Pool Homes for Sale in Winter Springs, FL
Buyers who want a pool search for the pool first. This page tracks every Winter Springs 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.
31 homes with a private pool are for sale or pending in Winter Springs, FL today across 28 communities. The median asking price is $650,000, from $359,900 to $3,998,000. Most listings right now: Winter Spgs Unit 4 (3), Huntridge (2), Lake Jessup (1). Updated September 8, 2026 from the MLS.
Winter Springs pool homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Pool Homes | New build | Median list | From |
|---|---|---|---|---|
| Winter Spgs Unit 4 | 3 | 0 | $624,000 | $539,900 |
| Huntridge | 2 | 0 | $734,950 | $644,900 |
| Lake Jessup | 1 | 0 | $3,998,000 | $3,998,000 |
| Dunmar Estates | 1 | 0 | $3,199,000 | $3,199,000 |
| Talis Crossing | 1 | 1 | $2,625,000 | $2,625,000 |
| Tuscawilla | 1 | 0 | $1,200,000 | $1,200,000 |
| Bear Creek Estates | 1 | 0 | $1,150,000 | $1,150,000 |
| Reserve At Tuscawilla Ph 1 The | 1 | 0 | $1,085,000 | $1,085,000 |
| Glen Eagle Unit 2 | 1 | 0 | $825,000 | $825,000 |
| Seville Chase | 1 | 0 | $799,900 | $799,900 |
| North Orlando Ranches Sec 01 | 1 | 0 | $799,000 | $799,000 |
| Tuscawilla Unit 12A | 1 | 0 | $799,000 | $799,000 |
| Chestnut Estates Ph 1 | 1 | 0 | $719,990 | $719,990 |
| Howell Creek Reserve Ph 3 | 1 | 0 | $689,900 | $689,900 |
| Tuscawilla Unit 14B | 1 | 0 | $674,900 | $674,900 |
| Tuskabay Ph 1 | 1 | 0 | $650,000 | $650,000 |
| Parkstone | 1 | 0 | $630,000 | $630,000 |
| Tuscawilla Unit 09 | 1 | 0 | $597,500 | $597,500 |
| Parkstone Unit 3 | 1 | 0 | $549,900 | $549,900 |
| Eagles Watch Ph 1 | 1 | 0 | $510,000 | $510,000 |
| Amherst | 1 | 0 | $480,000 | $480,000 |
| Stone Gable | 1 | 0 | $479,000 | $479,000 |
| Country Club Village Unit 2 | 1 | 0 | $439,000 | $439,000 |
| North Orlando Terrace Unit 2 Sec 8 | 1 | 0 | $399,000 | $399,000 |
| Sunrise Estates Unit 2 | 1 | 0 | $394,000 | $394,000 |
| North Orlando Ranches Sec 02 | 1 | 0 | $384,900 | $384,900 |
| North Orlando Terrace Unit 1 Sec 3 | 1 | 0 | $375,000 | $375,000 |
| Sunrise Village Unit 4 | 1 | 0 | $359,900 | $359,900 |
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 Springs?
What do pool homes cost in Winter Springs?
Which Winter Springs community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
Keep exploring Winter Springs
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 Springs, 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.