Grand Oak Drive, Kissimmee, FL
Everything we know about Grand Oak Drive in Kissimmee: 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.
28 homes sit on Grand Oak Drive in Kissimmee, FL (ZIP 34744), built 2006–2007, a typical 1,512 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $270,000.
The homes on Grand Oak Drive
Built by decade: 2000s 28.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 1999 Grand Oak Drive | $270,000 | 2025-06-11 | 2007 | 1,760 |
| 2043 Grand Oak Drive | $275,000 | 2025-06-04 | 2006 | 1,512 |
| 2015 Grand Oak Drive | $257,000 | 2025-06-04 | 2007 | 1,408 |
| 1995 Grand Oak Drive | $264,900 | 2025-01-31 | 2007 | 1,512 |
| 1985 Grand Oak Drive | $313,000 | 2024-08-09 | 2007 | 1,760 |
| 2057 Grand Oak Drive | $300,000 | 2022-06-24 | 2006 | 1,408 |
| 2023 Grand Oak Drive | $340,000 | 2022-06-20 | 2006 | 1,760 |
| 2013 Grand Oak Drive | $229,200 | 2021-11-05 | 2007 | 1,512 |
| 2053 Grand Oak Drive | $211,000 | 2021-09-10 | 2006 | 1,512 |
| 2027 Grand Oak Drive | $184,000 | 2021-03-24 | 2006 | 1,408 |
| 1993 Grand Oak Drive | $160,000 | 2020-03-09 | 2007 | 1,408 |
| 2019 Grand Oak Drive | $175,000 | 2019-11-13 | 2007 | 1,512 |
| 1975 Grand Oak Drive | $184,900 | 2019-06-17 | 2007 | 1,760 |
| 2021 Grand Oak Drive | $179,900 | 2019-05-10 | 2007 | 1,760 |
| 2041 Grand Oak Drive | $158,000 | 2019-04-15 | 2006 | 1,408 |
| 2003 Grand Oak Drive | $155,000 | 2018-12-31 | 2007 | 1,408 |
| 2045 Grand Oak Drive | $115,000 | 2016-06-22 | 2006 | 1,760 |
| 1963 Grand Oak Drive | $122,900 | 2016-02-12 | 2007 | 1,760 |
| 2007 Grand Oak Drive | $107,900 | 2015-09-11 | 2007 | 1,512 |
| 1967 Grand Oak Drive | $88,000 | 2015-03-16 | 2007 | 1,408 |
Communities along Grand Oak Drive
- Heritage Key Villas · 9 homes on the street
- Heritage Key Villas · 4 homes on the street
- Heritage Key Villas · 1 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 3,084 homes for sale in Kissimmee, homes for sale in 34744.