In Delaware / Dec 6, 2019

The Best Places to Retire in Delaware

The state of Delaware is a bit of a hidden gem when it comes to top spots for retirement. What makes it so attractive? Delaware is a low-tax state and is an easy drive to major metropolitan cities like Philadelphia and Baltimore, as well as the District of Columbia. "The First State" offers a wealth of culture and history, and is in close proximity to highly-rated health care facilities like Johns Hopkins Hospital. Surrounded by 19 state parks and trails to help retirees stay active and fit, learn more about Delaware’s retirement benefits here

Rehoboth Beach

Rehoboth Beach makes just about every list of top cities to retire in Delaware, and with good reason. If you think of retirement as a vacation you never have to come home from it makes sense why Rehoboth Beach, perhaps the most popular vacation spot in Delaware, is a favorite destination. Aside from its pristine beaches and coastal lifestyle, Rehoboth is home to a diverse community of all ages. Rehoboth boasts a vibrant restaurant scene and offers residents and visitors alike plenty of shopping opportunities (tax-free) at Tanger Outlets., which ranks Rehoboth Beach as #1 on its list of Best Places to Retire in Delaware, reports that the town has a population of 1,218, a median home value of $878,900, and a median rent of $1,231, with 82% of its residents owning their own homes. Learn more about Rehoboth Beach here.

Fun fact: Rehoboth Beach is known as the “Nation’s Summer Capital."


Just over a stone's throw from Rehoboth Beach, Lewes is another popular retirement spot in Delaware. As of February 2nd, 2019, SafeWise recognized Lewes as Delaware’s safest city -- but that isn’t the only reason we love Lewes. It is also famous for the beautiful Cape Henlopen State Park, which offers 5,193 acres of gorgeous trails and beaches. Whether you’re a water-lover seeking ocean swimming, kayaking, clamming, paddle-boarding, and sailing opportunities, or a hiker or cyclist hoping to hit the trails every day of your retirement, Lewes is the city for you. The town boasts an incredibly charming downtown featuring Second Street, where you can browse antique shops, fashion boutiques and sample delicious foods from a host of local restaurants.

Lewes has a population of 2,961, a median home value of $512,100, and a median rent of $882; and 81% of Lewes residents own their own homes. You can learn more about Cape Henlopen State Park here and more about the city of Lewes here.

Fun fact: Lewes is the first city in "The First State"!


If you’d like to spend your retirement years surrounded by friends who can join you in pursuing leisurely activities in and around a thriving town, check out Middletown’s The Ponds at Bayberry. With homes starting at $279,900, The Ponds at Bayberry is more affordable than tourist destinations like Rehoboth Beach and Lewes, while also offering plenty of resort-style amenities including an outdoor pool, tennis, bocce & pickleball courts, a beautiful fitness center, ballroom for special events, and more. The Ponds at Bayberry was carefully designed to create a vibrant 55+ community (and upon moving in, you’ll find an amazing built-in family of fellow retirees!). Bonus points: on-lot maintenance is included.

At 20,754, Middletown has a larger population than Rehoboth and Lewes. The median home value in Middletown is $282,200, and the median rent is $1,133. The city has a wonderfully open yet cozy suburban feel, with 79% of residents owning their own homes. While Middletown is a bustling suburban city full of things to do, it is also home to beautiful parks like Charles E. Memorial Park, which offers a fishing pond, trails, and picnic areas like Silver Lake Park. Explore the area to discover the dozens of restaurants, golf courses, shopping, and entertainment options in Middletown!

Fun fact: Middletown was originally a tavern stop on a road before it became an official town. Learn more about Middletown here.

North Star

Westhampton has officially SOLD OUT as of September 2021 but a beautiful new and exciting community is coming to Hockessin soon.


Introducing: Valley Grove. Learn all about this new community and sign up for the interest list to receive the latest news and updates at the community logo above!

Bordering Pennsylvania and the historic Brandywine Valley, North Star is packed with small-town charm and local amenities in the northern part of the state. Clocking in at just under 7 square miles, this small town is surrounded by country clubs, lush state parks, locally-owned shopping, dining, and coffee shops. If its small-town charm doesn’t reel you in, it might help to know that Niche ranks North Star as the #2 Best Suburb to live in Delaware and #7 on their retiree's list.

North Star has a population of 7,390, a median home value of $435,300, and a median rent of $1,891, with 95% of its residents owning their own homes. Check out Westhampton, a quiet luxury community nestled in preserved wooded space just a few miles outside of North Star.

Fun fact: North Star has its very own community creamery!

Ocean View

Loved by all, Ocean View ranks as number 2 for retirement towns on New Home Source and number 3 on As its name implies, Ocean View, Delaware provides scenic views of the Atlantic Ocean while also housing Holts Landing State Park, known for its crabbing and fishing, and Fenwick Island State Park, perfect for swimming and sunbathing. While the area was originally called Middlesex, local legend has it that it was renamed Ocean View after a young man climbed a tree and caught a glimpse of the Atlantic. and SafeWise both give Ocean View a high rating for safety. Its population is 2,150; its median home value is $337,600; its median rent is $1,189; and 88% of residents own their own homes.

Fun fact: Ocean View is known as the home of the commercial broiler chicken industry. Learn more about Ocean View here.


While Delaware towns like Rehoboth Beach, Lewes, and Ocean View are all prized for their proximity to the ocean, Greenville is a desirable location for retirees who prioritize proximity to city life while enjoying a quiet, suburban feel in their local neighborhood. Greenville is about ten minutes from Wilmington, Delaware’s largest city, so residents have several opportunities to participate in events, festivals and cultural experiences, enjoy a diverse food scene, and easily visit some of Delaware’s most historic areas. Among these are the Hagley Museum, Winterthur, and Nemours Estate.

Greenville has a population of 2,305 and is home to many retirees. The median home value is $667,400, the median rent is $1,334, and 51% of residents own their own homes.

Fun fact: several descendants of the famous DuPont family reside in Greenville.

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