There is an article on this family by Don C. Wood in "The Berkeley Journal, Back Creek Valley, Part I" issue 21, 1996:
"The 1782 land books for Berkeley County list James Winning with 157 acres.The earlier deed has not been located."
"On April 9, 1794 John Frank and wife Barbara sold for 100 pounds, 190 acres and 198 acres to Samuel Winning.The first tract had been granted to John Frank by Lord Fairfax 19 March 1769.The land was 1/2 mile from Back Creek on Barawicks Road."
"James Winning purhased 50 acres of land in Back Creek Valley 22 May 1794.Abraham Adlinger and Mary, his wife, sold to James Winning for 50 pounds Pennsylvania currency 50 acres on Back Creek adjoining Martin Houseman and Edward Beenson."
"On 21 April 1800 James Winning purchased for $2,000 two 50-acre tracts alongside Teter Myers and John Turner.James Winning wrote his will 24 August 1803 and it was probated 24 February 1804.To his wife Mary all the benefit of the plantation 'that James Cunningham now lives on.'Son Samuel Winning was to receive 80 pounds and 'what he has already gotten.'Son James was to get 40 pounds, daughters Peggy, Nancy and Elizabeth were to get 125 pounds each and Elizabeth 50 pounds more.To son John 'the plantation I now live on, he to pay legatees one half of what is coming to them.To Alexander the plantation where James Cunningham now lives."
"Alexander was dead by 1809.His will read; 'The place where James Cunningham now lives from my father's will to be sold, give 100 acres to Margaret (Peggy) Cunningham, rest to brother and sisters Samuel, John, Margaret and Nancy Cunningham.To brother John his saddle, to his brother Samuel daughter Jane my bed and bedding."
"Samuel Winning died in 1813 leaving a will.He named his wife Elizabeth Winning who was to have her one-third and the 50 pounds that was left to her by her father James Robinson.He did not name his children but the plantation was to be sold after her death.Prior to his death Samuel Winning had agreed to sell the interest he had inherited from his brother Alexander.A deed had not been drawn up.His heirs who were widow Elizabeth, Edward, James, George, Thomas and Isaac Winning sold their interest to the children of their uncle, John Winning."