1365 Westbrook Street. The Francis Waldo / Daniel Dole house.

Much has been said and written about General Samuel Waldo. War hero. Scoundrel. Promoter of colonial settlement. Opportunist. Above all of these, for our purposes, he was a powerful force in the early settlement of Portland and the area.

Waldo came to the area with Thomas Westbrook somewhere around 1720. Over the next 40 years, he would amass large holdings of land in the area and throughout what would become the State of Maine. His name would live on in Waldo County where many of his land holdings were located.


When Waldo died in 1759, his holdings in Stroudwater passed to his son Francis. Francis was a Harvard graduate and the first collector of customs for Falmouth along with being named to the General Court in 1762 & 1763. It was around this time that he built his home overlooking the Fore River and Stroudwater Landing.

I wonder when the Victorian era bay on the left was removed.

Francis Waldo died on April 16, 1770. In June of 1770, Daniel Dole purchased the property from Waldo’s estate.


The Francis Waldo – Daniel Dole house from Myrtle K Lovejoy’s “This Was Stroudwater”

The house is a pretty common, if a bit compressed, gambrel-roofed Georgian form. Any sort of flourishes often seen in contemporary examples seen on the coast of New England are limited and very low key. The aisle on the left is unique. It seems to be original given the details. The current form is probably original. The bay seen in the 1924 tax photo and the small vestibule on the street side seen in the photo above from the ’50s having been removed. Pity the white paint.


A classic Georgian entry motif

The home remained in the Dole family for the next 154 years before being sold in August of 1924 to the Maxfield brothers. They sold it to the Andrew family in 1953 and the Andrew family sold it to the current owner in 2009. This means through its 254-year life, the home has had only 5 owners. An amazing example of stability.

1.15.17 Update: I received a comment from the current owner of the property, John Ellingsworth.

4 thoughts on “1365 Westbrook Street. The Francis Waldo / Daniel Dole house.

  1. John Ellingsworth

    Hi alewifecove!

    Sorry for just getting back around to your article – I’ve been to the nether reaches of the interwebs; it’s a big place and takes some time. I am sure I found your post in my never ending research on the history of the house, Stroudwater, Falmouth, Portland, Maine, Waldo’s, Dole’s, Pearson’s, etc etc.

    I did want to point out something I believe significant to your post: This house probably belonged to Colonel Samuel Waldo, Jr. – son of the General – and brother of Francis Waldo. When Samuel Sr. died in 1759, 1/2 of his estate went to Samuel Jr. (the other quarters were divided between Jr.’s siblings Francis & Sarah). In 1770, when Jr. died, much of his estate then went to Francis, who by that time had more land and property than he knew what to do with. He promptly sold the land with the house to Daniel Dole in 1770; this is the first recorded reference to the house. Clearly it existed before 1770, and it is obvious Francis was not the original builder but certainly an owner.

    The outstanding question I continue to research is: was it built by Samuel, Jr. & when? Or was it built by Samuel, Sr. – the general – & when? Many people mix up father & son Samuel, so it makes seperating fact from speculation an interesting challenge.

    Alas, we may never know, but I will continue to search and update you with what I find. See you next time!


    1. Abbie A. Barber

      My father David Andrew, did much research on the house and found somewhere in the Portland Historical Society papers that the Daniel Dole House was built in 1745.



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