The Reynolds and Lois Greenman House was built in 1866 and lived in by one of the most successful and significant commercial businessmen in old Milton Junction, the west side of today’s City of Milton, Wisconsin. Reynolds Greenman was a lumber yard owner and contributed considerably to the growth and development of the community during its formative years.

Greenman came to the old settlement of Milton as a boy in 1851 and attended the old Milton Academy, the school that grew into Milton College. He studied law for a while, but gave that up when he saw an opportunity to make money developing a new community. In 1863, Greenman and his new wife, Lois, came to Milton Junction, where Greenman opened a lumber yard only a few years after Milton Junction was first platted. Greenman had an almost monopoly on building materials and for 27 years, he operated a successful business. This house, which Greenman built for himself and Lois in 1866, was a showplace for a lumber yard owner, with its up-to-date Italianate style and its abundant use of wood products.

After Greenman sold his lumber yard in 1891 he had already started his second commercial career in Milton. In 1889, he bought a joint interest in a newspaper, the Milton Junction News. For 10 years, Greenman was a part owner and editor for this newspaper. As such, he probably had a continued influenced on the development of Milton Junction.

Not only was Reynolds Greenman a significant businessman in the community at a very important time in its development, he was also a popular public servant, serving on numerous local boards. The Reynolds and Lois Greenman House, a large and fashionable residence, is a fitting local landmark for someone who was a commercial and community leader in 19th century Milton.

In the twentieth century, this house continued to have a role in the commercial history of Milton. Later owners of the house, S.C. Hull and Hubert Wright operated an insurance office since Hull founded it in 1936. An insurance office still operates out of this house.