59 New Island Ave Portland, ME 04108

Perched at the top of Whitehead Street, this charming year-round home enjoys one of the most scenic outlooks on Peaks Island, with sweeping views toward Cushing Island. Dotted with vintage cottages and gently sloping toward Hadlock Cove and Picnic Point, Whitehead Street captures the timeless coastal character that makes this island a Casco Bay favorite. With the shoreline just steps away, walks to the water become part of daily life. A welcoming covered porch sets the tone for relaxed island living, presenting the perfect perch to enjoy sea breezes and the vibrant neighborhood atmosphere. Inside, the thoughtfully preserved and well-maintained cottage features a bright, cheerful first floor with gathering spaces. Cozy up beside the propane stove or enjoy meals with water views from the dining area. The kitchen is flanked by a first-floor bath and laundry for added convenience. A practical mudroom and flex room--currently used as a music room--allows options for a den, or formal dining room. Upstairs, the primary bedroom opens to a private balcony nestled among the trees, creating a treehouse-like retreat with views. Two additional bedrooms await family and guests. Outdoor living shines here, with a wonderful exterior shower, easy-access storage, and a large sunny corner lot enhanced by fencing, mature trees, hardy shrubs, and perennial gardens. Just a short stroll from the island's beloved ''Down Front'' shops, restaurants, and ferry landing, this special property grants convenient access to both island charm and the energy of nearby Old Port. A quick ferry ride connects you to downtown Portland while allowing you to return home to the vibrant community of Peaks Island, known for its year-round spirit, creative energy, and welcoming neighbors. OPEN HOUSE Sat., May 23, 11-1:00