Madison Ave cottages are in a great location. Just a few blocks from pretty much Everything Bainbridge has to offer. Waterfront parks, Library, High School, Aquatic Center, Medical/ Dental, Groceries, Restaurants, Shopping, Performing arts, Galleries, Gyms, Ferry,,... you name it. Pretty much in the heart of downtown without being On the main commercial strip. There are a number of different cottages and homes/ townhomes in this vicinity so prices are great for buying and choices give options of maintenance included in HOA fees or not. Garden space or not, garage or not etc.
I'd say it's one of the best locations to enjoy Winslow and not even need a car.