Winona Avenue runs from Lake Flower Avenue south to Dorchester Road where it becomes Santanoni Avenue.
| Old Address | Post-911 Address | Building Name | Cure Evidence/Notes |
| 1 Winona Avenue | 1 Winona Avenue | TBSWC, DIS 1928 | |
| 3 Winona Avenue | 43 Winona Avenue | Slater Cottage 2 | TBSWC, DIS 1912-13 |
| 4 Winona Avenue | 47/50 Winona Avenue | 4 Winona Avenue | |
| 5 Winona Avenue | 39 Winona Avenue | 5 Winona Avenue | |
| 6 Winona Avenue | 44 Winona Avenue | 6 Winona Avenue | |
| 7 Winona Avenue | 33 Winona Avenue | 7 Winona Avenue | |
| 8 Winona Avenue | 40 Winona Avenue | 8 Winona Avenue | DIS |
| 9 Winona Avenue | 29 Winona Avenue | 9 Winona Avenue | |
| 10 Winona Avenue | 34 Winona Avenue | 10 Winona Avenue | |
| 11 Winona Avenue | 27 Winona Avenue | 11 Winona Avenue | DIS |
| 12 Winona Avenue | 28 Winona Avenue | 12 Winona Avenue | |
| 13 Winona Avenue | 23 Winona Avenue | Oldis Cottage | DIS 1929 |
| 13 1/2 Winona Avenue | 21 Winona Avenue | Aitken Cottage | DIS |
| 14 Winona Avenue | 22 Winona Avenue | 14 Winona Avenue | |
| 15 Winona Avenue | 19 Winona Avenue |
 15 Winona Avenue |
Cure Cottages, p. 18 |
| 16 Winona Avenue | 16 Winona Avenue | ||
| 17 Winona Avenue | 9 Winona Avenue | 17 Winona Avenue | |
| 18 Winona Avenue | 7 Dorchester Road | ||
| 19 Winona Avenue | "College Hall" |
 19 Winona Avenue |
TBSBC, DISNurses House |
| 20 Winona Avenue | 23 Santanoni Avenue |
 Saranac Lake General Hospital |
|
| 21 Winona Avenue | 3 Winona Avenue |
