As women of color in the 19th century, Mary and Eliza Freeman defied constraints of freedom, social innovation and entrepreneurship. Born in 1815 and 1805, respectively, Mary and Eliza lived as free African Americans. One sibling of Mary & Eliza’s, Joel Freeman, became a leader of the free black community in Bridgeport, known as “Little Liberia”. For previous years, the sisters lived in Derby & New York City and upon selling their family holdings in Derby, they purchased adjoining lots in Little Liberia. They constructed sizable homes that they leased as rental properties while they continued to live and work in New York over the next decade. The Freeman Houses stood tall: imposing sights on the 19th-century streetscape, donned with bright and expensive pigments, embodying the prosperity of this community. Both sisters developed, bought & sold real estate & managed property before women had the right to vote. When Mary Freeman died the only Bridgeporter of greater wealth was PT Barnum.