Many London houses were being made from stone and timber and even brick and timber, instead of just timber and mud. However, chimneys were still a luxury of the rich. They were made of stone, tile, or plaster. There were windows of glass and a guild of glaziers was chartered by the King. A typical merchant's house had a cellar; a ground floor with a shop and storage space; a first floor with a parlor to receive guests, a spacious hall for dining, and perhaps a kitchen; and at the top, a large family bedroom and a servant's room. Many single-roomed houses added a second-floor room for sleeping, which was approached by a wooden or stone staircase from the outside. Their goods were displayed on a booth outside the door of the house or hung in the windows. They were stored at night in the cellar. Over the booths swung huge signs, which had to be nine feet above street level to allow a man on horseback to ride underneath. There were no sidewalks. Street repair work for wages was supervised by a stone master. The streets sloped down from the middle so that the filth of the streets would run down the sides of the road. There were many wood chips in the streets due to cutting up of firewood before taking it indoors. People often threw the rubbish from their houses onto the street although they were supposed to cart it outside the city walls and to clean the frontage of their houses once a week. Dustmen scavenged through the rubbish on the streets. Pigs and geese were not longer allowed to run at large in the streets, but had to be fed at home. There were other city rules on building, public order, the use of fountains, precautions against fire, trading rights in various districts, closing time of taverns, and when refuse could be thrown into the streets, e.g. nighttime.

Aldermen were constantly making rounds to test measures and weights, wine cups, the height of tavern signs, and the mesh of the fishing nets, which had to be at least two inches wide. They saw that the taverns were shut when curfew was rung and arrested anyone on the street after curfew who had a weapon, for no one with a sword was allowed on the streets unless he was some great lord or other substantial person of good reputation. Wards provided citizens to guard the gates in their respective neighborhood and keep its key.

The city was so dense that nuisance was a common action brought in court, for instance, vegetable vendors near a church obstructing passageway on the street or plumbers melting their solder with a lower than usual shaft of the furnace so smoke was inhaled by people nearby.

Crime in London was rare. Murder, burglary, highway robbery, and gross theft were punishable by hanging. Forgery, fraud, was punishable by the placement in the pillory or stocks or by imprisonment. Perjury was punished by confession from a high stool for the first offense, and the pillory for the second. Slander and telling lies were punished by the pillory and wearing a whetstone around one's neck. There was an ordinance passed against prostitutes in 1351. London as well as other port towns had not only prostitutes, but syphilis.

Prominent Londoners sought to elevate their social position by having their family marry into rural landholders of position. For poor boys with talent, the main routes for advancement were the church, the law, and positions in great households.

Many master freemasons, who carved freestone or finely grained sandstone and limestone artistically with mallet and chisel, left the country for better wages after their wages were fixed by statute. The curvilinear gothic style of architecture was replaced by the perpendicular style, which was simpler and cheaper to build. Church steeples now had clocks on them with dials and hands to supplement the church bell ringing on the hour. Alabaster was often used for sepulchral monuments instead of metal or stone. With it, closer portraiture could be achieved.

In the 1300s and 1400s the London population suffered from tuberculosis, typhus, influenza, leprosy, dysentery, smallpox, diphtheria, measles, heart disease, fevers, coughs, cramps, catarrhs and cataracts, scabs, boils, tumors, and "burning agues". There were also many deaths by fires, burning by candles near straw beds when drunk, falling downstairs when drunk, and drowning in the river or wells. Children were often crushed by carts, trampled by horses, or mauled by pigs. Towns recognized surgery as a livelihood subject to admission and oath to serve the social good. Master surgeons were admitted to practice in 1369 in London in full husting before the mayor and the aldermen and swore to: faithfully serve the people in undertaking their cures, take reasonably from them, faithfully follow their calling, present to the said mayor and aldermen the defaults of others undertaking, so often as should be necessary; to be ready, at all times when they should be warned, to attend the maimed or wounded and others, to give truthful information to the officers of the city as to such maimed, wounded, or others whether they be in peril of death or not, and to faithfully do all other things touching their calling.

Some young girls of good families were boarded at nunneries to be taught there. Some upper class widows retired there. Only women were allowed to be present at a birth, at which they spread the knowledge of midwifery. As usual, many women died giving birth. Various ways to prevent pregnancy were tried. It was believed that a baby grew from a seed of the father planted in the woman's body.

Infant mortality was especially high in boroughs and burgess family lines usually died out. A three-generation family span was exceptional in the towns, despite family wealth.

Children's sweets included gingerbread and peppermint drops. After the plague, gentlemen no longer had their children learn to speak Norman. The grammar schools taught in English instead of Norman as of 1362. Bishops began to preach in English. English became the official language of Parliament, in 1363, and the courts, replacing Norman and Latin.