Waterfront Homes for Sale in Osprey, FL
This page tracks every Osprey 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.
27 waterfront homes are for sale or pending in Osprey, FL today across 17 communities. The median asking price is $749,900, from $99,500 to $9,750,000. Listings in Osprey without that feature have a median of $655,000. Most listings right now: Meridian At The Oaks Preserve (4), Casey Key (3), Blackburn Harbor Residences (3). Updated September 27, 2026 from the MLS.
Live waterfront homes in Osprey: the listings
21 active listings carry the flag today (30% of Osprey inventory), median asking $700,000, $392/sq ft, median 139 days on market. Photo cards link to the listing; refreshed nightly.
Newest waterfront homes in Osprey
The most expensive waterfront homes in Osprey
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 1216 N Casey Key Road | $9,750,000 | 8,050 | Casey Key |
| 121 N Casey Key Road | $6,475,000 | 4,096 | Casey Key |
| 313 Lookout Point Drive | $5,999,999 | 5,337 | Southbay Yacht & Racquet Club |
| 18 N Casey Key Road | $1,750,000 | 1,977 | Casey Key |
| 3603 N Point Road #702 | $1,395,000 | 2,545 | Meridian At The Oaks Preserve |
| 14021 Bellagio Way #404 | $999,900 | 2,187 | — |
| 14021 Bellagio Way #309 | $879,000 | 2,199 | — |
| 6100 Jessie Harbor Drive #202 | $798,000 | 3,771 | — |
| 260 Hidden Bay Drive #402 | $775,000 | 1,950 | — |
| 1328 Thornapple Drive | $749,900 | 2,174 | — |
Waterfront Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 4 | 19% |
| $300K–$500K | 1 | 5% |
| $500K–$750K | 7 | 33% |
| $750K–$1M | 4 | 19% |
| $1M+ | 5 | 24% |
Osprey 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 |
|---|---|---|---|---|
| Meridian At The Oaks Preserve | 4 | 0 | $1,000,000 | $629,400 |
| Casey Key | 3 | 0 | $6,475,000 | $1,750,000 |
| Blackburn Harbor Residences | 3 | 0 | $699,000 | $599,000 |
| Dry Slips At Bellagio Village | 3 | 0 | $109,000 | $99,500 |
| Villas At Bellagio Harbor Village | 2 | 0 | $849,950 | $700,000 |
| Southbay Yacht & Racquet Club | 1 | 0 | $5,999,999 | $5,999,999 |
| Bayside | 1 | 0 | $2,850,000 | $2,850,000 |
| Oaks 2 Ph 4 | 1 | 0 | $2,750,000 | $2,750,000 |
| Villas/Harbor Village | 1 | 0 | $879,000 | $879,000 |
| Edgewater/Hidden Bay Bldg B Ph | 1 | 0 | $775,000 | $775,000 |
| Willowbend Ph 1 | 1 | 0 | $749,900 | $749,900 |
| Baypointe Vista 1 | 1 | 0 | $700,000 | $700,000 |
| Park Trace Estates | 1 | 0 | $669,900 | $669,900 |
| Cordes Cove | 1 | 0 | $585,000 | $585,000 |
| Willowbend | 1 | 0 | $540,000 | $540,000 |
| Heron House | 1 | 0 | $395,000 | $395,000 |
| Windsor Lodge At The Oaks | 1 | 0 | $235,000 | $235,000 |
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 Osprey?
What do waterfront homes cost in Osprey?
Which Osprey community has the most waterfront homes for sale?
Is a waterfront home always in a flood zone?
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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 Osprey, 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.