Gerri Silver and her husband, Jay, also ended up in Weston by chance. Empty-nesters who sold their home in Ridgefield and were renting, the Silvers were looking to move into a contemporary home, a style fairly common in Weston. After a hunt in North Stamford turned up nothing, the Silvers eventually found a four-bedroom, single-level home in Weston with a pool and three-car garage for $865,000; they close in a few weeks.
Ms. Silver, 60, said she doesn’t mind driving to Westport to shop and dine — she works there as the business manager for a public relations firm. Her husband, who owns restaurants in Manhattan, commutes from the Westport station.

Dean Robert, a sales and marketing professional, and his wife, Susan, are on their second home in Weston, after moving there from New York 16 years ago. Its initial appeal was as a retreat from the city, but now that the couple has two children, Mr. Robert said, they have come to prize Weston’s top-notch school system.

“The value is incredible,” he said. “The student-teacher ratios are low, the classrooms are designed with high technology. My daughter, who is 12 now, has blossomed in the school system.”

Some residents frustrated by Weston’s rather sluggish real estate market recently started a website to help raise the town’s profile. Weston’s property tax rate is higher than that of most surrounding towns, which might discourage some buyers, but Nina Daniel, the first selectman, said there are no plans to alter the strict zoning to expand the tax base.

“When you come into Weston, you breathe a sigh of relief,” Ms. Daniel said. “You are not in traffic. You have a sense of being away from the hurly-burly of the world.”
What You’ll Find

A town of roughly 10,000, Weston has a history that goes back several centuries, and antique homes from earlier eras still grace the main roadways. Nature preserves abound, including the 1,756-acre Devil’s Den Preserve, which has 20 miles of hiking trails. Most social activities revolve around the schools and three private clubs: Aspetuck Valley Country Club, Weston Field Club and Weston Racquet Club.

Weston’s version of a hot spot these days is Lachat Town Farm, a 42-acre property left to the town and the Nature Conservancy in 1997. The farm went unused for years, but a community-led effort has revived it, creating a communal garden space and a monthly farmer’s market with live music and food trucks. “Lachat has been a real success so far,” said Vickie Kelley, the owner of Camelot Real Estate, in Weston. “It’s a much-needed gathering place.”
What You’ll Pay

The median sales price of a single-family home for the year to date is $795,500, barely changed from the 2016 median of $793,500, according to multiple listing data compiled by Ms. Kelley. Prices tend to be higher in the lower half of Weston, which is closer to Westport and the Merritt Parkway.

About 160 properties are currently listed, from $375,000 for a two-bedroom ranch built in 1930 to $2.94 million for a seven-bedroom, lodge-style house on almost eight acres.

The market is most active for properties priced below $900,000, said Kathleen O’Connell, an agent with Coldwell Banker. Bidding wars do happen occasionally, she said, noting that four buyers submitted offers on a midcentury-modern house she listed last spring: Priced at $875,000, it sold for $940,000.
About a half-dozen new-construction properties are listed, at prices ranging from $1.4 million for a four-bedroom on an acre to $2.2 million for a six-bedroom on 2.5 acres.

Weston has no condominiums or rental developments.

The Vibe

The resistance to change that has long defined Weston has lessened of late, as newcomers push for various amenities. As first selectman, Ms. Daniel is trying to straddle the divide, agreeing with those who want, for example, sidewalks connecting the school campus with the town center, while reassuring others that the town is not headed for mass commercialization. Also up for discussion: a town green, a community center and cluster-style housing for retirees.

The Schools

Weston is unusual in that all four of its public schools and athletic facilities are grouped together on a single, 117-acre campus. Hurlbutt Elementary School enrolls about 400 students in prekindergarten through second grade. Weston Intermediate School, for grades 3 through 5, enrolls about 520 students. Weston Middle School enrolls about 580 in grades six through eight. And Weston High School enrolls about 800 students.

Average 2016 SAT scores were 577 in reading and 582 in math, versus 494 and 508 statewide. U.S. News & World Report ranked the high school second highest in Connecticut this year.

The Commute

Most commuters use one of two Metro-North stations in Westport: Westport and Green’s Farms. The drive is about 10 to 15 minutes. The peak-time trip to Grand Central takes 70 to 80 minutes, and a monthly pass is $388.

The History

A weathered wood building opposite the shopping center is known to locals as the Onion Barn. It was originally used to store onions, a primary crop during Weston’s agricultural beginnings. Today, the circa-1830 barn serves as the town bulletin board, with posters announcing church fairs, summer concerts and other community happenings.