Nathan F. Cobb, Sr., a Cape Cod man, walked into Northampton County in October 1837 and opened a store on the seaside road. Two years later he bought an uninhabited barrier island just south of the Great Machipongo Inlet from a local fisherman called "Hard-Time" Fitchett. The price was $100 cash and a two-horse wagon-load of salt, to be delivered later. Cobb had a house framed up on Cape Cod and shipped down in pieces, erected it on the barrier sand, and opened the island as a public resort. He built a hotel for wealthy northern sportsmen who came to hunt waterfowl and fish. He built summer cottages and a church. With his sons Nathan Jr., Warren, and Albert, he hunted market ducks and salvaged the wrecks that piled up on the Cobb Island bars. Hard-Time had unloaded his island at a bargain. The Cobbs made it a small kingdom.

The Cobbs and their neighbors saved enough drowning sailors that in 1875 the United States Life-Saving Service commissioned a lifesaving station on Cobb's Island, the first formal recognition of the rescue work the family had been doing for free. Two years later that first station burned to the ground. A second was built around 1877. By the 1930s the second station too had been hammered by storms, and after the 1933 Chesapeake-Potomac hurricane swept the low barrier flat, the United States Coast Guard built a new three-story Colonial Revival station on the southern end of the island in 1936. By then the Cobbs had been gone for decades. The 1896 hurricane had destroyed the hotel and most of the town, and the residents who survived had moved their families to the mainland. The Coast Guardsmen at the new station were the only year-round residents of Cobb Island. In its eighty-nine years of operation the Cobb Island station responded to twenty-four major shipwrecks.

The Coast Guard closed Station Cobb Island in 1964. With the rescue radio gone, the island had no permanent inhabitants at all. In 1973 the federal government turned the abandoned station over to The Nature Conservancy as part of the Virginia Coast Reserve. For two decades the conservancy let the building stand where it was. But the barrier island was migrating westward, the way they all do, and by the 1990s the Atlantic was at the station's door. The choice was to lose the building to the sea or to move it. The conservancy chose to move it.

Expert Construction and House Movers, a Virginia Beach commercial firm, lifted the three-story Colonial Revival building onto a barge in early May 1998. The associated boathouse had already been moved to the new site by an earlier barge. On May 6 a tug pulled the barge with the station eight miles across Cobb Island Bay to a prepared foundation at Oyster, in Northampton County. On May 7 the building came off the barge and was rolled onto its new site. The conservancy restored it as a nature education center, a lodge, and a conference center, adding a keeper's cottage and other secondary buildings to complement the original station. Around 2006 the property passed to Cobb Island Station LLC, and from then until 2011 it was leased as a retreat by the World Healing Institute. The property has been listed for sale since 2018: 32.3 acres in all, including 17 acres of tidal salt marsh, 4 acres of intertidal wetlands, and 5 acres of high ground and forest. The Coast Guard station that watched twenty-four shipwrecks on Cobb Island now watches the quieter waters of Oyster harbor instead.