Nestled at the end of an exceptionally wide, tree-lined cul-de-sac on one of Westport's most picturesque streets, this timeless brick estate offers both elegance and privacy while remaining moments from town, beaches, and commuting conveniences. Set with a paver circular driveway and surrounded by mature landscaping, the property exudes warmth, scale, and classic sophistication at every turn. Designed for both grand entertaining and everyday living, the home features an extraordinary backyard anchored by a stunning pool and attached pool house, creating the ultimate resort-style setting. Inside, the thoughtfully designed floor plan includes a sought-after first-floor bedroom, expansive sun-filled living spaces, and seamless flow throughout. The dramatic family room showcases soaring 20-foot ceilings with striking wood beams, while the modern renovated kitchen beautifully blends contemporary style with everyday functionality. The second floor offers five spacious bedrooms along with an oversized playroom/flex space. A partially finished basement provides additional recreation room and storage possibilities. Zoned for highly desirable Long Lots Elementary and Bedford Middle School, this exceptional property combines timeless architecture, incredible outdoor living, and an unbeatable cul-de-sac location in the heart of Westport.