Jessie Harbor Drive, Osprey, FL
Everything we know about Jessie Harbor 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.
2 homes sit on Jessie Harbor Drive in Osprey, FL (ZIP 34229), built 1992–2004, a typical 1,425 sq ft with 2 bedrooms. 5 are for sale right now from $395,000 to $798,000.
For sale on Jessie Harbor Drive now
The homes on Jessie Harbor Drive
Built by decade: 1990s 1, 2000s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 1102 Jessie Harbor Drive | $315,000 | 2020-06-22 | 2004 | 1,425 |
| 4102 Jessie Harbor Drive | $170,000 | 2014-04-24 | 1992 | 1,425 |
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.