Welcome to this distinguished architectural shingle-style residence in the heart of Westbrook, where timeless design meets refined modern living. Set on over half an acre along a picturesque, tree lined street, this five bedroom, two bath home offers exceptional space, comfort, and versatility all within minutes of parks, dining, shopping, and just 4 miles to Portland offering an easy commute. Complete with a first floor flex space, ideal for an office, or can easily be a sixth bedroom. Step inside to discover a warm and inviting interior defined by generous proportions and thoughtful updates. The spacious living room provides an elegant setting for everyday living and entertaining, while the first floor primary suite offers a serene retreat complete with a private en suite bath. A versatile bonus room on the main level serves perfectly as a home office or additional bedroom, and the charming three season sunroom invites you to unwind and enjoy peaceful views. Upstairs, four additional bedrooms and a full bath provide abundant space for family and guests. Outside, the expansive backyard offers endless opportunities for outdoor enjoyment, complemented by an oversized detached garage ideal for hobbyists, collectors, or additional storage. Enhanced by central air, a standby generator, and efficient natural gas heat, this property seamlessly combines period craftsmanship with contemporary comfort. A classic Westbrook gem, reimagined for modern living.