Wellesley, MA

Just 15 miles west of Boston, Wellesley blends small-town charm with big-time prestige. Home to about 30,000 residents, it earned the title of 10th richest town in America from Newsweek in 2025. Forbes pegged the average household income at a comfortable $368,179 in 2024, and by May 2025 the average home value reached a cool $2,079,414. In other words — yes, Wellesley is gorgeous, but beauty comes at a premium. Here, $1.5 million might still buy you a home that needs central air, has only a one-car garage, or could use a renovation… and residents still consider it a great find.

Wellesley is postcard-perfect, with lush parks, Morses Pond, scenic walking paths, upscale shops, and a dining scene worth exploring. The public school system is among the state’s best, and the town also boasts world-class higher education with Wellesley College, Babson College (consistently ranked the #1 entrepreneurial school), and Olin College of Engineering right at its doorstep.

Getting “into town” (Boston, for newcomers) is easy — there are three commuter rail stops: Wellesley Square, Wellesley Hills, and Wellesley Farms. Drivers have quick access to Route 9, I-95/128, and the Mass Pike.

Shopping is a sport here. Wellesley Square tempts with boutiques like GrettaLuxe and Irresistibles, and you won’t want to skip dinner at Juniper or Alta Strada — followed, of course, by a cone from JP Licks. Linden Square offers more boutique browsing at Kenzie & Hope and Sara Campbell, plus popular dining at The Cottage, Lemon Thai, and Tatte Bakery & Café.

Historically, Wellesley has been known for its conservative character and deep-rooted New England families who have lived here for generations. Today, it continues to attract those who appreciate a refined community, a strong sense of tradition, and just the right amount of small-town sparkle.