The books here articulate the philosophy of education, classical and Orthodox, in the clearest manner we know of, but not all of them are easy reading. It is worth noting, as well, that some of these authors or not Orthodox, although they are chosen because they helpfully articulate a way of thinking about education that runs counter to practices and ideas in most modern schools.
We have listed the books in each category according to most accessible first, followed by those that are somewhat more challenging. All of them are worth the effort and time and will reward whatever you choose to invest in them.
Philosophy of Education
Consider This: Charlotte Mason and the Classical Tradition, by Karen Glass
Tending the Heart of Virtue: How Classic Stories Awaken a Child's Moral Imagination, by Vigen Guroian
The Abolition of Man, by C.S. Lewis
Beauty in the Word, by Stratford Caldecott
Poetic Knowledge: The Recovery of Education, by Dr. James S. Taylor
Norms and Nobility: A Treatise on Education, by David Hicks
Orthodox Parenting and Family Life
Children in the Church Today: An Orthodox Perspective, by Sister Magdalen
Following a Sacred Path: Raising Godly Children, by Elizabeth White
Raising them Right: A Saint's Advice on Raising Children, by St. Theophan the Recluse
On Marriage and Family Life, by St. John Chrysostom
Antiochian Archdiocese Department of Homeschooling
The Paideia Fellowship