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Hamden is too far from Chester. Hamden is technically a town but it's more like small city and sprawls. Thus, you can do a bit of driving just to get out of town. There is no fast, direct highway way to get there from Chester so its going to be a lot more than the 20-30 minutes you're looking to commute.
Maybe consider looking in Clinton. It's 20 minutes up to Chester on easy back roads -maybe 12-15 if your hubby is based at one of the facilities along CT Rt 145. And it's 25 minutes to the New Haven area ( traffic permitting ) along CT 1-95.
You'll find some townhouse type condo rentals, some units in 2 family homes and perhaps even a small, year round house to rent. It's safe and quiet with enough local shopping for most needs.
And If I were you, I would still explore Middletown. It's really close to Chester and close enough to New Haven to make it a possibility, if you look for housing in southern Middletown.
While most of Hamden is safe, it is well outside your 30 minute commuting distance. It would be closer to an hour. Middletown would be your closest city area. Or as Willow wind suggested look into the shoreline towns east of New Haven. Old Saybrook is very nice and has some rentals. Jay
Haddam is lovely- it's the town north of Chester. It's perfectly safe- but it's another fairly small town.
There are no apartments in complexes or condos to rent. You might be able to find a house to rent ( few and far between but not impossible ) or maybe the rare apartment in a two family house.
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