Highland Oaks Circle, Sarasota, FL
Everything we know about Highland Oaks Circle in Sarasota: 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.
32 homes sit on Highland Oaks Circle in Sarasota, FL (ZIP 34235), built 1987–1992, a typical 2,350 sq ft with 3 bedrooms. 1 is for sale right now from $813,000. Homes that sold since 2023 went for a median $729,000.
For sale on Highland Oaks Circle now
The homes on Highland Oaks Circle
32 single-family. Built by decade: 1980s 25, 1990s 7.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 4322 Highland Oaks Circle | $655,000 | 2026-08-19 | 1991 | 2,374 |
| 4305 Highland Oaks Circle | $729,000 | 2026-07-10 | 1990 | 2,612 |
| 4348 Highland Oaks Circle | $730,000 | 2026-03-17 | 1990 | 2,820 |
| 4444 Highland Oaks Circle | $700,000 | 2025-06-30 | 1992 | 2,026 |
| 4369 Highland Oaks Circle | $880,000 | 2025-03-27 | 1989 | 3,044 |
| 4524 Highland Oaks Circle | $760,000 | 2024-05-03 | 1988 | 3,395 |
| 4556 Highland Oaks Circle | $675,000 | 2024-01-22 | 1988 | 1,896 |
| 4571 Highland Oaks Circle | $750,000 | 2023-12-21 | 1988 | 2,921 |
| 4427 Highland Oaks Circle | $660,000 | 2023-12-05 | 1988 | 2,067 |
| 4557 Highland Oaks Circle | $799,000 | 2023-08-09 | 1987 | 2,326 |
| 4470 Highland Oaks Circle | $590,000 | 2023-02-27 | 1989 | 1,862 |
| 4415 Highland Oaks Circle | $750,000 | 2022-12-08 | 1988 | 2,046 |
| 4313 Highland Oaks Circle | $775,000 | 2022-06-21 | 1989 | 2,862 |
| 4492 Highland Oaks Circle | $950,000 | 2022-04-01 | 1988 | 2,261 |
| 4438 Highland Oaks Circle | $831,500 | 2021-09-01 | 1990 | 2,094 |
| 4439 Highland Oaks Circle | $719,000 | 2020-11-30 | 1989 | 2,756 |
| 4489 Highland Oaks Circle | $499,000 | 2020-09-09 | 1989 | 2,997 |
| 4372 Highland Oaks Circle | $520,000 | 2020-08-31 | 1989 | 2,551 |
| 4395 Highland Oaks Circle | $400,000 | 2019-12-20 | 1989 | 2,236 |
| 4533 Highland Oaks Circle | $575,000 | 2018-07-26 | 1987 | 2,858 |
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 2,420 homes for sale in Sarasota, homes for sale in 34235.