Another of Andrew's daughters, Elizabeth, married coal miner Thomas Black and lived in the house from around 1855. They were still there in the both the 1861 and 1871 census, along with their children (most of whom were likely born in the house). One of their daughters, born in 1857, was named 'Helen Lundin Brown Black' - her middle names presumably taken from the then minister of the Free Church in Largo, Rev. Robert Lundin Brown.
Elizabeth Black died in 1879 aged 54. By the 1881 census her widower, Thomas, was living in the smaller part of what was then named 'Wynd House'. One of his daughters (Ann) lived in the main part of the house with her second husband William Cowan (a flax scutcher), her 3 children from first marriage (to Walker Harris), plus their 2 children together. In 1891, Ann Cowan was in the main part of the house with six of her children, while two lodgers were in the annex. By 1901, the house has been renamed 'Woodwell House' although still occupied by Ann Cowan, two of her daughters and a domestic servant. The annex was occupied by one lodger - local police constable, William Mitchell.
In the 1911 census three Cowan sisters were living at Woodwell - Rose Ellen, Edith and Caroline, along with Edith's husband John Warrender. Their mother Ann Cowan (daughter of Elizabeth Dall and Thomas Black) lived at Earnest Cottage just down the road from her daughters until she died there in 1915 aged 69. The children of Ann Cowan collectively owned Woodwell for decades after that. Edith and John Warrender lived in the main house, while the annex had various tenants. Peter and Agnes Bloomfield lived there in the early '40s until Agnes's death at the house in 1943 aged 81. The Bloomfields relatives, John Mackie (gardener at Kellie Castle) and his wife Janet Younger, then lived there. Janet Younger Mackie died at Woodwell in 1944.
During the late 1940s and early 1950s the house was occupied by David and Jane Erskine and their daughter Jessie. When Jessie married John Aitken in 1950, they lived in Woodwell House also, until it was condemned. Both the Erskines and the Aitkens were rehoused in Durham Cresent, Lower Largo, when it was newly built. Although that marked the end of an era for Woodwell House, the site was reconfigured to become a garage/workshop - in which form it can still be seen today on the east side of Largo Road (see image below).