Pleasant Valley, Calvert County, Maryland

Sunderland is an unincorporated community located at the crossroads of Maryland routes 2, 4, and 262, Dalrymple and Pushaw Station roads in Calvert County, Maryland, United States, approximately five miles south of Dunkirk and 10 miles north of Prince Frederick. Although Sunderland is not incorporated and does not have a central business district, it does have a zip code, 20689. However, as of November 2007, the former Sunderland post office had closed its doors due to a lease dispute, without opening a new location, and postal officials are determining where to locate a new post office.All Saints' Church, circa 1774-1777, was listed on the National Register of Historic Places in 1973. The Joseph D. Lyons House was listed in 1998.

All Saints' Church is a historic Episcopal church located at 100 Lower Marlboro Road (near the intersection of Southern Maryland Boulevard MD 4 and Solomons Island Road MD 2), in Sunderland, Calvert County, Maryland. All Saint's Parish was one of the thirty original Anglican parishes created in 1692 to encompass the Province of Maryland. In 1693 its first parish church, a log structure, was built on an acre of land called Kemp's Desire donated by Thomas Hillary. This log church was expanded in 1703-1704 and repaired at least 4 times before being replaced on top of the hill between MD routes 4, 262, and 2 by the present brick building.Built between 1774 and 1777, the present church building is a Georgian structure of Flemish bond brick with random glazed headers. Since All Saint's Parish was part of the established church of the Province of Maryland, the published volumes of the Archives of Maryland contain pertinent documented source material on the building showing that it was built with county taxes while future bishop Thomas Claggett served as its rector.All Saints' Church was listed on the National Register of Historic Places in 1973.All Saints' Church remains an active parish in the Episcopal Diocese of Maryland. Its current rector is the Rev. Andrew Rutledge.

The Joseph D. Lyons House is a historic home in Sunderland, Calvert County, Maryland, United States that is listed on the National Register of Historic Places. It is privately owned and not open to the public. It is a large, two-story frame structure with a hip roof and full-width front and rear porches. The house is five bays in width, front and back, and four in depth on both sides, with all of the openings evenly spaced and precisely aligned at both floor levels. It was completed in 1924, and built in Colonial Revival-style by a local contracting firm known as Lyons, Gibson & Company who were responsible for many of Calvert County's more important early-20th century public buildings and private residences. A number of agricultural buildings contemporary with the house survive, including a garage, several sheds, and a sprawling, multi-use bank barn.The Joseph D. Lyons House was listed on the National Register of Historic Places in 1998.

Chaneyville is a small, rural unincorporated community located at the crossroads of MD 4, Chaneyville Road, and Fowler Road in Calvert County, Maryland, United States. It is generally considered part of either Owings or Dunkirk.

Owings is a town center and census-designated place (CDP) in northern Calvert County, Maryland, United States. The population was 2,149 at the 2010 census, up from 1,325 in 2000.

Huntingtown High School is located at 4125 North Solomons Island Road, Huntingtown, Maryland (MD), United States. Completed and opened in 2004, HHS is currently home to approximately fifteen hundred students from grades 9 to 12. Huntingtown High School (HHS) is in Calvert County, and is part of the Calvert County Public Schools (CCPS).

Northern High School is a public secondary school located in Owings, Calvert County, Maryland, United States. In 2023 it had 1553 students attending the school.

Huntingtown, established 1683, is a census-designated place (CDP) in Calvert County, Maryland, United States. The population was 3,311 at the 2010 census, up from 2,436 in 2000. Many large estate homes have recently been built in small developments off routes 2/4. It has a public high school called Huntingtown High. The Calverton School is located just south of the town center. State-operated commuter buses and private vanpools carry residents to Washington.

Holly Hill, also known as Holland's Hills or Rose Valley, is a historic house at Friendship, Anne Arundel County, Maryland, United States. It was initially named as Holland's Hills for Francis Holland, who bought the land in 1665. Richard Harrison, a Quaker planter and shipowner, bought the land and built a home on it. Harrison owned about 6,000 acres total. It was originally a primitive, two-room, 1+1⁄2-story frame dwelling constructed in the fall or winter of 1698. An addition was made in 1713, and c. 1730, the entire structure was encased in brick and another addition was constructed. The house is an example of Medieval Transitional architecture built in Maryland during the mid-seventeenth century. It was a quarter plantation of Richard Harrison, who likely built the original structure for his son, Samuel Harrison (1679–1733). The inventory of Samuel Harrison's estate (1733) lists thirteen rooms, including a kitchen as well as a library of 195 books. Harrison's "store" or storeroom contained abundant supplies of everything from cooper's tools to tobacco boxes to India silk. Interesting features of the house include original brick vaulting in the cellar, fine paneling and moldings, ancient glass panes, batten doors with original hardware, a wall of rare marbleized paneling; and three eighteenth-century paintings on wood. In 1825, the will of Benjamin Harrison bequeathed half of the household furniture and three African-American slaves to his daughter Ann Tongue. Ownership of Holly Hill continued in the Harrison family until 1850; then, after a brief period, it was owned by the Scrivener family until Captain and Mrs. Hugh P. LeClair purchased it in the late 1930s. The LeClair family completed an extensive restoration of the house and added a kitchen wing and a detached garage in faithful Tidewater style. In 1968, Holly Hill was purchased by attorney Brice McAdoo Clagett (1933–2008) and his wife Virginia Parker Clagett. Brice was a descendant of the original builder, Richard Harrison. Clagett and his wife added extensive ornamental plantings and gardens to the grounds near the house.Holly Hill was listed on the National Register of Historic Places in 1971. Holly Hill is protected by conservation easements that are held by Maryland Environmental Trust and Maryland Historical Trust. It comprises 585.6 acres (237.0 ha).

Friendship is an unincorporated community and census-designated place (CDP) in Anne Arundel County, Maryland, United States. As of the 2010 census, its population was 447.Friendship covers 1.794 square miles (2.887 km2), and is located at the southern tip of Anne Arundel County along Maryland Route 2, by which road it is 22 miles (35 km) north to Annapolis, the state capital, and 15 miles (24 km) south to Prince Frederick, the seat of Calvert County.

Maidstone is an old southern Maryland plantation located in Owings, Calvert County, Maryland. The oldest extant part of the house was built in 1751 by a yeoman planter, Lewis Lewin on or near the site of an earlier wood structure., though a brick in one of the chimneys is dated 1678.

Chesapeake Beach is a town in Calvert County, Maryland, United States. Its major attractions include the Chesapeake Beach Railway Station, the Chesapeake Beach Rail Trail, a water park, marinas, piers, and charter boat fishing. The town's population was recorded as 5,753 in the 2010 census.