Urban redevelopment in Portland, Maine’s historic waterfront has given the state’s largest city fresh life in recent years. Beautiful, historic landmarks now coexist with trendy eateries and art galleries. The 69.4 square-mile city was founded in 1786. Set on a peninsula extending into Casco Bay, its population has a median age of 35.6 (2022) and an economy that relies mostly on tourism and the service sector.

Homes in Colonial, Federal, Greek Revival, Italianate, Gothic, Queen Anne, and Shingle styles line residential streets, where the typical home value is $501,738, up 10.4% over the past year (Zillow, 2022). Events ranging from live concerts to art walks occur nearly every evening throughout Portland’s unique neighborhoods.

Portland is accessible from I-95, I-295, and U.S. Route 1. Right off I-295 is the city’s East End neighborhood, offering up a mix of stately homes, shops, and funky, upscale restaurants. West End is also close to I-295. Historic brick homes from the 19th century, with climbing ivy and original iron fencing, add charm to the area.

Portland, despite its redevelopment, is still a bustling fishing port that offers a little bit of grit along with its graciousness. It’s a charming fusion of old and modern that includes historic landmarks, cultural sophistication, and, of course, world-famous lobster.