Pros:
Set between a busy main drive and a residential area, Winsor Park is a small but well utilized park space with a lot going for it. Great for beginners to middle amateurs, the park has rolling hills, fast sloping greens, and some moderate to tight fairways.
Variety - You'll find quite a bit of variety for a 9-hole course with right/left turns, up/down hills, tight/open fairways, and pins which sometimes have precarious positions. The dual tees on every hole frequently add variety and different looks at the fairways. I wouldn't go so far as to say it plays like 18 unique holes but it is definitely a course bonus. Many of the holes have great complementary features which accentuate the courses variety such as the first two opening holes. Hole 1 is a slight hyzer midrange or putter poke under a low-ceiling to an ever so slightly sloping green while 2 allows for a high ceiling, longer turnover which fades right of a blocking fence to a shaded pin.
Maintenance - From the time you pull up, you can tell this course is well-maintained and well-loved. A huge sign directed towards the parking lot describes course sponsors and donors. The fairways reflect the same level of care and are unanimously well-groomed and pruned. The one exception to this is a few of the natural tees which need some work.
Cons:
Crowded holes - Because of the extremely small size of park acreage, fairways are tightly jammed together and you will almost certainly find yourself near/on another fairway at some point or even worse buzzing another group's obscured from view tee box.
Challenge - Highly skilled players aren't going to work very hard except on the few holes which require a pinpoint drive. Usually, a putter through an easily achieved open window will suffice for birdie or even ace run.
Other Thoughts:
More traditional than its neighbor, Mingus Park, Winsor scores higher for design, upkeep, and 'feel' although it lacks some of the more extreme elements that make Mingus interesting.