Richard was born about 1677, a date indicated by the time of his coming of age and being able to distribute his father's estate. 
He was the son of Adam Shipley. There has been persistent speculation that his mother Lois was the daughter of Cornelius Howard, however, the evidence, shown in The Legend of Lois Howard Shipley is that Cornelius had no daughter Lois.
His occupation, in addition to "planter" -- the owner and manager of large estates, was carpenter.
His father died about 1698 when Richard, the eldest, was just 21 and his brothers and sisters were not yet of age.
Richard was the eldest son and by right of primogeniture the heir of his father. He made a fair distribution of the estate to his brothers and sisters, retaining 300 acres of Adam the First for himself."  Along Maryland 108, adjacent to the Adam Shipley cemetery, is an historical marker commemorating the patenting of Adam the First by Adam Shipley over 300 years ago in 1687. This was the first large patent in the area that later becaome Howard County, Maryland.
In his gifts of property to his younger brothers and sisters he gives as his motive, "natural love and affection."
In 1698, Richard SHIPLEY for love and affection towards his younger brothers gave them land.
What happened was that since someone couldn't find a deed of the SHIPLEYs buying the land, they speculated that it may have been inherited, and that Lois may have been a HOWARD. Someone else came along and dropped the speculation, stating it as fact she was a HOWARD. The progression was that someone then decided she must be the daughter of Cornelius HOWARD. Many early Anne Arundel deeds were burned in a courthouse fire, which is why they did not find a deed. The details of how Adam SHIPLEY acquired the land are, though, contained in a HOWARD deed that after the fire was rerecorded at the request of Ruth HOWARD, widow of Philip HOWARD. On 19 Jan. 1687 Cornelius HOWARD, son and heir of Cornelius HOWARD conveyed 500 acres of *Howard and Porters Range* to Philip HOWARD. It was stated that the parcel by survivorship descended from Peter PORTER to Cornelius HOWARD, and that Cornelius HOWARD had sold 150 acres to Lancelott TODD, and sold 100 acres to Addam SHIPLEY. [AALR 1H1:243] So, although the deed from Cornelius HOWARD to Adam SHIPLEY was not rerecorded, this shows how he acquired the tract. It was not by inheritance through his wife Lois, but by a simple sale. Cornelius HOWARD died in 1680, and did not name a daughter Lois in his will. [Maryland wills 2:107-110] 
About 1703 he married Susannah Stevens. There have been several different theories about her parentage, especially since his brother married an Elizabeth Stevens at roughly the same time, but the two are not believed to be sisters. More detailed discussion on Susannah's profile.
Richard's will was made October 5, 1724, proved in Baltimore County on 24 August, 1725. (BCW 1:205)  His estate was inventoried on 30 Sep 1725 by Joshua Dorsey and John Dorsey and valued at L147.3.6. His brothers Peter and Robert signed the inventory as did his executrix, Susanna Shipley (BCI 4:46). His executrix administered his estate on 4 Jul 1727 (BCAA 3:66). 
The Will of Richard Shipley, planter, Baltimore Co.,was made 5th Oct., 1724 and proved 24th Aug., 1725. It's provisions included:
What is the relationship of Susannah and Benjamin?
Richard claimed no virtue for his justice and made a fair distribution of the estate. His will breathes piety and faith in God and makes ample provision that the family might be kept together. He died a comparatively young man, having made his last will and Testament October 5, 1724, which was probated October 24, 1725, between which dates his death certainly occurred. At the time of his passing, none of his children were of age. 
His descendants are probably the most numerous of all the Shipley's who trace their ancestry back to Adam.
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