A unique yet quintessential historic Sag Harbor estate was analyzed for potential extension and modernization. With two different stylistic options for a modern living wing and a transitional great room in the old house, this property would be brought to current living standards while maintaining the charm and integrity of the old house. We think it would be perfect for a couple with differing tastes. Special existing details including a whaling-themed handmade iron fence are echoed in the balustrade of the modern portion, warming and deepening the connection with the past.