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. Winthrop has an unusually large stock of pre-World War II architecture, making it one of the older and more historic cities.

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.

One interesting thing about the economy is that relatively large numbers of people worked from their home: 12.91% of the workforce. While this number may seem small overall, as a fraction of the total workforce this is high compared to the rest of the county. 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.

In Winthrop, however, the average commute to work is quite long. On average, people spend 34.41 minutes each day getting to work, which is significantly higher than the national average. One bright side is that local public transit is widely used, so it may be an option to avoid the headache of driving in the heavy traffic by leaving the car at home and taking transit. In addition, the city is also quite pedestrian-friendly, because many neighborhoods are very dense and have amenities close enough together that people find it feasible to get around on foot.

Despite being a small city, Winthrop has a lot of people using the subway to get to and from work every day. Most of these people on the subway are using it to get to good jobs in other cities.

The citizens of Winthrop are among the most well-educated in the nation: 43.70% of adults in Winthrop have a bachelor's degree or even advanced degree, whereas the average US city has 21.84% holding at least a bachelor's 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.