Stephen and Charles Smith House

Springbank is a historic home located at Roslyn Harbor in Nassau County, New York. It was built about 1835 and expanded and modified in 1880. A two-story rear addition was completed in 1959. It exhibits building construction and stylistic details from a number of periods. The first renovation was a conversion of the original simple dwelling to a Swiss cottage style building. Details added include the Dutch door main entry, full front porch, overhanging roof, front dormer, and a seven-foot addition. It features a deep front porch on the front elevation with sawn brackets. The property was once owned by the family of William Cullen Bryant.It was added to the National Register of Historic Places in 1999.

Clifton is a historic mansion located at Roslyn Harbor in Nassau County, New York. The main house is a large, 2+1⁄2-story, Flemish Revival building constructed about 1863 and altered twice between 1876 and 1932. It features a complex roof plan, including numerous gables in the forms of cross gables, wall dormers and roof dormers, most of which are Flemish gables with bold molding. Also on the property are a contributing boathouse and rustic gazebo.It was listed on the National Register of Historic Places in 1999.

The Clayton-Cedarmere Estates are located in Roslyn Harbor, New York, United States, listed jointly on the National Register of Historic Places in 1986. Clayton, the bulk of the property, is the large landscaped Bryce/Frick estate, now home to the Nassau County Museum of Art. Cedarmere, the smaller of the two, is William Cullen Bryant's estate, currently undergoing interior renovation, is located on the west side of Bryant Avenue; overlooking Hempstead Harbor, now a historic house museum. The grounds are open to the public. The two combined properties, with input from several notable architects, illustrate the development of estates on the North Shore of Long Island over a period of nearly a century.Bryant originally owned almost the entire property. Fifteen years after Bryant's death, in 1893, Lloyd Bryce bought the largely undeveloped inland portion of the estate and hired Ogden Codman, Jr. to design a mansion for it. In 1919, the dying Henry Clay Frick purchased the estate for his son Childs, who, after renovating it and expanding it, lived there with his family until his 1965 death. Four years later, it was turned over to the county for use as a museum.

Willowmere, also known as Pearsall House, is a historic home located at Roslyn Harbor in Nassau County, New York. It was originally constructed about 1750 as a 2+1⁄2-story, gambrel-roofed dwelling with a five-bay front facade. It was expanded in 1893. It was the property of Admiral Aaron Ward (1851-1918), a rose lover. The portico was added in 1926, when the house was renovated to the Colonial Revival style.It was added to the National Register of Historic Places in 1999.

Clapham-Stern House, also known as Wenlo and originally known as Stone House, is a historic mansion located at Roslyn Harbor in Nassau County, New York. It was originally built between 1868 and 1872 and turned into a premier estate in 1906 after being purchased by department store magnate Benjamin Stern. It is an asymmetrical 2+1⁄2-story dwelling resting on a full basement. It consists of a main block with wings to the north and south, a tower, and a piazza wrapping around the south and west sides. It is constructed of rough-faced gray Greenwich granite accented by limestone. It has a moderately pitched hipped slate roof with copper cresting. After a major fire in 1960, the house was returned to a High Victorian Gothic style. Also on the property there is a contributing bathhouse dated to the 1920s.It was listed on the National Register of Historic Places in 2005.

The 1919 PGA Championship was the second PGA Championship, which is now considered one of golf's major championships. It was held September 16–20 at the Engineers Country Club in Roslyn Harbor, New York, east of New York City on Long Island in Nassau County. The PGA Championship was not held in 1917 or 1918 due to World War I. The field of 32 golfers qualified by sectional tournaments. They competed in 36-hole match play rounds in a single-elimination tournament. Defending champion Jim Barnes defeated Fred McLeod, 6 & 5, in the final.

Trinity Church Complex is a historic church off of Northern Boulevard in Roslyn, New York. It is located on the westbound off-ramp from the William Cullen Bryant Viaduct and Church Street, the latter of which also leads to the St. Mary's Roman Catholic Church of Roslyn, on the northeast corner of Bryant and Summit Avenues.

Engineers Country Club is a historic country club located in Roslyn Harbor, New York, on the historic Gold Coast on the north shore of Long Island.

Mudge Farmhouse is a historic home located at Roslyn Harbor in Nassau County, New York. It was moved to its present location about 1920. It dates to the 18th century and is built of oak timbers. It features the original front Dutch door entry. Alterations and additions occurred when the house was moved. They are believed to have been designed by John Russell Pope, brother-in-law of the owner at the time, Robert Patchin.It was added to the National Register of Historic Places in 1999.

My Father's Place was a music venue in Roslyn, New York. It first opened in 1971, and according to The New York Times, "created a scene that would influence music for decades to come."In the nearly sixteen years the club was open before it closed in 1987, My Father's Place presented more than 6,000 shows from over 3,000 diverse artists. Its promoter Michael "Eppy" Epstein refused to book cover bands, and so the club became known as a place aspiring artists could perform. Young unknown musicians such as Billy Joel, Bruce Springsteen, Madonna, Aerosmith, The Police, Tom Petty, as well as hopeful comics Billy Crystal, Eddie Murphy, and Andy Kaufman, and a host of others graced the stage. In the summer of 2018 Epstein opened a new version of the club in a location not far from the original venue, in the newly renovated Roslyn Hotel (formerly the Roslyn Claremont Hotel).

Willet Titus House is a historic residential building located at Roslyn in Nassau County, New York. It was built about 1860 and is a 2-story Italianate-style frame house with an above-grade basement story at the west end. It consists of a 2-story, rectangular main block with a three-bay side entrance facade and a recessed 1+1⁄2-story two-bay wing. It features porches at the front of the main block and wing.It was listed on the National Register of Historic Places in 1986.

The Rescue Hook & Ladder Company No. 1 Firehouse is a historic fire station located in Roslyn, Nassau County, New York. Although the department was established on November 1, 1852, the Colonial Revival style firehouse itself was built in 1937. It was subsequently sold and renovated as a Temple, and now houses a retail business. The new Roslyn Hook & Ladder Company No. 1 firehouse, dedicated in 1986, is a Brobdingnagian structure containing five fire trucks and larger equipment, towering over the Roslyn Plaza, which had fallen victim to the Town of North Hempstead's asphalt- and concrete- philosophy, demolishing 19th century structures for the Long Island Railroad's expansive parking lot. The volunteer firefighter brigade has claimed several championships over the years in competitions with other firehouses.It was added to the National Register of Historic Places on May 6, 1991.