Owners of the Campobello Company hoped to enhance their one million-dollar investment by subdividing their land and selling the smaller lots to hotel guests, island residents, and others. Only a few of the lots were actually sold and built upon. however, at least nine cottages were constructed between 1884 and 1902 on land purchased from the company. In addition, two existing homes were purchased and transformed into more elaborate summer homes. These summer residences became Campobello's summer colony.
The summer cottages had oil lamps and candles for lighting. A butcher's cart brought vegetables and meat three days a week and a dairyman delivered milk, cream, butter and eggs. Colonists went or sent to Eastport for fruit, vegetables, mail and newspapers - items not readily available on Campobello. Towels and bedding were collected weekly by the laundry wagon; housekeepers laundered personal clothing. Cottage owners brought their own staff with them and/or employed local workers. Drinking water either came from the hotels or was delivered weekly. Ice was available at the hotels or, in later years, from icehouses built by the cottage owners.
At least some summer residents developed close ties with Campobello families. FDR and his family enjoyed long-standing relationships with the Calders, Lanks, and others. Summer colonists also took an active part in the community, donating funds for a library (still in existence) and raising money for a church hall.
Victorian-era resorts eventually experienced a decline in popularity. Families aged or lost interest in Campobello, maintenance costs and taxes increased, and cottage owners wanting to sell or rent their summer homes were unable to do so. Subsequently, several summer colony homes were torn down. Only the FDR, Hubbard, Prince, Wells-Shober, and Johnston cottages remain.