• Portland’s Parkside neighborhood, on the north side of the city’s peninsula, takes its name from Deering Oaks, the 55-acre, multi-use park that dates to 1879 and is on the National Register of Historic Places. A mix of house styles – many multifamily, many architecturally distinctive – and high-profile local businesses, Parkside is where you can find Hadlock Field, home of the Portland Sea Dogs, and the venerable Expo, where the NBA G League Maine Red Claws play.

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Premier Properties

  • No. 96 Emery St. has been in the Napolitano clan since 1951; No. 94, since 2007.
  • The Jesse & Isabel Alden House (c. 1820) has been beautifully restored.
  • “Many of Portland’s most prominent figures in business, industry, politics and the professions grew up as residents of a Bayside with tree-lined streets and open trolley cars,” a 1968 City of Portland neighborhood report noted. Today, Bayside is undergoing “an energetic transformation … into a first-rate, mixed-use urban district … with a wide range of housing development" (portlandmaine.gov) whose attractions include craft breweries and restaurants, music and theater, galleries, trails – and, of course, a landmark ten-pin bowling alley.