Welcome to this one-of-a-kind property in Trumbull, offering over 7,000 sf of living space across two separate ranch-style units-perfect for multi-generational living, extended family, or flexible use. With a total of 17 rooms, 6 bedrooms, 5 full & 2 half baths, these two residences blend spaciousness, comfort, and luxury in a breathtaking setting. Upper level has a private entrance. Each unit boasts a beautifully updated kitchen and remodeled baths, with many thoughtful finishes throughout. The expansive walkout lower level adds even more versatile living space, with a third kitchen, huge wet bar, a stage, and several seating & dining areas. This space is ideal for entertaining, recreation, or private guest or in-law quarters. Step outside to resort-style amenities, including a heated saltwater inground pool, a stunning new stone patio and fire pit area, a deck on each level, and a stone terrace off the main level sunroom, all perfect for relaxing or hosting gatherings. Perched atop Tashua Hill, the highest point on the East Coast between Florida and Rhode Island within 7 miles of the shore, this property offers panoramic, sweeping views that are simply unmatched. The home is part of the award-winning Jane Ryan school district, and just minutes away from beautiful town parks, golf course, walking trails & recreation areas. This is more than just a home-it's a lifestyle, combining privacy, space, elegance & spectacular surroundings in one of Trumbull's most coveted locations.