Shenandoah Oaks was built circa 1848 by Nathaniel and Martha (Patsy) Manning. It was originally named Buena Vista (beautiful view) because in earlier days before the fields grew into forests, it "commanded a view of the Valley, the River and the Blue Ridge Mountains embracing the Valley." Mr. Manning, grandson of General William Darke who was a delegate to the Virginia Constitutional Convention in 1788, was a planter and brick kiln proprietor. "At Buena Vista, during the Civil War, officers from both sides were quartered in turn from time to time." The Mannings supported the South during the Civil War and were left in "reduced circumstances" at war's end. They lost ownership of the mansion but were allowed to stay until 1872.

The mansion changed hands several times, and was purchased by Brooke Wyncoop in the late 1920's. Mr. Wyncoop changed the name of the home to Willowbrooke and completely renovated it. It was a place of entertainment for the Wyncoops. Long-time residents of Jefferson County can recall lovely and lavish parties on the front verandah in the summertime.

Mr. Wyncoop sold the mansion to the Pickering family of New York as a summer home. Mr. Pickering was president of Remington Rand Corporation. His wife Betty and daughter Aretha spent their summers at Willowbrooke. Aretha, a silent movie actress, married Frank Muska, a prize fighter who trained with Gene Tunney. Many famous people are said to have frequented the house during the summers, among them painter Norman Rockwell. Letters that were found in the house were from people such as James Cagney and Ernest Hemmingway.

After the deaths of Aretha and Frank Muska, the house was purchased by the Catholic Diocese of West Virginia. The Church leased then sold the mansion to the Homeless Coalition who ran a homeless shelter in the home for several years.

In October of 1998, General and Mrs. Parker purchased the mansion. They changed the name of the home from Willowbrooke to Shenandoah Oaks, celebrating the beauty of the Shenandoah River and the grand old oak trees that grace the grounds.

The Parkers spent over two years renovating and restoring the home to its original grandeur. The 31-room mansion has seven fireplaces, formal parlor, great room, formal dining room, library, six bedrooms and six full baths. The home is filled with period antiques, reproductions and family heirlooms. A beautiful 1840's square grand piano is the focal point of the great room, while the Library is filled with a collection of military books and memorabilia. Family portraits and photos are displayed throughout.

In the fall of 2003, Doctor and Mrs. Bridwell purchased Shenandoah Oaks. Their first contribution to the estate was renovation of the seven fireplaces. The Bridwell family, and their four friendly dogs extend a warm welcome to visitors from around the world.