So You Want to Live in Weston?

Photo by Drone Home Media / Listing agent: Melissa Dailey, Coldwell Banker

1. Pick Your Price Point

It’s no secret that this “W” town is expensive—here, homes sell for a median price of $2.2 million after spending an average of 42 days on the market. Like its neighbor Wellesley, Weston has an ample selection of sprawling estates on plenty of land—some of which can be priced upward of $10 million. If you aren’t looking for that level of investment, you’ll usually be able to find a few homes in town priced between $1 million and $2 million. These three-to-five-bedroom beauties may be smaller than their neighbors, but many are modern and recently renovated.

Photo by John Phelan/Creative Commons

2. Plot Your Commute

Although Weston is only about 16 miles west of Boston, residents can see their 30-minute drive into the city turn into an hour during peak commuting times. If you’d prefer to avoid that hassle, the commuter rail offers service between North Station and Weston’s Kendal Green station, and you can usually count on a half-hour ride.

Photo by Jennifer Potter

3. Take in the Vibe

Weston may not be known for its shopping or lively nightlife, but if you love the outdoors, this is the place for you. The town has about 1,800 acres of conservation land preserved as parks, fields, wetlands, and forests. Of that, there are about 90 miles of trails available for hiking, horseback riding, and cross-country skiing. If you aren’t keen on venturing out on your own, Weston Forest and Trail members host guided walks.

Photo courtesy of the Golden Ball Tavern Museum

4. Check out the Culture

Colonists arrived in Weston in the mid-17th century, and several areas in town are on the National Register of Historic Places. Dive head-first into the Revolutionary-era history at the Golden Ball Tavern Museum, or catch a show at the Weston Friendly Society, one of the oldest theater groups in the country. The town is also home to the Spellman Museum of Stamps and Postal History, which houses more than 2 million postal artifacts, including president Dwight D. Eisenhower’s personal stamp collection.

Photo by Chris Jylkka

5. Scope out the Schools

Weston’s five public schools—including three elementary schools—are high-ranking both nationally and within the state. (Weston High School ranked No. 2 in our 2024 Top Public High Schools list.) A large portion of Weston’s students, however, are enrolled at one of the town’s three private schools, which include the Meadowbrook School, the Cambridge School, and the Rivers School.