The Residence

Woodberry Forest School is a private, all-male boarding school located in Woodberry Forest, Madison County, Virginia, in the United States. Woodberry's current enrollment is 391. Students come from 34 U.S. states, Washington, D.C., and 36 countries. The school's endowment and managed funds total $432,000,000 as of June 30, 2023. Comprehensive tuition for 2023–2024 is $65,350; 41% of the students receive financial aid.

Grelen is a historic home located near Orange, Orange County, Virginia. The main house was built in 1935–1936, and consists of a 2+1⁄2-story, five-bay, brick Georgian Revival style main block flanked by 1+1⁄2-story brick wings. The house is topped by a slate hipped roof and has a recessed centrally located six-panel front door surrounded by fluted pilasters. It features two massive interior brick chimneys with corbeled caps that rise above the roof of the main block of the house.It was listed on the National Register of Historic Places in 1998.

Brampton, also known as Buena Vista Farm, is a historic home located near Orange, in Madison County, Virginia. It was built about 1846, as a two-bay, side passage plan with a flat roof, two-story portico, and a small wing. It is a temple-form Greek Revival-style residence. A rear addition was built about 1900, and the front portico was redesigned with a pedimented form. Also on the property are the contributing brick kitchen, smokehouse, and dairy.It was listed on the National Register of Historic Places in 1985.

Five Forks is an unincorporated community located in Madison County, Virginia, United States.

Willow Grove Inn (officially known as The Inn at Willow Grove) is a hotel in Orange, Virginia, United States. The basic structure of the building was built by Joseph Clark in 1778. In 1820, his son added a brick wing.The exterior of the building reflects Thomas Jefferson's Classical Revival architecture, but the interior reflects Federal-style architecture.The Inn at Willow Grove has also been a member of Historic Hotels of America, the official program of the National Trust for Historic Preservation, since 2017.

Willow Grove, also known as the Clark House, is a historic plantation house located near Madison Mills, Orange County, Virginia. The main brick section was built about 1848, and is connected to a frame wing dated to about 1787. The main section is a 2+1⁄2-story, six-bay, Greek Revival-style brick structure on a high basement. The front facade features a massive, 2+1⁄2-story, tetrastyle pedimented portico with Tuscan order columns, a full Tuscan entablature, an arched brick podium, and Chinese lattice railings. Also on the property are numerous 19th-century dependencies and farm buildings, including a two-story schoolhouse, a one-story weaving house, a smokehouse, and a frame-and-stone barn and stable.It was listed on the National Register of Historic Places in 1979.

Greenway, also known as Prospect Hill, is a historic home and farm complex located at Madison Mills, Madison County, Virginia. The original section was built about 1780, and is a 1+1⁄2-story, heavy timber-frame structure, on a hall-and-parlor plan. A shed-roofed rear addition was added shortly before 1800. A rear wing was added in the early-20th century and enlarged in 1986. Also on the property are the contributing wood frame dairy / maids house; brick dairy / smokehouse; pumphouse (c. 1920); garage, corncrib, and the Madison/Taliaferro family cemetery. Greenway was built by Francis Madison, brother of President James Madison.It was listed on the National Register of Historic Places in 1988.

Madison Mills is an unincorporated community located in Madison County, Virginia, United States. It is located at the intersection of U.S. Route 15 and Virginia State Route 230. Greenway and Willow Grove are listed on the National Register of Historic Places.

Belle Plaine is a historic farm property at 2488 South United States Route 15 in rural Madison County, Virginia, south of Locust Dale. The main farmhouse is a five-bay two-story frame structure attached to a somewhat older log structure, finished like the main block in wooden clapboards. The log portion is believed to be one of the oldest surviving structures in the county. The property illustrates the changing trends of agricultural use over more than two centuries.It was listed on the National Register of Historic Places in 2016.

The Robinson River is a 34.2-mile-long (55.0 km) tributary of the Rapidan River in Madison County, Virginia, in the United States. It flows southeast through White Oak Canyon and Berry Hollow, under Routes 231, 29 and 15. From its start in Shenandoah National Park as Cedar Run and Tims River, it has confluences with the Rose River, Quaker Run, Shotwell Run, Leathers Run, Mulatto Run, White Oak Run, Deep Run, Dark Run, Beaverdam Run and Great Run before its confluence with the Rapidan River. A 19-mile (31 km) section of the Robinson River from Syria to Locust Dale is Class II whitewater, with an average gradient of 15 feet per mile (2.8 m/km). In the Syria area, both the Rose River and Robinson River are stocked with Rainbow trout and Brook trout by the state of Virginia.

Tanners is an unincorporated community located in Madison County, Virginia.

Hare Forest Farm is a historic home and farm complex located near Orange, Orange County, Virginia, United States. The main house was built in three sections starting about 1815. It consists of a two-story, four-bay, brick center block in the Federal style, a two-story brick dining room wing which dates from the early 20th century, and a mid-20th-century brick kitchen wing. Also on the property are the contributing stone garage, a 19th-century frame smokehouse with attached barn, an early-20th-century frame barn, a vacant early-20th-century tenant house, a stone tower, an early-20th-century frame tenant house, an abandoned storage house, as well as the stone foundations of three dwellings of undetermined date. The land was once owned by William Strother, maternal grandfather of Zachary Taylor, and it has often been claimed that the future president was born on the property.It was listed on the National Register of Historic Places in 1992.