Top 5 Places to Retire in Fenwick Island, Delaware

Nestled between Bethany Beach and Ocean City, Maryland, is the small coastal community of Fenwick Island, Delaware.

Known for its historic lighthouse and the serene Fenwick Island State Park, this quiet resort community is a great place to retire.

With its low taxes and beautiful coastline, southern Delaware is a great place to lay down roots in your golden years and stretch those 401k and IRA dollars as much as possible.

If you're searching for the perfect place to retire, Fenwick Island, Delaware, may just be the place.

There are several great communities in the area that cater to the 55 and up demographic. Here are five top choices at or near Fenwick Island, Delaware.

Bayside Fenwick Island

If you're searching for the true beach life experience, there's perhaps no better choice in the Fenwick Island area than Bayside.

With the first Jack Nicklaus Signature Golf Course in Delaware, as well as a huge recreational area that includes two swimming pools, a splash zone for the kids, tennis courts, bocce ball courts and much more, there's always plenty going on at Bayside Fenwick Island.

The community also features a health and aquatic club that includes an indoor swimming pool, a hot tub, an aerobics room and a fitness area. There's also an on-site dog park for those residents who have pets.

The Point at Bayside is the place for residents to enjoy hiking trails and water sports like kayaking and paddle boarding.

An on-site beach shuttle also provides transportation to the Fenwick Island beaches during the summer season.

Learn more about Bayside Fenwick Island by clicking here.

Fenwick Acres

Fenwick Acres is a small oceanfront gated community that consists of just 22 homes. Homes here are a bit pricier due to the oceanfront location, but certainly worth a look if you're searching for a luxury retirement home at the Delaware beaches.

Located on the northern edge of Fenwick Island State Park, between Bethany Beach, Delaware, and Ocean City, Maryland, Fenwick Acres offers upscale living in Delaware's southern resort region.

Homes here don't hit the market often. So if you're interested in an oceanfront home in Fenwick Acres, have someone at the Oldfather Group keep an eye out for you.

Learn more about Fenwick Acres by clicking here.


One of Delaware’s premier retirement communities is located in Millsboro, just a short drive from the state's coastal resort towns.

Independence consists of more than 400 single-family homes with first-floor owner’s suites.

The heart of the community is the award-winning clubhouse, Independence Hall, which boasts a large meeting space, a bar, a yoga studio, a grand ballroom and much more.

Homes in the Independence community are specifically designed for buyers who are 55 years of age and older and there are many hobbies and activities for residents to enjoy, including the Garden Club, the Art Club, movies and a popular book club.

There are also several group activities, including walking, billiards, ballroom dancing, poker, yoga, and tai chi.

Learn more about Independence by clicking here.

Feet in the Ocean Waves

Friendship Creek

Just a few miles west of Fenwick Island and Bethany Beach is the community of Friendship Creek, a perfect spot to retire in Delaware's coastal region.

Billed as the "only villa community" close to Fenwick Island, Friendship Creek is designed to be a close-knit, private community with easy access to all of the fun and excitement of the Delaware beaches.

If you're searching for that perfect retirement spot that combines a coastal lifestyle with an ideal location, Friendship Creek could be the spot.

Townes at Bayshore Village

The Townes at Bayshore Village is a townhome community that rests on the shores of the Little Assawoman Bay and provides easy access to Fenwick Island, as well as to neighboring Ocean City, Maryland.

The community is within walking distance to many top spots in Fenwick Island, including restaurants, shopping, boating and, of course, the beach.

When finished, the Townes at Bayshore Village will feature a swimming pool, boat slips and a boardwalk, among other amenities.

Rehoboth Dunes

For much more on the benefits of retiring in Fenwick Island or anywhere else at the Delaware and Maryland beaches, contact the Oldfather Group today at 302-260-7244 or visit

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Google Reviews

⭐⭐⭐⭐⭐ "We worked with Linda O'Reilly, and she was excellent! We purchased a 2nd home in W Fenwick Island DE, with us being 3 hours away she handled everything for us flawlessly! She knew the areas, she listed to what we wanted, she maximized our time when we came to view homes, she treated our sale like she was spending her own money, we never once felt like she was a "sales person". I would highly recommend her, she is a honest, hardworking professional." - Rick Bogdanski on Google
⭐⭐⭐⭐⭐ "Searching for a home is always challenging but Linda O’Reilly, in the Fenwick Island office, has been really amazing. She is incredibly knowledgeable about the intricacies of buying a home. She is a true professional, and such a pleasure to work with in this unusually tight market! Thank you Linda for your patience and dedication in finding me a new place to call home!" - Karen G on Google
⭐⭐⭐⭐⭐ "Dustin & Mariya helped us to find our forever retirement home, they are professional and family oriented and they treat you like family from the get go!!! We highly recommend anyone looking for your forever home, first home or vacation home call The Oldfather Group you will not be disappointed! Thank you for all you do for your clients it makes a difference." - Robin Webber on Google
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