Middlesex County · Massachusetts

Real Estate in Winchester, Massachusetts

Winchester is one of Greater Boston's most prestigious suburbs, consistently ranked among the top communities in Massachusetts for schools, safety, and quality of life. Its beautiful town center and proximity to the Middlesex Fells Reservation make it highly desirable.

$1,732,500

Median Sale Price (last 90 days)

27 days

Avg Days on Market

59

Active Listings

18 min via commuter rail to North Station

Commute to Boston

Why Live in Winchester?

Winchester is the gold standard for families seeking top-tier education, a safe community, and beautiful New England charm — all within a quick commute to Boston.

#1 ranked public schools in MAMiddlesex Fells ReservationHistoric downtown centerCommuter rail to North StationStrong property values

Neighborhoods

Winchester CenterWedgemereWinchester HighlandsSymmes Corner

Top Schools

Winchester High SchoolMcCall Middle SchoolAmbrose Elementary

Thinking about Winchester?

Whether you're buying your first home, selling, or looking for an investment opportunity in Winchester — I can help you navigate this market with confidence.

Plato Asadov — Real Estate Consultant serving Greater Boston

Plato Asadov

Real Estate Consultant, Investor, Developer

Steve Bremis Realty Group

Get Started in Winchester

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Data provided by MLS Property Information Network