S Shore Drive, Osprey, FL
Everything we know about S Shore 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.
34 homes sit on S Shore Drive in Osprey, FL (ZIP 34229), built 1963–2019, a typical 2,189 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $818,750.
The homes on S Shore Drive
34 single-family. Built by decade: 1960s 12, 1970s 12, 1980s 7, 1990s 1, 2000s 1, 2010s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 432 S Shore Drive | $529,000 | 2026-09-29 | 1988 | 1,704 |
| 353 S Shore Drive | $977,500 | 2026-07-23 | 1968 | 1,840 |
| 437 S Shore Drive | $492,500 | 2026-05-13 | 1976 | 1,947 |
| 525 S Shore Drive | $1,700,000 | 2025-06-12 | 1972 | 2,315 |
| 505 S Shore Drive | $999,000 | 2025-03-21 | 1980 | 2,301 |
| 433 S Shore Drive | $660,000 | 2023-11-16 | 1984 | 1,868 |
| 429 S Shore Drive | $595,000 | 2023-07-06 | 1969 | 1,406 |
| 345 S Shore Drive | $1,750,000 | 2023-03-24 | 1995 | 3,740 |
| 504 S Shore Drive | $1,020,000 | 2022-04-05 | 2004 | 3,098 |
| 365 S Shore Drive | $1,200,000 | 2022-03-04 | 1968 | 1,824 |
| 346 S Shore Drive | $350,000 | 2021-01-04 | 1963 | 2,006 |
| 441 S Shore Drive | $460,000 | 2020-07-16 | 1965 | 2,060 |
| 420 S Shore Drive | $379,900 | 2020-07-09 | 1986 | 1,872 |
| 459 S Shore Drive | $730,000 | 2020-05-08 | 1973 | 4,560 |
| 341 S Shore Drive | $650,000 | 2019-12-30 | 1980 | 2,644 |
| 509 S Shore Drive | $1,125,000 | 2019-11-05 | 1972 | 2,537 |
| 421 S Shore Drive | $600,000 | 2019-07-18 | 1975 | 2,325 |
| 529 S Shore Drive | $850,000 | 2019-05-06 | 1974 | 2,128 |
| 521 S Shore Drive | $1,189,636 | 2018-12-14 | 2019 | 3,827 |
| 386 S Shore Drive | $809,900 | 2018-08-24 | 1979 | 2,321 |
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.