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 88 communities. The median asking price is $1,004,950, from $289,000 to $5,995,000. Listings in Winter Garden without that feature have a median of $898,000. Most listings right now: Lakeshore Preserve Ph 4 (4), Lakeshore Preserve Ph 1 (4), Avalon Cove (3). Updated September 8, 2026 from the MLS.
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 | $2,345,000 | $1,450,000 |
| Lakeshore Preserve Ph 1 | 4 | 0 | $1,196,000 | $585,000 |
| Avalon Cove | 3 | 0 | $1,999,000 | $1,389,000 |
| Waterleigh Ph 2B | 3 | 0 | $989,900 | $849,900 |
| Sunset Lakes | 2 | 0 | $2,394,450 | $989,900 |
| Hickory Hammock Ph 1D | 2 | 0 | $1,579,500 | $1,060,000 |
| Lakeshore Preserve Ph 2 | 2 | 0 | $1,570,000 | $1,190,000 |
| West Lake Hancock Estates | 2 | 0 | $1,542,500 | $1,335,000 |
| Waterside/Johns Lake Ph 1 | 2 | 0 | $1,304,500 | $1,159,000 |
| Bronsons Lndgs F & M | 2 | 0 | $1,242,500 | $860,000 |
| Watermark Ph 1B | 2 | 0 | $1,174,000 | $1,150,000 |
| Twinwaters | 2 | 0 | $1,117,500 | $775,000 |
| Lakeview Pointe/Horizon West P | 2 | 0 | $1,022,500 | $650,000 |
| Waterleigh Ph 3B 3C & 3D | 2 | 0 | $993,000 | $787,000 |
| Waterleigh Ph 1A | 2 | 0 | $989,000 | $679,000 |
| Orchard Hills Ph 3 | 2 | 0 | $879,950 | $849,900 |
| Johns Lake Pointe A & S | 2 | 0 | $852,000 | $839,000 |
| Carriage Pointe A-I & L | 2 | 0 | $769,950 | $715,000 |
| Winding Bay Ph 3 | 2 | 0 | $760,500 | $722,000 |
| Crown Point Spgs | 2 | 0 | $477,450 | $475,000 |
| 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 |
| 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 |
| Winter Grove | 1 | 1 | $1,498,440 | $1,498,440 |
| Overlook 2/Hamlin Ph 2 & 5 | 1 | 0 | $1,359,999 | $1,359,999 |
| Mcallister Lndg | 1 | 0 | $1,349,000 | $1,349,000 |
| Hawksmoor-Phase 1 | 1 | 0 | $1,349,000 | $1,349,000 |
| Overlook 2/Hamlin Ph 1 & 6 | 1 | 0 | $1,250,000 | $1,250,000 |
| Westhaven At Ovation | 1 | 1 | $1,249,000 | $1,249,000 |
| Lake Roberts Lndg E | 1 | 0 | $1,200,000 | $1,200,000 |
| 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 |
| Highlands/Summerlake Grvs Ph 3 | 1 | 0 | $1,139,000 | $1,139,000 |
| Oakland Park | 1 | 0 | $1,125,000 | $1,125,000 |
| Watermark Ph 2A | 1 | 0 | $1,100,000 | $1,100,000 |
| Johns Lake Pointe | 1 | 0 | $1,095,000 | $1,095,000 |
| Westfield Lakes | 1 | 0 | $1,095,000 | $1,095,000 |
| 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 |
| Johns Cove 43/104 | 1 | 0 | $1,075,000 | $1,075,000 |
| Bradford Creek Phase Ii | 1 | 0 | $1,060,000 | $1,060,000 |
| Winter Garden Shores First Add | 1 | 0 | $1,020,000 | $1,020,000 |
| Country Lakes | 1 | 0 | $969,000 | $969,000 |
| Del Webb Oasis | 1 | 0 | $969,000 | $969,000 |
| 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 |
| Watermark Ph 2B | 1 | 0 | $880,000 | $880,000 |
| 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 |
Also with pool homes for sale: Stoneybrook West Ut 4`` (1), Summerlake Pd Ph 3B (1), Harvest/Ovation (1), Glynwood 51 32 (1), Lakeshore Preserve (1), Bronson'S Landing (1), Watermark (1), Panther View (1), Stoneybrook West Un 06 (1), Covington Chase Ph 2B (1), Overlook At Hamlin (1), Fries Winter Garden (1), Lake Star At Ovation (1), Waterleigh Ph 3B-3D (1), Roper Reserve (1), Del Webb Oasis Ph 3 (1), Summerlake (1), Winter Oaks (1), Bradford Creek (1), Wintermere Harbor Ph 02 48 21 (1), Reserve/Carriage Point Ph 1 (1), Waterleigh Ph 1C (1), Mt Park Orange Grove (1), Wintermere Pointe (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
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.