He fought Confederates. He tangled with Indian fighters. Now John Upham's St. Augustine cottage is for sale again -- for a whopping $3.2 million

An eye-catching design, bath with a view and a welcoming outside area (Evan Ulsh/Good Things Homes)

If Lt. Col. John Jaques Upham were alive today, he would be pleased to see that the interior of the winter cottage he built in St. Augustine, Fla., for his bride has been returned to something he would recognize.

That’s because the owners have spent about as much renovating the striking residence at 268 Saint George St. as they did after purchasing it in late 2023 for $1.045 million.

If you are brave – and rich – enough to take on the upkeep and hefty taxes, the 5,800-square-foot dwelling can be yours for a cool $3.2 million – three times its previous purchase price.

When it was built in 1892-1893, the Queen Anne Victorian was a real showpiece in a neighborhood full of showpieces.

Upham, 54, married Caroline Hoppin Williams – 10 years his junior -- in Milwaukee on Sept. 23, 1891. Having soldiered through bouts of poor health, the Civil War veteran and U.S. 8^th Cavalry officer (Indian Wars) retired just four months later. He focused on building the cottage. (At left, photo of Upham while cadet, courtesy of U.S. Military Academy Library)

The couple happily wintered in St. Augustine and summered in Wisconsin until 1898, when Upham died of kidney disease.

The Uphams could not have foreseen what would happen to the luxuary house years later.

“The last time we listed it, the property was difficult to sell because it needed a lot of work, and it had a disjointed – and somewhat confusing – layout,” said Elizabeth Jennings. She and Kate Mitchell have marketed the property for ONESotheby’s International Realty in St. Augustine.

“Because it had been converted to five units at some point, there were additional staircases and a landing space to enter the units,” said Jennings in an email. “Although it had been used as a single-family home for a few decades, none of the previous owners had done the work that it needed in order to restore it to a single-family home with a cohesive layout.”

A staircase was built to the third floor (Evan Ulsh/Good Things Homes)

That's all been remedied through an exhaustive renovation.

Upham Cottage is part of the St. Augustine historic district, which is listed on the National Register of Historic Places; the National Park Service says the three-story cottage is one of a few remaining of that style in the coastal city.

The Upham Cottage’s sales price has varied widely in the past 15 or so years, according to Zillow. Like other houses of that age with such features, upkeep is paramount.

Upham took part in Civil War, Indian Wars

John J. Upham was born in Wilmington, Del., in 1837. His family moved to Milwaukee, where his father, Don A.J. Upham, served as mayor in 1849 and 1850. The younger Upham attended West Point, graduated in 1859 and joined the regular army.

First in the infantry, the officer was stationed at Governor’s Island, N.Y., and California before the Civil War broke out.

He was engaged in the defense of Washington, D.C., the 1862 Peninsula Campaign in Virginia and the Battle of Gettysburg, where he was promoted to brevet major for “gallant and meritorious service,” according to his The Milwaukee Sentinel obituary (provided to the Picket by the Wisconsin Historical Society). He later became a disbursing officer in the North and occupied South.

Cullum’s Register, an index of graduates of the U.S. Military Academy, had a biography of Upham, listing numerous stations in the West during the Indian Wars, after he had switched to the cavalry. The officer took several leaves of absence, at least some for health reasons. The register said he served “despite constant poor health.”

Upham was in a few regiments in his time in Texas, Kansas and Indian Territory. He took command of Oklahoma’s Fort Gibson in 1875 and was in the field in the summer of 1876 as part of the Yellowstone and Big Horn expeditions (George A. Armstrong and much of his command were killed at Little Big Horn in June 1876).

Upham fought at War Bonnet Creek and Slim Buttes and later was stationed at Fort D.A. Russell, Fort Wahaskie and Fort Niobrara, according to his obituary.

Jennings said the owner – is from the Atlanta area – is intrigued with the Upham story. They had planned to stay in the house longer, but had a change of plans.

Property is not for the 'faint of heart'

(Evan Ulsh / Good Things Homes)

The sellers created a more cohesive and less funky interior by removing two staircases, building one new staircase to the third floor, converting the landing space into a modern sized primary bath and adding a new staircase that flows directly from the second floor to the third floor.

Upgrades included a new roof, kitchen renovation, lighting and extensive landscaping.

“Historic properties like this are very delicate and not for the faint of heart. Because of the current price point of $3.2 million, the new buyer will be someone with high net worth,” said Jennings.

In other words, most folks aren’t in the running for the seven-bedroom, five-bathroom house.

“They will be someone who loves history, loves St. Augustine and someone who likes the hustle and bustle of downtown living. This home is located on historic St. George Street, which is the most well-known street in St. Augustine. All of the shops, restaurants and cultural icons – like the Bridge of Lions, the Lightner Museum, the Castillo San Marcos – are only steps away.”

The global real estate adviser said the sellers have done all the hard work. The buyer will have to be serious, too, taking on high taxes, insurance and the unforeseen on the quarter-acre property.

“The last time we had this property listed, we showed it to dozens and dozens of buyers. Most of them were afraid to take on this project because the costs associated with renovations are largely unknown,” said Jennings.

(Evan Ulsh / Good Things Homes)

The payoff?

Lots of admiring eyes, spaces to socialize and a place for multigenerational living or a means to earn extra income.

‘This remarkable home showcases the graceful blend of Queen Anne Victorian architecture with examples of Moorish Revival in the courtyard arches,” says the listing. “With stunning original millwork, wood floors and unique octagonal shape, this home will take you back to the splendor of the Gilded Age.”

The Upham Cottage is in the white rectangle toward the center bottom of aerial photo