The Calderwood cottage was built in 1880 by a woman from Kansas City who used it in the summertime. In the garage, there was a horse stall and a place for a carriage, as well as a 3 hole lavatory (outhouse). Next to the garage was a windmill for pumping water from a well. The cement stanchions for the tower still exist. The 10′ diameter well hole was filled in by Mr. Calderwood for safety. The cottage was built of first-cut pine tongue & groove which made it strong. The driveway for the cottage is off Cliff Road; most of Cliff Road eroded from the top of the Bluff in the 1940’s. The Calderwood driveway is all that is left of it.
Up until approximately 1940, it was owned by the Brierly family who had owned it for a number of years. It was then bought by the Croll family around 1942. Mr. Calderwood bought the cottage from Mrs. Croll in 1958 for $14,500.
The cottage now has 2 1/2 bathrooms and 4 bedrooms and is heated with oil hot water. It sits high above the Nauset inner harbor about 50 feet from the edge of the Bluff and has spectacular views.