This was where the school office and Senior Leadership team were based as well as 2 halls and classrooms for English, Maths, Languages and PE.

Onsite was also a "Caretaker's House with part of this being used as a Music Classroom and a "Dining Centre" where hot food was available at break and lunch time.

Winton Academy was inspected by Ofsted between 11–12 December 2018, who found the school to be outstanding in all areas – effectiveness of leadership and management, quality of teaching, learning and assessment, personal development, behaviour and welfare and outcomes for pupils.

[5] Additionally, inspectors found that the academic outcomes and personal development of boys attending Winton Academy to be outstanding, recognising that boys attending the school made very strong progress from their starting points, with this having been the case previously between 2015–2018.

Again, Winton Academy was named the top performing non-selective boys' school in Bournemouth and Poole in 2015, and was recognised in 2016 as the top-performing non-selective school in Bournemouth, Poole and Christchurch, with 74% of boys achieving GCSE Level 5 A*-C grades, including in English & Maths.

[10] In 2017, Winton Academy received a Performance 8 score of +0.65, recognising the success of 70% of boys achieving GCSE A* - C (or 4+) in both English & Mathematics.

A waiting list is operational for boys who were either refused a place, or missed out on a space at Winton Academy, due to being out-with the schools catchment area.

[14] A house system is in place at Winton Academy alongside the school year groups, with the house system designed to develop a sense of community, offer boys the chance to work with other year groups whilst feeling more connected with the community across the school and out–with.