
If a local Rip Van Winkle woke up today in Middletown, he might find that, while he was snoozing, his farm had been turned into a residential community with a clubhouse and a pickleball court.
In 2000, this northernmost town south of the C&D Canal had a population of slightly over 6,000 people. U.S. Route 301 meandered through its western edges like a cow ambling across a meadow. And the most-exciting happening each spring was seeing whether the local farmers were going to plant soybeans or corn.
Now, just over 20 years later, Middletown has almost quadrupled in size to 23,000 residents. Route 301 is now a limited-access highway that has been nicknamed the “Middletown Autobahn.” And the fastest growing crop is not corn nor beans, but housing developments, especially 55-plus communities.
While retirement communities are hardly a new thing in Delaware, builders and buyers alike seem to be especially drawn to the 55-plus concept, where most residents must be at least that age. It attracts a slightly younger, more-active crowd of retirees looking primarily to downsize and to simplify their lives but who are not yet interested in on-site medical and care facilities. They are a development within developments that isn’t going away anytime soon.
“There are approximately 15 55-plus communities now being built in Delaware,” said Fox & Roach real estate agent and vice president, Jerry Strusowki, who said that demand is exceeding supply and that he sends out letters to established residents seeing if they are interested in selling to one of his clients.

Five of these communities – a third of all – are under construction in the Middletown area, which has emerged as Delaware’s 55-plus epicenter. Starting prices per single or duplex range between $370,000 and $737,000 per unit. Middletown’s attractions are obvious – it’s in the country, prices are more affordable than elsewhere in the state and it’s still only 30 minutes from Interstate 95 and Delaware’s largest hospital.
Typical of these is Traditions at Whitehall, located between the canal and where Route 301 sweeps across from Route 1 before turning south. The site is still under construction, with earth being moved and the skeletons of housing rising above the flatlands.
“We have the first phase of the site work completed, and have just started on the second phase,” said Rich Julian, president of Benchmark Builders, a local company which was early into 55-plus community development. “There will be four phases and 229 homes in total.”
“The attraction of the 55-plus communities is that people are at that stage of life when they want maintenance-free living and a turn-key operation where they can just lock the door and leave on vacation without worrying,” said Jason Giles, senior vice president and managing broker for realtor Patterson Schwartz.
“They cost less than other types of communities,” Strusowski added. “[And residents] still feel independent and able to live on their own – which is very attractive.”
Many Delaware residents want to downsize but still stay near friends and family, while outsiders are drawn to the state for other reasons.
“Delaware is hard to beat – great East Coast location, great health care system, low taxes,” Julian said.
Charles Durante, partner and investment adviser at Connolly Gallagher, said that, unlike Pennsylvania, which imposes an inheritance tax even on modest estates, Delaware has no inheritance tax. And while the state has other economic negatives, the optics of no sales tax has a draw perhaps greater than its value.
Choosing a 55-plus that has the most appeal depends on several factors – location, cost per unit, amenities, size of the community, and, in the case of cars parked in driveways that have black license plates, how near the rest of the family lives.
“Kent County is the least expensive, while Sussex County on average is most expensive and has the most luxury units. A lot of the buyers there come from Washington, D.C., and have bigger budgets,” Julian said.
By being more rural, Sussex also has more land available for building. However, the most-expensive community under development in Delaware is the small, 26-unit Crooked Billet in Greenville, with homes starting at $1.45 million, and the least-expensive is Village at Cinderberry in Georgetown, starting at just over $340,000.
Most 55-plus developments usually have three or so different house plans as well as a number of two-family units, often called carriage houses. The mix of these may be more the dictates of local use plans and codes and not an economic consideration of the developer.
Basic amenities desired in communities are almost universal, Julian said. That includes complete living on the first floor, with two bedrooms there, and wider hallways and doorways. Garages and a basement, even an unfinished one, are also important.
In fact, for downsizing, most have more living space – even though much is open-designed – than needed, although not enough space to always hold all the “stuff” accumulated.
Beyond that, the demand for other amenities and overall look varies. Some communities have a very similar, button-up look with many restrictions. That is not the case, however, at Traditions. While most garages will face an alleyway, all have an informal look with covered front porches. Additionally, Julian said, “We are one of the few, if not the only, 55-plus communities in the area that allows residents to fence their backyards. That has been a selling feature for buyers who have pets or prefer a fenced-in yard.”
Not that competitive selling features are always needed.
“Sales have been good. Over the past year, we have sold about 30 homes at Traditions,” Julian said.
Real estate agent Giles reported one September morning that there were 66 active listings [for 55-plus housing] with 38 under contract in New Castle County, while Sussex was the opposite, with 15 active and 55 under contact. While there are not a lot of bidding wars, Giles said that buyers “very frequently waive contingencies and other fees.”
Longtime Middletown residents appear to like the amenities that newcomers have brought with them – more shopping and dining opportunities among them. Or, as Julian puts it, “Businesses follow when you get up enough roofs.”
Roxanne Ferguson, head of the Middletown Chamber of Commerce, also points out that the arrival of the new communities has meant updated infrastructure, including improvements now underway to traffic-choked Route 299 to Odessa.
“People in the 55-plus communities provide tremendous support, both as volunteers and employees. Some have started up their own small businesses, and they generally come to the town meetings,” she noted.
Paradoxically, aided by the influx of seniors, more business has meant more local employment, and thus Middletown has “become less of a bedroom community” for Wilmington and Newark, Ferguson said.
Sad news for Rip, though.