Lookout Point Drive, Osprey, FL
Everything we know about Lookout Point 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.
35 homes sit on Lookout Point Drive in Osprey, FL (ZIP 34229), built 1978–2016, a typical 2,738 sq ft with 3 bedrooms. 3 are for sale right now from $2,095,000 to $5,299,999. 2 closed in the last 12 months at a median of $1,880,000. Homes that sold since 2023 went for a median $1,060,000.
For sale on Lookout Point Drive now
Recent sales on Lookout Point Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 321 Lookout Point Drive | $2,910,000 | 2026-10-07 | 3 / 3.5 | 3,122 |
| 157 Lookout Point Drive | $850,000 | 2026-08-07 | 3 / 2.0 | 1,859 |
The homes on Lookout Point Drive
34 single-family, 1 condo/townhome/other. Built by decade: 1970s 11, 1980s 17, 1990s 3, 2000s 2, 2010s 2.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 321 Lookout Point Drive | $2,910,000 | 2026-10-07 | 1978 | 3,122 |
| 157 Lookout Point Drive | $850,000 | 2026-08-07 | 1981 | 1,859 |
| 275 Lookout Point Drive | $3,525,000 | 2025-06-06 | 2007 | 5,279 |
| 284 Lookout Point Drive | $1,020,000 | 2025-05-22 | 1986 | 2,909 |
| 229 Lookout Point Drive | $1,100,000 | 2025-04-23 | 2013 | 2,388 |
| 181 Lookout Point Drive | $975,000 | 2023-10-31 | 1997 | 2,899 |
| 228 Lookout Point Drive | $1,150,000 | 2022-10-14 | 1980 | 2,738 |
| 297 Lookout Point Drive | $3,900,000 | 2022-02-16 | 1997 | 4,159 |
| 154 Lookout Point Drive | $995,000 | 2021-11-12 | 1979 | 4,578 |
| 241 Lookout Point Drive | $650,000 | 2021-07-15 | 1979 | 1,802 |
| 160 Lookout Point Drive | $650,000 | 2021-05-14 | 1979 | 2,288 |
| 148 Lookout Point Drive | $754,000 | 2021-03-24 | 1979 | 3,270 |
| 208 Lookout Point Drive | $765,000 | 2020-10-28 | 1988 | 3,289 |
| 266 Lookout Point Drive | $900,000 | 2020-07-27 | 1989 | 4,022 |
| 257 Lookout Point Drive | $750,000 | 2020-06-24 | 1993 | 3,215 |
| 147 Lookout Point Drive | $330,000 | 2019-11-18 | 1980 | 2,173 |
| 288 Lookout Point Drive | $925,000 | 2019-04-29 | 1987 | 4,357 |
| 238 Lookout Point Drive | $375,000 | 2018-04-16 | 1981 | 2,676 |
| 267 Lookout Point Drive | $570,000 | 2017-11-09 | 1978 | 2,899 |
| 242 Lookout Point Drive | $430,000 | 2017-04-05 | 1978 | 2,413 |
Communities along Lookout Point Drive
- Southbay Yacht & Racquet Club · 31 homes on the street
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.