Middletown 55+ Active Adult Retirement Communities

8 Communities near Middletown

Select one...
# Homes (High-Low)


A small town with easy access to larger cities, Middletown is a growing city popular among traveling retirees. As one of the most affordable Mid-Atlantic cities, Middletown is quickly becoming a hot spot for active adults looking for the amenities of nearby major metropolitan areas and the quiet charm of a tight-knit community. Besides that, residents can enjoy local markets, art exhibits, and unique festivals.

Climate & Geography 

Located in Northern Delaware, Middletown is situated between the Delaware River to the east and the Chesapeake Bay to the west. It is directly between the Philadelphia and Baltimore metro areas, and experiences similar weather patterns: warm summers, cool winters with snow, and higher than average rainfall. Middletown experiences all four seasons, but its proximity to the Atlantic coast means it rarely experiences extreme weather.

Middletown is the fastest growing area in Delaware because of recent annexations of land. The growth is characteristic of suburban sprawl, with increasing developments in the town center as well as to the north.

Recreation, Culture, & Entertainment 

Many of Middletown’s amenities highlight its history and quaint, small-town charm. Middletown Main Street is a historic downtown area with boutique shops, restaurants and bars, and art galleries. The Dutch Country Farmers Market is another draw for residents, offering everything ranging from local produce to handmade furniture. Nearby Wilmington has many notable history museums, and several historic buildings and homes in Middletown are open to the public.

For outdoor activities, water recreation is accessible to the east and west, and Charles E. Memorial Park is within town limits. Its 100 acres offer walking trails, nine pavilions, an eight-acre catch and release fishing pond, dog park, and open fields. The town also hosts the annual Olde Tyme Peach Festival, an annual event with a parade, live music, and peach-flavored food and drinks.

Cost of Living & Taxes 

Middletown’s cost of living is higher than the U.S. average, mainly because housing is much more expensive. All other factors, including groceries, transportation, health care, and utilities, are also slightly above average. However, Delaware’s cost of housing in comparison to other Mid-Atlantic states is much lower.

Delaware is tax friendly for retirees. It does not levy income tax on Social Security, and although other forms of retirement income are taxed, they are eligible for deductions. The property taxes in Delaware are also below average, and are the fourth lowest in the country. There are no sales taxes at the state or local level, which is great for retirees looking to spend more money on entertainment, shopping, and travel. 

Health Care

Middletown is considered part of the Philadelphia-Camden-Wilmington metro area. This community ranks within the top 100 across the country in Gallup’s Well-Being Index.

Although there are no nationally ranked hospitals within Middletown, the closest hospital is Union Hospital in Elkton, Maryland just half an hour away. Also nearby, ChristianaCare Hospital in Newark, is nationally ranked by U.S. News as the No. 1 hospital in the state. Johns Hopkins Hospital in Baltimore, 50 miles away, is the No. 1 hospital in Maryland, nationally ranked, and the No. 3 hospital in the country.

Take me back to the top
Scroll to Top