Five Forks, Madison County, Virginia

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.

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.

The Residence, also known as Woodberry, is a historic home located on the grounds of Woodberry Forest School at Woodberry Forest, Madison County, Virginia. It was built in 1793, reputedly after the plans of Thomas Jefferson. In 1884, the house was extensively enlarged and altered. It is a 1+1⁄2-story, wood frame, Federal-style residence. The front facade features a pedimented Tuscan order portico. The house is covered with weatherboarding and is topped by its original hipped roof. Also on the property is the contributing smokehouse. The house was built for William Madison, brother of President James Madison.It was listed on the National Register of Historic Places in 1979.

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

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.

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.

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.

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.

Locust Dale is an unincorporated community in Madison County, Virginia, United States.Locust Hill was listed on the National Register of Historic Places in 2002.

Locust Hill is a historic home and farm complex located at Locust Dale, Madison County, Virginia. The two-story frame house incorporates an original side-passage- plan section dating to 1834. which was enlarged and given a two-tier Doric order front porch probably about 1849. About 1900 a three-story bathroom tower, a summer kitchen, and a brick greenhouse wing were added. The house includes Federal and Greek Revival style elements. Also on the property are the contributing Willis's School (1897), smokehouse, cistern, dairy, brick lined pit, the site of a water tower, chicken house, Locust Dale store and Post Office (1880s), and Fertilizer House (1934).It was listed on the National Register of Historic Places in 2002.