Waterfront Homes for Sale in Winter Park, FL
This page tracks every Winter Park listing whose MLS record reports waterfront (ocean, bay, Intracoastal, river, canal or lake frontage), by community, with live counts and asking prices, and the costs that come with the water.
30 waterfront homes are for sale or pending in Winter Park, FL today across 20 communities. The median asking price is $1,324,500, from $130,000 to $6,900,000. Listings in Winter Park without that feature have a median of $630,000. Most listings right now: South Lakemont Shores (3), Killarney Estates (3), Lake Killarney Condo (3). Updated September 27, 2026 from the MLS.
Live waterfront homes in Winter Park: the listings
20 active listings carry the flag today (8% of Winter Park inventory), median asking $1,262,500, $743/sq ft, median 37 days on market. Photo cards link to the listing; refreshed nightly.
Newest waterfront homes in Winter Park
The most expensive waterfront homes in Winter Park
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 1260 Alabama Drive | $6,900,000 | 6,396 | J Kronenberger |
| 313 Sylvan Drive | $5,500,000 | 4,775 | Sylvan Park |
| 2240 Venetian Way | $3,500,000 | 4,036 | Maitland Shores |
| 311 E Morse Boulevard #1-5 | $2,475,000 | 2,316 | Phillips Circle |
| 1803 Barker Drive | $2,190,000 | 3,463 | South Lakemont Shores |
| 1420 Aloma Avenue | $1,949,500 | 2,422 | Sylvan Lake Shores |
| 1113 Via Del Mar | $1,595,000 | 2,012 | Tuscany Terrace |
| 1841 Lake Spier Drive | $1,498,000 | 2,467 | South Lakemont Shores |
| 1881 Lake Spier Drive | $1,350,000 | 1,750 | South Lakemont Shores |
| 240 Killarney Drive | $1,275,000 | 1,329 | Killarney Estates |
Waterfront Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 5 | 25% |
| $500Kâ$750K | 1 | 5% |
| $750Kâ$1M | 1 | 5% |
| $1M+ | 13 | 65% |
Winter Park waterfront homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Waterfront Homes | New build | Median list | From |
|---|---|---|---|---|
| South Lakemont Shores | 3 | 0 | $1,498,000 | $1,350,000 |
| Killarney Estates | 3 | 0 | $1,250,000 | $1,250,000 |
| Lake Killarney Condo | 3 | 0 | $285,000 | $269,000 |
| Cloisters Condo | 2 | 0 | $1,547,000 | $1,299,000 |
| Lakeside Manor Apts Condo | 2 | 0 | $157,200 | $130,000 |
| J Kronenberger Sub | 1 | 0 | $6,900,000 | $6,900,000 |
| Alabama Oaks | 1 | 0 | $5,900,000 | $5,900,000 |
| Sylvan Park | 1 | 1 | $5,500,000 | $5,500,000 |
| Lake Maitland | 1 | 0 | $4,750,000 | $4,750,000 |
| Maitland Shores 1St Add | 1 | 0 | $3,500,000 | $3,500,000 |
| Phillips Circle Rep | 1 | 0 | $2,475,000 | $2,475,000 |
| Sylvan Lake Shores | 1 | 0 | $1,949,500 | $1,949,500 |
| Whispering Waters/Phillips Circle Rep | 1 | 0 | $1,825,000 | $1,825,000 |
| Tuscany Terrace | 1 | 0 | $1,595,000 | $1,595,000 |
| Lake Forest Park | 1 | 0 | $1,100,000 | $1,100,000 |
| Lords Sub | 1 | 0 | $1,050,000 | $1,050,000 |
| Lake Spier Xing | 1 | 0 | $925,000 | $925,000 |
| Killarney Circle | 1 | 0 | $899,000 | $899,000 |
| Albert Lee Ridge Add 02 | 1 | 0 | $549,900 | $549,900 |
| Killarney Bay Condo | 1 | 0 | $389,000 | $389,000 |
What waterfront ownership really costs
Waterfront homes carry costs inland homes do not: flood insurance where the parcel sits in a FEMA special flood hazard area, higher windstorm premiums closer to open water, and upkeep for seawalls, docks and lifts. Before you offer, pull the FEMA flood zone for the specific parcel, ask for the seawall’s age and any inspection reports, and get an insurance quote in hand, not an estimate. Our flood insurance calculator and wind mitigation savings calculator show what the parcel will actually cost to insure.
Questions to ask about any waterfront listing
Is the water frontage deeded or association-owned? Is there a fixed bridge between the dock and open water, and what is the clearance? What did the seller pay for flood and wind coverage last year, and with which carriers? Has the seawall or dock been permitted and inspected? What is the finished-floor elevation? A local agent who works waterfront deals will know which canals hold depth at low tide and which carriers are writing in the area.
Common questions
How many waterfront homes are for sale in Winter Park?
What do waterfront homes cost in Winter Park?
Which Winter Park community has the most waterfront homes for sale?
Is a waterfront home always in a flood zone?
Keep exploring Winter Park
- All homes for sale in Winter Park
- Winter Park ZIP codes with prices
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- Winter Park gated community homes
- Winter Park 4-bedroom homes
- Winter Park homes under $300K
- Winter Park homes $300Kâ$500K
- Waterfront Homes in every city
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 Park, FL whose MLS record reports waterfront. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.