A brief piece of Winchester History
From a copy of "Broadneck Maryland's Historic Peninsula"
published by the Broadneck Jaycees in 1976. As quoted directly from p. 53:
"Located to the north of Pendennis Mount, the sites of the present communities of Severnside, Winchester and the Manresa Retreat House were purchased by Jacob Winchester in 1849 and 1854. His home was called Severnside or Severn Heights. Originally from the eastern shore, Mr. Winchester was married to Mary Ridout, granddaughter of John Ridout. His land stayed in the hands of descendants until 1900s. Samuel Lucas lived on the site of the present community of Winchester on the Severn in 1878.
These 80 acres were purchased in the 1920s by the four Matthews brothers who were manufacturers of paper boxes in Baltimore. Each brother built a house on the land and the houses were connected by an oyster shell road. Three of the houses are still in use as the private homes of the Dr. Gerald Church family, the Capt. Harry D. Helfrich family and the Douglas C. Smith family. The Matthews lost the estate in a bank foreclosure during the Great Depression. A Catholic religious order held the estate briefly and then resold to the Charles L. Pumphrey Company. Pumphrey surveyed the land for individual home sites, installed waterlines and set aside two areas for swimming beaches and several sites as potential dock sites.
In 1963, the
remaining lots were sold to Charles Steffey's Lexington Construction
Company. Steffey built several private homes and also contributed the land
for the Chase Creek Swim Club. 
Winchester on the Severn, Inc., became a recognized association in the
1950s. It has purchased additional community owned property and has annexed
a bulkhead and built docks and slips."
If you have more facts about the history of Winchester and would like to contribute to this page, please send to Winchester History.