Classic farmhouse charm meets modern flexibility in the heart of Portland. This 4 bedroom, 3 full-bath Colonial is ideally located just minutes from the Connecticut River Waterfront Park and offers an easy commute to Middletown. A two-story addition completed in 2005 adds unexpected space and versatility to this inviting home. A covered front porch sets the tone as you step into a bright living room featuring hardwood floors and a cozy wood stove. The main level flows effortlessly into a kitchen with built-ins, stainless steel appliances, and ample white cabinetry, opening to a dining area highlighted by additional built-ins and updated lighting. An extra living space on the main floor provides the perfect spot for relaxing, working from home, or entertaining guests. The primary suite offers a unique private retreat with its own staircase and full bath-ideal for a guest suite, in-law potential, or secluded owner's space. Three additional bedrooms and another full bath complete the upper level. Additional features include thermopane windows, a walk-up attic for extra storage or future expansion, solar panels, and a patio that opens to a spacious, lovingly maintained backyard. The outdoor space is beautifully adorned with fruit trees and flowering plantings, creating a peaceful setting for gatherings or quiet enjoyment. A rare opportunity to own a well-cared-for home that blends timeless character, thoughtful updates, and a prime central location.