Welcome to a rare opportunity to own an extraordinary 10-acre estate (2 separate 5 acre plots) on the highly desirable Rudder Lane. This private compound features a luxurious 10,187 sq. ft. main residence featuring 5 bedrooms (each with their own private bath), 8.5 total bathrooms, meticulously designed for refined living and grand-scale entertaining. Step inside to discover flooring that includes Russian black oak, French pillow limestone, Vermont bluestone, and hardwood, complementing the home's timeless architecture and elegant finishes. Highlights include seven fireplaces (two of which are located in upstairs bedrooms), two wet bars, two laundry rooms, custom lighting, and a whole house generator. The gourmet kitchen is a chef's dream, outfitted with two new Bosch dishwashers, a Sub-Zero refrigerator, Wolf gas range with double ovens, a Thermador warming drawer, and a limestone arch carved in Mexico over the cooking center. Outside, an expansive saltwater pool and in-ground hot tub overlook professionally designed landscaping and fully stocked pond, creating a true resort-like setting. The wine cellar provides the perfect space for curated collections. A rustic 2-bedroom, 2-bath guest house offers comfortable accommodations with its own private charm, while the carriage house impresses with a basketball court, full kitchen, 2 additional bathrooms, and space to house up to nine vehicles, including room for a boat and RV. The classic horse barn, built in the 1940's, consists of four stalls and completes the package of everything you could possibly want in a dream property. This one-of-a-kind estate offers the perfect blend of luxury, privacy, and functionality in one of the area's most prestigious addresses. Buyer to verify all measurements.