Edith Walks Through Leeholm and the Water View
in June of 1885 Edith went to Oyster Bay to stay at Aunt Anna’s home Gracewood. (Former Anna Bulloch who married James Gracie).
While on a short walk through the woods Edith came upon Leeholm. Inside Anna (Bamie) was preparing for a 5 week visit from TR.
That was the first time Edith saw the house that would eventually become her home for the rest of her life. She strolled through the 22 rooms, 8 had fireplaces with dumb waiters to bring logs up from the basement.
TR changed the name to Sagamore Hill shortly after running into Edith coming down the stairs from the parlor in Bamie’s house in New York City. He proposed to Edith on November 17, 1885.
There has always been the question whether, or not they had an unobstructed view of the sound from the piazza.
Below is believed to be the earliest photo view looking out toward the Long Island Sound. It was stashed away in one of Edith’s photo albums. On the back of the photo Edith wrote, “Taken years ago before the trees grew up to hide the View.”
The date of the photo is unknown and could have been taken before the house was built. Sagamore Hill is the highest point in Cove Neck.

It’s probably safe to say in the summer months the trees were full enough and high enough to prevent an unobstructed view clear down to the shoreline from the piazza. There is evidence the Roosevelts could see the sound looking out toward the right above the trees. In this photograph you can vaguely see the sound above the dip in the trees

We do know that above the tree line the Roosevelts could see the Fall River Line sailing ships into New York Harbor from Stonington, Ct. In the summers the Roosevelt Family rule was when the last ship could no longer be seen sailing into New York (around 9:00pm) the youngest had to go to bed.