Exploring Weston, Massachusetts: The Quaint Home Of America’s Billionaires

Massachusetts is a state of wealth—a wealth of history, education, and wealth itself.

According to the U.S. Census Bureau, Massachusetts is the second wealthiest state in the U.S., with a median household income of $85,843 compared to the national median of $65,712.

While much of the state’s most expensive properties are set in Boston, many of the most affluent of Massachusetts’ residents live outside the city in smaller towns like Dover, Sherborn and Carlisle.

One such town, Weston, is the wealthiest.

Located just 15 miles west of downtown Boston, Weston is not only one of the richest towns in Massachusetts but also in the nation, with a median household income of $206,250.

It’s no accident, however, that this small, New England suburb is largely unknown to those from out of state—residents pride themselves on their well-kept town but often brush off its moneyed reputation.

“Sure, the town is home to billionaires, but you see behavior so uncharacteristic of that,” says Catherine Bassick of Bassick Real Estate Advisors, one of Wall Street Journal’s top 100 agents in the U.S. and a resident of Weston. “People are putting out messages during snowstorms that say their kids can come shovel snow for the elderly. Someone even brought me chicken broth when I got a cold! There’s still a strong sense of community.”

With over 300 years of history, the town is currently at something of a crossroads. The pandemic-fueled urban migration has brought a new wave of interested buyers, straining a supply primarily consisting of long-established homes.

But while this demand may give rise to new construction, an array of building and zoning restrictions have kept over-development at bay, maintaining the town’s quiet and idyllic charm, Bassick shares. “People love it here because it’s an authentic community. Plus, the setting looks like a Hallmark movie.”

Homes In Weston

While the town may possess a certain rustic quaintness, the luxury homes are anything but.

Large estates reaching well above 10,000 square feet can be found about town, including stately manors of Colonial and Georgian designs dating back to the early 20th century.

Many of these sizable luxury homes feature classical rooms like libraries, ballrooms, and wine cellars and housing more modern spaces like gyms, movie theaters, and indoor spas.

Exterior space is also ample in Weston—the town’s population of about 11,800 is spread out over 17.3 square miles, meaning the density breaks down to roughly one acre per person—and many homes are located on multi-acre lots. Well-maintained gardens, walking paths and patches of forest are common on estate grounds.

Though the area may be famous for its more illustrious homes, a variety of residences can be found.

“Not everyone lives in a big mansion. There are people here who live in more modest homes,” Bassick says. “But the magnificent homes are truly magnificent.”

Real Estate Prices In Weston

According to data from Redfin.com, the median sale price for homes in Weston was $2,453,000. In November 2021, the median was about $1.29 million. This disparity results from so few homes being on the market and thus few homes selling per month, meaning one sale can greater alter averages.

Lower price points in the area still hover around $1 million. For that price, buyers can expect single-family homes ranging from about 2,000-3,000 square feet in more densely populated neighborhoods.

Multi-acre estates make up the most expensive properties in the area, with prices reaching upwards of $15 million.

The Vibe Of Weston

Given the town’s long history, notable historical landmarks are in abundance, including many structures that pre-date the American Revolution.

The area’s downtown recently underwent an $18-million face-lift, improving the town center’s look, function, and safety. These improvements ranged from new public spaces to installing four-way stop signs.

Although the downtown area is home to many businesses, you won’t find a bar, as Weston is a dry town. For bars and restaurants, many residents head to nearby Boston.

The population age in Weston is fairly evenly dispersed, with residents under the age of 18 making up 25.9% and residents over the age of 65 making up 20.8%, per the most recent data from the U.S. Census Bureau.

Schools in Weston

There are five schools in the Weston Public School District—three elementary, one middle and one high school. The district serves roughly 2,100 students. Nearly 25% of students in Weston attend a private school.

Prominent institutions in the area include the Meadowbrook School of Weston, a pre-kindergarten through eight-grade co-ed school located on a 26-acre campus and the Cambridge School of Weston, a day and boarding school founded in 1886.

Surrounding Weston

Roughly 100 miles south of Weston is Martha’s Vineyard, with another popular destination, Nantucket, located about 20 miles beyond. Boston Logan International Airport is 17 miles east or about a 30-minute drive.

Bassick Real Estate Advisors is an exclusive member of Forbes Global Properties, a consumer marketplace and membership network of elite brokerages selling the world’s most luxurious homes.