Isle of Wight Academy

Isle of Wight is an unincorporated community in and the county seat of Isle of Wight County, Virginia, United States. Originally, Isle of Wight County was named Warrosquyoake Shire. This was changed to the current name of Isle of Wight in 1637.

Boykin's Tavern is a historic inn and tavern located at Isle of Wight, Isle of Wight County, Virginia. The original structure was built about 1790, and expanded to two stories with a 1+1⁄2-story gambrel-roofed wing in the early 19th century. A two-story wing and two-story porch were added in 1900–1902. It has four brick external end chimneys and a standing seam metal gable roof. The interior reflects the transition between the Colonial and Federal styles. It is the only surviving structure associated with the Isle of Wight Courthouse of 1800. The building is occupied by a local history museum. It was listed on the National Register of Historic Places in 1974.

Isle of Wight County is a county located in the Hampton Roads region of the U.S. state of Virginia. It was named after the Isle of Wight, England, south of the Solent, from where many of its early colonists had come. As of the 2020 census, the population was 38,606. Its county seat is Isle of Wight, an unincorporated community. Isle of Wight County is located in the Virginia Beach-Norfolk-Newport News, VA-NC Metropolitan Statistical Area. Its northeastern boundary is on the coast of Hampton Roads waterway. Isle of Wight County features two incorporated towns, Smithfield and Windsor. The first courthouse for the county was built in Smithfield in 1750. The original courthouse and its associated tavern (The Smithfield Inn) are still standing. As the county population developed, leaders thought they needed a county seat near the center of the area. They built a new courthouse near the center of the county in 1800. The 1800 brick courthouse and its associated tavern (Boykin's Tavern) are still standing, as are the 1822 clerk's offices nearby. Some additions have been made. The 1800 courthouse is used daily, serving as the government chambers for the Board of Supervisors, as well as the meeting hall for the school board. The chambers are sometimes used as a court for civil trials if the new courthouse is fully in use. The new courthouse opened in 2010; it is across the street from the sheriff's office and county offices complex.

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.

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.

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.

Wolftrap Farm was a historic home located near Smithfield, Isle of Wight County, Virginia. The house was built about 1820, and is a 2+1⁄2-story, three-bay, Federal style frame dwelling. It was a one-story rear elevation surmounted by a double tier of dormer windows. The house has a double-pile, hall-parlor plan and measures approximately 32 feet, 6 inches, square. The house has been dismantled.It was listed on the National Register of Historic Places in 1974, and was delisted in 2017

William Scott Farmstead, also known as the Roberts House and Ennis Pond House, is a historic home located near Windsor, Isle of Wight County, Virginia. The house was built about 1775, and is a two-story, five-bay, gable roofed brick dwelling. It has a rear frame addition dated to the mid- to late-19th century. The front facade features a pedimented one bay porch supported by Doric order columns. The interior retains much of its early Federal interior woodwork. Also on the property are the contributing servants' quarters, smokehouse, barn, and corn crib.It was listed on the National Register of Historic Places in 1991.

Windsor High School is a public high school located in Windsor, Virginia in Isle of Wight County.

Henry Saunders House is a historic home located near Windsor, Isle of Wight County, Virginia, United States. The house was built about 1796, and is a 1+1⁄2-story, three bay Georgian style frame dwelling. It has a gable roof with dormers and a one-story side wing. Also on the property are four additional contributing buildings and one contributing structure.It was listed on the National Register of Historic Places in 1991.

Windsor is an incorporated town in Isle of Wight County in the Hampton Roads region of southeastern Virginia in the United States. It is located near the crossroads of U.S. Route 460 and U.S. Route 258. The population was 2,626 at the 2010 census, up from 916 at the 2000 census.

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.