Gated Communities in Osprey, FL: Homes for Sale
This page tracks every Osprey listing whose MLS record reports a gated community (manned gate, unmanned gate or security gate), by community, with live counts and asking prices, and the fee questions that come with the gate.
43 homes in gated communities are for sale or pending in Osprey, FL today across 21 communities. The median asking price is $798,000, from $235,000 to $2,850,000. Listings in Osprey without that feature have a median of $639,000. Most listings right now: Meridian At The Oaks Preserve (15), Bay Street Village (4), Oaks 2 Ph 1 (3). Updated September 28, 2026 from the MLS.
Live gated community homes in Osprey: the listings
27 active listings carry the flag today (38% of Osprey inventory), median asking $789,000, $389/sq ft, median 165 days on market. Photo cards link to the listing; refreshed nightly.
Newest gated community homes in Osprey
The most expensive gated community homes in Osprey
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 236 Saint James Park | $2,700,000 | 6,246 | Oaks 2 Ph 2 |
| 852 Macewen Drive | $2,395,000 | 4,519 | Oaks 2 Ph 2 |
| 401 N Point Road #1001 | $1,995,000 | 3,029 | Meridian At The Oaks Preserve |
| 909 Macewen Drive | $1,595,000 | 4,241 | Oaks 2 Ph 2 |
| 226 Saint James Park | $1,495,000 | 2,591 | Oaks 2 Ph 2 |
| 3603 N Point Road #702 | $1,395,000 | 2,545 | Meridian At The Oaks Preserve |
| 17 Bayhead Lane | $1,295,000 | 2,850 | — |
| 409 N Point Road #601 | $1,250,000 | 2,594 | Meridian At The Oaks Preserve |
| 385 N Point Road #304 | $1,100,000 | 2,778 | Meridian At The Oaks Preserve |
| 14021 Bellagio Way #404 | $999,900 | 2,187 | — |
Gated Community Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 2 | 7% |
| $300K–$500K | 2 | 7% |
| $500K–$750K | 8 | 30% |
| $750K–$1M | 6 | 22% |
| $1M+ | 9 | 33% |
Osprey gated community homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Gated Community Homes | New build | Median list | From |
|---|---|---|---|---|
| Meridian At The Oaks Preserve | 15 | 0 | $795,000 | $445,000 |
| Bay Street Village | 4 | 0 | $308,000 | $289,000 |
| Oaks 2 Ph 1 | 3 | 0 | $1,800,000 | $1,495,000 |
| Oaks 2 Ph 2 | 2 | 0 | $2,147,500 | $1,900,000 |
| Villas At Bellagio Harbor Village | 2 | 0 | $849,950 | $700,000 |
| Blackburn Harbor Residences | 2 | 0 | $748,500 | $699,000 |
| Bayside | 1 | 0 | $2,850,000 | $2,850,000 |
| Oaks 2 Ph 4 | 1 | 0 | $2,750,000 | $2,750,000 |
| 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 |
| Oaks 2 Phase 2 | 1 | 0 | $1,595,000 | $1,595,000 |
| Bishops Court At Oaks Preserve | 1 | 0 | $1,295,000 | $1,295,000 |
| Emerald Woods At Oaks 03 Ph 02 | 1 | 0 | $1,050,000 | $1,050,000 |
| Villas/Harbor Village | 1 | 0 | $879,000 | $879,000 |
| Bishopscourt At The Oaks Preserve | 1 | 0 | $789,000 | $789,000 |
| Edgewater/Hidden Bay Bldg B Ph | 1 | 0 | $775,000 | $775,000 |
| Baypointe Vista 1 | 1 | 0 | $700,000 | $700,000 |
| Blackburn Point Marina Village | 1 | 0 | $540,000 | $540,000 |
| Blackburn Harbor Waterfront Villas | 1 | 0 | $480,000 | $480,000 |
| Heron House | 1 | 0 | $395,000 | $395,000 |
| Windsor Lodge At The Oaks | 1 | 0 | $235,000 | $235,000 |
What the gate costs and what it actually does
A gate is an HOA amenity, so it shows up in dues: an unmanned keypad or transponder gate adds little; a 24-hour manned gate is a six-figure annual staffing line shared by the homeowners, and the roads behind it are usually private, which means the association, not the county, pays to repave them. Ask for the current HOA budget and reserve study, whether the roads are private, and whether a gate or road assessment is pending. The MLS field records the gate, not its staffing, so confirm which kind it is before you value it. Our true cost of ownership calculator puts HOA dues, taxes and insurance into one monthly number.
Questions to ask about any gated-community listing
Is the gate manned, and during what hours? Are the roads private, and what do the reserves look like for repaving? What are the HOA dues today and what did they run three years ago? Is there a CDD or a special assessment on the books? What are the guest-access and delivery rules? A local agent who works the community will know which gates are staffed and which associations are underfunded.
Common questions
How many homes in gated communities are for sale in Osprey?
What do gated community homes cost in Osprey?
Which Osprey community has the most gated community homes for sale?
Are gated communities more expensive to own?
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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 a gated community. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.