Set across two separate lots totaling 2.24 acres-21 Congdon (0.68 acres with residence and "artist studio" shell) and 23 Congdon (1.56 acres)-this exceptional property offers 186 feet of frontage on the peaceful waters of Lily Pond. Made for modern day entertaining, a wide front porch sets the tone for the gracious interiors. Step into the welcoming entry foyer where original stained glass windows transoms scatter dappled light across the interiors in every room on both floors, infusing the space with timeless character throughout the home. To the left, a light-filled parlor with a fireplace and ornately carved original stone mantel opens into a cozy library nook featuring a window seat, custom built-ins, and space for intimate conversation. Toward the rear of the home, a generous open-plan kitchen and lounge area with skylights and a fireplace is perfect for entertaining or unwinding. A large island with cooktop and proper exterior ventilation anchors the kitchen, while a nearby powder room adds convenience. Sliding glass doors lead to a spacious and newly updated deck perfect for alfresco dining while enjoying views of Lily Pond. Off the kitchen, the formal dining room dazzles with original millwork, a grand crystal chandelier, and access to the outdoor veranda-perfect for relaxing in the shade with a book. Upstairs, the sunlit primary suite features dramatic half-moon windows, two walk-in closets, and a serene ensuite bath. Two additional rooms, perfect for children, guests or office space -one with vaulted ceilings-and a full bath complete the second level. Modern upgrades include a whole-house generator (installed in 2017) and a new gas heating unit. Also on the property is a 1,518-square-foot, two-story artist's studio-currently a blank canvas ready to be transformed to suit your vision. Centrally located and one block from Coecles Harbor, this home blends historic charm, natural beauty, and sprawling grounds-an exceptional opportunity in one of Shelter Island's most private enclaves. Anchored in local history, this Shelter Island Classic sits on the site of Jonathan Nicoll Havens' former estate, the "Great Central Mansion," and where the affectionately named historic "Sweet House" once stood circa 1886. Recent property taxes for 21 Congdon Road were $8,224.71 and property taxes for 23 Congdon Road were $2,380.05.