4 Bedroom Homes for Sale in Osprey, FL
Four bedrooms is the most-searched size in most Florida and Georgia markets. This page tracks every Osprey listing whose MLS record reports four or more bedrooms, by community, with live counts and asking prices, and how the price compares with smaller homes in the same city.
22 homes with four or more bedrooms are for sale or pending in Osprey, FL today across 15 communities. The median asking price is $1,925,000, from $525,000 to $9,750,000. Listings in Osprey without that feature have a median of $649,000. Most listings right now: Southbay Yacht & Racquet Club (4), Park Trace Estates (3), Casey Key (2). Updated October 2, 2026 from the MLS.
Live 4-bedroom homes in Osprey: the listings
15 active listings match today (20% of Osprey inventory), median asking $1,399,000, $430/sq ft, median 31 days on market. Photo cards link to the listing; refreshed nightly.
Newest 4-bedroom homes in Osprey
The most expensive 4-bedroom 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 |
| 275 Lookout Point Drive | $4,590,000 | 5,279 | Southbay Yacht & Racquet Club |
| 650 Oaks Creek Court | $3,700,000 | 4,314 | Oaks 2 Ph 2 |
| 236 Saint James Park | $2,700,000 | 6,246 | Oaks 2 Ph 2 |
| 154 Lookout Point Drive | $2,095,000 | 4,578 | Southbay Yacht & Racquet Club |
| 1417 Landview Lane | $1,399,000 | 3,255 | Southbay Yacht & Racquet Club |
| 296 Pine Ranch Trail | $1,100,000 | 3,354 | — |
| 907 Eagle Isle Court | $1,100,000 | 3,984 | — |
4-Bedroom Homes by price
| Band | For sale | Share |
|---|---|---|
| $500K–$750K | 4 | 27% |
| $750K–$1M | 1 | 7% |
| $1M+ | 10 | 67% |
Osprey 4-bedroom homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | 4-Bedroom Homes | New build | Median list | From |
|---|---|---|---|---|
| Southbay Yacht & Racquet Club | 4 | 0 | $3,342,500 | $1,399,000 |
| Park Trace Estates | 3 | 0 | $824,900 | $669,900 |
| Casey Key | 2 | 0 | $8,112,500 | $6,475,000 |
| Oaks 2 Ph 2 | 2 | 0 | $2,800,000 | $1,900,000 |
| Southbay Yacht & Racquet Club | 1 | 0 | $4,590,000 | $4,590,000 |
| Oaks 2 Ph 4 | 1 | 0 | $2,750,000 | $2,750,000 |
| Oaks 2 Ph 1 | 1 | 0 | $2,700,000 | $2,700,000 |
| Oaks 2 Ph 4C Part 1 | 1 | 0 | $2,600,000 | $2,600,000 |
| Oaks 2 Ph 4-C Pt 3 | 1 | 0 | $1,950,000 | $1,950,000 |
| Pine Ranch East | 1 | 0 | $1,100,000 | $1,100,000 |
| Rivendell The Woodlands | 1 | 0 | $1,100,000 | $1,100,000 |
| Rivendell Woodlands | 1 | 0 | $700,000 | $700,000 |
| Rivendell, Unit 3-A | 1 | 0 | $630,000 | $630,000 |
| Bay Oaks Estates | 1 | 0 | $529,000 | $529,000 |
| Palms/Casey Key | 1 | 0 | $525,000 | $525,000 |
What the fourth bedroom costs
The answer block above compares the median asking price of four-plus-bedroom homes with the median of everything else listed in the city; the gap is what the extra room, and usually the extra square footage and lot, is priced at today. Compare on price per square foot, not price alone: a four-bedroom home at 2,000 square feet and one at 2,800 are different purchases, and the MLS square footage on each listing page makes that comparison in seconds. Newer subdivisions tend to deliver four bedrooms in less square footage than older ones; the community pages show year-built ranges so you can see which is which.
Questions to ask about any four-bedroom listing
Is the fourth bedroom a true bedroom with a closet and window, or a converted den, garage bay or bonus room? Are the bedrooms split (owner’s suite away from the others) or all on one side? Is there a second full bath near the secondary bedrooms? What does the seller pay for insurance and, in an HOA community, what do the dues cover? A local agent who works the area will know which builders’ four-bedroom plans hold their value.
Common questions
How many homes with four or more bedrooms are for sale in Osprey?
What do 4-bedroom homes cost in Osprey?
Which Osprey community has the most 4-bedroom homes for sale?
How much more does a 4-bedroom home cost?
Keep exploring Osprey
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- 4-Bedroom Homes in every city
4-Bedroom Homes in nearby Sarasota County cities
- Sarasota 4-bedroom homes (609 for sale)
- North Port 4-bedroom homes (221 for sale)
- Venice 4-bedroom homes (120 for sale)
- Nokomis 4-bedroom homes (98 for sale)
- Longboat Key 4-bedroom homes (48 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 Osprey, FL whose MLS record reports four or more bedrooms. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.