Glimpses. 499 Ocean Avenue

Built ca: 1860 by Moses Dow

A small Italianate near Payson Park.


The history books note 499 Ocean Street for it being owned by a rather famous veteran of the Civil War. And, while this is indeed true, the period said veteran owned our subject is less than 5 years out of the 160 since it was built. Also, the house had existed for almost 60 of those years before being purchased by the GAR founder. There’s a lot more of a story at 499 Ocean Street.

The Second Parish Presbyterian, aka ‘Payson Memorial’, Church at the corner of Pearl and Congress streets. Maine Memory Network

The Payson family had owned property on the north side of Back Cove for some time when Henry sold the land for our subject to Moses Dow in 1858. Henry was one of 8 children born to Edward and Anna Payson. Edward was a minister and noted theologian in the early part of the 19th century. The Second Parish Church that once stood on Congress Street was long known as the ‘Payson Church’. Henry was born in 1821. His first wife and son died in 1849 and Henry, with nothing left to lose, headed west in 1850 to make his fortune in the goldfields of California. With little success there, he moved back to Portland in 1854 and opened a small stock and securities office on Exchange Street. That small start would become a successful business that exists to this day.

The Payson house on Back Cove. Maine Memory Network

In the early 1850’s, Henry’s brothers Edward and George contracted with the local architect Henry Rowe to design and build a gothic cottage near where our subject was later built. The cottage was built of brick made of mud dredged from the cove nearby. Legend is that the bricks were found to be too porous and the building had to be stuccoed afterwards to keep the moisture out. This oddly fascinating structure stood in what is now Payson Park until the late 1950’s.


499 Ocean Street is a two storey house in a vaguely Italianate mode. Details are few. The windows of the first floor are quite deep in an almost Greek Revival manner. The entry portal is arched and rests on paired posts with Doric capitals. These posts could be described as ‘Colonial Revival’ if that term had been invented in 1860. The roof is so low hipped as to be almost flat. A covered porch ran the entire length of the south west side of the house as seen in the 1924 tax photo. The handsome barn, suitable for horse and carriage and perhaps some chickens, was built at the same time as the house.


Moses Dow was a merchant who sold salt and corn meal that was ground in his mills on the Presumpscot River in Westbrook where he lived. He ran a wholesale office at the head of Long Wharf between Fore and Commercial Streets. Dow owned the property until February of 1861 when he sold it to a hat seller originally from Norridgewock named Moses Palmer. Moses Palmer, his brother John and their families shared a house on Oxford Street and the brothers operated out of the same space on Middle Street where Moses sold premade inventory and John handled custom orders or ‘jobbing’ as it was known. In August of 1863, Moses sold 499 Ocean Avenue to John Palmer for $1000. In March of 1865, John sold it to Margaret Purington.


Margaret was a widow who lived in Westbrook with her son Albert and his family when she purchased our subject from John E Palmer for $1500 in 1865. In 1871 she took a mortgage for $1475 from a Nathan D Hill of Rollinsford New Hampshire. Hill and his wife Mary were English born and had come to the US in the late 1840s. Nathan worked as a clerk for one of the cotton mills on the Salmon Falls River that runs through the New Hampshire/Maine border town. In early 1871, Nathan started writing mortgages in the Portland area. Between February of that year and October of 1875, he wrote 125 mortgages of which Margaret’s was an early one. What happened with her mortgage is an odd story.

  • October 16, 1871. Margaret takes the above mentioned mortgage. Note carries 8% interest and requires semi annual payments and a 5 year term.
  • December 1, 1871. Nathan Hill assigns his entire portfolio of loans, including Margarets, to the Rollinsford Savings Bank.
  • April 29, 1872. Nathan Hill files a note of discharge stating Margaret has satisfied the conditions of the note and now has complete ownership of 499 Ocean Avenue.
  • April 21, 1874. Margaret Purington dies at the age of 67 and is buried in Evergreen Cemetery.
  • April 27, 1881. The Rollinsford Savings Bank files a ‘Certificate of Entry for Foreclosure’ on 499 Ocean Avenue.
  • September 18, 1883. The Rollinsford Savings Bank assigns the mortgage to John Proctor. Proctor is a Portland realtor whose father was a pioneer of the industry in Portland.
  • January 17, 1884. John Proctor assigns the mortgage to Ryerson Pride of Westbrook.

Not being an expert on real estate law in the late 19th century, I have no idea how the above scenario happens. If the mortgage was assigned in 1871, how was Hill allowed to file a note of discharge in 1872? There is no will or probate on file for Margaret so we cannot determine how the property was handled after her death. None of her children show up in the Registry of Deeds for the property. It’s a very odd mystery.


When Ryerson Pride bought 499 Ocean Street from John Proctor in 1884, he was a prosperous farmer in Westbrook. His wife Rachel had died in 1865 and he was raising their daughter Martha on his own. I do not believe they lived in our subject. The Prides sold it 1887 and Ryerson died in 1889. The purchaser in 1887 was Caroline Record. Caroline’s husband worked as a stable hand and then in the shoe shops in Westbrook. He died in 1907. Caroline sold the house to Joshua Lawrence Chamberlain in 1909.

Joshua Lawrence Chamberlain. Bowdoin College

Joshua Lawrence Chamberlain needs no introduction. From a simple upbringing in Brewer Maine to the Civil War, Governorship of Maine and presidency of Bowdoin College, his name is writ large on the state’s history. By the time he enters our story however, he is in the twilight of his life. Chamberlain had retired from Bowdoin when he accepted the position of Collector of Customs for the Port of Portland in 1899. His health was suffering from wounds suffered in the war. More importantly, he was destitute. A series of poor investments had drained any financial resources he had.

Falmouth Hotel in 1900. Maine Memory Network

Initially, Chamberlain took a room at the Falmouth Hotel in Middle Street but by 1906, the year after his wife’s death, was renting our subject. He died on February 24th of 1914. His funeral was a major event for both Portland and Brunswick where he was buried with his wife. On March 21st of 1914, his will was probated and 499 Ocean Street was transferred to his daughter Grace Allen and her husband Horace. They rented the property to a dentist and Bowdoin College Alumni named Henry Gilman and his wife Maude before selling it to them in 1918. 

499 Ocean Street in 1924. Maine Memory Network

Maude Gilman died in 1955 at which time Henry inherited it. Upon his death in 1968, his entire estate, including 499 Ocean Avenue was donated to Bowdoin College. The following year, Bowdoin College sold it to a Catholic priest from Old Town Maine named Romeo A St Pierre. St Pierre would own it until 1992

499 Ocean Street is currently listed as a single family residence. The owners are a trial attorney and contractor. Condition is excellent.

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