The 43rd Street sections of the building are topped by a set back five-story attic, interrupted by a seven-story tower with a pyramidal hip roof.

The facade is constructed of light-colored Indiana limestone, brick, and terracotta and is divided horizontally into a two-story base, a nine-story midsection, and the attic and tower stories.

Prior to the New York Times Annex's development, the site was part of the Astor family estate and contained several brownstone townhouses.

[22] After the first expansion in 1924, an account by the New York Times Company described the building as measuring 399 ft 6 in (121.77 m) from the lowest basement to the pinnacle of the rooftop flagpole.

[25] At the extreme east end of the building, the four-story wing has a brick facade and three single-hung windows on either of the third and fourth stories.

[40] A freight elevator was at the eastern end of the building and traveled between the ground-floor loading dock and the sub-basement; it was used exclusively to transport paper.

[43] The ground level had a neo-Gothic entrance, three loading docks, two storefronts, and a passageway leading to Weber and Fields' Music Hall (later the 44th Street Theatre).

[69] The addition was to be designed in a similar style to Fox's original building, making the structures appear as though they were built at the same time.

[97] The northward expansion, which was completed in 1947, involved expanding the printing presses' capacity by 50 percent, as well as adding bedrooms on the 14th story for executives.

[82][98] Three memorial plaques were unveiled inside the renovated lobby in 1948, commemorating Times employees who had fought in the two world wars.

[53] The surrounding section of 43rd Street was widened in 1951 to accommodate delivery-truck traffic, and Shreve, Lamb and Harmon designed an auditorium on the ninth story, which opened the next year.

[82] A computer, capable of printing type with even margins, was installed on the third floor in 1964, but it subsequently went unused for several months due to disputes with the Times's labor unions.

[82][109] By the late 1960s, crime in the area was increasing; one-third of the building's night-shift printers had been assaulted or robbed,[110] and an official for a newspaper-deliverers' union said the structure was one of the most dangerous places in the city for news-truck drivers.

[117] The Times was also looking to relocate its printing plant outside of New York City, with 2,000 employees in the business and news departments to remain at 229 West 43rd Street.

[24] Concurrently in 1999, state and city officials were planning to launch a request for proposals for a nearby vacant site on Eighth Avenue between 40th and 41st Streets.

[132][133][11] Tishman Speyer planned to renovate the building's 770,000 sq ft (72,000 m2) of office space as soon as the Times moved out, as well as add retail to the base.

[132][11] Tishman Speyer announced plans in 2006 to convert the ground-level loading bays into 100,000 sq ft (9,300 m2) of storefronts, designed by Gabellini Sheppard Associates.

[24] Amid a shortage of Midtown office space, ESPN and several law firms expressed interest in leasing at 229 West 43rd Street.

[135] The Times shifted its publishing operations from 43rd Street to its new Eighth Avenue headquarters on June 11, 2007,[136][137] and the paper's collection of 5 million print materials was relocated as well.

[139] The same month, Lev Avnerovich Leviev's Africa Israel Investments (subsequently AFI USA) acquired it for $525 million, three times the price Tishman Speyer had paid.

[38] That December, Leviev announced plans to convert the building into a mixed-use structure with retail at the base, 379 hotel rooms in the midsection, and 26 residential condominiums in the attic.

[142] Fashion designer Tommy Hilfiger and investment firm JSR Capital had considered buying eight floors for $110 million and operating a hotel there, but they withdrew their offer.

[157][158] In 2011, The Blackstone Group purchased the top 11 office stories for $160 million, though AFI USA and Five Mile retained ownership of the 245,000 sq ft (22,800 m2) of retail on the four lowest floors.

[159][160] After buying the office floors, Blackstone spent $105 million on renovations, aiming to attract startups and technology companies[161][162] with incentives such as private entrances, parking, and terraces.

[166][167] Several technology companies including Facebook reportedly expressed interest in leasing space at 229 West 43rd Street.

[180][181] A month later, Kushner signed National Geographic Encounter to operate an educational entertainment attraction about the ocean, replacing Discovery Times Square Exposition.

[189][190] Guy Fieri's restaurant announced plans to close at the end of 2017,[191] and the food hall was canceled after English and Kushner sued each other in February 2018.

[192] That April, Kushner replaced Guy Fieri's former space with a new outpost of The Ribbon, a popular Upper West Side restaurant.

[199] In March 2020, when the COVID-19 pandemic in New York City forced many physical businesses to close, Kushner fell behind on loan payments yet again.

[210] Conversely, the paper's former architecture critic Paul Goldberger said "it was never a wonderful place to work" because it merged "the worst qualities of a factory and an office".