Assignment of Membership Interest by and between Chesapeake Custom Homes, L.L.C. and Old Line Bancshares, Inc. dated as of November 1, 2008

Exhibit 10.44

For and in consideration of the payment of Two Hundred Five Thousand ($205,000.00) Dollars and other good and valuable consideration, the receipt and sufficiency of which is hereby acknowledged, the undersigned CHESAPEAKE CUSTOM HOMES, L.L.C., a Maryland limited liability company ("Assignor") does hereby sell, assign, transfer and convey to OLD LINE BANCSHARES, INC., a Maryland corporation ("Assignee"), its successors and assigns, all of Assignor's right, title and interest to a twelve and one-half percent (12.5%) Membership Interest (as defined in the Company's Operating Agreement, as amended) and Percentage of Membership Interest (as defined in the Company's Operating Agreement, as amended) in Pointer Ridge Office Investment, LLC, a Maryland limited liability company (the "Company").

In Witness Whereof, the undersigned has hereunto set his hand

and seal this 1st  day of November, 2008.

		CHESAPEAKE CUSTOM HOMES
		L.L.C., a Maryland limited liability
		company
Katie Stewart		By: Greg S. Wilby                (SEAL)
		Greg S. Wilby, General Manager