I live in Sindlesham, which is next to Winnersh.
Winnersh is located within Wokingham Borough, not Reading. Wokingham Borough also encompasses Lower Earley, Wokingham Town, Arborfield, Barkham, Finchampstead, Woodley, Twyford and some others.
All areas are nice and Wokingham has good schools, who mostly perform above the national average, DS is four so we've been looking and he starts school next week. There is a train line from Reading to Wokingham which goes further on and stops at Winnersh and a business park called Winnersh Triangle.
Wokingham and Woodley have the most shops, cafes etc but everywhere is well served by road and buses. Traffic in winnersh can be bad but they are building a relief road.
Woosehill is a very residential area between Wokingham and Winnersh, and there are plenty of houses in Winnersh itself. Finchampstead is further away by car from Winnersh but again very residential and desirable. There's a variety of houses in Lower Earley and there is a very large ASDA. Earley falls under Reading Borough so know less about there.
Wherever you choose you won't be far from Winnersh.