Hemingway Drive, Oldsmar, FL
Everything we know about Hemingway Drive 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.
52 homes sit on Hemingway Drive in Oldsmar, FL (ZIP 34677), built 1997–1999, a typical 1,452 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. 3 closed in the last 12 months at a median of $300,000. Homes that sold since 2023 went for a median $354,500.
Recent sales on Hemingway Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 271 Hemingway Drive | $350,000 | 2026-09-04 | 3 / 2.5 | 1,452 |
| 208 Hemingway Drive | $300,000 | 2026-06-25 | 2 / 2.0 | 1,207 |
| 248 Hemingway Drive | $276,000 | 2026-03-24 | 2 / 2.0 | 1,086 |
The homes on Hemingway Drive
4 single-family, 48 condo/townhome/other. Built by decade: 1990s 52.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 271 Hemingway Drive | $350,000 | 2026-09-04 | 1998 | 1,452 |
| 208 Hemingway Drive | $300,000 | 2026-06-25 | 1997 | 1,207 |
| 248 Hemingway Drive | $276,000 | 2026-03-24 | 1998 | 1,086 |
| 284 Hemingway Drive | $350,000 | 2025-09-02 | 1998 | 1,604 |
| 217 Hemingway Drive | $398,000 | 2025-05-09 | 1998 | 1,604 |
| 201 Hemingway Drive | $359,000 | 2024-12-06 | 1997 | 1,604 |
| 252 Hemingway Drive | $387,500 | 2024-10-29 | 1998 | 1,604 |
| 206 Hemingway Drive | $340,200 | 2023-11-07 | 1997 | 1,207 |
| 205 Hemingway Drive | $375,000 | 2023-08-18 | 1997 | 1,604 |
| 245 Hemingway Drive | $389,000 | 2023-06-29 | 1998 | 1,452 |
| 219 Hemingway Drive | $357,000 | 2022-10-19 | 1998 | 1,452 |
| 216 Hemingway Drive | $395,000 | 2022-06-25 | 1997 | 1,452 |
| 203 Hemingway Drive | $389,000 | 2022-06-21 | 1997 | 1,452 |
| 269 Hemingway Drive | $391,000 | 2022-05-31 | 1998 | 1,452 |
| 236 Hemingway Drive | $370,000 | 2022-01-19 | 1998 | 1,604 |
| 228 Hemingway Drive | $308,000 | 2021-11-10 | 1997 | 1,452 |
| 200 Hemingway Drive | $325,000 | 2021-10-27 | 1997 | 1,604 |
| 218 Hemingway Drive | $315,000 | 2021-07-07 | 1997 | 1,604 |
| 226 Hemingway Drive | $255,000 | 2020-11-30 | 1997 | 1,604 |
| 232 Hemingway Drive | $250,500 | 2020-08-10 | 1998 | 1,604 |
Communities along Hemingway Drive
- Sun Ketch Townhomes At Cypress Lakes · 40 homes on the street
- Sun Ketch Townhomes At Cypress Lakes · 4 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 165 homes for sale in Oldsmar, homes for sale in 34677.