The original Cherrymount Cottage, was constructed in 1956 by Robert “Bob” Doherty, who was a great-uncle of the current owner. The cottage was home to Bob, along with his wife Lily and their daughter Myrtle.

The cottage was built on a plot of land which the family purchased from local landowner Mrs. Crosse-Kelly for £84, the purchase of the site was financed by selling a field at nearby Drumgay. Bob had farmed this field using traditional methods for many years prior.

Originally, the planned cottage was intended for the Drumgay field. However, the Cherrymount site presented a more convenient location closer to Enniskillen. The adjacent orchard field, which they purchased a few years later, allowed the family to maintain their smallholding.

In 2002, Myrtle replaced the original cottage with a new, larger, and more modern Cherrymount Cottage which still stands on the site today.