From the Estate Beautiful to Neighborhood: Loudoun and the Castlewood Subdivision, Lexington, Kentucky

Historic real estate advertising is one of those rabbit holes I tumble happily into while researching (usually researching other topics entirely). In 1923, a handsome brochure was published in Lexington, Kentucky, announcing the development of new subdivision known as Castlewood. The lots were part of what had been the Loudoun estate, a farm anchored by an extraordinary Gothic Revival house designed by A.J. Davis.

Loudoun House, designed by A. J. Davis and built by John McMurtry.

And since the transition from farmland to “developed” land is a conversation I have often with my oldest child (you can never start too early to think about conservation and preservation), I began musing about the farm that once formed the northern boundary of Lexington, and the street that took its name from the estate.

The cover of the 1923 brochure.

The brochure did not show any new houses – none had been built. But the slim, 12-page volume contained several images of existing nearby houses – all large and lovely. I was intrigued to learn that one of the pictured houses was built for the one of the former occupants of Loudoun House – Annie Clay Goodloe Leonard.

A 1924 advertisement for the Castlewood neighborhood.

Loudoun House was built between 1850-1852 for Francis Key Hunt, but in 1884 the estate was purchased by Colonel William Cassius Goodloe, an ambassador to Belgium. The Goodloe family would live at Loudoun until 1921, when it was sold to the man who would sell much of the land off for development.

Annie Clay was the second oldest child of eight, and didn’t grow up at Loudoun House. Her four younger siblings did – the youngest was only five years old when their father died in 1889 at the age of 47. Following his death, his widow sold off 40 acres of the “front yard” and those parcels became building sites along Loudon Avenue (spelled entirely differently than the estate).

Some of the Goodloe children on the lawn of Loudoun House in the late 19th century.

On June 30, 1891, in a small ceremony at Loudoun House, Annie Clay married Andrew G. Leonard. Her groom was “in horses” (it is Kentucky, after all) and served as a racing official. The introduction of the electric streetcar system made Loudon Avenue, only recently opened, the place to live. And after all, it was the former front yard of Annie Clay’s family home.

An excerpt from an article in The Kentucky Leader on June 30, 1891, about the wedding of Annie Clay Goodloe to Andrew Leonard.

In July 1895, Mr. and Mrs. Leonard and their two children, Mary and Frederick, were living in the house built for them on Loudon Avenue. Their new brick home was the height of fashion, with an irregular footprint, Richardsonian Romanesque touches, a tower, a lovely arched window on the façade, and was within walking distance of her widowed mother and younger siblings.

The Andrew and Annie Clay Goodloe Leonard House, photograph from 2016.

By 1900 , the Leonard family had moved to Gratz Park and resided in another late 19th century home on North Mill Street. The handsome house on Loudon Avenue became the home of Andrew J. Riley and family. Riley was described in 1916 as a “retired grocer and capitalist. ”

The house, June 2021.

In February 1920, Annie Clay’s mother, Mary Elizabeth Mann Goodloe, died at Loudoun House. By May, the house and farm – 95 acres total – was on the market.

In December 1921, Judge J. F. Bailey of Paintsville, Kentucky, purchased the property. A newspaper account of the sale put the selling price for the house and land at $90,000.00 – equivalent to around $1.3 million today.

Advertisement from the May 2, 1920 edition of the Lexington Herald.

Obviously, Loudoun did not remain a stock farm and its “virgin soil” would go onto sprout new homes – bungalows, Tudor Revivals, and charming Colonial Revival houses to meet the growing demand for housing in Lexington.

The 1923 plat of Castlewood.

Judge Bailey did not develop the land himself, and so the the promoters of the land deal included photographs of the large trees and park-like setting, and the many large and stately homes from  the late 19th century lining Loudon Avenue.

A page from the 1923 Castlewood brochure showing the Andrew and Annie Leonard House.

At the time the Leonard house was featured in the Castlewood brochure, it still retained the original graceful and arched portico over the entry door, and interestingly, ivy creeps up a corner of the house, much as it does today.  The current porch spanning the façade was likely added in the 1930s.

One of the many houses built in Castlewood in the 1930s.

When the subdivision of Loudoun was announced in the spring of 1923, it was accompanied by  a pledge to save as many as possible of the 450 oak trees on the estate. I can only imagine how gorgeous the setting would have been at that time.

I wonder what happened to this tree? Image from the 1923 Castlewood brochure.

By 1932, the city of Lexington had purchased 32 acres from Judge Baily to create a new city park. (Bailey sold the acreage for only $5,000 less than what he paid for the entire parcel in 1921.) The Castlewood neighborhood was taking shape.

Another home constructed in the new Castlewood subdivision.

Today, the remaining small parcel of land from the Loudoun Estate is a gem of greenspace on the north side of Lexington. The historic house still stands and is home to the Lexington Art League. I fear the pledge to save all 450 magnetics old oak trees was nothing more than hot air, but many venerable trees do still grace the spot.

It’s a common story, of progression from farm to neighborhood, but I do wonder what Annie Clay thought about seeing her former home and its fields transformed in such a manner. She would have been alive to see bungalows sprout along new streets, and to witness the streetcars leaving Loudon Avenue, and the rise of the automobile on more and bigger streets in Lexington. I think the transition to park was one of the best outcomes possible, and one that provided a small sense of context and history in a rapidly changing landscape.