Pleasant Pine Circle, Winter Park, FL
Everything we know about Pleasant Pine Circle in Winter Park: 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.
53 homes sit on Pleasant Pine Circle in Winter Park, FL (ZIP 32792), built 2013–2016, a typical 2,319 sq ft with 4 bedrooms. Nothing is listed for sale on the street today. 4 closed in the last 12 months at a median of $603,000. Homes that sold since 2023 went for a median $645,000.
Recent sales on Pleasant Pine Circle
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 7917 Pleasant Pine Circle | $581,000 | 2026-05-26 | 4 / 2.5 | 2,157 |
| 7895 Pleasant Pine Circle | $719,000 | 2025-11-19 | 5 / 3.5 | 3,568 |
| 7888 Pleasant Pine Circle | $625,000 | 2025-11-03 | 4 / 2.5 | 2,267 |
| 7864 Pleasant Pine Circle | $550,000 | 2025-10-23 | 4 / 2.5 | 2,182 |
The homes on Pleasant Pine Circle
53 single-family. Built by decade: 2010s 53.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 7917 Pleasant Pine Circle | $581,000 | 2026-05-26 | 2014 | 2,157 |
| 7895 Pleasant Pine Circle | $719,000 | 2025-11-19 | 2014 | 3,568 |
| 7888 Pleasant Pine Circle | $625,000 | 2025-11-03 | 2016 | 2,267 |
| 7864 Pleasant Pine Circle | $550,000 | 2025-10-23 | 2016 | 2,182 |
| 7988 Pleasant Pine Circle | $596,500 | 2025-10-02 | 2016 | 2,267 |
| 7945 Pleasant Pine Circle | $735,000 | 2025-05-13 | 2015 | 3,496 |
| 8073 Pleasant Pine Circle | $635,000 | 2025-02-21 | 2014 | 2,319 |
| 8057 Pleasant Pine Circle | $750,000 | 2024-10-31 | 2013 | 3,215 |
| 7921 Pleasant Pine Circle | $660,000 | 2024-06-03 | 2015 | 2,572 |
| 8097 Pleasant Pine Circle | $555,000 | 2024-02-21 | 2015 | 2,003 |
| 8000 Pleasant Pine Circle | $655,000 | 2024-02-16 | 2015 | 2,535 |
| 7875 Pleasant Pine Circle | $560,000 | 2023-12-28 | 2014 | 2,268 |
| 7984 Pleasant Pine Circle | $750,000 | 2023-12-18 | 2016 | 3,496 |
| 7904 Pleasant Pine Circle | $690,000 | 2023-08-23 | 2014 | 3,496 |
| 8001 Pleasant Pine Circle | $589,000 | 2023-07-20 | 2015 | 2,267 |
| 7909 Pleasant Pine Circle | $675,000 | 2023-05-15 | 2014 | 3,496 |
| 8077 Pleasant Pine Circle | $680,000 | 2022-09-15 | 2013 | 3,215 |
| 7913 Pleasant Pine Circle | $545,000 | 2022-08-08 | 2014 | 2,003 |
| 7884 Pleasant Pine Circle | $570,000 | 2022-07-28 | 2015 | 2,319 |
| 7985 Pleasant Pine Circle | $590,000 | 2022-05-31 | 2014 | 2,267 |
Communities along Pleasant Pine Circle
- Enclave At Aloma · 53 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 402 homes for sale in Winter Park, homes for sale in 32792.