Incorporated in 1861, the city of Middletown sits close to Delaware’s border with Maryland and is home to over 24,000 people. Predominantly residential, Middletown consists of many neighborhoods and subdivisions branching out from a commercial center, which in turn offers its residents a blend of suburban living and the convenience of more urban amenities a short drive away. Delaware is popular due to its lack of a sales tax and attracts those from out-of-state. “Downsizing people from northern Delaware, or New Jersey and New York, seek new construction and active adult communities,” says Will Webber, a licensed Realtor and broker with Keller Williams Realty. “Delaware has really affordable taxes compared to Pennsylvania, New Jersey and New York, so that’s part of it. It’s where you get a lot of house for your money and you get the feeling of community.” The city has continued to grow, with many of its properties having been built after the turn of the millennium. It serves as a midpoint between two major cities in Delaware. “Middletown is an exploding, booming, growing neighborhood,” Webber says. “It became the bedroom community for people, as it’s midway between Dover and Wilmington.” Both cities are less than 30 miles south and north, respectively. “Delaware all by itself is kind of a hidden gem, because it’s without as much traffic and it’s not as expensive as Connecticut or Massachusetts,” Webber says. “People escape New York and New Jersey to come to Delaware.”
Thanks to the proximity of Route 1, which winds its way past the east side of Middletown, residents stay linked to major areas in Delaware and beyond. “It’s well-connected, because you can fly up and down Route 1,” Webber says. “Years ago, that wasn’t a road. It was corn fields. Middletown’s not a small town anymore, but it used to be. Now, it’s suburbia with upscale houses and lots of choices, including active adults.”
Stop in the boutique stores along Main St for a day of shopping in Middletown.
A sculpture of an eagle stands at the center of town square in Middletown.
Main Street in Middletown is a restaurant hub with plenty of new favorites popping up.
Kids can enjoy a small petting zoo which has several types of animals at the Peach Festival.
Single-family homes are the most common housing found in Middletown. Cape Cod, colonial and ranch-style homes are the most popular architectural styles, and single-family properties rarely cost below $500,000; they often range between $500,000 and $800,000. The median home price for homes in Middletown is $524,617, which exceeds the national median of $416,700, and most homes date to 2000 or later. “You do get a lot of house for your money, as far as cost per square foot,” Webber says. “It’s very attractive and has kind of gotten a reputation for being amazing, so it’s more competitive.”
Some properties, mostly custom homes, cost over $1 million, and are mostly part of the Bohemia Mill Pond community near the Maryland border. Listings tend to sit on the market for 35 days, up from September 2023’s duration of 26 days. Grid-style, organized streets and subdivisions fan out from the commercial hub in Middletown, perched on modest, landscaped lots. “Each neighborhood is slightly different, built one, two, three years apart and by different builders,” Webber says. “It’s houses that are convenient to shopping, but nobody ever buys a house just for shopping, because it’s also convenient to work.”
Just north of Middletown, the town of Whitehall is a more recently incorporated area for Delaware residents. “It’s kind of a special enclave, hamlet or village,” Webber says. “You’ll see a really well-thought-out, planned community where the driveways are behind the house. There’s little alleys that connect to them, and all generations from single families can live within walking distance. The grandparents can walk the kids to the elementary school or the library. It’s kind of a unique concept.”
On an annual basis, Middletown’s 45 inches of rain on average are higher than the national mean of 38, though it gets a below-average amount of snowfall. “It’s moderate, weather-wise,” Webber says. “It’s close enough to the coast and the Chesapeake Bay that if it snows, everybody panics for a day or two, but then it’s done.”
A large traditional home in Middletown is the perfect place to raise a family.
Charming Cape Cod homes with plenty of street parking on E Cochran St in Middletown.
A beautiful Victorian home in Middletown that makes you feel like you've stepped back in time.
Ranch homes typically come with attached driveways in Middletown.
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Route 1 runs just east of Middletown
The largely residential landscape of Middletown means locals often commute by car, but the Delaware Authority for Regional Transit (DART) operates buses for public transportation. As far as main roads go, Delaware state Route 1 winds its way past Middletown to the east. “Route 1 goes due south and connects to the beaches like Rehoboth and Dewey,” Webber says. “If you go just west, 301 connects to Annapolis.” Routes 71 and 299 make up the primary commercial stretch of the city, while Route 301 runs along and through parts of the west side.
Drivers can reach the state capital of Dover around 25 miles south, while Philadelphia sits about 60 miles northeast. “Dover is real convenient, within 15 to 20 minutes or less, and Philadelphia might be an hour and a half depending on time of the day,” Webber says. “Baltimore is close, but you have to go further south to catch 301 and the interstate and Beltway, or you go further north to catch I-95 and the Beltway." In terms of distance, Baltimore is just under 90 miles via the northern route and slightly over 90 miles by way of the southern route.
ChristianaCare is the second-largest employer in Delaware, with over 11,000 employees, and has several medical outlets in and around Middletown.
Green spaces of varying sizes in Middletown
Small tracts of land serve as most of Middletown’s green spaces, and Charles E. Price Memorial Park is the city’s largest park. Kids clamber across a pair of playgrounds, anglers cast lines in a pond on its grounds and dogs can run free in two parks for furry friends. Paved walking trails wind around the park, which is surrounded by agricultural land.
Towards the center of the city, Silver Lake Park encompasses six ballfields, used by the MOT (Middletown-Odessa-Townsend) Little League during the fall. The Appoquinimink River is another prominent feature of the natural landscape and is sometimes used for fishing or paddling. “It’s kind of marshy and kind of in a flood zone,” Webber says. Golfers hit the links at Frog Hollow Golf Club & Restaurant. Vacationers can head to Rehoboth Beach or Lewes Beach, each over 60 miles south. “There are real, official beaches with sand and places where you can buy t-shirts, flip-flops, swimwear and kayaks if you go to Rehoboth, Lewes and Bethany,” Webber says.
Catch a local little league game at Silver Lake Park in Middletown.
Charles E. Price Memorial Park has a popular dog park among local dog owners.
Play a game of pickleball with friends on the new pickleball courts at Silver Lake Park.
Book a tee time at Frog Hollow Golf Club, an 18 hole course in Middletown.
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A wide variety of stores and restaurants for locals
Middletown Warwick Road and Main Street serve as the area’s retail and dining hubs. Bakeries, breweries and food markets sit along and branch off of Main, while more commercial options are concentrated around Middletown Warwick Road. These include major retailers and chain restaurants, as well as an assortment of local eateries. “You would not believe how convenient everything is, if you don’t mind some traffic on heavier days,” Webber says. “Every store you can imagine is here, and so is everybody else.”
Grocery shoppers can head to Sprouts, Aldi or Lidl on the west side of the city, while ACME and Giant are located on the east side. Shopping complexes like Dove Run Shopping Center house more retail options. From Route 1 on the east side, shopping on the stretch of Middletown Warwick is about 4 miles west.
Pick up fresh meats and produce at the Dutch Country Farmers Market in Middletown.
Check off your grocery list in Middletown at the local Aldi.
First State Brewing Company in Middletown prides themselves on their variety of craft brews.
Find the perfect new outfit at F+L Boutique in Middletown.
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Community events and entertainment outlets
Several annual festivals mark the calendar for locals, including the Middletown Olde-Tyme Peach Festival. It has endured for over 30 years, kicks off with a parade and commemorates the area by showcasing local food and crafts, filling the air with live music and more. “The Peach Festival is one of the bigger, more memorable and noteworthy things,” Webber says. “Every town like this has a car club, Boy Scout-sponsored activities or where the local rotary gets out and cleans the highway. It’s a lot of cooperative, friendly, volunteer activities, where you can be cool and join this or that group. It has a huge sense of community.”
Westown Movies and Putters Paradise sit alongside one another on the west side. When residents are vacationing near Rehoboth Beach, there’s more options on the coast. “It’s 10 minutes to a bicycle-friendly brew pub,” Webber says. “I was there last summer and they had tents, taps and outside areas with rows of tables and sandwiches. It was good.”
A stage is set up in the center of town for a variety of acts at the Peach Festival.
Make sure to browse through the many vendors at the Delaware Renaissance Festival.
Local vendors fill the streets of downtown Middletown for the Olde Tyme Peach Festival.
Pick up your favorite sweet treats from local bakeries at the Olde Tyme Peach Festival.
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An A-rated school district for Middletown students
The Appoquinimink School District serves students in the area, awarded an A rating by Niche and also ranked as the best school district in the entire state. It includes 13 elementary schools, four middle schools and three high schools. The nearest major college is Wilmington University, situated about 20 miles north, which enrolls around 14,000 total students.
Students can begin their education at Brick Mill Elementary School.
Silver Lake Elementary School has 578 students in grades 1-5.
Louis L. Redding Middle School has 660 students in grades 6-8.
Middletown High School has an A rating on Niche, and is home of the Cavaliers.
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Crime in Middletown tends to be property-based
According to Neighborhood Scout’s crime data sourced from the FBI, Middletown makes record of 31.50 offenses per 1,000 residents each year. It is considered safer than 9% of cities nationwide, and property crimes make up almost 27 of the 31.50 average offenses.
Written By
Adam Cheek
Photography Contributed By
Bill Marrs
Video By
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GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Middletown, DE sell after 145 days on the market compared to the national average of 52 days. The median sale price for homes in Middletown, DE over the last 12 months is $510,000, down 3% from the median home sale price over the previous 12 months.
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