Head of the Harbor, New York

Kate Annette Wetherill Estate is a national historic district located at Head of the Harbor in Suffolk County, New York. The district encompasses an estate with three contributing buildings, two contributing sites, and two contributing structures. The estate house was designed by Stanford White in 1895 in the Colonial Revival style The main block of the house is two stories with a full attic formed of facade gables corresponding to an octagonal form. A large 2+1⁄2-story, gable-roofed service wing projects to the east. Also on the property is a pump house, rose garden, stone entrance piers with iron gate, carriage barn, and superintendent's cottage.It was added to the National Register of Historic Places in 1993.

The Saint James General Store is a general store located on the northwest corner of Moriches and Harbor Hill Roads in Saint James, New York. Established in 1857, it is a contributing property of the Saint James District, which is primarily in the vicinity of New York State Route 25A in St. James, although the store is located northwest of Route 25A.

Shore Cottage, also known as the Lawrence Grant White and Laura Chanler White Estate, is a national historic district located at Head of the Harbor in Suffolk County, New York. The district encompasses an estate with two contributing buildings. The estate house was designed in 1913 and is a 2+1⁄2-story, rectangular block clad in stucco under a gable slate roof. It was the summer home of the Lawrence Grant White family; he was a son of Stanford White. Also on the property is a contributing barn.It was added to the National Register of Historic Places in 1993.

Mills Pond District is a national historic district located at St. James in Suffolk County, New York. The district includes nine contributing buildings. Prominent buildings within the district are the Mills Homestead (1837), Wegrzyn Barn, ice house, Wegrzyn House (c. 1730), Dougherty House (c. 1730), Papadakos House (c. 1820), Gyrodene Gambrel Roofed House (c. 1800), and Perry House (c. 1880).It was added to the National Register of Historic Places in 1973.

Saint James District is a national historic district located at St. James in Smithtown Town, Suffolk County, New York. The district includes 21 contributing buildings, two contributing sites, and one contributing structure. Prominent buildings within the district are the Timothy Smith House (ca. 1800) and dependencies, "Deepwells" (1845–47) and dependencies, St. James Episcopal Church and dependencies, the St. James Railroad Station (built in 1873), and St. James General Store (built in 1857). The newest structure, the 1922-built Saint James Fire Department was also included in the district, but was modernized in recent decades.It was added to the National Register of Historic Places in 1973.

St. James is a historic station on the Port Jefferson Branch of the Long Island Rail Road. The station is located on Lake Avenue and Railroad Avenue, just south of New York State Route 25A in St. James, Suffolk County, New York.

Harbor House, also known as the George C. Case Estate, is a national historic district located at Nissequogue in Suffolk County, New York. The district encompasses an estate with two contributing buildings, one contributing site, and two contributing structures. The estate house is a two story with full attic structure with a gambrel roof designed in 1910. Also on the property are a contributing carriage barn / stable and a well house.It was added to the National Register of Historic Places in 1993.

East Farm, also known as the Archibald M. Brown Estate, is a national historic district located at Head of the Harbor in Suffolk County, New York. The district encompasses an estate with seven contributing buildings and one contributing site. The estate house was originally built in the 18th century about 1690 and as the Smith family farmhouse, then greatly enlarged by its architect-owner in 1910. It is a wood framed, clapboarded structure with a wood shingle roof, and Colonial in style. Also on the property are a contributing barn with shed, milk house, two cottages, and barn and garage complex. The estate also retains an intact formal garden.It was added to the National Register of Historic Places in 1993.

Box Hill Estate is a national historic district located in St. James in Suffolk County, New York. The district encompasses an estate that includes five contributing buildings and one contributing structure. The estate house was the summer home of Stanford White. It was built in 1885 and is a rambling, multi-gabled structure surfaced in pebblestone dashed stucco. It features a one-story verandah defined by a range of fluted columns. Also on the property are a contributing cottage, barn, carriage house, stable, and water tower.It was added to the National Register of Historic Places in 1973.

Flowerfield was a station along the Port Jefferson Branch of the Long Island Rail Road in Saint James, New York. The station opened in 1910 on a 1,000-acre (400 ha) parcel purchased by John Lewis Childs to grow plants and seeds, which was later acquired by the Gyrodyne Company of America. The second floor of the station even had a small greenhouse. The station agency closed in 1944. On July 2, 1959, the LIRR petitioned with the New York State Public Service Commission for permission to discontinue all passenger services and team tracks at the station.Reopening the Flowerfield station, along with a closure of the St. James station, was proposed in the mid-1990s as part of a plan to redevelop the Gyrodyne site.

By-the-Harbor, also known as the Prescott Hall Butler and Cornelia Smith Butler Estate, is a historic home located at Nissequogue in Suffolk County, New York. It was built about 1878 as the first of a group of country homes built on Stony Brook Harbor and one of Charles F. McKim's earliest projects. It is a long and narrow, two story, Shingle Style structure with a low attic level at each end. The south facade features a massive asymmetrical gable that rises from the first floor to the ridge of the roof. Also on the property are the original flanking stone entrance piers and rusted iron gates and casino building. The casino is a sprawling two story Colonial Revival style building with shingled facades and a hipped roof. The original section, holding a squash court and plunge baths, was designed in the 1890s by McKim, Mead, and White. In 1905, a wing containing a ballroom and designed by Stanford White, was added.It was added to the National Register of Historic Places in 1993.

The Mallows, also known as Alida Chanler Emmet and Christopher Temple Emmet Estate, is a historic home located at Head of the Harbor in Suffolk County, New York. It is a Colonial Revival estate home designed in 1906 by architect Charles A. Platt (1861–1933). It is an imposing structure, finished in stucco with powerful wooden detailing at the principal doorways, roof cornice and porch. It is a large rectangular mass, two full stories in height, seven bays long, with projecting wings. It features a simple pitched gable roof and a two-story porch on the west wing with large Doric order piers.It was added to the National Register of Historic Places in 1993.