Main Street, Windermere, FL
Everything we know about Main Street in Windermere: 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.
42 homes sit on Main Street in Windermere, FL (ZIP 34786), built 1942–2015, a typical 2,114 sq ft with 3 bedrooms. 2 are for sale right now from $1,572,000 to $2,099,000. 2 closed in the last 12 months at a median of $769,500. Homes that sold since 2023 went for a median $850,000.
For sale on Main Street now
Recent sales on Main Street
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 811 Main Street | $690,000 | 2026-09-22 | 2 / 1.5 | 1,398 |
| 111 Main Street | $849,000 | 2026-07-01 | 3 / 2.0 | 2,272 |
The homes on Main Street
42 single-family. Built by decade: 1940s 4, 1950s 5, 1960s 7, 1970s 4, 1980s 11, 1990s 2, 2000s 4, 2010s 5.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 811 Main Street | $690,000 | 2026-09-22 | 1985 | 1,398 |
| 111 Main Street | $849,000 | 2026-07-01 | 1984 | 2,272 |
| 1209 Main Street | $925,000 | 2026-01-05 | 1979 | 2,095 |
| 720 Main Street | $850,000 | 2025-10-21 | 1980 | 2,778 |
| 729 Main Street | $2,065,000 | 2025-07-14 | 2015 | 3,950 |
| 116 Main Street | $695,000 | 2025-06-13 | 1958 | 1,269 |
| 904 Main Street | $3,650,000 | 2025-04-30 | 2003 | 6,079 |
| 19 Main Street | $1,150,000 | 2025-02-05 | 1959 | 2,331 |
| 133 Main Street | $550,000 | 2024-10-31 | 1963 | 1,166 |
| 1027 Main Street | $690,000 | 2024-03-22 | 1988 | 1,596 |
| 1003 Main Street | $705,000 | 2024-03-06 | 1988 | 2,005 |
| 925 Main Street | $940,000 | 2023-09-18 | 1984 | 2,971 |
| 323 Main Street | $1,150,000 | 2023-07-10 | 2015 | 2,106 |
| 106 Main Street | $592,500 | 2023-07-10 | 1979 | 1,995 |
| 11 Main Street | $1,050,000 | 2023-04-13 | 1955 | 1,638 |
| 905 Main Street | $650,000 | 2022-11-04 | 1981 | 1,921 |
| 1017 Main Street | $640,000 | 2022-08-12 | 1988 | 1,925 |
| 835 Main Street | $799,000 | 2022-06-10 | 1984 | 2,489 |
| 5 Main Street | $1,062,000 | 2021-12-08 | 1966 | 2,160 |
| 63 Main Street | $749,000 | 2021-12-03 | 2014 | 2,186 |
Communities along Main Street
- windermere town · 21 homes on the street
- Windermere · 11 homes on the street
- Davis Shores · 5 homes on the street
- Lake Butler Park · 1 homes on the street
- Lake Butler Park · 1 homes on the street
- Lake Butler Park · 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 October 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 236 homes for sale in Windermere, homes for sale in 34786.