There’s something quietly exceptional about life in Westport’s Long Lots neighborhood, especially when your home sits close to Bedford Middle School (grades 6 - 8) and Staples High School. It’s not just about convenience—though there’s plenty of that—it’s about being woven into the everyday rhythm of one of Westport’s most family-centered, connected, and livable communities.
Living near the Bedford/Staples campus means school is part of daily life, not a logistical puzzle. Morning walks or quick bike rides with your children get them to school. Alternatively, familiar faces at the bus stop foster independence for kids and peace of mind for parents. As students get older, that independence grows naturally—no long bus rides, no rushed carpool schedules, just a seamless transition from middle school to high school within the same neighborhood orbit.
This part of Long Lots has a unique continuity: families put down roots and stay. You see it in the way neighbors know each other, in the ease of organizing playdates or study groups, and in the shared milestones—first days of school, homecoming parades, graduation season. Living close to the schools keeps you plugged into the social and civic life of the Westport, from school plays and concerts to Friday nights watching Wreckers football games, all feel like true community events.
Bedford and Staples are more than highly regarded schools—both A+ graded by Niche, with Staples taking the #1 spot for public high schools in Connecticut, they’re community anchors. Being nearby makes it easier for students to take advantage of extracurriculars, athletics, and after-school programs without the stress of long commutes.
Staples, Bedford then Wakeman Park line North Avenue, where recent sidewalk additions make walks even more enjoyable. At Wakeman Park, there is a fenced baseball field, a softball field and 4 multipurpose fields that hosts games almost year round. Soccer, lacrosse, field hockey, football, summer sports camps—you name it, the kids (and adults) are playing it with organized leagues and pick-up games.
Opposite the baseball field, along Cross Highway, you find Wakeman Town Farm. While the farm is officially a model facility, an “organic demonstration homestead” serving the Westport community, it is in practice much, much more. Saturday farmstands, youth farm programs, summer camps, cooking classes for all ages, adult educational and volunteer opportunities, and community events are just some of the happenings on the farm. A great place to get involved in the community.
From a housing perspective, Long Lots is known for its larger lots, mature trees, and sense of openness. Even near the schools, the area retains a peaceful, residential feel—classic New England suburbia with room to roam. Streets are ideal for evening walks, dog-walking conversations, and kids shooting hoops or riding bikes until dusk. It’s a lifestyle that feels relaxed but never disconnected.
Perhaps what makes this area most special is the balance. You’re close to schools, friends, and daily routines, yet still just minutes from Westport’s beaches, town center, train station, and cultural life. It’s a place where days feel manageable, neighbors feel familiar, and life feels intentionally well-paced.
Living in Long Lots isn’t just about where your house is—it’s about how your days unfold, how your kids grow up, and how connected you feel to the town around you. It’s the kind of place people move to for the schools—and stay for everything else.