Family forests represent the largest proportion of forestland within the United States; however, the processes of forest conversion, fragmentation, and parcelization are drastically impeding the ability to manage these lands and maintain the benefits they provide. One factor suggested as driving this trend is the inability of landowners to meet the property tax burden on their land. We evaluated the effectiveness of three tools commonly suggested for meeting the financial demands of property taxes: (1) use of economic returns from timber management, (2) enrollment in a current-use tax program, and (3) sale of a conservation easement, within a rural watershed in western Massachusetts. Our results indicate that revenue from timber management is insufficient at covering property taxes and that application of measures such as the sale of conservation easements will be critical in maintaining the viability of forest ownership in areas of rising land values and property taxes.