The Pilgrims started constructing their living houses and storehouses in late December 1620, but only managed to get a couple built before and during the first winter; and they were hindered further by occasional fires, usually caused by a spark or ember from the fire making it onto the roof, which was constructed of dried thatch.  On 28 December 1620, the Pilgrims assigned out house-plots to the 19 family groups--each family was responsible for building their own house, as well as supplying labor to build community storehouses, a defensive fort, and sheds.  They were assigned land plots that were 50 feet deep.  The width of the lot was about 8 feet multiplied by the number of members in the family--so a family of six would have received a plot of land approximately 50 feet by 50 feet.  But without the time, good weather, and enough manpower to quickly build a house, many of the Pilgrims continued to live onboard the Mayflower throughout the winter.  In December 1621, Mayflower passenger Edward Winslow wrote a letter in which he said "we have built seven dwelling-houses, and four for the use of the plantation."  In 1622, the Pilgrims built a fence around the colony for their better defense--the perimeter was nearly half a mile, and the fence was about 8 to 9 feet high.

In late 1623, Emmanual Altham wrote a letter from Plymouth to his brother back in England, and reported that there were about twenty houses, but only about five of them were "very fair and pleasant".  By that time, several additional ships carrying passengers, including the Fortune in 1621, and the Anne in 1623, had arrived.  The Fortune brought mostly young, undisciplined men, who the company hoped would contribute labor.  The Anne brought many of the wives and children to the colony--many of the men had left behind their wives and children in England until the colony was better established.  In 1624, Captain John Smith recorded that Plymouth had about 32 houses, "whereof 7 were burnt the last winter." 

In 1628, Plymouth was visited by the Dutchman named Isaac de Rasieres, and he wrote a more detailed description of what he saw: 

"New Plymouth lies on the slope of a hill stretching east towards the sea-coast, with a broad street about a cannon shot of 800 feet long, leading down the hill; with a crossing in the middle, ... The houses are constructed of clapboards, with gardens also enclosed behind and at the sides with clapboards, so that their houses and courtyards are arranged in very good order, with a stockade against sudden attack; and at the ends of the streets there are three wooden gates. ... Upon the hill they have a large square house, with a flat roof, built of thick sawn planks stayed with oak beams, upon the top of which they have six cannon."

The earliest houses in Plymouth had thatched roofs, but because they were more likely to catch on fire, the colony eventually passed a law that required new homes be built with plank instead.  Most houses had dirt floors, not wooden floors, and each had a prominent fire and chimney area, since this was the only source of heat as well as the only way to cook.  Each house would have had its own garden, where vegetables and herbs could be grown.  Each family was also assigned a field plot just outside of town, where they could grow corn, beans, peas, wheat, and other crops that required more space to grow, as well as to raise larger livestock.

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