These Neighborhoods in Delaware Are Great Places to Live

Looking to relocate in the 302? These booming neighborhoods offer distinct qualities catering to different lifestyles.

Delaware, at a slow and steady pace, finally cracked the 1 million residents mark last year after decades of incremental growth, according to the U.S. Census Bureau. Where’s everyone going? We tracked down just a few hot spots where new homes collide with local history and historic towns feel rejuvenated.


Rob Stigler knows better than most that Arden can be a lot to take in for the uninitiated.

The funky lawn décor. The odd, old, Frankenstein houses with mismatched extensions and outré curb appeal. Even the neighborhood’s cherished annual festival, the Arden Fair, may confuse first-time patrons seeking a run-of-the-mill block party.

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Arden neighborhood

“People see us for the first time and think, Why the hell are these Arden people dressed up like wizards?

Stigler, a Realtor with Keller Williams, is a lifelong Arden resident and today sells homes there and beyond. Dressing in Shakespearean garb for the annual fair is just part of the quirky package.

“I’ve lived in Arden my whole life, so I feel like it’s OK for me to say this: Arden is weird,” he says. “And you either love that weirdness or you don’t. It caters to a specific buyer.

“There are some houses in Arden that will sell for a price that seems kind of ridiculous considering what you get on an objective basis. But what drives some of those prices is maybe how unique the house is or some of the quirks about it that people just, for whatever reason, love Arden for.”

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The vast majority of the 450-plus homes in Arden are totally original. No cookie-cutters or McMansions here.

Stigler’s house, for instance, is the only octagonal house in the neighborhood, and one of only a couple in the state. There are plenty of other homes that have their own sense of uniqueness in the neighborhood, he says, “and that can be both a blessing and a curse because not everybody wants that weird one-off house that doesn’t cater to today’s kind of norms.”

Arden Delaware
Beyond a sign that reads, “You Are Welcome Hither,” Arden is a funky arts community where old Frankenstein houses with mismatched extensions meet Tudor-style cottages with whimsical gardens.

Find everything here from cozy ranch cottages to fixer-uppers to historic Tudor-style homes—and oddballs and artists galore.

“There’s a bit of a premium placed on some of that uniqueness, charm, quirkiness, whatever you want to call it,” Stigler says. Home prices here can range from anywhere between $180,000 and $850,000. A one-bedroom house recently sold for $400,000. Between the variety of architecture, a happening summer music festival, swim club and Arden’s famous Gild Hall, residents are happy to embrace the weirdness.


Few spots in the First State are witnessing the kind of new construction explosion as Milton, the small Sussex town once known for Dogfish Head Craft Brewery, a beloved theater…and not a whole lot else.

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Things are far different today. “There’s so much slated new construction coming to Milton that I can’t even keep up,” says Jaime Hurlock, a Realtor with Long & Foster. Young families, downsizers and out-of-staters continue to flock to Milton thanks to its friendly, small-town feel, its proximity to the beaches and outlets, and a raft of affordable new inventory on the market. Single-family homes fetch prices in the $300,000 to $400,000 range, while properties with water views like Broadkill Beach and Wagamons Pond are going for more. Such neighborhoods as Preserve on the Broadkill and Cannery Village offer walkability and tailored amenities galore.

Milton neighborhood

“Downtown is coming back again,” Hurlock asserts. “Milton has had a lot of stores turning over, but another couple of cafés showed up this wintertime that seem to be doing well.” Shops like Maggiemade and Cape Treasure Gallery sell hip and locally inspired housewares, and nearby spots like Revelation Brewery provide the kind of wide-open, relaxed vibe only found downstate and away from the bustle of the beach.

Milton Delaware
The small Sussex town of Milton, home to Dogfish Head Craft Brewery and its charming namesake theater, is witnessing a new explosion of construction: Downtown is coming alive again with shops and cafes as the area draws downsizers and young families to its cozy single-family and waterfront homes.

Who knows for how long, though. Open space is also being converted into destinations like Schellville—the “enchanted winter celebration” operated by the development giants Schell Brothers. The drive-through lights show and miniature Christmas village—complete with scale-model homes to explore, an ice rink, train rides and more—continues to attract enormous crowds in the winter months.

Beyond the amenities, families and guardians can also plug into the excellent Cape Henlopen School District. Thanks to the population growth, most families can send their kids to new—“brand-spanking new” in many cases, Hurlock says—school buildings. “The growth and financial stability of this school district just keeps building up,” she says.


Unlike its neighbors to the south, Milford has mostly resisted the new construction boom. And that’s a good thing, in a way. “Milford’s definitely that town that has the old town, small charm still,” Hurlock says.

That also means 30- to 40-year old homes with old charms and mature landscaping, and average home prices near the $300,000 mark, with a handful of bargains to be had near historic downtown Milford.

Still, it seems impossible to deny Milford’s growing profile. “There’s a lot of reinvestment happening in town,” Hurlock says. “It has that walkable riverfront area. It’s an area that’s seeing a lot of families, especially because of the price point.”

Historically blue-collar, Milford’s small-town feel is the main attraction for most who settle (or never move away from) here. A walkable riverfront and opening of a new hospital campus has diversified residents and home prices, and were the impetus for major reinvestment into downtown.

Milford has a strong blue-collar presence, as it has throughout its history, with a chicken plant, a concrete plant, and manufacturers of electronics, thermoplastics and more among its major job providers—as well as the recently built Bayhealth Sussex Campus. That helps lead to a diverse range of home prices and a few newer condo options like Hearthstone Manor.

“And you’re starting to see the larger grocery stores, and just everybody popping up around that area now,” Hurlock adds.

Who can resist buzzy local favorites like My Sister’s Fault (the heralded Puerto Rican bakery and café), Surf Bagel and Arena’s Deli? Suddenly, they, along with Mispillion Brewery and Easy Speak Distillery, comprise a formidable lineup of dining and drinking options.


There are a few newer neighborhoods with larger homes and water views that command much higher sums, especially in spots along Haven Lake, like North Shore Drive, Haven Lake Avenue and Evergreen Lane.

“There’s a lot of cool stuff going on in Milford, as I see a lot of people I grew up with from a little bit farther north going to that area,” Hurlock says. “And then anybody [who] grew up in Milford stays there, raises their families and are reinvesting themselves back in the community, too.”

Related: New Neighborhoods in Delaware Where You can Have It All


Great schools, flocking young families, and buzzy retail, breweries and restaurants? Check.

A Panera Bread and a Target? Now you’re officially on the map, Middletown.

After decades of rapid residential growth, Middletown’s surrounding amenities are beginning to catch up with the monumental demand for family-friendly dining and activities.

The beloved national chains join cool local hangouts like First State Brewing Company and Crooked Hammock, boutiques like F+L, and new and improved green spaces near Shallcross Road and Levels Park. Micro entertainment hubs see places like Putters Paradise mini golf and Westown Movies attract big crowds on warm nights.

Middletown continues to buzz with new business and housing options.

The highly rated Appoquinimink School District still tops families’ wish lists when considering Middletown, Realtor Megan Aitken says. “A lot of people find that Middletown is a healthy balance for both top education and price point and location, and in proximity to where they have to work,” she says.

Coveted new neighborhoods include the Estates at St. Anne’s, nestled between some of the town’s newer, hipper shopping and restaurant options. A similar vibe is unfolding on the southwest side of Middletown near the Westown Shopping Plaza, Aitken says.

Planned “active” communities like Bayberry and the Town of Whitehall continue to spark interest, offering loads of community events and gatherings.

With a possible downshift in the economy looming, rising interest rates and inflation, home prices around Middletown—which hover around $500,000—could start adjusting back down the bell curve.

“The big buzz is really what’s coming next,” Aitken says. “What’s coming? Panera Bread was such a big deal when they opened up here and then it was onto the next thing. Just an insatiable audience here.”

Trolley Square

The 20-somethings who staggered around the Trolley Square bar loops have grown up, raised kids of their own and are now settling down in the historic neighborhood once again.

Realtor and Trolley Square resident Vince Garman says the neighborhood is experiencing a changing of the guard, along with nearby Forty Acres, both old, proud Irish neighborhoods. “It’s a known sexy area,” he says. “It’s charming, attractive. A lot of folks from the Wilmington area are leaving for college, then coming back in their late 20s and buy a place here.”

And why not rekindle your glory years in one of Wilmington’s consistently strong hangout spots, always teeming with nightlife and restaurants? It’s home to one of BrewHaha!’s most luxuriously hip locations and both long-standing and newer establishments.

Trolley Square
Trolley Square, a beloved hangout among 20-somethings, is on the upswing for residents of all ages.

The Trolley Square Oyster House, the narrow but knockout oyster bar that opened in 2016, remains a hot spot, Garman says. “One of the coolest, funnest places out there. A definition of a vibe.” The backyard at Grain Craft Bar + Kitchen is another pivotal place to see and be seen, along with stalwarts like Kelly’s Logan House.

Garman—who, along with his wife Mary, runs an Instagram account called Trolley Trends spotlighting local businesses and residents—says the area’s on a certified upswing. “When houses go up here, they’re going super quickly,” he says. “It’s the place to be. It has the best of both worlds: suburbia mixed with walkable city life.”

Homes can be had reasonably here, too—with their old-world charm and abundant brickwork, as long as you don’t mind a creak or two.

And who says parents can’t hire a babysitter (via the bulletin board at St. Anne’s Church, perhaps?) and still participate in a bar loop once in a while?

Related: How to Stage Your Delaware Home for the Best Results

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