The John and Maria Webb House is significant as an intact example of a stylistically-transitional residential building that incorporates both Federal- and Greek Revival-style elements and also as a rare surviving domestic building on Bridgton?s Main Street. Located in western Cumberland County in the southwesterly corner of the state, the house is a well-preserved, vernacular interpretation of two of Maine?s most popular nineteenth-century architectural styles, the Federal and the Greek Revival. While Bridgton?s Main Street once had numerous other houses from this era, the Webb House is one of the last to have escaped alteration, relocation or demolition. It is also a rarity among the residences on Main Street in that is has not been converted to retail or service use. It was listed in the National Register of Historic Places at the local level of significance as a good example of domestic architecture that illustrates the transition between two stylistic periods.