[1] In 1785, John Sterrett purchased 1,626 wooded acres with several buildings named "Felicity" from Mathias Hammond, a participant in the 1774 sinking of the Peggy Stewart.

The site known as "Oakland Mills" served as a postal stop, and the name was later used for one of the Rouse development company villages.

Charles Sterrett Ridgely forfeited the house in 1826, selling it to Robert Oliver for $47,000 after failing to make payments toward the property.

He sold it for $58,459.95 in 1838 to George Riggs Gaither, who operated the manor as a productive slave plantation producing wheat, corn, oats and hay.

[5] In October 1862, six Union troops from New Jersey raided the Oakland Manor as a Southern sympathizing plantation with the owners joining the Confederate Army.

In 1877, Morris began a significant grounds improvement program removing Hawthorn hedges and replacing them with wood fencing throughout the property manufactured at the Oakland Mills sawmill.

Attorney Bernard F. Goldberg negotiated the deal early in his career before his prison term for misappropriation of land development funds.