Oak Bay Drive, Osprey, FL
Everything we know about Oak Bay Drive in Osprey: what is for sale, what has sold, what the homes are like and which communities the street runs through — from the MLS record and county parcel data, refreshed nightly.
39 homes sit on Oak Bay Drive in Osprey, FL (ZIP 34229), built 1995–2003, a typical 2,216 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $530,000.
The homes on Oak Bay Drive
39 single-family. Built by decade: 1990s 36, 2000s 3.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 523 Oak Bay Drive | $540,000 | 2026-08-07 | 1998 | 2,399 |
| 562 Oak Bay Drive | $511,500 | 2026-06-17 | 1995 | 2,414 |
| 566 Oak Bay Drive | $520,000 | 2026-02-26 | 1997 | 2,559 |
| 629 Oak Bay Drive | $500,000 | 2025-03-21 | 1996 | 1,867 |
| 502 Oak Bay Drive | $495,000 | 2024-12-27 | 1995 | 2,116 |
| 515 Oak Bay Drive | $512,500 | 2024-09-06 | 1995 | 1,977 |
| 603 Oak Bay Drive | $600,000 | 2024-07-31 | 1997 | 2,312 |
| 590 Oak Bay Drive | $609,000 | 2023-10-30 | 1999 | 1,892 |
| 506 Oak Bay Drive | $655,000 | 2023-09-27 | 1995 | 1,944 |
| 574 Oak Bay Drive | $625,000 | 2023-07-14 | 1999 | 2,325 |
| 599 Oak Bay Drive | $595,000 | 2022-12-29 | 2002 | 2,037 |
| 514 Oak Bay Drive | $672,000 | 2022-11-30 | 1999 | 1,846 |
| 579 Oak Bay Drive | $830,000 | 2022-08-09 | 1995 | 2,721 |
| 554 Oak Bay Drive | $440,000 | 2022-06-30 | 1999 | 1,749 |
| 500 Oak Bay Drive | $700,000 | 2022-01-28 | 1996 | 2,459 |
| 520 Oak Bay Drive | $565,000 | 2021-11-09 | 1998 | 1,958 |
| 595 Oak Bay Drive | $435,000 | 2021-04-06 | 1996 | 2,241 |
| 542 Oak Bay Drive | $375,000 | 2020-12-31 | 1996 | 2,046 |
| 608 Oak Bay Drive | $350,000 | 2020-06-22 | 1998 | 2,058 |
| 530 Oak Bay Drive | $371,100 | 2020-04-14 | 1997 | 2,369 |
How to read this
Home counts, build years, sizes and last sales come from the county parcel record joined to MLS history; listings and 12-month closings from the live MLS feeds as of October 14, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 85 homes for sale in Osprey, homes for sale in 34229.