Retiring to Florida isn’t as affordable or achievable as it previously was for most retirees. The Sunshine State’s house prices increased more than any other U.S. state between 2000 and 2024, according to House Price Index data from the Federal Housing Finance Agency. But while Florida may be too expensive now for most, there are many other enticing cities and towns around America for retirees. One of these, Middletown, sits on America’s idyllic East Coast and was recently featured by Fortune as one of its Best Places to Retire Affordably.
Like Florida, Delaware is renowned for being tax-friendly, offering no state or local sales tax, no tax on Social Security, and some of the lowest property taxes (0.54%) in the country. Middletown benefits from this, offering retirees affordability in a charming small-town setting with historical architecture, a lively and walkable Main Street, various outdoor spaces, and numerous community events. The town’s low crime rates, nationally recognized healthcare system of ChristianaCare hospitals, and numerous aged-care homes also make it an appealing choice for senior Americans.
One reason Middletown is so lovely to visit or move to is its small and walkable downtown. Walk Score gives the town a solid 75/100 score for walkability, indicating that most day-to-day tasks can be accomplished simply by using your feet. Downtown is a big part of Middletown’s great walkability. It centers on Main Street, fanning out across intersecting streets where you can stumble upon various local restaurants, boutiques, and community hubs. One of these hubs, The Everett, is a historic theater that’s been part of the local fabric since 1863. It stages live plays and musicals, screens movies, and hosts special events, such as singalongs. The theater also takes on volunteers — a great way for new residents to feel part of the community.
Downtown Middletown’s dining and shopping
Retirees looking for fresh and delicious food need only stroll around Downtown Middletown to find their next meal or ingredients. Those who prefer to cook at home have multiple farmers markets to choose from. The Middletown Farmers Market runs on Saturdays from May to October. You can often find vendors selling baked goods, goat’s milk soap, farm-fresh produce, bee-made honey, and other wholesome products. The Dutch Country Farmer’s Market is just a 20-minute walk from Main Street and open Thursdays, Fridays, and Saturdays year-round. It’s more of a mall setting but still a great spot to find fresh produce, meat, and dairy goods. Retirees can also browse handmade goods at Simply Crafty or eclectic homewares and decorations at Danny Mertz Discount Decor…