Middletown, DE 55+ Active Adult Retirement Communities

Active adult homebuyers looking for a small town with easy access to larger cities should consider 55+ communities in Middletown. Middletown is one of the most affordable of the mid-Atlantic cities and 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.

Active adult homebuyers looking for a small town with easy access to larger cities should consider 55+ communities in Middletown. Middletown is one of the most affordable of the mid-Atlantic cities and 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. Middletown weather patterns consist of 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.

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 Middletown 55+ community residents 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.


Communities Near Middletown
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8 communities near Middletown

0 Homes for Sale

The Ponds at Bayberry - Middletown DE

The Ponds at Bayberry

For Sale
  • Low $500ks - High $500ks
  • 572 Homes (2 for sale)
  • 55+ Age Restriction
  • New And Resale Homes
  • 2015 - Present
  • No Reviews
Springmill - Middletown DE

Springmill

For Sale
  • High $300ks - High $400ks
  • 362 Homes (1 for sale)
  • 55+ Age Restriction
  • Resale Homes Only
  • 2000 - 2007
  • 1 reviews

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Spring Arbor - Middletown DE

Spring Arbor

For Sale
  • High $400ks - Mid $500ks
  • 317 Homes
  • 55+ Age Restriction
  • Resale Homes Only
  • 2007 - 2018
  • 3 reviews
Four Seasons at Silver Maple - Middletown DE

Four Seasons at Silver Maple

For Sale
  • Mid $500ks - Mid $500ks
  • 299 Homes
  • 55+ Age Restriction
  • Resale Homes Only
  • 2011 - 2017
  • No Reviews

Four Seasons at Baymont Farms

For Sale
  • High $400ks - High $600ks
  • 288 Homes (5 for sale)
  • No Age Restrictions
  • New Homes Only
  • 2019 - Present
  • No Reviews

Traditions at Whitehall

For Sale
  • Mid $400ks - Mid $600ks
  • 250 Homes (10 for sale)
  • 55+ Age Restriction
  • New Homes Only
  • 2019 - Present
  • No Reviews
Legacy at The Preserve at Deep Creek - Middletown, DE

Legacy at The Preserve at Deep Creek

For Sale
  • Mid $500ks - High $500ks
  • 205 Homes
  • 55+ Age Restriction
  • New And Resale Homes
  • 2016 - Present
  • No Reviews
Whispering Woods - Middletown, DE

Whispering Woods

For Sale
  • Mid $400ks - Mid $500ks
  • 178 Homes (3 for sale)
  • 55+ Age Restriction
  • New And Resale Homes
  • 2017 - Present
  • No Reviews

42 More Communities Found in Delaware

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$369,000

1056 Southern Hills Drive, Banning, CA

Meadow Ranch Community

  • 3 bed
  • |
  • 3 bath
  • |
  • 2320 SqFt
MLS CV23099287
Call Us: (888) 625-4885

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