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.
38 homes with a private pool are for sale or pending in Maitland, FL today across 27 communities. The median asking price is $860,000, from $349,000 to $2,999,000. Listings in Maitland without that feature have a median of $307,500. Most listings right now: Forest Brook 5Th Sec (3), Maitland Club Rep (2), Oakleigh Third Add (2). Updated September 27, 2026 from the MLS.
Live pool homes in Maitland: the listings
12 active listings carry the flag today (22% of Maitland inventory), median asking $869,500, $345/sq ft, median 62 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 |
|---|---|---|---|
| 1166 N Lake Sybelia | $2,999,000 | 5,355 | Lake Sybelia Shores |
| 220 Adams Drive | $1,925,000 | 3,005 | Kings Row |
| 755 Cranes Court | $1,345,500 | 4,566 | Lake Sybelia Cove |
| 2491 Lauder Drive | $1,199,000 | 2,695 | Highland Park Estates |
| 900 Brightwater Circle | $1,125,000 | 3,857 | Maitland Club |
| 313 Macarthur Place | $940,000 | 3,044 | Sybelia Place |
| 2051 Dyan Way | $799,000 | 3,136 | Dommerich/Maitland Highlands |
| 2624 Tuscarora Trail | $785,500 | 1,959 | Dommerich Hills |
| 2130 Deloraine Trail | $750,000 | 2,175 | Highland Park Estates |
| 553 Arapaho Trail | $599,000 | 1,602 | Dommerich Estates |
Pool Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 1 | 8% |
| $500K–$750K | 2 | 17% |
| $750K–$1M | 4 | 33% |
| $1M+ | 5 | 42% |
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 |
|---|---|---|---|---|
| Forest Brook 5Th Sec | 3 | 0 | $595,000 | $525,000 |
| Maitland Club Rep | 2 | 0 | $1,110,000 | $1,095,000 |
| Oakleigh Third Add | 2 | 0 | $1,012,500 | $950,000 |
| Highland Park Estates First Add | 2 | 0 | $974,500 | $750,000 |
| Dommerich Hills | 2 | 0 | $920,000 | $895,000 |
| Bretton Woods | 2 | 0 | $699,500 | $650,000 |
| English Woods | 2 | 0 | $479,500 | $394,000 |
| Floridahaven 1St Add | 2 | 0 | $405,000 | $350,000 |
| 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 | $1,925,000 | $1,925,000 |
| Woodbridge | 1 | 1 | $1,800,000 | $1,800,000 |
| Lake Colony Ph 02 | 1 | 0 | $1,695,000 | $1,695,000 |
| Lake Sybelia Cove | 1 | 0 | $1,345,500 | $1,345,500 |
| Lake Sybelia Cove Ph 01 | 1 | 0 | $1,150,000 | $1,150,000 |
| Wellington | 1 | 0 | $949,000 | $949,000 |
| Sybelia Place | 1 | 0 | $940,000 | $940,000 |
| Dommerich Hills First Add | 1 | 0 | $825,000 | $825,000 |
| Dommerich/Maitland Highlands | 1 | 0 | $799,000 | $799,000 |
| Dommerich Hills Second Add | 1 | 0 | $785,500 | $785,500 |
| English Estates Unit 3 | 1 | 0 | $725,000 | $725,000 |
| Dommerich Estates 1St Add | 1 | 0 | $699,000 | $699,000 |
| Dommerich Estates 1St Add Maitland | 1 | 0 | $599,000 | $599,000 |
| Roosevelt Place | 1 | 0 | $535,000 | $535,000 |
| Forest Brook 4Th Sec | 1 | 0 | $499,900 | $499,900 |
| Winfield | 1 | 0 | $435,000 | $435,000 |
| Maitland House | 1 | 0 | $349,000 | $349,000 |
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?
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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.