In the New Haven area there are a number of condominium communities catering exclusively to over-55ers. These communities offer a step up in the quality of life of such adults: they offer sensible home architecture, maintenance-free park-like grounds, and community amenities (eg. gardens, recreational facilities) far beyond what most typical homes offer. Above all, these communities often offer -with unsurpassed convenience- a social environment (through both their formal programs and their informal settings) that contributes immensely to the well-being of the residents.
With the population aging and the over-55 demographic wealthier and more demanding than in generations past, I suggest that these "Active Adult" condominium communities are bound to grow in popularity. I suggest that you look into such condominium communities in the New Haven area, focusing on active adult condominium communities close to town centers and within close proximity to libraries, senior centers, restaurants, professional/medical offices. I am quite familiar with two such communities in Hamden: The Commons at Mill River and The Summit at Hamden Hills.
I encourage you to consider what I've written here, look into these two communities, and refer to realtor.com for properties listed for sale at both the Commons and the Summit.
Wishing you the best,