Following the development of the nearby Grand Central Terminal and office buildings during the early 20th century, Fred F. French began planning a residential enclave in Midtown Manhattan.

The site was historically part of the Turtle Bay Farm, which had been acquired in 1795 by Francis Winthrop, who named the area Prospect Hill because it overlooked the East River.

Soon afterward, the blocks east of First Avenue were taken over by noxious industries: abattoirs and meat packing houses, a gasworks, an animal glue factory, and the Waterside Generating Station.

[12][13][15] A real estate operator named Leonard Gans believed there was a market for middle-class apartments within walking distance of Grand Central Terminal and that Prospect Hill was an advantageous location for it.

[15] According to author Lawrence R. Samuel, Prospect Hill's topography and proximity to the East River made it "an ideal spot to situate a group of high-rise buildings that would offer thousands of residents sanctuary from the various transportation woes that plagued the city".

[23][24] In contrast to French's earlier apartment buildings on Park Avenue, which mainly attracted wealthy people because of their upscale addresses, the new Tudor City targeted middle-class managers and professionals who had previously commuted from the suburbs.

[73] Advertisements also promoted the area's "old-world charm" and sense of community, though the writer Lawrence Samuel says the wording may have implied that the residents were largely white.

[91] As a wartime precaution, air-raid drills were frequently conducted inside the buildings; a scrap-metal pile was created on 42nd Street; and first-aid stations were established in their basements.

[96][97] Tudor City's popularity in the 1940s was attributed in part to the complex's recreational facilities,[97][95] which included the tennis courts, five sun decks, and a water playground.

[77] The French Company finally acquired the site 8 Tudor City Place in June 1945,[61][103][77] at which point all of the structures surrounding that lot had been demolished several years prior.

[116][113] French Company vice president Charles N. Blakeley also objected to the plan, saying it would force tenants of the affected buildings to use stairs or escalators to reach their own front doors.

[120][121] The board provisionally authorized the street widening in June 1949, and Manhattan's borough president announced in December 1949 that work would commence shortly.

[127] After the service roads were removed, the main entrances to the Hotel Tudor, Church of the Covenant, and Woodstock Tower were stranded up to 17 feet (5.2 m) above the new grade of 42nd Street.

[5] During the late 1940s and early 1950s, rumors persisted that the French Company was planning to sell Tudor City, prompting further fears that existing residents would be evicted.

[146] The French Company leased the site west of the Hotel Tudor and announced plans in 1962 to develop a 17-story office building there, designed by William Lescaze.

The project included redecorating each building's lobby; installing electric ranges in studio apartments; replacing the elevators; and adding wallpaper and carpeting in hallways.

[5][164] Over the next decade, residents stalled the redevelopment of Tudor City's parks by stealing construction materials, filing lawsuits,[165] and, in one case, placing themselves in front of a bulldozer.

[196] Mayor Ed Koch, an initial supporter of the plan, announced in March 1981 that he would oppose the project[197][198] after rival developer Donald Trump argued that the playground was more valuable than Helmsley's proposed building.

[207] After his revised plan was rejected, Helmsley announced in January 1982 that he would again try to develop the private parks,[199] since Fred F. French had originally intended to build towers on these sites.

[214] The structure remained a rental building but was resold several times,[213] including to developer John Zaccaro, husband of U.S. vice-presidential candidate Geraldine Ferraro.

[225] Helmsley sold his three remaining apartment buildings—Hatfield House, Hardwicke Hall, and Haddon Hall—to Tudor City I Associates, a partnership of Pilevsky, Michael H. Gold, and Alfred S. Friedman.

[240] After the Black Monday stock market crash of 1987, Pilevsky and Greenburger began offering the studio apartments for as low as $77,000 to anyone who had a good credit rating.

[242] New York magazine recalled in 2008 that Time Equities ended up selling apartments at a significant discount, reporting: "In 1992, if the new owner were willing to assume the accrued debts, a Tudor City one-bedroom could be had for $3,500.

It is also ten stories high and is mostly clad with brick; the corners of the facade contain terracotta ornamentation patterned after that of the Sutton Place estate in Surrey, England.

By the time of Tudor City, the Neo-Tudor style had already been used on a limited number of urban apartment buildings, including Hudson View Gardens in Washington Heights, Manhattan, and several erected by the Fred F. French Company.

[321][322] The use of the Tudor and Elizabethan styles also contrasted with the increasing popularity of Art Deco architecture in New York City, giving each building an "old world" feeling.

[324][325] The wooden entrance doors are carved with such Tudor forms as linenfold panels and fish-bladder tracery, and decorated with hardware based on sixteenth-century precedents.

Public lobbies include half-timbering, carved woodwork, beamed ceilings, arched openings, plaster friezes and rosettes, and Tudor-style fixtures and furnishings.

[336] The Tudor City Tennis Club attracted players such as Pancho Segura, Bobby Riggs, Bill Tilden, Rudy Vallée, and Katharine Hepburn from the 1930s to the 1950s,[140] and the courts hosted the United States Pro Championship for the only time in 1936.

[338] In 1995, the co-op board of Prospect Tower requested the LPC's permission to remove the sign, calling it ugly and dangerous, but the commission refused, on the ground of historical significance.