Mansion on a Hill

Mountain vacation home for Virginia millionaire is a fascinating homage to excess

Jun 23, 2026

Welcome to this week’s Visual Story. This series, published on Tuesdays, focuses on a specific place or theme with a short narrative. Most of the “Visual Stories” are too long to be carried in most email browsers. If that’s the case, view it on a web browser or on the Substack app.

This week, we are visiting a Gilded Age mansion located in the Blue Ridge Mountains with the largest Tiffany window found in a private home in North America. A window that is a portrait of the first owner’s beloved wife, no less.

The Swannanoa Mansion was built in 1912 on the top of Afton Mountain as a summer home for James Dooley and his wife, Sallie Mae. Dooley, then 70, was a Richmond native and lawyer who amassed his millions in the late 19th century due to investments in railroads, steel, insurance, and banking. He wanted Swannanoa to be a place where he and his wife of almost 50 years could escape Richmond’s heat and humidity during the summer months.

Although Swannanoa was only one-sixth the size of the infamous Biltmore Estate, the 23,000-square-foot mansion was not tiny — or lacking in eccentricity — by any means.

A Second Place

Five years ago, my wife and I bought a small one-bedroom condo at Wintergreen, Virginia, to have a place to get away from the craziness that comes from living in close proximity to the nation’s capital.

Our logic at the time was sound. In January 2021, we were 10 months into what seemed like a never-ending pandemic. The bottom had fallen out of the real estate market, making the purchase affordable, yet a sound investment. While my business was limited at best during this time, Jill was getting settled into a new leadership role and working nonstop. Both of us were going stir crazy for totally different reasons.

Located 40 miles southwest of Charlottesville and 110 miles northwest of Richmond, Wintergreen is about three hours from our townhouse in Alexandria. It also is about three hours from Chapel Hill, where Jill’s brother and sister-in-law live, and had become a place for our families to meet for the holidays and at other times over the years.

Jill and her brother, Michael, grew up in the mountains of North Carolina and always spoke of feeling at home whenever we went to Wintergreen. Several months before we purchased our place, Michael and his wife Jennifer bought one nearby.

Over the next several months, I went to Wintergreen almost once a week, exploring parts of rural central Virginia with my camera. That May, when photographer friend Gary Rubin mentioned that Swannanoa would be open for a rare weekend tour about 20 miles from the condo, I jumped at the chance to join him.

About Swannanoa

Dooley, who served with his father and brother in the Confederate Army during the Civil War, was no stranger to building large homes that featured homages to his wife. In 1893, he built Maymont, a stone mansion on a 100-acre Victorian estate overlooking the James River, and named it after Sallie May.

For Swannanoa, Dooley purchased 763 acres on top of Afton Mountain from a local farmer and spared no expense building the mansion. The exterior is constructed from white Georgian marble from the United States, but all of its interiors are imported Italian marble. The 10-foot stained-glass window of Mrs. Dooley is at the top of the house’s grand staircase; the home also has an elevator.

Dooley died in 1922, leaving the majority of his estate to build a hospital, orphanage, and library in Richmond. Maymont also was left to the city; the house is now a museum. On the Maymont estate property now are an arboretum, an Italian and Japanese garden, a carriage collection, and a nature center with native wildlife exhibits and a petting zoo.

Dooley’s wife lived at Swannanoa until her death in 1925 and willed the mansion to her husband’s sisters, who sold it the following year. The mansion became a country club and golf course, but it went bankrupt during the Great Depression and was completely abandoned for a dozen years.

In 1944, Skyline Swannanoa Inc. purchased the estate and leased it four years later to the University of Science and Philosophy, a nonprofit “devoted to the Science of Spiritual Man and the Cosmos, with the aim of teaching the essentials of harmony found in the world’s religions/philosophies and in the fine arts and sciences.” The university rented the property for 50 years before moving into a building in nearby Waynesboro.

Since 1998, Swannanoa has been unoccupied. An exterior restoration was completed in 2006 at a cost of $3 million, but the effects of time and limited funds have not been kind to this house on the hill. The estate operates as a private venue through bookings, seasonal tours and ticketed events; it is reopening this summer after “an important period focused on deferred and necessary maintenance to better preserve and care for the property for years to come.”