Bayside Real Estate

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Browse real estate for sale in Portland's Bayside. Contact Benchmark Real Estate | Maine with questions or to schedule a private showing. Sign up to save your favorite Bayside listings and custom searches, and we'll email you when similar properties become available.

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Bayside Homes For Sale in Portland Maine

Bayside, Portland, ME, is a vibrant downtown neighborhood nestled between the Old Port and Back Cove. A mix of residential and commercial properties, Bayside features an eclectic blend of old and modern architecture. The neighborhood, bounded by Forest Avenue, I-295, Congress Street, and Franklin Street, boasts a diverse array of homes, including Federal and Greek Revival styles that survived the Great Fire of 1866. Notable landmarks include the historic Schlotterbeck and Foss Building, now apartments, and the iconic Franklin Towers. Bayside offers a dynamic lifestyle with Portland High School, Baxter Academy, Whole Foods, and Trader Joe’s all within walking distance. The area has also seen significant redevelopment, with former public works buildings transformed into restaurants, breweries, exercise studios, and new apartment complexes.

Community living in Bayside is lively and evolving, thanks to attractions like Bayside Bowl, which hosts the PBA League Elias Cup, and the scenic Bayside Trail, which connects the neighborhood to East Bayside and the Back Cove Trail. Residents enjoy access to the Stone Street Playground, complete with a splash pad, as well as a community garden on Chestnut Street. Here are the top 5 things to do in Bayside:

  1. Bayside Bowl – Enjoy bowling and rooftop views at this popular venue.
  2. Explore the Bayside Trail – Walk or bike along this scenic trail connecting to other parts of Portland.
  3. Stone Street Playground – A perfect summer spot for kids, featuring a splash pad. 
  4. Drink and Dine along Lancaster Street – Grab a hearty dish of Southern comfort from pit-smoke experts over at Wilson County Barbeque. Then hop next door to Baston River Distilling to experience an impressive distillery and tasting room experience, which is especially festive in the winter months.
  5. Bayside American Cafe – Open daily, eggs benedict and mimosa are the stars of this local brunch landmark, a landmark since 1990.
  6. Isa – This brick-walled bistro serves a seasonally-inspired, eclectic menu which is inspired by the chef’s Mexican roots, executed with Italian and French techniques.

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