Pool Homes for Sale in Maitland, FL
Buyers who want a pool search for the pool first. This page tracks every Maitland 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.
33 homes with a private pool are for sale or pending in Maitland, FL today across 30 communities. The median asking price is $879,000, from $339,000 to $4,999,000. Listings in Maitland without that feature have a median of $339,750. Most listings right now: Maitland Club Rep (2), Hidden Estates Unit 3 (2), English Woods (2). Updated November 8, 2026 from the MLS.
Live pool homes in Maitland: the listings
23 active listings carry the flag today (23% of Maitland inventory), median asking $899,000, $296/sq ft, median 71 days on market. Photo cards link to the listing; refreshed nightly.
Newest pool homes in Maitland
The most expensive pool homes in Maitland
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 360 Lake Seminary Circle | $4,999,000 | 6,466 | — |
| 1166 N Lake Sybelia | $2,999,000 | 5,355 | Lake Sybelia Shores |
| 220 Adams Drive | $1,879,000 | 3,005 | kings row |
| 1130 Mechanic Street | $1,800,000 | 3,567 | — |
| 755 Cranes Court | $1,345,500 | 4,566 | Lake Sybelia Cove |
| 120 Minnehaha Road | $1,249,000 | 2,464 | Packwood |
| 2491 Lauder Drive | $1,174,999 | 2,695 | Highland Park Estates |
| 900 Brightwater Circle | $1,125,000 | 3,857 | Maitland Club |
| 229 Flame Avenue | $969,000 | 4,055 | — |
| 1951 Mohican Trail | $925,000 | 2,367 | — |
Pool Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 1 | 4% |
| $500K–$750K | 6 | 26% |
| $750K–$1M | 8 | 35% |
| $1M+ | 8 | 35% |
Maitland 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 |
|---|---|---|---|---|
| Maitland Club Rep | 2 | 0 | $1,277,450 | $1,125,000 |
| Hidden Estates Unit 3 | 2 | 0 | $884,000 | $799,000 |
| English Woods | 2 | 0 | $454,500 | $394,000 |
| Floridahaven | 1 | 1 | $4,999,000 | $4,999,000 |
| Lake Sybelia Shores | 1 | 0 | $2,999,000 | $2,999,000 |
| Hollieanna Shores 1St Add | 1 | 1 | $2,150,000 | $2,150,000 |
| Kings Row | 1 | 0 | $1,879,000 | $1,879,000 |
| Woodbridge | 1 | 1 | $1,800,000 | $1,800,000 |
| Lake Sybelia Cove | 1 | 0 | $1,345,500 | $1,345,500 |
| Packwood Sub | 1 | 0 | $1,249,000 | $1,249,000 |
| Highland Park Estates First Add | 1 | 0 | $1,174,999 | $1,174,999 |
| Wellington | 1 | 0 | $1,139,500 | $1,139,500 |
| Windsor Park | 1 | 0 | $925,000 | $925,000 |
| Dommerich Hills 5Th Add | 1 | 0 | $925,000 | $925,000 |
| Sybelia Place | 1 | 0 | $919,000 | $919,000 |
| Maitland Grove | 1 | 0 | $899,000 | $899,000 |
| Dommerich Hills Second Add | 1 | 0 | $879,000 | $879,000 |
| Dommerich Hills First Add | 1 | 0 | $825,000 | $825,000 |
| Dommerich Hills 6Th Add | 1 | 0 | $824,900 | $824,900 |
| Dommerich/Maitland Highlands | 1 | 0 | $789,000 | $789,000 |
| Druid Hills Park | 1 | 0 | $769,000 | $769,000 |
| Dommerich Woods | 1 | 0 | $749,000 | $749,000 |
| Bretton Woods | 1 | 0 | $650,000 | $650,000 |
| Lake Sybelia Shores Second Add | 1 | 0 | $645,000 | $645,000 |
| English Estates Unit 2 | 1 | 0 | $625,000 | $625,000 |
| Dommerich Estates 1St Add Maitland | 1 | 0 | $599,000 | $599,000 |
| Forest Brook | 1 | 0 | $525,000 | $525,000 |
| Indian Hills Unit 1 Rep | 1 | 0 | $519,900 | $519,900 |
| Floridahaven 1St Add | 1 | 0 | $440,000 | $440,000 |
| Maitland House | 1 | 0 | $339,000 | $339,000 |
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 Maitland?
What do pool homes cost in Maitland?
Which Maitland community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
Keep exploring Maitland
- All homes for sale in Maitland
- Maitland waterfront homes
- Maitland gated community homes
- Maitland 4-bedroom homes
- Maitland homes under $300K
- Maitland homes $300K–$500K
- Pool Homes in every city
Pool Homes in nearby Orange County cities
- Orlando pool homes (847 for sale)
- Winter Park pool homes (152 for sale)
- Windermere pool homes (146 for sale)
- Winter Garden pool homes (117 for sale)
- Apopka pool homes (93 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 Maitland, 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.