What makes these five so-called “W” towns so appealing?

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There are five so-called “W” towns in Massachusetts that are consistently rated as being among the best municipalities to live in. What makes Wayland, Wellesley, Weston, Westwood, and Winchester stand out to both residents and prospective buyers? All five of these towns are located within 25 miles of Boston and offer easily accessible routes into the city. Most importantly, the town administrations focus heavily on education spending and low crime rates. There is a prestige associated with these “W” towns, but these luxuries come at a cost.

Wayland allocated a significant amount of resources towards education with 52.1 percent of their budget going towards the public schools. This equates to annual per pupil spending of $17,981. A similar trend is observed in Westwood, which in 2022 allocated 51.7 percent of its budget towards K-12 education with per pupil spending of $17,672.

Winchester has allocated a smaller portion of its budget (47.3 percent) towards education, which results in a much smaller per-pupil spending of $13,300. This same trend of lower percentages of the budget allocated to education is seen in Weston and Wellesley; however, a significant increase in spending per pupil is also present in these two towns – most likely a result of their higher tax revenue. Wellesley, allocated 48 percent of its total budget to education, which allotted $20,210 per student. Weston, with an even smaller portion of its budget going towards education (44.6 percent), spent $24,292 per student. In 2022, Weston landed 25th in the state for most money spent per child towards education. 

Figure 1: Created from Data on MassAnalysis

When analyzing violent crime rates in Massachusetts for 2021, Wayland ranks third for the lowest frequency of these crimes. Weston, Wellesley, Winchester, and Westwood all fell close to one another, but not quite matching the infrequency of violent crime seen in Wayland. Despite differing from Wayland, which has virtually no violent crime in relation to its total population, these four towns still rank alongside Wayland as being among the safer towns in Massachusetts.

There is, however, a cost associated with living in a town that prioritizes educational success and crime prevention: housing prices. Although the residential tax rates in all these towns fell right around the Massachusetts average, the single family tax bill in these five towns in 2023 were among the highest in Massachusetts. The taxes are so high per household because the average house values in these towns are exponentially higher than in other municipalities. Weston’s single-family tax bills average $23,893, which places them highest in the state. Wellesley is fourth with average single-family tax bills of $18,087 in 2023. Winchester and Wayland take the 11th and 12th spots for highest taxes, totalling $16,215 and $15,958 for the year, respectively. Westwood comes in at the lowest rank of the five “W” towns, in the 21st spot, which is still in the top 6 percent statewide. The average tax bill in Westwood in 2023 was $13,270. What is clear by these numbers is that purchasing homes in these towns comes with a significant cost that many residents and buyers see as worthwhile. 

Figure 2: MassAnalysis (2023)

While there are a number of factors that might influence why a resident chooses to locate in a particular town, safety and quality of education will always be top of the list for families. With high per-pupil education spending and consistently low crime rates, it is no wonder the five Massachusetts “W” towns are attractive places to live. However, high property values lead to residential taxes in these towns being among the highest in the state, a factor that residents must consider when buying a home in one of these towns.     


Dana DiChiro is a Roger Perry Government Transparency Intern at the Pioneer Institute for Summer 2024.  She is a rising senior studying Government & Politics and Economics at the University of Maryland, College Park.