Glimpses. 501-509 Cumberland Avenue

Built in 1887 for John W Deering & Jacob S Winslow.

Design by John Calvin Stevens

Built by Portland’s largest ship owner and a successful lumber merchant as an income property. Jacob Winslow was incredibly wealthy and lived on Deering Street. We will spend more time on him in an upcoming post. John W Deering owned a wholesale lumber business and was just finished with his second term as mayor when the houses were built.


The houses are brick, 5 bay wide by 2 bay deep units with rear ells. Details are in wood and brownstone.

Overall, the design is Queen Anne in character but there are early hints of Stevens interest in the ‘new’ Colonial Revival movement. It’s hard to say it would be new for John Calvin as the examples being published in publications of the day, mostly colonial-era buildings in locations like Maine and New Hampshire, would have been every day things for him.

The dentils at the eaves and trim of the pediment and bay windows are all colonial in form and style. Whereas, the details of the facade bays and entries are distinctly Queen Anne.

We also see Stevens beginning to develop a program for the design of double houses on urban lots. This rigidly symmetrical form with the entries on the ends would become a regular device for the firm in many projects over the coming decades.

Both houses are in good shape with 509 showing the ravages of some very unsympathetic renovations. The box store awning window in the dormer could possibly be overlooked if there weren’t those heater vents pushed through the walls.


507-509 Cumberland Avenue would be sold by Jacob’s widow, Melvina, to Stanwood Soule in 1912. Soule subdivided the property. 507 was sold a separate unit the following year. By 1924 it was owned by Raffaele Romano. Soule would hold on to 509 until May of 1916. Perhaps he resided there during this period. The owner of record in 1924 was James Romito. He and his wife Mary also owned 2 family homes on May & Carroll Streets in 1924. The roles list 507-509 as boarding houses.

509 Cumberland Avenue, Portland, 1924

507-509 Cumberland Avenue, Portland, 1924

John Deering sold 501 Cumberland Ave to William Alden in 1892. Alden sold the home to Henry Peters, the owner of record in 1924, in January of 1919. Deering would hold onto 503 until his death in 1914 when it passed to his son, Fred W. He is listed as the owner in 1924. Deering, in 1924, owned 6 properties in the city. 1, at Avon Court, appears to have been his residence. The other 5 are all multi-family, apartments or rooming houses. As with 507-509 Cumberland, 501-503 were shown as rooming houses in 1924.

499-501 Cumberland Avenue, Portland, 1924

499-501 Cumberland Avenue, Portland, 1924

The current tax roles show 501 as condominiums with 503, 507 & 509 as apartments.

This slideshow requires JavaScript.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.