Jolly Roger Drive, Cudjoe Key, FL
Everything we know about Jolly Roger Drive in Cudjoe Key: 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.
40 homes sit on Jolly Roger Drive in Cudjoe Key, FL (ZIP 33042), built 1963–2020, a typical 1,561 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $1,700,000.
The homes on Jolly Roger Drive
40 single-family. Built by decade: 1960s 2, 1970s 9, 1980s 18, 1990s 3, 2000s 2, 2010s 4, 2020s 2.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 22410 Jolly Roger Drive | $1,500,000 | 2026-08-10 | 1982 | 1,587 |
| 22562 Jolly Roger Drive | $1,700,000 | 2026-01-30 | 1987 | 2,074 |
| 22521 Jolly Roger Drive | $1,030,000 | 2025-11-19 | 2010 | 1,728 |
| 28595 Jolly Roger Drive | $2,599,000 | 2025-06-18 | 1975 | 1,153 |
| 22440 Jolly Roger Drive | $2,025,000 | 2025-05-13 | 1988 | 1,292 |
| 22572 Jolly Roger Drive | $3,300,000 | 2025-02-18 | 1963 | 3,225 |
| 22727 Jolly Roger Drive | $800,000 | 2025-01-31 | 2001 | 1,008 |
| 22903 Jolly Roger Drive | $685,000 | 2024-11-27 | 1972 | 1,152 |
| 22532 Jolly Roger Drive | $1,600,000 | 2024-11-14 | 2019 | 1,288 |
| 22766 Jolly Roger Drive | $1,800,000 | 2024-11-14 | 1989 | 1,884 |
| 22684 Jolly Roger Drive | $2,450,000 | 2024-04-17 | 1977 | 1,819 |
| 22856 Jolly Roger Drive | $2,575,000 | 2024-03-15 | 2016 | 1,953 |
| 22542 Jolly Roger Drive | $1,250,000 | 2023-07-28 | 1982 | 2,440 |
| 22892 Jolly Roger Drive | $1,670,000 | 2022-05-20 | 2020 | 1,767 |
| 22896 Jolly Roger Drive | $1,600,000 | 2022-05-09 | 2020 | 1,767 |
| 22757 Jolly Roger Drive | $598,000 | 2021-07-12 | 1963 | 600 |
| 22888 Jolly Roger Drive | $1,250,000 | 2021-07-08 | 1981 | 1,250 |
| 22832 Jolly Roger Drive | $1,125,000 | 2021-01-19 | 1981 | 1,282 |
| 28585 Jolly Roger Drive | $900,000 | 2020-10-21 | 1970 | 1,152 |
| 22358 Jolly Roger Drive | $990,000 | 2020-08-24 | 1978 | 2,319 |
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 46 homes for sale in Cudjoe Key, homes for sale in 33042.