Historical Information


A History of Chesopeian Colony as Told by Those Who Lived It (1957-2017) – Betty B Kennedy

This was published in the Chesopeian Colony Newsletter in 2017.

Some of the following information about Chesopeian Colony and how it started was taken from an article in The Virginian Pilot from October 2008 by a Joanne Kimberlin. I will repeat here some of the things that she investigated about the beginning history of our beautiful and unique neighborhood and further information shared by former early residents and personal observations. Our peninsula and the areas of Virginia Beach, Norfolk and Chesapeake were once inhabited by an Indian tribe known as the Chesapeakes. They may have lived in the area for thousands of years. “The people took their name from the Chesapeake Bay, whose name in Algonquin means ‘Mother of Water’.” It is believed that Chief Powatan, to the west, who had built a nation of many tribes, was told by a priest that “an enemy from the east would conquer his empire.”

Since the Chesapeakes to the east had refused to join with Powhatan and wanted to maintain their independence, Powatan believed this referred to the Chesapeakes; therefore, Powhatan destroyed all of their men and women and took the children into his tribes, including the Nansemond Tribe, who were allies nearby. Little did he realize that the true threat to his kingdom was to come from the East later, but in the form of the English Colonists. Relics found show evidence of the existence of tribes in the area.

An amateur archaeologist named Floyd Painter retrieved many ancient relics from various areas in Virginia Beach, including the grave of an American Indian king, “whose remains were draped in the finery of 30,000 shell beads.” Over the years many Indian relics have been found, including some in our own Colony by various residents digging in their yards. I have what appears to be a stone hatchet head that my son found on my property on the point at the end of Cattayle Run.

Wayne McLeskey, who developed Chesopeian Colony around 1957, was told by an historian that the Indians had favored this spot because of its inlets, tall pines and the beautiful waters. Mr. Hunt (McLeskey’s step-father) owned the peninsula, and he and his mother, Maybelle Hunt, turned it over to McLeskey to be developed. He was so entranced with the area that he moved with his wife Faye and two children into the large old white house on the west side of the point, the oldest home in Chesopeian Colony, built in 1922. It has since been renovated several times but maintains its original charm. It currently is owned and occupied by Floyd and Angela Sawyer who purchased the home in 1982 and is known as 665 Chesopeian Point. McLeskey built the white house on Cattayle Run for his mother where she lived until she died at the age of 101 (?).

Nestled along the wooded pathway, on the opposite side of the point, (on the east side) is the 2nd oldest home in the Colony, built in 1939. It currently is owned by Jim and Sharon LaVier and is listed as 664 Chesopeian Point. At the time that these first two homes were built, there was only a dirt road to Virginia Beach Blvd. We believe that these two houses were part of a farm where two sisters lived, one in each house. It is said that when Fred and Florence Michaels purchased this vintage home in 1959 from a Sarah W. Adams, they found a tomahawk stuck in the trunk of a tree. The Laviers have been living there since 1981. Prior to moving there, they lived on Pine Ridge Lane from 1974 until 1980 when they moved to Richmond. They missed the Colony and Virginia Beach so much that they were thrilled to find this piece of history for sale in Chesopeian Colony.

After purchasing the property, Mr. and Mrs. Hunt (McLeskey mother) turned it over for development to their son Wayne, he proceeded to fulfill his vision of a very special waterfront community hidden away on a peninsula on high land with the beautiful dogwood, pine and oak trees. He named it Chesopeian Colony after the Chesapeake Indians who had once resided here. He laid out the plats and the plans for dredging of channels and submitted them to the city. He built a boat ramp at the end of Queen Anne Rd for the exclusive use of the residents so that all could enjoy boating, even those who were not on the water. He erected the walls at the entrance with the name of his new development and put it on the market. At that time, there was only an open space where the Wal-Mart is today, except for Carol’s Hamburgers.

There were just the two houses on the point and the red brick home built in 1930 just to the right of Chesopeian Colony on Virginia Beach Blvd where the Smiths lived and now operate Smith Electric. McLeskey opened his office across the street at 2859 Virginia Beach Blvd, where it remains today. McLeskey’s company was known as M&S Construction Company, Inc.; today, it is McLeskey and Associates. The first house built by McLeskey, the tri-level house at 400 Chesopeian Trail, has been renovated again by the current owners, Chris Bryant and Skip Cole. The house was built in 1956 for the mother of Betty Spiegel who was married to the famous producer in Hollywood, Sam Spiegel (Bridge Over the River Kwai.). When Betty’s mother moved into the house, the road was nothing but mud. Years later, Betty joined her mother and remained there after her mother died. Betty moved to Mill Creek in Great Neck in 2004.

Six houses were built in 1957. Some of the lots were sold to other builders by McLeskey. One of those homes located at 425 Chesopeian Trail was purchased by a young couple moving from North Carolina – Bill and Madeline Cox. Even though working in Chesapeake, they were entranced by the beauty of the area and Mrs. Cox remained here after Mr. Cox died until she had to go to an assisted living home. When I first wrote this article in 2009, they had the honor of being among the first who purchased here and still lived in the same house, thus making them the resident with the most longevity. Their two daughters, Debbie and Pat, grew up here and graduated from Cox High School. Madeline was honored in 2007 as the queen of the Chesopeian Colony Garden Club’s 50th anniversary float in the 4th of July Parade. She was chosen for being the only original charter member who was still a resident at the time.

It was with great jubilance and enthusiasm that Madeline told the stories of wonderful comradeship among the neighbors, most of whom were young at the time. They were constantly having parties together, helping each other out when needed and having a wonderful life. At Christmas, they would put up and decorate a big tree at the entrance.

They would then get together and sing carols. Dot and Clyde Francis were among those who shared their companionship. Dot, who was a musician, lived just down the street and used to set up a speaker system to play holiday music that could be heard all the way to the entrance. The colony residents would get together for neighborhood parties throughout the year. Some of those other couples were John and Fern Garrow, Peggy and Jim Quinn, Joe and Imogene Phelps. Everyone knew Max (known as Sandy) Sanders, who ran Williams Hardware store, near Kings Grant, where all the Colony went for years, until it finally had to give way to all the new big hardware stores. Sandy lived with his wife Pearl at 2804 Pine Ridge Lane; he always had a helping hand for all. Others were Margaret and Admiral McCune, Max and Florence Rosen, and Lorin and Vinnie Hay. After Vinnie died, he remarried and his new wife Lois, now widowed, still lives in the same house on Chesopeian Trail. At age 92, Lois remains an active member of the Garden Club.


Serving Chesopeian Colony and Surrounding Neighborhoods

Catherine Dozier who lives on Cattayle Run has been living here since before 1969. I believe she has been living here longer than any other resident. I may be 2nd since I bought the property in 1966 and moved in the house in 1969. If you know of anyone who was here before Sept. 1969, please let me know. Florence and Max Rosen moved from Norfolk in 1958 to purchase the contemporary home just off of Chesopeian Trail at 429 to the west in back of the Cox’s home. It was featured in Better Homes and Gardens for its upto-date and contemporary style. Many a party was held there among the young couples with great times had by all. Florence passed away after being in a nursing home and the property was purchased after sitting on the market for some time due to its “outdated style” and wear and tear. The new residents, Chris Hahn (a naval officer) and his wife Emily (an emergency room physician) saw the potential in this home worthy of any Frank Lloyd Wright home and have worked diligently remodeling the home. It is unique in its style and it is a pleasure to see someone willing to tackle a home that once appeared in Better Homes and Gardens restored to its original splendor, yet suited to their needs today. Congratulations to a job well done!

Since then, many homes are worthy of Better Homes and Gardens. It is truly a very special neighborhood with beautiful trees and lawns. We hope that all newcomers will appreciate the special value of our trees and other fauna and do all they can to preserve our neighborhood as it is with our stately and flowering trees. Most residents have done much to enhance and maintain its special beauty. We hope that future changes will maintain the flavor of our special community. What has grown into our active Civic League today started in late 1957 with 4 people at the home of Max Sanders (“Sandy”). Attending were Bill Cox, Lorin Hay, Margaret McCune and Max Sanders (“Sandy”.) Lorin Hay was voted the first president and the Chesopeian Colony Civic League was born. Madeline Cox was then appointed secretary. The Garden Club also was started in 1957 by Margaret McCune. …