Winthrop is a medium-sized coastal city (i.e. on the ocean, a bay, or inlet) located in the state of Massachusetts. With a population of 18,510 people and five associated neighborhoods, Winthrop is the 100th largest community in Massachusetts. Much of the housing stock in Winthrop was built prior to World War II, making it one of the older and more historic cities in the country.

Housing costs in Winthrop are among some of the highest in the nation, although real estate prices here don't compare to real estate prices in the most expensive communities in Massachusetts.

Also of interest is that Winthrop has more people living here who work in computers and math than 95% of the places in the US.

Telecommuters are a relatively large percentage of the workforce: 12.91% of people work from home. While this number may seem small overall, as a fraction of the total workforce it is high relative to the nation. These workers are often telecommuters who work in knowledge-based, white-collar professions. For example, Silicon Valley has large numbers of people who telecommute. Other at-home workers may be self-employed people who operate small businesses out of their homes.

One of the nice things about Winthrop is that it is nautical, which means that parts of it are somewhat historic and touch the ocean or tidal bodies of water, such as inlets and bays. Because of this, visitors and locals will often go to these areas to take in the scenery or to enjoy waterfront activities.

One downside of living in Winthrop is that it can take a long time to commute to work. In Winthrop, the average commute to work is 34.41 minutes, which is quite a bit higher than the national average. On the other hand, local public transit is widely used in the city, so leaving the car at home and taking transit is often a viable alternative. In addition, it is also a pedestrian-friendly city. Many of Winthrop’s neighborhoods are dense enough and have amenities close enough together that people find it feasible to get around on foot.

Even though Winthrop is a smaller city, it has many people who hop on public transportation – mostly the subway for their daily commute to work. Typically, these people are commuting to good jobs in the surrounding cities.

The education level of Winthrop ranks among the highest in the nation. Of the 25-and-older adult population in Winthrop, 43.70% have at least a bachelor's degree. The typical US community has just 21.84% of its adults holding a bachelor's degree or graduate degree.

The per capita income in Winthrop in 2022 was $57,278, which is upper middle income relative to Massachusetts, and wealthy relative to the rest of the US. This equates to an annual income of $229,112 for a family of four. However, Winthrop contains both very wealthy and poor people as well.

Winthrop is a very ethnically-diverse city. The people who call Winthrop home describe themselves as belonging to a variety of racial and ethnic groups. The greatest number of Winthrop residents report their race to be White, followed by Black or African-American. Winthrop also has a sizeable Hispanic population (people of Hispanic origin can be of any race). People of Hispanic or Latino origin account for 18.20% of the city’s residents. Important ancestries of people in Winthrop include Italian, Irish, English, German, and Albanian.

Foreign born people are also an important part of Winthrop's cultural character, accounting for 18.67% of the city’s population.

The most common language spoken in Winthrop is English. Other important languages spoken here include Spanish and Portuguese.