Chesterwood Road, St. Augustine, FL
Everything we know about Chesterwood Road in St. Augustine: 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 Chesterwood Road in St. Augustine, FL (ZIP 32084), built 2023–2024, a typical 1,655 sq ft with 3 bedrooms. 1 is for sale right now from $349,000. Homes that sold since 2023 went for a median $328,140.
For sale on Chesterwood Road now
The homes on Chesterwood Road
38 single-family. Built by decade: 2020s 38.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 95 Chesterwood Road | $352,990 | 2024-06-28 | 2024 | 2,205 |
| 242 Chesterwood Road | $296,990 | 2024-06-27 | 2024 | 1,222 |
| 210 Chesterwood Road | $324,990 | 2024-06-27 | 2024 | 1,526 |
| 194 Chesterwood Road | $287,990 | 2024-06-27 | 2024 | 1,222 |
| 250 Chesterwood Road | $328,290 | 2024-06-18 | 2024 | 1,655 |
| 103 Chesterwood Road | $372,250 | 2024-06-13 | 2023 | 2,492 |
| 211 Chesterwood Road | $340,990 | 2024-06-05 | 2024 | 1,778 |
| 178 Chesterwood Road | $337,290 | 2024-05-31 | 2024 | 1,778 |
| 243 Chesterwood Road | $351,990 | 2024-05-30 | 2024 | 1,778 |
| 260 Chesterwood Road | $305,990 | 2024-05-30 | 2024 | 1,222 |
| 218 Chesterwood Road | $297,990 | 2024-05-30 | 2024 | 1,222 |
| 234 Chesterwood Road | $317,990 | 2024-05-30 | 2024 | 1,526 |
| 226 Chesterwood Road | $324,990 | 2024-05-30 | 2024 | 1,655 |
| 251 Chesterwood Road | $323,990 | 2024-05-29 | 2024 | 1,526 |
| 267 Chesterwood Road | $332,130 | 2024-05-29 | 2024 | 1,655 |
| 219 Chesterwood Road | $320,990 | 2024-05-28 | 2024 | 1,526 |
| 203 Chesterwood Road | $325,990 | 2024-05-28 | 2024 | 1,655 |
| 259 Chesterwood Road | $340,990 | 2024-05-28 | 2024 | 1,778 |
| 227 Chesterwood Road | $342,000 | 2024-05-24 | 2024 | 1,778 |
| 193 Chesterwood Road | $316,990 | 2024-05-24 | 2024 | 1,526 |
Communities along Chesterwood Road
- Ravenswood Village · 37 homes on the street
- Ravenswood · 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 September 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 1,076 homes for sale in St. Augustine, homes for sale in 32084.