Hi kiechanner and best of luck on the new home search. Very exciting times in your household I am sure.
In order to best answer your questions, what is your budget range and what years in school are your children? Do you see this being a permanent home where your kids will attend all K-12 grades, or only a portion?
Within close proximity of Boston and cities / towns similar to Milton, I would recommend checking out Westwood, Sharon, Canton, Needham, Stoughton, Norton, Norwell, Hingham and Scituate are all towns that strike me as similar to Milton, strong schools systems and may offer some inventory at your price range.
Feel free to give me a shout as I am happy to refine some search options for your specific needs.