Wolftrap Farm

Four Square is a historic home and farm located near Smithfield, Isle of Wight County, Virginia. The original structure was built in 1807, and is a two-story, five-bay, L-shaped frame dwelling. Also on the property are eight contributing domestic outbuildings, and a variety of barns and other farm buildings.It was listed on the National Register of Historic Places in 1979.

Poplar Hill is a historic home located near Smithfield, Isle of Wight County, Virginia. The house was built about 1793, and is a 1+1⁄2-story, frame, hall and parlor-plan dwelling. It has an early 19th-century lean-to rear addition, a post American Civil War kitchen addition, a 1920s one-room addition, and a screened-in front porch on the main facade. Also on the property are the contributing wash house, shed, garage, and stable, and the sites of a smokehouse, kitchen, carriage house, and ice house.It was listed on the National Register of Historic Places in 1995.

Robert Tynes House, also known as Tynes Plantation, is a historic plantation house located near Smithfield, Isle of Wight County, Virginia. The house was built in 1750 and is a two-story, three-bay, Georgian style brick dwelling with a gambrel roof. The interior features a center-passage single-pile plan. Also on the property are the contributing garden and well, smokehouse / frame shed, and kitchen foundation. In 1802, its owner Timothy Tynes granted manumission of his 81 slaves and the division of his 4,000 acre estate primarily to his slaves.It was listed on the National Register of Historic Places in 2007.

Ivy Hill Cemetery is a historic rural cemetery and national historic district located at Smithfield, Isle of Wight County, Virginia. It was established in 1886, and is a privately owned cemetery. Grave markers within the cemetery date from the mid-19th century to the present day. It includes a number of notable funerary monuments.Notable burials include: Pembroke Decatur Gwaltney (1836–1915), founder of the highly successful Gwaltney ham and peanut business Congressman Joel Holleman (1799–1844) Congressman Dr. John W. Lawson (1837–1905) Hardy Cross (1885–1959), Pioneer in the field of Structural EngineeringIt was listed on the National Register of Historic Places in 2007.

William Rand Tavern, also known as Rectory of the Christ Episcopal Church, Sykes Inn, and Smithfield Inn, is a historic inn and tavern located at Smithfield, Isle of Wight County, Virginia. It was built about 1752, and is a two-story, five-bay, Georgian style brick and frame building. It has a standing-seam metal hipped roof with parged brick chimneys at the building ends. A rear addition was built in 1922–1923. It opened as a tavern in 1759, and operated as such until 1854, when the Vestry of Christ Church purchased it. The church sold the property in 1892, and it resumed use as an inn in 1922. It is now operated as a bed and breakfast. It was listed on the National Register of Historic Places in 2004. It is located in the Smithfield Historic District.

The Old Isle of Wight Courthouse was built in 1750-51 and was used as the main courthouse for Isle of Wight County, Virginia until a new courthouse was built at Isle of Wight, Virginia in 1800. It is located in the Historic District in the town of Smithfield.

Smithfield Historic District is a national historic district located at Smithfield, Isle of Wight County, Virginia. It encompasses 289 contributing buildings and 2 contributing structures in the historic downtown and surrounding residential areas of Smithfield. There are 211 houses, 37 commercial buildings, 1 warehouse, 4 churches, 10 barns, 1 smokehouse, 23 garages, 1 farm office, 1 colonial kitchen, and 2 corncrib structures. Notable buildings include the original county clerk's office (1799), county jail, Wentworth-Barrett House (c. 1752), Wentworth–Grinnan House (c. 1780), King-Atkinson House (c. 1800), Smith-Morrison House (1770s), Hayden Hall (c. 1810, c. 1846), Boykin House (c. 1876), Goodrich House (1886), Thomas House (1889), Smithfield Academy (1827), Christ Episcopal Church (1832, 1892), and Hill Street Baptist Church (1923). Located in the district and separately listed are the Old Isle of Wight Courthouse, Smithfield Inn, Windsor Castle Farm, and P. D. Gwaltney Jr. House.It was listed on the National Register of Historic Places in 1973.

The Isle of Wight County Museum is located in Smithfield, Virginia.

The Wentworth–Grinnan House (ca. 1780) is listed on the National Register of Historic Places and located on the river side of South Church Street within the Smithfield Historic District in Smithfield, Virginia. Smithfield is a colonial seaport town on the Pagan River in Isle of Wight County with colonial trading ties to Bermuda and the West Indies.

Joseph Jordan House, also known as Boykin's Quarter, Jordan's, and Hatty Barlow Moody Farm, is a historic home located near Raynor in Isle of Wight County, Virginia, United States. The original structure was built about 1795, and is a 1+1⁄2-story, three-bay, frame structure with brick ends. It was later expanded with a two-story, one room, frame addition and a one-bay kitchen ell. The house features clerestory monitors that were probably added about 1820–1840. Also on the property are a variety of contributing outbuildings.It was listed on the National Register of Historic Places in 1979.

P. D. Gwaltney Jr. House is a historic home located at Smithfield, Isle of Wight County, Virginia. The house was built about 1900, and is a large two-story, rectangular, Queen Anne style wood frame mansion with three porches. It features an elaborate profile punctuated by a corner turret, projecting bays, and a complex roof form. It was the primary residence of Pembroke Decatur Gwaltney Jr. of the Gwaltney meat empire.It was listed on the National Register of Historic Places in 1999. It is located in the Smithfield Historic District. The mansion remained in the Gwaltney family until 2016.

Windsor Castle is a former plantation and now a public park in Smithfield, Virginia, United States. It is located in the Smithfield Historic District.