2 houses in a restrained Greek Revival manner.
Both have simple proportions. Closed gables facing the street. Pilastered corners supporting an undecorated frieze. All hallmarks of the Greek Revival. The extra width of 108 gives a little better balance to the design. The narrowness of 110 is very visible in the roof pitch. A bit too steep for the style. It tends to make 110 seem taller than 108 when they are in fact the same height to the second-floor plate line.
Dating is difficult. The 1924 tax records say 50 years old. My 1871 Beers Atlas map of Portland shows them. If they are ca 1870, they would be stylistic hold outs as Greek Revival had been surpassed as a residential style everywhere but rural backwaters. Portland was certainly not a rural backwater in 1870. Deed records for 108 Winter first mention ‘buildings’ in 1839. That was when the style was near its apex of popularity. I am going with ca 1835.
1924 Tax photos and information.
108 Winter. Owned by the heirs of Mary Ward. The valuation was $4958.00. The 1873 Beckett directory lists a Mrs. Priscilla Ward at 82 Winter. Currently the property is listed as 2 families.
110 Winter Street. 1924 owner is one Charles A Davis. The valuation was $4216.00. There is no listing for a Davis on Winter in 1873. Currently, the property is listed as 4 condos.