Countryside Key Boulevard, Oldsmar, FL
Everything we know about Countryside Key Boulevard in Oldsmar: 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.
152 homes sit on Countryside Key Boulevard in Oldsmar, FL (ZIP 34677), built 1995–1998, a typical 1,110 sq ft with 2 bedrooms. 2 are for sale right now from $229,500 to $275,000. 9 closed in the last 12 months at a median of $235,000. Homes that sold since 2023 went for a median $275,000.
For sale on Countryside Key Boulevard now
Recent sales on Countryside Key Boulevard
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 382 Countryside Key Boulevard | $225,000 | 2026-07-13 | 2 / 1.5 | 1,105 |
| 244 Countryside Key Boulevard | $191,000 | 2026-07-06 | 2 / 2.5 | 1,110 |
| 388 Countryside Key Boulevard | $234,000 | 2026-07-02 | 2 / 1.5 | 1,105 |
| 273 Countryside Key Boulevard #N/A | $235,000 | 2026-03-19 | 2 / 2.5 | 1,110 |
| 477 Countryside Key Boulevard | $220,000 | 2026-03-04 | 2 / 1.5 | 1,105 |
| 421 Countryside Key Boulevard | $245,000 | 2025-12-29 | 2 / 2.5 | 1,105 |
| 367 Countryside Key Boulevard | $235,000 | 2025-12-09 | 2 / 1.5 | 1,105 |
| 239 Countryside Key Boulevard | $245,000 | 2025-12-01 | 2 / 1.5 | 1,105 |
| 467 Countryside Key Boulevard | $240,000 | 2025-10-20 | 2 / 2.5 | 1,110 |
The homes on Countryside Key Boulevard
3 single-family, 149 condo/townhome/other. Built by decade: 1990s 152.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 382 Countryside Key Boulevard | $225,000 | 2026-07-13 | 1997 | 1,105 |
| 244 Countryside Key Boulevard | $191,000 | 2026-07-06 | 1996 | 1,110 |
| 388 Countryside Key Boulevard | $234,000 | 2026-07-02 | 1997 | 1,105 |
| 477 Countryside Key Boulevard | $220,000 | 2026-03-04 | 1995 | 1,105 |
| 421 Countryside Key Boulevard | $245,000 | 2025-12-29 | 1998 | 1,105 |
| 367 Countryside Key Boulevard | $235,000 | 2025-12-09 | 1997 | 1,105 |
| 239 Countryside Key Boulevard | $245,000 | 2025-12-01 | 1998 | 1,105 |
| 467 Countryside Key Boulevard | $240,000 | 2025-10-20 | 1997 | 1,110 |
| 267 Countryside Key Boulevard | $260,000 | 2025-09-29 | 1996 | 1,110 |
| 309 Countryside Key Boulevard | $227,500 | 2025-09-05 | 1996 | 1,110 |
| 232 Countryside Key Boulevard | $230,000 | 2025-07-16 | 1996 | 1,285 |
| 297 Countryside Key Boulevard | $279,000 | 2025-07-01 | 1996 | 1,110 |
| 441 Countryside Key Boulevard | $236,000 | 2025-04-09 | 1998 | 1,110 |
| 324 Countryside Key Boulevard | $275,000 | 2025-03-07 | 1996 | 1,110 |
| 325 Countryside Key Boulevard | $275,000 | 2025-01-06 | 1996 | 1,105 |
| 233 Countryside Key Boulevard | $249,900 | 2024-11-27 | 1998 | 1,110 |
| 360 Countryside Key Boulevard | $274,000 | 2024-11-19 | 1997 | 1,110 |
| 314 Countryside Key Boulevard | $283,500 | 2024-10-18 | 1996 | 1,110 |
| 380 Countryside Key Boulevard | $285,900 | 2024-08-08 | 1997 | 1,110 |
| 345 Countryside Key Boulevard | $285,000 | 2024-05-31 | 1997 | 1,141 |
Communities along Countryside Key Boulevard
- Countryside Key · 128 homes on the street
- Countryside Key · 10 homes on the street
- Countryside Key · 4 homes on the street
- Countryside Key · 4 homes on the street
- Countryside Key · 3 homes on the street
- Countryside Key · 2 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 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 174 homes for sale in Oldsmar, homes for sale in 34677.