Welcome to 169 Milton Road, a once-in-a-lifetime opportunity to own one of Rye's most iconic properties once known as the sea captain's house. This home offers an unparalleled lifestyle in a sought after, walk-to-all location. The elegant 7-bedroom home is set on a sprawling one-acre lot, offering both historical charm and modern sophistication. The property underwent a significant transformation in 2016 to create outdoor living space designed by renowned Sean Jancski Landscape Architects. The outdoor resort space features a stunning 20x44 swimming pool, a luxurious hot tub, and a meticulously designed entertainment area with two handsome fireplaces, a built-in BBQ, bar, and pergola. Enjoy the tranquil sound of fountains amid lush new plantings, all enhanced by state-of-the-art outdoor lighting and sound systems. In 2021, the original four-car garage was reimagined into a versatile two-car garage with an adjoining pool house. This sanctuary includes a lounge area with a built-in bar and fireplace, a full bath, and flexible space for fitness pursuits-perfect for retreating and relaxing in a resort-like setting and great for guest. Inside, the home exudes elegance with its high ceilings, built-in cabinetry, and beautifully scaled rooms, ideal for both grand entertaining and intimate gatherings. The sophisticated dining area features a charming fireplace, complemented by a butler's pantry for seamless hosting. The kitchen boasts modern upgrades while maintaining its classic appeal. Additional enhancements include new flooring throughout, updated bathrooms, and essential infrastructure upgrades such as new A/C units, a new boiler, and a new roof. The exterior has been refreshed with new paint, shutters, and shingles, ensuring this home is as striking outside as it is within. This residence offers a harmonious blend of retreat and convenience, situated in the heart of Rye less than minutes to the vibrant, quaint town of Rye, schools and beach. Walk to all schools, nursery schools, town, train and beach.