166 Pleasant Avenue, Portland, ME, 04103

Tucked into a quiet, tree-lined pocket of Deering Center, this sun-drenched two-bedroom, one-bath condo lives inside the historic Captain Matthews House—a home that feels storied, warm, and timeless the moment you step inside.

Situated on the second floor, the space is filled with natural light thanks to oversized east- and south-facing windows. The kitchen and bathroom have been thoughtfully updated, blending classic character with modern comfort, and a heat pump ensures cool, easy living during Maine's warm summer months. The HOA covers heat and hot water, laundry is conveniently located on the first floor, and—rare for the neighborhood—this unit includes two private off-street parking spaces.

Step outside and you're moments from everything that makes this area so special: peaceful walks through Evergreen Cemetery and Baxter Woods, plus some of Portland's most beloved local stops. Morning pastries at Norimoto Bakery, sandwiches from Pats Meat Market and Deli, coffee at Rambler Café, and pizza nights at Noble Pizzeria & BBQ—all just steps away.

Offered for the first time in 25 years, this is a rare opportunity to own a piece of Deering Center history, where walkability, charm, and community come together beautifully.