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 94 communities. The median asking price is $927,500, from $245,000 to $5,995,000. Listings in Winter Garden without that feature have a median of $575,000. Most listings right now: Lakeshore Preserve Ph 4 (3), Lakeshore Preserve Ph 2 (3), Waterleigh Ph 2B (3). Updated November 7, 2026 from the MLS.
Live pool homes in Winter Garden: the listings
84 active listings carry the flag today (12% of Winter Garden inventory), median asking $996,250, $312/sq ft, median 65 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 Winter Garden |
| 7723 Green Mountain Way | $2,695,000 | 5,174 | Summerlake Pd |
| 7693 Green Mountain Way | $2,600,000 | 5,115 | Summerlake Pd |
| 15505 Shorebird Lane | $2,500,000 | 5,287 | Lakeshore Preserve Winter Garden |
| 13377 Lake Butler Boulevard | $2,500,000 | 4,961 | â |
| 15633 Panther Lake Drive | $2,395,000 | 4,556 | Lakeshore Preserve Winter Garden |
| 14656 Pylon Court | $2,300,000 | 4,634 | Isles Lake Hancock |
Pool Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 1 | 1% |
| $300Kâ$500K | 2 | 2% |
| $500Kâ$750K | 14 | 17% |
| $750Kâ$1M | 26 | 31% |
| $1M+ | 41 | 49% |
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 |
| Lakeshore Preserve Ph 2 | 3 | 0 | $2,395,000 | $1,950,000 |
| Waterleigh Ph 2B | 3 | 0 | $930,000 | $840,000 |
| Wintermere Harbor | 3 | 0 | $699,000 | $699,000 |
| Summerlake Pd Ph 3A | 2 | 0 | $2,647,500 | $2,600,000 |
| Highlands/Summerlake Grvs Ph 3 | 2 | 0 | $1,515,000 | $1,080,000 |
| Canopy Oaks Ph 1 | 2 | 0 | $1,512,450 | $1,499,900 |
| Hickory Hammock Ph 1D | 2 | 0 | $1,509,999 | $1,020,000 |
| Country Lakes | 2 | 0 | $1,322,000 | $969,000 |
| Lake Roberts Lndg E | 2 | 0 | $1,299,999 | $1,200,000 |
| Watermark Ph 1B | 2 | 0 | $1,174,000 | $1,150,000 |
| Panther View | 2 | 0 | $1,017,500 | $835,000 |
| Orchard Hills Ph 3 | 2 | 0 | $874,950 | $839,900 |
| Lakeshore Preserve Ph 1 | 2 | 0 | $809,500 | $550,000 |
| Winding Bay Ph 3 | 2 | 0 | $744,000 | $689,000 |
| Stoneybrook West 44/134 | 2 | 0 | $697,500 | $640,000 |
| Black Lake Park Ph 02 | 2 | 0 | $684,500 | $669,000 |
| 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 |
| Signature Lks-Pcl 01D Ph 02 - Independence | 1 | 0 | $2,400,000 | $2,400,000 |
| Isles/Lk Hancock Ph Iii | 1 | 0 | $2,300,000 | $2,300,000 |
| Sanctuary/Twin Waters | 1 | 0 | $2,250,000 | $2,250,000 |
| Lake Cove Pointe Ph 02 | 1 | 0 | $2,249,999 | $2,249,999 |
| 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 | $2,100,000 | $2,100,000 |
| Avalon Cove | 1 | 0 | $1,999,000 | $1,999,000 |
| Lakeview Preserve | 1 | 0 | $1,999,000 | $1,999,000 |
| Oakland Hills | 1 | 0 | $1,899,999 | $1,899,999 |
| Lake Avalon Groves Rep | 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 |
| Hull Island/Oakland | 1 | 0 | $1,599,000 | $1,599,000 |
| Lakeview Reserve 46/149 | 1 | 0 | $1,450,000 | $1,450,000 |
| Hawksmoor-Phase 1 | 1 | 0 | $1,325,000 | $1,325,000 |
| Lakeview Pointe/Horizon West P | 1 | 0 | $1,225,000 | $1,225,000 |
| Winter Garden Shores Rep | 1 | 0 | $1,200,000 | $1,200,000 |
| Crown Point Town | 1 | 0 | $1,150,000 | $1,150,000 |
| 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 |
| Oakland Park | 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 |
| Northlake At Ovation | 1 | 0 | $997,500 | $997,500 |
| Hickory Hammock Ph 2A | 1 | 0 | $995,000 | $995,000 |
| Winter Garden Shores First Add | 1 | 0 | $985,000 | $985,000 |
| Verde Park Ph 2 | 1 | 0 | $925,000 | $925,000 |
| Lakeshore Preserve Ph 5 | 1 | 0 | $924,900 | $924,900 |
| Wincey Grvs Ph 2 | 1 | 0 | $900,000 | $900,000 |
| Oakland Parka F1 & F2 | 1 | 0 | $899,000 | $899,000 |
| Glynwood Ii | 1 | 0 | $888,000 | $888,000 |
| 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 |
| Hamlin Reserve | 1 | 0 | $859,000 | $859,000 |
| Signature Lakes | 1 | 0 | $850,000 | $850,000 |
| Lakeview Preserve Ph 2 | 1 | 0 | $849,000 | $849,000 |
Also with pool homes for sale
- Lakeshore Preserve (1)
- Watermark (1)
- Watermark Ph 4A (1)
- Glynwood 51 32 (1)
- Harvest/Ovation (1)
- Windward Cay (1)
- Bronsons Landing (1)
- Carriage Pointe A-I & L (1)
- Windward Cay 48 125 (1)
- Covington Chase Ph 2B (1)
- Lake Star At Ovation (1)
- Stoneybrook West Un 06 (1)
- Wintermere Pointe (1)
- Waterleigh Ph 3B-3D (1)
- Emerald Ridge (1)
- Wintermere Harbor Ph 02 48 21 (1)
- Signature Lakes Ph 02 A B H I J (1)
- Waterleigh Ph 3B 3C & 3D (1)
- Latham Park North (1)
- Carriage Pointe (1)
- Mt Park Orange Grove (1)
- Hawksmoor Ph 4 (1)
- Waterleigh Ph 1C (1)
- Stoneybrook West D (1)
- Magnolia Wood Fifth Add (1)
- The Harbor (1)
- Independence / Signature Lakes Ph 02 (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
- All homes for sale in Winter Garden
- Winter Garden ZIP codes with prices
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- Winter Garden golf course homes
- 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 (856 for sale)
- Winter Park pool homes (154 for sale)
- Windermere pool homes (151 for sale)
- Apopka pool homes (96 for sale)
- Maitland pool homes (34 for sale)
- Ocoee pool homes (30 for sale)
- Oakland pool homes (16 for sale)
- Belle Isle pool homes (14 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.