From the book "Pembroke" part of the Bermuda's Architectural History Series published by the Bermuda National Trust in 2017:
Olive Hill
I had no idea that our family had a substantial connection to this property (#47 on the lower portion of the map). A house was built here ca. 1715, which was significantly expanded after 1861. The brothers Edward (died 1790) and William bought the property about 1789, just before Edward died. Edward left his Spanish Point property to his son John, and his Olive Hill property to his other son, Josiah William, with the stipulation that his wife Christianna could live there for the rest of her life. Josiah died, apparently childless, in 1816. John inherited the house and 12 acres when his mother died in 1831. John died in 1847 and the property went to his son Edward (1806-1895). Edward sold it to Solomon Sears in 1861. These are the notes from the Pembroke book on Olive Hill:
Demolished 1994, 46 Pitts Bay Road, built before 1715. The Dunscomb's owned this property from 1789 till 1861. Pitts Bay Road turns north and away from the waterfront at Olive Hill. The original house of that name at 46 Pitts Bay Road was demolished in 1994 but for over two centuries it had been an important part of that area. It is possible that the earliest part of the house dated back to the early 18th century, either when mariners Adamson Eve and Benjamin Wood owned the property or after Capt. William Joell purchased the land sometime before 1715. Photographs taken in 1990 show the house as a one and two-story building, with ancient elongated rectangular chimneys and a roof whose contours were softened by numerous layers of whitewash. The chimney at the western gable was separated slightly from the roof, suggesting that the house was originally thatched. It is believed that the purpose of the gap was to prevent fire damage, common in early houses. The gable ends of the house were flush with the wall, another characteristic of some very early houses, and there was an old domed tank nearby.
The first, confirmed owner, William Joell, owned Olive Hill until his death in 1715 when he left his dwelling house and land to his son Thomas Joell Sr. Another Thomas Joell, either the son or the grandson of Thomas Joell Sr., inherited the property in the mid 1700's. That Joell moved to South Carolina, and the 1789 assessments record his total Bermuda property as comprising 40 acres worth 480 pounds and houses worth 283 pounds, 6 shillings, 8 pence and 233 pounds, 6 shillings, 8 pence. In the same year he sold Olive Hill with 25 acres to two mariners, brothers William and Edward Dunscomb. Edward died in 1790, stipulating in his will that his wife should have the option of living in the house but that ultimately Olive Hill should pass to their son, Dr. Josiah William Dunscomb. Edward's wife lived there until her death in 1831but their son died 15 years before his mother. An 1826 parish assessment evaluated her house and land at a substantial 1,200 pounds.
Edward's other son, John, the same John Dunscomb who had owned St. John's Hill and later owned Godfrey's Point, inherited the house and 12 acres after his mother's death. He lived in Newfoundland and mariner Capt. Benjamin Tuzo and his wife rented the property. Louisa's father, John Jauncey Ketchum, moved there and lived with them until his death in 1841. The property passed to John's son, another Edward, who lived in Georgia and in 1861 he sold it to Solomon Sears Masters. In an 1860 advertisement, the property was described as "a dwelling house (in good order), outhouses, tank, etc., a nursery of cedars - about 25 acres, the greater part excellent for planting or grazing purposes…situated on an eminence overlooking that pretty little inlet called Pitt's [sic] Bay.. It would be a splendid site for the erection of a modern dwelling." It seems that this is just what the new owner Solomon Sears Masters thought. Without demolishing the old section, he more than doubled the house's size by adding a two and three-story wing with large plain pilasters, heavily moulded gable ends and an enclosed wooden porch.
The land was subdivided over the years but in 2015 part of it is still owned by the Masters family, although the old house was demolished in 1994 and replaced by a modern one.
This traces the ownership:
Owner (relationship) Dates Owned
Adamson Eve & Benjamin Wood ?
Capt. William Joell ?-1715
Thomas Joell Sr.(son of William Joell) 1715-ca. 1750
Thomas Joell Jr.(son or grandson of Thomas Joell Sr. ca. 1750-1789
Edward Dunscomb & William Dunscomb 1789-1790 (sons of Edward who died 1733)
Christian Dunscomb (widow of Edward above) 1790-1831
John Dunscomb (son of Edward & Christian) 1831-1848
Edward Dunscomb (son of John above) 1848-1861
Solomon Sears Masters (by purchase) 1861-1864
House was extended after 1861
Samuel Alexander Masters, Alonzo Wallace
Masters, Elizabeth Susan Boyle (children of
Solomon Sears Masters) 1864-1882
Samuel Alexander Masters & Elizabeth
Susan Boyle 1882-1889
Samuel Alexander Masters 1889-1898
Elizabeth Susan Masters & Mary Sigismunda
Masters (daughters of Samuel Alexander Masters 1898-1936
Elizabeth Susan Masters 1936-1960
Dorothy Forster Masters (widow of the nephew of
Elizabeth Susan Masters) 1960-1989
Hugh Clarendon E. Masters or heirs ½ share;
Steven Lloyd Richardson Masters & Julie Lee
Masters or heirs ½ share 1989-1994
The early ownership of the house and 25 acres was explained in Book of Deeds, Sept. 5, 1789. The 25 acres were easily traced through accessories, deeds, and wills. Researchers Mercer/Zuill notes on the Wood family provided information on Capt. Benjamin Tuzo and his wife Louisa Ketchum who rented Olive Hill until it was sold to Masters in 1861. Louisa's brother Alfred had died in Nevis in 1852 while on board the Medora and his widow Elizabeth Wood returned with her children to live at Olive Hill where they were treated callously by their Tuzo relatives. The property was purchased by Capt. Solomon Sears Masters (1799-1864), the eldest son of John J. Masters of Old Homestead, and has remained in the Master's family.