Here are several communities I recommend you look into, that work with your price range and services you're looking for:
West Hartford - located between Hartford and Waterbury, closer to Hartford. Theater in the center, lots of amenities and town services, good schools and many neighborhoods that are walkable. There are currently about 30 properties activley for sale that are under 500k and around 2500 sf. Several grocery stores such as Whole Foods as well as some smaller markets.
Farmington-Further west than West Hartford but not immediately off of Rt 84. Not as many walkable neighborhoods or amenities but good schools. Also have about 30 properties actively for sale under 500k and around 2500 sf.
Southington-Movie theatre and lots of amenities in town including many chain restaurants and grocery stores. Good schools. Easy access to highway, RT 84. There are currently about 60 actively for sale properties meeting your basic criteria.
Berlin-Movie theatre, many town amenities, easy access to Rt 9, Rt 5/15, Rt 91 (can connect to 691 which brings you into Waterbury). Good schools, but not as many houses currently on the market - about 20. Easy access to Berlin Tpk which has hundreds of stores like Target, Walmart, Lowes but there is also a historic area as well as the Kensington area which is less big box commercial.