Chesham Drive, Orlando, FL
Everything we know about Chesham Drive in Orlando: 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 Chesham Drive in Orlando, FL (ZIP 32817), built 1987–1988, a typical 1,510 sq ft with 3 bedrooms. 2 are for sale right now from $370,000 to $405,000. 4 closed in the last 12 months at a median of $380,000. Homes that sold since 2023 went for a median $395,000.
For sale on Chesham Drive now
Recent sales on Chesham Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 10120 Chesham Drive | $408,000 | 2026-08-05 | 4 / 2.0 | 1,647 |
| 10159 Chesham Drive | $355,000 | 2026-07-29 | 3 / 2.0 | 1,510 |
| 9913 Chesham Drive | $405,000 | 2026-05-04 | 3 / 2.0 | 1,510 |
| 10025 Chesham Drive | $350,000 | 2025-12-19 | 3 / 2.0 | 1,510 |
The homes on Chesham Drive
35 single-family. Built by decade: 1980s 35.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 10120 Chesham Drive | $408,000 | 2026-08-05 | 1987 | 1,647 |
| 10159 Chesham Drive | $355,000 | 2026-07-29 | 1987 | 1,510 |
| 9913 Chesham Drive | $405,000 | 2026-05-04 | 1987 | 1,510 |
| 10025 Chesham Drive | $350,000 | 2025-12-19 | 1987 | 1,510 |
| 10018 Chesham Drive | $405,000 | 2025-08-01 | 1988 | 1,510 |
| 10042 Chesham Drive | $405,000 | 2025-02-28 | 1987 | 1,525 |
| 10049 Chesham Drive | $359,900 | 2025-02-14 | 1987 | 1,253 |
| 10103 Chesham Drive | $395,000 | 2024-07-24 | 1987 | 1,510 |
| 10009 Chesham Drive | $410,000 | 2024-05-15 | 1987 | 1,510 |
| 10066 Chesham Drive | $360,000 | 2023-08-15 | 1988 | 1,289 |
| 10135 Chesham Drive | $375,000 | 2023-06-03 | 1987 | 1,289 |
| 9930 Chesham Drive | $389,000 | 2022-10-28 | 1987 | 1,510 |
| 10136 Chesham Drive | $318,000 | 2021-12-21 | 1987 | 1,510 |
| 10082 Chesham Drive | $280,000 | 2021-10-27 | 1987 | 1,479 |
| 10041 Chesham Drive | $278,100 | 2021-07-14 | 1987 | 1,510 |
| 9912 Chesham Drive | $275,000 | 2020-03-12 | 1988 | 1,811 |
| 9921 Chesham Drive | $232,500 | 2020-01-31 | 1987 | 1,289 |
| 9937 Chesham Drive | $240,000 | 2020-01-20 | 1987 | 1,289 |
| 10143 Chesham Drive | $266,500 | 2019-12-18 | 1987 | 1,632 |
| 10127 Chesham Drive | $311,000 | 2019-12-02 | 1987 | 1,930 |
Communities along Chesham Drive
- Deans Landing At Sheffield Forest · 25 homes on the street
- Sheffield Forest · 2 homes on the street
- Deans Landing At Sheffield Forest · 2 homes on the street
- Deans Landing At Sheffield Forest · 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 4,337 homes for sale in Orlando, homes for sale in 32817.