Chapter 26


THE WHITE HERON HOUSE – This home is now located near Blind Pass on Sanibel-Captiva Road. It appears to be a farmhouse, which it was when it was built over 100 years ago. Thomas Holloway, a partner with Josiah Dinkins in the Wulfert farming community, owned this home and acres of vegetable fields and citrus groves during the thriving first 25 years of the 20th century. After the hurricane of 1926 and the subsequent “bust,” farmers fled to the mainland. Holloway’s property, a stretch of land across the top of the Wulfert area peninsula, was sold to John Oster. Land in the southeast was sold to Clarence Chadwick. When Oster wanted to move this house to the land he owned on Clam Bayou, Chadwick refused to let him cross the Chadwick land he owned on Clam Bayou, claiming the road he’d travel on was private. Oster found evidence to the contrary. The feud was on. The house was raised and put on a flatbed to be hauled by a tractor led by Oster. Chadwick, in his limousine, had the driver block the road. Picture two men cursing at each other and threatening to call in the law. As the tractor got closer and closer to the limo, the young driver panicked and, in spite of Chadwick’s orders, drove the car off the road and into a tomato field. Oster moved his house, renamed it White Heron, and built a small cluster of cottages around it.
Later the house was owned by a descendant of Wild Bill Hickok. The cottages were sold off as the land surrounding White Heron was developed for homes. Still later, White Heron was placed on the city’s historic register. A large addition was built to the rear and a pool installed. Recently the home has changed hands and the new owners have restored and remodeled it, staying true to the historic nature of this lovely old home.

GRAY GABLES – The Nutt family home is the oldest residence on Sanibel. Laetitia Ashmore Nutt was the widow of Louisiana state senator, Confederate captain, and attorney, Leroy Nutt. In 1889, she brought her three grown daughters, her brother, and her mother-in-law to Sanibel and was granted a 160-acre homestead. The family built Gray Gables, their charming home, on beachfront land with an eye to using it as a boarding school or boarding house. All the Nutt sisters (Cordie, Lettie, and Nanny) and their mother taught school in Lee County. Ernest Bailey stayed in The Gables (as it was known then) when he first explored Sanibel as a place to relocate with his widowed mother and brothers. Laetitia Nutt was an un-reconstructed Southerner, a stern disciplinarian, and the backbone of the islands’ cultural scene. The Nutt family gave land for the Community House, donated generously to Jones-Walker Hospital (known as Gulf Coast Hospital today), and proudly gave Laetitia’s name to the local chapter of the Daughters of the Confederacy.
Their home was placed on the city’s historic register and moved closer to the road and family cemetery. It has been extensively remodeled on the inside. The present owner is the great-grand niece of Laetitia Nutt and has published her aunt’s Civil War diary and developed a “history hall” at Gray Gables.

THE COOPER HOUSE – This home was built by George Madison Cooper, a man who wore many hats in his lifetime. He was the owner of a lumber mill near the Caloosahatchee on Yellow Fever Creek, a merchant with a small fleet of steamers that traded locally and, in Honduras, a storeowner, a farmer and an early homesteader on Sanibel. Cooper’s home was constructed on the corner of what is now Periwinkle and Tarpon Bay Road almost as soon as he claimed his homestead. He then built a bigger two-story home in 1891.
Cooper was the island’s mailman. He would travel to Pine Island, collect the mail, and put it on his wife’s sewing machine when he returned to Sanibel. Islanders would collect their letters and packages at the Cooper home. The home is located near today’s post office and is now incorporated into the Olde Sanibel Shoppes. It has been placed on the city’s historic register as the “Cooper House” and has been restored to an earlier appearance. The home’s second story was reached by an outside staircase, a feature that is now hidden in the back. The Cooper family had a well inside their home. This is no longer visible, but a shop patron must “step down” into a second room. Something else not visible is the ghost, which is reported by the owner to rearrange merchandise in the shop.

THE BAILEY HOUSE – This house started out in 1896 as a hip-roofed square with an option to add a porch for $50 (which Mary Bailey passed on as being “too expensive”). The Fort Myers Press reported, “The Baileys are here to stay and have recently erected a home on Sanibel.” Mary Beers Bailey, the widow of Samuel Major Bailey, a Virginia tobacco farmer and owner of a tobacco products manufacturing company that failed after the Civil War, came to Sanibel in 1884 with her three youngest children, Harry, Ernest, and Frank. She was described as a woman of strong will and pioneering spirit. She acquired a homestead and her sons farmed the land. In 1899, the brothers purchased a plantation store on Mathews Wharf that was the start of the Sanibel Packing Company. As the matriarch of the family, Mrs. Bailey was the recipient of a fine, high-wheeled buggy similar to the surrey exhibited in the shed attached to the museum’s replicated Packing House. Mrs. Bailey was an artist who drew the sketches in the Rutland House dining room and owned the chocolate set in the display case. She, Hallie Matthews, and Laetitia Nutt were the grand dames of genteel Southern society.
The Bailey home, which is situated on Periwinkle Way where Donax comes in, was added onto (including a front porch) as the years passed and the family increased. Frank Bailey married Annie Meade Matthews in 1919 and they welcomed three sons, Francis, Sam, and John. Harry was married and moved to Fort Myers, but Ernest Bailey continued to live in the Bailey House with his brother’s family. When Frank’s wife died at a young age, her sister, Charlotta Matthews, occasionally stayed there to help with the cooking and laundry. As long as the Baileys have owned the property, the house has been painted a dark green.
In 2011, the Bailey Homestead was sold to the Sanibel-Captiva Conservation Foundation for $4 million, along with the attached 28 acres. SCCF intends to preserve the Bailey House and surrounding land, and after restoration, it will be open to the public on a schedule to be determined as an environmental education center.