There is 1 golf course in Winchester, Massachusetts and 0 are municipal courses. There are also another 99 golf courses within 20 miles of Winchester, including 28 public, 27 municipal and 42 private courses. The oldest course in the Winchester area is the The Country Club which was designed by Wiiliam S Flynn and. The longest course is The Golf Club At Turner Hill, which is 7,033 yards. Unicorn Golf Course is rated the best course near Winchester.