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.
118 homes with a private pool are for sale or pending in Winter Garden, FL today across 93 communities. The median asking price is $905,000, from $245,000 to $5,995,000. Listings in Winter Garden without that feature have a median of $570,000. Most listings right now: Lakeshore Preserve Ph 4 (3), Avalon Cove (3), Waterleigh Ph 2B (3). Updated October 17, 2026 from the MLS.
Live pool homes in Winter Garden: the listings
86 active listings carry the flag today (12% of Winter Garden inventory), median asking $925,000, $309/sq ft, median 50 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 |
|---|---|---|---|
| 13377 Lake Butler Boulevard | $5,995,000 | 6,000 | â |
| 15614 Espalier Way | $4,300,000 | 6,601 | signature lakes |
| 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 |
| 13377 Lake Butler Boulevard | $2,500,000 | 4,961 | â |
| 7301 Wild Blackberry Trail | $2,400,000 | 5,403 | â |
| 15675 Panther Lake Drive | $2,399,000 | 4,213 | Lakeshore Preserve |
| 234 N Lakeview Avenue | $2,199,900 | 3,350 | Cooper Sewell |
Pool Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 1 | 1% |
| $300Kâ$500K | 2 | 2% |
| $500Kâ$750K | 19 | 22% |
| $750Kâ$1M | 24 | 28% |
| $1M+ | 40 | 47% |
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 | 3 | 0 | $2,500,000 | $2,075,000 |
| Avalon Cove | 3 | 0 | $1,999,000 | $1,339,000 |
| Waterleigh Ph 2B | 3 | 0 | $960,000 | $849,900 |
| Panther View | 3 | 0 | $835,000 | $770,000 |
| Wintermere Harbor | 3 | 0 | $729,000 | $715,000 |
| Lakeshore Preserve Ph 2 | 2 | 0 | $2,174,500 | $1,950,000 |
| Hickory Hammock Ph 1D | 2 | 0 | $1,509,999 | $1,020,000 |
| 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 |
| Watermark Ph 1B | 2 | 0 | $1,174,000 | $1,150,000 |
| Orchard Hills Ph 3 | 2 | 0 | $874,950 | $839,900 |
| Lakeshore Preserve Ph 1 | 2 | 0 | $822,000 | $575,000 |
| Carriage Pointe A-I & L | 2 | 0 | $762,449 | $699,999 |
| Hawksmoor Ph 4 | 2 | 0 | $755,000 | $620,000 |
| Winding Bay Ph 3 | 2 | 0 | $753,500 | $708,000 |
| Black Lake Park Ph 02 | 2 | 0 | $684,500 | $669,000 |
| Crown Point Spgs | 2 | 0 | $477,450 | $475,000 |
| Signature Lakes Ph 2 | 1 | 0 | $4,300,000 | $4,300,000 |
| Sunset Lakes | 1 | 0 | $3,799,000 | $3,799,000 |
| 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 | $2,400,000 | $2,400,000 |
| Sanctuary/Twin Waters | 1 | 0 | $2,250,000 | $2,250,000 |
| Grove/Oakland | 1 | 1 | $2,210,000 | $2,210,000 |
| Cooper & Sewell Add | 1 | 0 | $2,199,900 | $2,199,900 |
| Summerlake Pd Ph 2A & 2B | 1 | 0 | $2,150,000 | $2,150,000 |
| Lakeview Preserve | 1 | 0 | $1,999,000 | $1,999,000 |
| Oakland Hills | 1 | 0 | $1,924,999 | $1,924,999 |
| Hull Island/Oakland | 1 | 0 | $1,699,000 | $1,699,000 |
| West Lake Hancock Estates | 1 | 0 | $1,690,000 | $1,690,000 |
| Lakeview Reserve | 1 | 0 | $1,675,000 | $1,675,000 |
| Lakeview Reserve 46/149 | 1 | 0 | $1,500,000 | $1,500,000 |
| Bronsons Lndgs F & M | 1 | 0 | $1,499,990 | $1,499,990 |
| Deer Island | 1 | 0 | $1,495,000 | $1,495,000 |
| Hawksmoor-Phase 1 | 1 | 0 | $1,349,000 | $1,349,000 |
| Overlook 2/Hamlin Ph 2 & 5 | 1 | 0 | $1,348,900 | $1,348,900 |
| Lakeview Pointe/Horizon West P | 1 | 0 | $1,255,000 | $1,255,000 |
| Winter Garden Shores Rep | 1 | 0 | $1,200,000 | $1,200,000 |
| Avalon Ridge | 1 | 0 | $1,150,000 | $1,150,000 |
| Watermark Ph 2A | 1 | 0 | $1,100,000 | $1,100,000 |
| Black Lake Park Ph 01 | 1 | 0 | $1,089,000 | $1,089,000 |
| Highlands/Summerlake Grvs Ph 3 | 1 | 0 | $1,080,000 | $1,080,000 |
| Oakland Park | 1 | 0 | $1,075,000 | $1,075,000 |
| Northlake At Ovation | 1 | 0 | $1,075,000 | $1,075,000 |
| Bradford Creek Phase Ii | 1 | 0 | $1,060,000 | $1,060,000 |
| Watermark Ph 3 | 1 | 0 | $1,050,000 | $1,050,000 |
| Encore/Ovation Ph 2 | 1 | 0 | $1,049,000 | $1,049,000 |
| Winter Garden Shores First Add | 1 | 0 | $995,000 | $995,000 |
| Country Lakes | 1 | 0 | $969,000 | $969,000 |
| Wintermere Pointe Ph 02 46/141 | 1 | 0 | $925,000 | $925,000 |
| Verde Park Ph 2 | 1 | 0 | $925,000 | $925,000 |
| Oakland Parka F1 & F2 | 1 | 0 | $910,000 | $910,000 |
| Wincey Grvs Ph 2 | 1 | 0 | $900,000 | $900,000 |
| Hamlin Reserve | 1 | 0 | $899,000 | $899,000 |
| Bay Isle 48 17 | 1 | 0 | $870,000 | $870,000 |
| Johns Lake Pointe A & S | 1 | 0 | $865,000 | $865,000 |
| Summerlake Pd Ph 3B | 1 | 0 | $859,000 | $859,000 |
| Stoneybrook West Ut 4`` | 1 | 0 | $859,000 | $859,000 |
| Glynwood 51 32 | 1 | 0 | $850,000 | $850,000 |
| Lakeshore Preserve | 1 | 0 | $849,900 | $849,900 |
Also with pool homes for sale
- Storey Grove Ph 1B-2 (1)
- Lakeview Preserve Ph 2 (1)
- Watermark (1)
- Harvest/Ovation (1)
- Windward Cay (1)
- Windward Cay 48 125 (1)
- Covington Chase Ph 2B (1)
- Lake Star At Ovation (1)
- Stoneybrook West Un 06 (1)
- Cypress Reserve (1)
- Wintermere Pointe (1)
- Winter Oaks (1)
- Waterleigh Ph 3B-3D (1)
- Westfield Lakes (1)
- Twinwaters (1)
- Del Webb Oasis Ph 3 (1)
- Emerald Ridge (1)
- Wintermere Harbor Ph 02 48 21 (1)
- Signature Lakes Ph 02 A B H I J (1)
- Reserve/Carriage Point Ph 1 (1)
- Waterleigh Ph 3B 3C & 3D (1)
- Latham Park North (1)
- Mt Park Orange Grove (1)
- Waterleigh Ph 1C (1)
- Stoneybrook West D (1)
- Magnolia Wood Fifth Add (1)
- Glenview Estates 1St Add (1)
- Magnolia Wood Third Addition (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)
- Suburban Shores (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
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- Winter Garden ZIP codes with prices
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- Winter Garden gated community homes
- Winter Garden 4-bedroom homes
- Winter Garden homes under $300K
- Winter Garden homes $300Kâ$500K
- Pool Homes in every city
Pool Homes in nearby Orange County cities
- Orlando pool homes (826 for sale)
- Winter Park pool homes (151 for sale)
- Windermere pool homes (125 for sale)
- Apopka pool homes (101 for sale)
- Maitland pool homes (39 for sale)
- Ocoee pool homes (28 for sale)
- Oakland pool homes (14 for sale)
- Belle Isle pool homes (13 for sale)
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.