The medieval Madrid was a walled city with controlled access points known as Gates. As the city grew, the wall became part of the population and new gates were relocated. Various Toledo Gates were placed along the axis of Toledo Street.
In the original city wall built in the 11th century, there was a Toledo Gate near the Hospital de la Latina, from where the road to Toledo began. This first Toledo Gate was at the intersection of Toledo Street and Santa Ana Street. It was surrounded by a wall extending to Embajadores, crossing Lavapiés, and running via Magdalena to Antón Martín Square (location of Antón Martín Gate). In 1625, with the construction of the Alfonso XIII wall, a second gate was built, closer to the city center on Toledo Street, near the Casa-Matadero. This area housed livestock slaughter and was near leather tanning and leather goods industries. The gate was made of brick, as depicted in Texeira's plan.
The current gate's construction began during the Napoleonic occupation under Joseph Bonaparte, intending to enhance the entrance to Madrid via the old Andalusia royal road. This initial project was not completed; after Bonaparte's expulsion, the municipal authorities commissioned a new design from architect Antonio López Aguado. He designed it as a triumphal arch honoring the restored Fernando VII. The old Toledo Gate was demolished, and the new gate was moved to its current location in 1813, with construction finishing in 1827. A time capsule containing coins, Madrid guides, calendars, and Joseph I's government constitutions was buried beneath it. Later, after Joseph I's departure, Madrid's City Council unearthed the capsule, replacing some contents with the 1812 Constitution and Fernando VII medals. When Fernando VII abolished the constitution, he ordered its excavation, replacing it with the contemporary Madrid Diary, Guide for Strangers, and Sarrabal de Milán (a type of almanac). By the late 19th century, public executions moved from Plaza de la Cebada to the outskirts, near the Toledo Gate.
In the 19th century, animal entry into the city was restricted to the Toledo Gate, making Toledo Street and its gate Madrid's primary livestock passage. This changed in the early 20th century with the establishment of the Legazpi Slaughterhouse. Following Carlos María de Castro's 1868 plans for Madrid's expansion, the Toledo Gate became part of the city, losing its gate function. The old Casa-Matadero, relocated to the Legazpi Slaughterhouse, became the Central Fish Market. In 1848, the Gas Factory (Gasómetro) was installed nearby.
Today, the Toledo Gate is a city monument. Restorations by the Madrid City Council in 1995 partly restored its original appearance. However, the diminishing importance of Toledo Street throughout the 20th century and reduced traffic along the Ronda de Toledo - Bailén axis have left the gate as a visitable monument. The nearby Puerta de Toledo Market and the current Rastro of Madrid make it a distinctive symbol of Madrid.
Currently, it is located in the middle of a roundabout and surrounded by a landscaped area, so there is no passage of people or vehicles through it. The construction of an underground tunnel beneath the gate has caused the ground on which it sits to slightly subside and the central arch to be deformed, although this is barely noticeable.
Its structure is made up of granite blocks, and the decorative elements are made of Berroqueña limestone. Some authors describe it as a 'heavy' gate compared to the Alcalá Gate.
In neoclassical style, it is composed of a central semicircular arch and two linteled doors on its sides. The decoration consists of fluted Ionic half-columns on either side of the central arch, and pilasters of the same style framing the sides.
The Gate of Toledo is crowned by a stone sculptural group designed by José Ginés and carved by Ramón Barba and Valeriano Salvatierra. On the north facade, held by two children, is the coat of arms of Madrid. Military trophies rest above the side doors, facing south.
On the facade facing south (exterior), an allegory of Spain is depicted in the center, supporting a shield placed over two hemispheres. The allegory is shown receiving a genius from the provinces, personified by a matron placed to the right of Spain. This is to pass it to the arts on the left, represented by another matron with their attributes.
The military trophies facing south appear in different arrangements. Some of them resemble those already present on the Puerta de Alcalá, previously designed by Sabatini. Among the trophies, the banners, plumes, and various armaments (mortars and piled projectiles) stand out.
With the completion of the current Puerta de Toledo at the beginning of the 19th century, inscriptions were made. Part of them were torn off during the revolution of 1854, leaving only the inauguration date. Today, after its restoration, the complete inscription is once again displayed.