Chicago Avenue, Valparaiso, FL
Everything we know about Chicago Avenue in Valparaiso: 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 Chicago Avenue in Valparaiso, FL (ZIP 32580), built 1947–2023, a typical 1,726 sq ft with 3 bedrooms. 1 is for sale right now from $339,000. Homes that sold since 2023 went for a median $311,500.
For sale on Chicago Avenue now
The homes on Chicago Avenue
32 single-family. Built by decade: 1940s 1, 1950s 18, 1960s 2, 1970s 2, 1980s 2, 1990s 1, 2010s 3, 2020s 3.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 348 Chicago Avenue | $303,000 | 2026-06-30 | 1954 | 1,824 |
| 186 Chicago Avenue | $172,000 | 2026-02-17 | 1947 | 1,572 |
| 318 Chicago Avenue | $515,000 | 2025-12-22 | 2010 | 2,898 |
| 346 Chicago Avenue | $289,900 | 2025-09-30 | 1955 | 1,212 |
| 345 Chicago Avenue | $372,500 | 2025-06-12 | 1955 | 2,013 |
| 183 Chicago Avenue | $699,900 | 2024-06-18 | 2023 | 2,656 |
| 357 Chicago Avenue | $375,000 | 2024-01-25 | 1955 | 1,803 |
| 344 Chicago Avenue | $320,000 | 2023-12-13 | 1955 | 1,350 |
| 215 Chicago Avenue | $260,000 | 2023-05-15 | 1950 | 1,822 |
| 359 Chicago Avenue | $275,000 | 2023-04-24 | 1955 | 1,416 |
| 334 Chicago Avenue | $352,000 | 2022-08-01 | 1956 | 1,423 |
| 222 Chicago Avenue | $581,000 | 2022-07-14 | 2022 | 2,354 |
| 220 Chicago Avenue | $581,000 | 2022-06-28 | 2022 | 2,354 |
| 236 Chicago Avenue | $395,900 | 2022-04-01 | 1951 | 1,894 |
| 180 Chicago Avenue | $260,000 | 2022-03-11 | 1966 | 1,364 |
| 176 Chicago Avenue | $472,700 | 2021-12-09 | 2018 | 2,027 |
| 326 Chicago Avenue | $235,000 | 2021-11-30 | 1954 | 1,032 |
| 340 Chicago Avenue | $335,000 | 2021-07-09 | 1955 | 1,600 |
| 200 Chicago Avenue | $235,000 | 2021-03-25 | 1966 | 1,913 |
| 235 Chicago Avenue | $159,900 | 2019-06-28 | 1951 | 1,200 |
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 18 homes for sale in Valparaiso, homes for sale in 32580.