The plans are part of a larger scheme to regenerate the area with 229 new homes alongside a community space and food and café outlets on the banks of Maidenhead waterways.
The York Road site is the first of four sites which will bring more affordable homes for residents.
The rejuvenation of York Road also includes a £1 million investment to enhance and improve existing buildings and public realm.
Cllr Simon Dudley, leader of the council and lead member for Maidenhead regeneration and Maidenhead, said: "I am delighted that this planning application has been considered and approved in principle.
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"This is a major milestone for Maidenhead's regeneration and I looking forward to seeing the site being transformed as we look to build a borough for everyone.
"I am delighted the council is able to deliver an additional 20 affordable homes for shared ownership on this site meaning a total of 88 new affordable homes (38%) will be created in the heart of Maidenhead to give residents struggling to get onto the housing ladder a place to call home.
"It will provide much needed homes for our residents and create a much needed new neighbourhood in the town centre with a mixture of homes, retail outlets and community facilities to meet the needs of our residents now and in the future."
Malcolm Wood, Project Director at Countryside, added: "We are delighted that the council has resolved to grant planning permission for this important site.
"We look forward to continue to work closely with the council and the community as we deliver the much needed new homes, modern community facilities, cafes and restaurants as well as fabulous new public spaces."
Building work is expected to start on the site in Spring 2019 with the first homes expected to be completed by Autumn 2020.
(CM)
