In 1846 this property was described as being in the occupancy of Dr. J. E. Hooper. The original house on this lot would have been built as early as 1796 or as late as the 1840s. After the property was purchased in 1796 by Thomas Jackson, he passed it to Mary Jackson who married William Harrison, who passed the property to Elizabeth Ann Harrison, who married Thomas B. Sherman. After 1796, the next deed recorded was in 1846. The original house was moved to the back of the property when the current house was built on the front of the lot in 1929. A 1943 deed excepts from the conveyance "a three room house on the rear of the lot with the right to remove the same at any time on or before 1 January 1944." Brian Tolley reports that the original three room house was demolished.
James Cheesman (b. 1895) stated in 1990 that this was where Dr. Jacobs had an office. He stated "the house has been built and the office moved back." On the 1877 map there is a house at this location and an office on the Edmondson House lot. However, by 1922 the office no longer existed and the original house on this lot remained. Perhaps the original office of Dr. Jacobs was moved or destroyed and later he used the house that was on this lot in 1877 as his office.
Notes from Brian Tolley
My parents currently live at 11 main street where the JR Webster property is. Their house was built in the late 1920's. Apparently the newer house was built by the Webster sisters and they lived there for a few years before selling it. Mom and Dad bought the house from Johnnie Rickwood in 1974. He may have bought it from the Webster sisters in the 1950's. There was an earlier house on their property that was demolished and is shown on the 1877 and 1922 map. There are still bricks and an old well that was filled in sometime ago. The back wheels of a tree trimming truck sunk into the well back in the early 80's so we filled it in more. The older house was located a little further back than my parents house and was a little smaller.
The Light Post between the Webster property and Edmondson House was typical of East New Market at the turn of the century.