Middletown, Delaware
- StateDelaware
- CountyNew Castle
- Population24,875
Having graced Fortune’s Best Places to Live for Families list in 2023 and 2024, Middletown now takes a seat as a Best Place to Retire Affordably. It’s no surprise considering that Delaware is so tax-friendly: Bankrate recently dubbed it as the top state for retirees. It has no sales tax or estate tax and has a low property tax of 0.55%.
Located at the midpoint between Dover and Wilmington, Middletown offers retirees an affordable cost of living and a safe and close-knit community. The small town is brimming with historical charm, and features a Main Street lined with restaurants and boutiques.
There’s plenty to enjoy on the recreational front, from a film at Everett Theatre to regular farmers’ markets to the annual Olde-Tyme Peach Festival, celebrating the first cash crop that kicked off the town’s population boom way back when. For a taste of bigger cultural moments, Philadelphia and Baltimore are only an hour and hour and a half away, respectively.
Retirees can also bask in Middletown’s moderate climate, walking around Charles E. Price Memorial Park, playing golf at Back Creek Golf Club, or watching the shoreline at nearby Augustine Beach.
Middletown also plays host to a branch of ChristianaCare services, a network of nonprofit private hospitals that has been ranked as a top health system nationwide. And there are 25 above-average nursing homes within 50 miles, per Healthgrades.
Town Information
| Number of above-average home care services within 50 miles, per 100,000 households | 40,757 |
| Median sale price for single-family residences (2023) | $516,004 |
| Average property taxes for single-family homes and condos | $3,178 |
| Sharecare Community Well-Being Index Score (out of 100) | 64 |
| Risk of social isolation for adults age 65+ (out of 100, with a higher value indicating a greater risk) | 46 |
| Percentage of residents who believe the city or area where they live is a perfect place | 55.31% |