Bobtail Drive, Maitland, FL
Everything we know about Bobtail Drive in Maitland: 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.
58 homes sit on Bobtail Drive in Maitland, FL (ZIP 32751), built 1995–1999, a typical 1,678 sq ft with 3 bedrooms. 1 is for sale right now from $519,999. 3 closed in the last 12 months at a median of $372,000. Homes that sold since 2023 went for a median $400,000.
For sale on Bobtail Drive now
Recent sales on Bobtail Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 1866 Bobtail Drive | $350,000 | 2026-09-21 | 3 / 2.0 | 1,322 |
| 2040 Bobtail Drive | $372,000 | 2026-06-24 | 3 / 2.0 | 1,382 |
| 1662 Bobtail Drive | $525,000 | 2026-05-07 | 5 / 2.5 | 2,398 |
The homes on Bobtail Drive
57 single-family, 1 condo/townhome/other. Built by decade: 1990s 58.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 1866 Bobtail Drive | $350,000 | 2026-09-21 | 1996 | 1,322 |
| 2040 Bobtail Drive | $372,000 | 2026-06-24 | 1998 | 1,382 |
| 1662 Bobtail Drive | $525,000 | 2026-05-07 | 1997 | 2,398 |
| 1758 Bobtail Drive | $545,000 | 2025-09-10 | 1997 | 2,304 |
| 1787 Bobtail Drive | $489,000 | 2024-09-10 | 1998 | 2,365 |
| 1733 Bobtail Drive | $370,000 | 2023-12-14 | 1997 | 1,642 |
| 1769 Bobtail Drive | $400,000 | 2023-06-28 | 1998 | 1,822 |
| 1938 Bobtail Drive | $399,900 | 2022-09-23 | 1996 | 1,495 |
| 1914 Bobtail Drive | $430,500 | 2022-07-05 | 1996 | 1,715 |
| 2034 Bobtail Drive | $398,700 | 2022-04-15 | 1997 | 1,307 |
| 2010 Bobtail Drive | $398,835 | 2022-03-24 | 1998 | 2,154 |
| 1632 Bobtail Drive | $348,500 | 2022-03-08 | 1999 | 1,822 |
| 1902 Bobtail Drive | $316,000 | 2021-07-13 | 1996 | 1,617 |
| 1770 Bobtail Drive | $299,000 | 2021-01-22 | 1997 | 1,642 |
| 1860 Bobtail Drive | $285,000 | 2021-01-13 | 1997 | 1,740 |
| 1848 Bobtail Drive | $290,000 | 2020-09-30 | 1996 | 1,617 |
| 1795 Bobtail Drive | $283,500 | 2020-06-26 | 1995 | 2,045 |
| 1763 Bobtail Drive | $285,500 | 2019-09-18 | 1998 | 1,802 |
| 1939 Bobtail Drive | $245,000 | 2019-07-26 | 1996 | 1,494 |
| 2065 Bobtail Drive | $260,000 | 2019-05-28 | 1996 | 1,769 |
Communities along Bobtail Drive
- Winfield · 24 homes on the street
- Winfield · 14 homes on the street
- Winfield · 9 homes on the street
- Winfield · 5 homes on the street
- Winfield · 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 113 homes for sale in Maitland, homes for sale in 32751.