Chesterfield Circle, Winter Springs, FL
Everything we know about Chesterfield Circle in Winter Springs: 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.
38 homes sit on Chesterfield Circle in Winter Springs, FL (ZIP 32708), built 1984–1986, a typical 2,064 sq ft with 4 bedrooms. Nothing is listed for sale on the street today. 2 closed in the last 12 months at a median of $487,000. Homes that sold since 2023 went for a median $517,500.
Recent sales on Chesterfield Circle
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 1017 Chesterfield Circle | $535,000 | 2026-05-01 | 3 / 3.0 | 1,882 |
| 1073 Chesterfield Circle | $439,000 | 2025-12-05 | 4 / 2.0 | 2,064 |
The homes on Chesterfield Circle
38 single-family. Built by decade: 1980s 38.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 1017 Chesterfield Circle | $535,000 | 2026-05-01 | 1984 | 1,882 |
| 1073 Chesterfield Circle | $439,000 | 2025-12-05 | 1985 | 2,064 |
| 1003 Chesterfield Circle | $410,000 | 2025-08-15 | 1985 | 1,759 |
| 1000 Chesterfield Circle | $429,900 | 2025-07-03 | 1984 | 1,756 |
| 1069 Chesterfield Circle | $500,000 | 2025-01-23 | 1984 | 2,033 |
| 1030 Chesterfield Cir | $620,000 | 2024-04-09 | 1985 | 3,131 |
| 1031 Chesterfield Circle | $550,000 | 2023-04-06 | 1984 | 2,402 |
| 1051 Chesterfield Circle | $549,999 | 2023-01-30 | 1985 | 2,416 |
| 1056 Chesterfield Circle | $540,000 | 2022-03-21 | 1985 | 2,050 |
| 1037 Chesterfield Circle | $480,000 | 2021-10-25 | 1984 | 1,671 |
| 1027 Chesterfield Circle | $564,500 | 2021-08-09 | 1985 | 3,072 |
| 1076 Chesterfield Circle | $485,000 | 2021-06-22 | 1985 | 2,402 |
| 1039 Chesterfield Circle | $475,000 | 2021-03-10 | 1986 | 2,402 |
| 1055 Chesterfield Circle | $310,000 | 2021-01-12 | 1984 | 1,665 |
| 1071 Chesterfield Circle | $375,000 | 2020-09-25 | 1984 | 1,929 |
| 1061 Chesterfield Circle | $340,000 | 2020-05-07 | 1985 | 2,064 |
| 1001 Chesterfield Circle | $345,000 | 2019-11-06 | 1985 | 2,064 |
| 1002 Chesterfield Circle | $300,000 | 2019-09-13 | 1985 | 1,956 |
| 1042 Chesterfield Circle | $348,500 | 2019-07-26 | 1985 | 2,081 |
| 1007 Chesterfield Circle | $375,000 | 2017-10-23 | 1984 | 3,140 |
Communities along Chesterfield Circle
- Amherst · 38 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 129 homes for sale in Winter Springs, homes for sale in 32708.