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Annapolis Roads grew in four distinct spurts over nearly 80 years. Here is a brief account of those building booms and of their characteristic building styles. The graph below charts the number of new houses built each year from the community's inception in 1926 until the end of 2003, for a total of 328 dwellings. Between the years 1953 and 1973, Annapolis Roads experienced sustained growth with 209 new houses, an average of ten per year. The latest growth spurt occurred between 1988 and 2003, with 65 new builds averaging five per year. With the exception of one house on Ogleton, all of the pre-1950 houses were built near the Annapolis Roads Beach Club house, which burned in 1953. Claibourne and the "Land's End" portions of the community were the first sections platted; developer Rella Abell Armstrong intended the proceeds from lot sales to support construction of a hotel (the Beach Club house) and golf course.
Certainly the episodic character of Annapolis Roads' growth accounts for some of the diversity in style and the abandonment of what developer Armstrong had envisioned: a community of Colonial Revival houses encircling a resort constructed in the same style.