Overseas Highway, Upper Matecumbe Key Islamorada, FL
Everything we know about Overseas Highway in Upper Matecumbe Key Islamorada: 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.
136 homes sit on Overseas Highway in Upper Matecumbe Key Islamorada, FL (ZIP 33036), built 1940–2026, a typical 2,444 sq ft with 3 bedrooms. 28 are for sale right now from $399,000 to $29,000,000. Homes that sold since 2023 went for a median $3,525,000.
For sale on Overseas Highway now
The homes on Overseas Highway
114 single-family, 22 condo/townhome/other. Built by decade: 1940s 2, 1950s 17, 1960s 19, 1970s 22, 1980s 24, 1990s 17, 2000s 18, 2010s 7, 2020s 8.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 87950 Overseas Highway | $3,600,000 | 2026-10-22 | 1973 | 2,464 |
| 75840 Overseas Highway | $11,500,000 | 2026-09-11 | 2025 | 5,900 |
| 87200 Overseas Highway Unit O 6 | $500,000 | 2026-08-26 | 1980 | 1,354 |
| 75560 Overseas Highway | $5,325,000 | 2026-06-22 | 2005 | 3,228 |
| 75851 Overseas Highway | $5,475,000 | 2026-05-05 | 1992 | 3,978 |
| 76434 Overseas Highway | $2,000,000 | 2026-05-01 | 1986 | 1,509 |
| 82260 Overseas Highway | $880,000 | 2026-04-15 | 1964 | 2,314 |
| 82238 Overseas Highway | $8,300,000 | 2025-10-17 | 2015 | 6,866 |
| 76180 Overseas Highway | $27,750,000 | 2025-10-06 | 2024 | 10,228 |
| 75621 Overseas Highway | $1,650,000 | 2025-07-23 | 1959 | 1,322 |
| 75061 Overseas Highway | $2,850,000 | 2025-05-06 | 1983 | 1,616 |
| 85331 Overseas Highway | $2,700,000 | 2025-05-01 | 2024 | 2,880 |
| 85327 Overseas Highway | $3,300,000 | 2025-01-17 | 2024 | 2,880 |
| 80908 Overseas Highway | $3,560,000 | 2024-12-20 | 2000 | 5,244 |
| 75261 Overseas Highway | $5,250,000 | 2024-10-15 | 2020 | 3,014 |
| 75091 Overseas Highway | $2,300,000 | 2024-07-25 | 1986 | 1,534 |
| 75631 Overseas Highway | $3,500,000 | 2024-02-12 | 1992 | 2,502 |
| 76200 Overseas Highway | $2,990,000 | 2024-01-16 | 1958 | 1,361 |
| 75751 Overseas Highway | $7,625,000 | 2023-12-15 | 1997 | 3,113 |
| 80980 Overseas Highway | $4,000,000 | 2023-10-31 | 1973 | 3,992 |
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 29, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 28 homes for sale in Upper Matecumbe Key Islamorada, homes for sale in 33036.