Nestled atop Pine Street in the acclaimed Meeting House Hill neighborhood, this stately Victorian offers more than just a place to live—it has the potential for a fulfilling lifestyle. Whether you're seeking room for extended family, looking to generate rental income, or hoping to find a peaceful retreat near the city, you have found it. A single or two-family home, 311 provides remarkable flexibility to suit your needs. Originally part of the historic Marriner Estate, this beloved home gave Pine Street its name with its towering pine tree gracing the lush landscape. From the moment you step onto the inviting screened porch—a perfect spot for quiet mornings or evening relaxation—you'll feel the warmth of a home that has been both cherished and cared for. Original hardwood floors, detailed moldings, and abundant natural light blend beautifully with modern updates to create a harmonious balance between character and functionality. Spanning three levels, the home features 4 bedrooms and 3 full bathrooms, with a thoughtful layout that supports both privacy and connection. The first floor exudes a calm, welcoming energy with a cozy foyer, a formal dining room, and comfortable living room. Upstairs, the spacious second floor is filled with natural light & the third floor offers expansion options and a tranquil perch with seasonal glimpses of Casco Bay. Ideally set up for multi-generational living, or rental use, upper level access from either of two separate entrances lends privacy to each fully-applianced unit. Many system updates and new roofing offer peace of mind. A dry and partially finished basement includes laundry and storage. A two-car garage also offers lower level storage. The fenced yard is perfect for gardening or hosting summer gatherings. 311 Pine is minutes from the heart of Portland and all that coastal living offers. Peaceful and convenient with charm, comfort & investment potential. Don't miss this one.