Due to the difference between the orbital periods of the Earth and Venus, Venus can be "above" on any day of an Earth year. It's not constrained by the seasons of the Earth.

One item of clarification re the transits of Venus: for the past couple of thousand years they have been occurring mainly in either June or December. This is due to the way the nodes of Venus' orbit line up as seen from Earth. For example the last non-June/December transit was on May 23rd in the year 1526 CE. This June/December pattern will continue for many more thousands of years, unless there's an event that perturbs either Venus and/or the Earth.

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