West Side Homes for Sale

The West Side neighborhood in Winchester offers a blend of early- to mid-20th-century architecture, with homes ranging from 1920s and 1930s Colonials to midcentury Cape Cods, ranch-styles, split-levels, and more recent Modern Traditional builds from 2015 to 2024. Two-unit townhouses are also present on the south side. The area is characterized by large front and back lawns, wooded lots, and winding suburban streets without sidewalks. Residents enjoy proximity to natural features like Mount Pisgah and Whipple Hill, which offer hiking trails and off-leash areas for dogs. The Winchester Country Club provides an 18-hole golf course, while Upper Mystic Lake is a spot for fishing. The Minuteman Commuter Bikeway offers a flat, 9-mile trail for cyclists. Essential shopping is accessible with Whole Foods 3 miles away, and Market Basket and H-Mart 4 miles north in Burlington. The Burlington Mall, less than 5 miles away, features over 185 retailers and restaurants. Downtown Winchester is known for its boutiques and dining options. Community events, such as Spirit Weekend and activities at the Arthur Griffin Photography Museum, foster a strong local spirit. Route 3 and Interstate 95 provide connectivity, with Wedgemere train station offering a 20-minute ride to Boston's North Station. Logan International Airport is about 14 miles southeast. The neighborhood is served by highly rated schools, including Vinson-Owen Elementary, McCall Middle, Winchester High, and Lexington Christian Academy. The crime rate in the area is lower than the national average, contributing to a sense of security for residents.