Waterside Drive, Kissimmee, FL
Everything we know about Waterside 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.
23 homes sit on Waterside Drive in Kissimmee, FL (ZIP 34747), built 2000–2002, a typical 1,640 sq ft with 3 bedrooms. 3 are for sale right now from $469,000 to $1,399,000. 4 closed in the last 12 months at a median of $387,500. Homes that sold since 2023 went for a median $417,500.
For sale on Waterside Drive now
Recent sales on Waterside Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 914 Waterside Drive | $1,225,000 | 2026-09-25 | 5 / 4.0 | 3,896 |
| 1038 Waterside Drive | $295,000 | 2026-07-17 | 2 / 2.0 | 1,465 |
| 1050 Waterside Drive #0 | $480,000 | 2026-06-22 | 3 / 2.0 | 1,640 |
| 1054 Waterside Drive | $295,000 | 2025-11-17 | 2 / 3.0 | 1,465 |
The homes on Waterside Drive
9 single-family, 14 condo/townhome/other. Built by decade: 2000s 23.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 914 Waterside Drive | $1,225,000 | 2026-09-25 | 2001 | 3,896 |
| 1038 Waterside Drive | $295,000 | 2026-07-17 | 2001 | 1,465 |
| 1054 Waterside Drive | $295,000 | 2025-11-17 | 2001 | 1,465 |
| 1042 Waterside Drive | $325,500 | 2025-10-06 | 2001 | 1,640 |
| 1056 Waterside Drive | $350,000 | 2025-09-08 | 2001 | 1,640 |
| 1008 Waterside Drive . | $390,000 | 2025-02-27 | 2001 | 1,640 |
| 1034 Waterside Drive | $445,000 | 2024-05-13 | 2001 | 1,640 |
| 1028 Waterside Drive . | $600,000 | 2023-12-20 | 2001 | 1,640 |
| 1060 Waterside Drive | $500,000 | 2023-04-17 | 2001 | 1,465 |
| 1000 Waterside Drive | $540,000 | 2023-02-20 | 2001 | 1,640 |
| 1012 Waterside Drive | $376,000 | 2022-04-26 | 2001 | 1,465 |
| 912 Waterside Drive | $834,500 | 2021-07-29 | 2000 | 3,908 |
| 1044 Waterside Drive | $250,000 | 2020-12-07 | 2001 | 1,465 |
| 904 Waterside Drive | $668,000 | 2020-11-20 | 2001 | 3,523 |
| 908 Waterside Drive | $645,000 | 2020-07-28 | 2001 | 3,051 |
| 1014 Waterside Drive | $280,000 | 2018-12-14 | 2001 | 1,640 |
| 918 Waterside Drive | $475,000 | 2018-12-03 | 2001 | 2,236 |
| 910 Waterside Drive | $505,000 | 2017-12-29 | 2002 | 2,713 |
| 906 Waterside Drive | $577,500 | 2015-03-30 | 2000 | 3,523 |
| 902 Waterside Drive | $460,000 | 2012-03-15 | 2000 | 2,987 |
Communities along Waterside Drive
- Celebration · 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 34747.