Oliver Chapman's Cottage · 1882 - 1938 Oliver E. Chapman was one of the founders of Winter Park. His cottage was considered the first house built in Winter Park. Built in the spring of 1882, it was located at the corner of Interlachen and Canton Avenues, on the shore of Lake Osceola. Mr. Chapman purchased the land for his cottage at $ 45.00 per acre! Less grand than other "cottages," Chapman's home appeared more like a lodge, with its massive sloping shingled roof and sheltered porch. The cottage was torn down long ago, c. 1938.