,000 | $575,000 |
| Waterleigh Ph 2B | 3 | 0 | $960,000 | $849,900 |
| Waterleigh Ph 3B 3C & 3D | 3 | 0 | $787,000 | $699,000 |
| Sunset Lakes | 2 | 0 | $2,394,450 | $989,900 |
| Hickory Hammock Ph 1D | 2 | 0 | $1,559,500 | $1,020,000 |
| Overlook 2/Hamlin Ph 2 & 5 | 2 | 0 | $1,354,449 | $1,348,900 |
| Lake Roberts Lndg E | 2 | 0 | $1,299,999 | $1,200,000 |
| Waterside/Johns Lake Ph 1 | 2 | 0 | $1,279,000 | $1,159,000 |
| Bronsons Lndgs F & M | 2 | 0 | $1,232,500 | $840,000 |
| Watermark Ph 1B | 2 | 0 | $1,174,000 | $1,150,000 |
| Twinwaters | 2 | 0 | $1,112,500 | $765,000 |
| Westfield Lakes | 2 | 0 | $922,000 | $749,000 |
| Orchard Hills Ph 3 | 2 | 0 | $874,950 | $839,900 |
| Panther View | 2 | 0 | $802,500 | $770,000 |
| Carriage Pointe A-I & L | 2 | 0 | $762,449 | $699,999 |
| Winding Bay Ph 3 | 2 | 0 | $753,500 | $708,000 |
| Wintermere Pointe | 2 | 0 | $670,000 | $550,000 |
| Crown Point Spgs | 2 | 0 | $477,450 | $475,000 |
| Summerlake Pd Ph 3A | 1 | 0 | $2,600,000 | $2,600,000 |
| Summerlake Pd Ph 3A | 1 | 0 | $2,600,000 | $2,600,000 |
| Signature Lks-Pcl 01D Ph 02 - Independence | 1 | 0 | $2,600,000 | $2,600,000 |
| Sanctuary/Twin Waters | 1 | 0 | $2,250,000 | $2,250,000 |
| Grove/Oakland | 1 | 1 | $2,210,000 | $2,210,000 |
| Summerlake Pd Ph 2A & 2B | 1 | 0 | $2,150,000 | $2,150,000 |
| Lake Avalon Groves Rep | 1 | 0 | $1,775,000 | $1,775,000 |
| West Lake Hancock Estates | 1 | 0 | $1,750,000 | $1,750,000 |
| Hull Island/Oakland | 1 | 0 | $1,699,000 | $1,699,000 |
| Lakeview Reserve | 1 | 0 | $1,675,000 | $1,675,000 |
| Hull Island/Oakland Ph 2 | 1 | 0 | $1,500,000 | $1,500,000 |
| Hawksmoor-Phase 1 | 1 | 0 | $1,349,000 | $1,349,000 |
| Lakeview Pointe/Horizon West P | 1 | 0 | $1,295,000 | $1,295,000 |
| Winter Garden Shores Rep | 1 | 0 | $1,200,000 | $1,200,000 |
| Orchard Hills Ph 1 | 1 | 0 | $1,199,000 | $1,199,000 |
| Avalon Ridge | 1 | 0 | $1,150,000 | $1,150,000 |
| Oakland Park | 1 | 0 | $1,125,000 | $1,125,000 |
| Watermark Ph 2A | 1 | 0 | $1,100,000 | $1,100,000 |
| Highlands/Summerlake Grvs Ph 3 | 1 | 0 | $1,099,000 | $1,099,000 |
| Watermark Ph 3 | 1 | 0 | $1,090,000 | $1,090,000 |
| Black Lake Park Ph 01 | 1 | 0 | $1,089,000 | $1,089,000 |
| Estates At Lakeview Preserve | 1 | 0 | $1,089,000 | $1,089,000 |
| Bradford Creek Phase Ii | 1 | 0 | $1,060,000 | $1,060,000 |
| Winter Garden Shores First Add | 1 | 0 | $995,000 | $995,000 |
| Country Lakes | 1 | 0 | $969,000 | $969,000 |
| Wincey Grvs Ph 2 | 1 | 0 | $950,000 | $950,000 |
| Courtlea Oaks Ph 01A | 1 | 0 | $939,000 | $939,000 |
| Wintermere Pointe Ph 02 46/141 | 1 | 0 | $925,000 | $925,000 |
| Hamlin Reserve | 1 | 0 | $899,000 | $899,000 |
| Oakland Parka | 1 | 0 | $890,000 | $890,000 |
| Hawksmoor Ph 4 | 1 | 0 | $890,000 | $890,000 |
| Lake Forest Sec 10A | 1 | 0 | $880,000 | $880,000 |
| Storey Grove Ph 1B-2 | 1 | 0 | $875,000 | $875,000 |
| Bay Isle 48 17 | 1 | 0 | $870,000 | $870,000 |
| Johns Lake Pointe A & S | 1 | 0 | $865,000 | $865,000 |
| Glynwood 51 32 | 1 | 0 | $860,000 | $860,000 |
| Summerlake Pd Ph 3B | 1 | 0 | $859,000 | $859,000 |
| Stoneybrook West Ut 4`` | 1 | 0 | $859,000 | $859,000 |
| Lakeshore Preserve | 1 | 0 | $849,900 | $849,900 |
Also with pool homes for sale
- Bronson'S Landing (1)
- Watermark (1)
- Harvest/Ovation (1)
- Covington Chase Ph 2B (1)
- Fries Winter Garden (1)
- Lake Star At Ovation (1)
- Stoneybrook West Un 06 (1)
- Waterleigh Ph 3B-3D (1)
- Del Webb Oasis Ph 3 (1)
- Summerlake (1)
- Winter Oaks (1)
- Wintermere Harbor (1)
- Emerald Ridge (1)
- Wintermere Harbor Ph 02 48 21 (1)
- Signature Lakes Ph 02 A B H I J (1)
- Latham Park North (1)
- Mt Park Orange Grove (1)
- Stoneybrook West D (1)
- Waterleigh Ph 1C (1)
- Grova Residence & Spa Hotel Condo 3 (1)
- Oak Park At Winter Garden (1)
- Grove Residence & Spa Hotel (1)
- Grove Residence & Spa Hotel Condo 3 (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 Garden?
What do pool homes cost in Winter Garden?
Which Winter Garden community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
Keep exploring Winter Garden
- All homes for sale in Winter Garden
- Winter Garden ZIP codes with prices
- Winter Garden waterfront homes
- Winter Garden golf course homes
- Winter Garden gated community homes
- Winter Garden 4-bedroom homes
- Winter Garden homes under $300K
- Winter Garden 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 Garden, 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.