Exploring the 55+ Communities of Chesapeake, Virginia

If you want to live near the water in Virginia, check out these Chesapeake communities.

Virginia Beach is also just thirty minutes east of Chesapeake, giving residents easy access to the boardwalk and classic beach stops like golf courses and the aquarium.

The Hampton Roads area is also popular for older adults. According to The Virginian-Pilot, the region has more active adults than any other region in Virginia. The Census Bureau also estimates that the percentage of retired-age people will continue to grow. This means that many people who have lived and worked in the region will continue to live there even into retirement age.

The good news for active adults who want to stay in the region is that Chesapeake alone offers six age-restricted communities. Here’s a brief overview of those six communities.

Eagle Pointe at Cahoon Plantation

Low $300s – Mid $400s

Since 2005, Eagle Construction has been building Eagle Pointe at Cahoon Plantation. As the largest of Chesapeake’s six communities, Eagle Pointe at Cahoon Plantation will have 501 homes at completion.

Home styles include attached and single-family models, providing easy living and low-maintenance for homeowners.

The centerpiece of the community is The Isles Golf Links, an 18-hole course for all levels of play. Residents also enjoy The Bay Club, a 10,000 square-foot clubhouse with many spaces for residents to take classes and meet neighbors, plus an indoor and outdoor pool and fitness center.

The Retreat at Greenbrier

Low $300s – High $400s

The Retreat at Greenbrier is a smaller, established community with 184 homes. Prospective residents can find quadriplexes, townhomes, and single-family homes offered for resale. 

Although smaller, the Retreat at Greenbrier offers amenities of a larger community. Residents can stay fit, learn new skills, or just relax at the Lakeside Clubhouse. Outside the clubhouse, the pool and pool deck provide a calm place to enjoy the summer weather, while the gazebo and fire pit offer residents great outdoor socializing space.


Low $300s – Mid $400s

Sommerton is an intimate community of just 90 homes. Prospective residents can choose from new or resale homes starting in the low $300s.

Stephen Alexander Homes offers four different models of townhomes, with three bedrooms plus or minus a bonus room, and two-and-a-half bathrooms. With more of a neighborhood feel, residents can get to know each other at the gazebo or picnic area, or just enjoying the natural areas of the community.

The Commons at Hunningdon Lakes

Mid $200s – Low $300s

The Commons at Hunningdon Lakes is another intimate attached home community in Chesapeake. The neighborhood includes just 87 attached homes, offered for resale in the mid $200s to low $300s range. The condos include three bedrooms and two-and-a-half baths.

Residents have plenty of time to enjoy all that the region has to offer, since exterior building maintenance, lawn care, and common area lawn care are all maintained by the homeowners’ association.

Retreat at Kemps River

Low $300s – Low $400s

Retreat at Kemps River offers a neighborhood of attached homes for active adult residents. . The completed community will include 80 homes that are customizable. Attached homes include vaulted ceilings, open kitchens, fireplaces, and covered porches, with options for first- or second-floor suites.

Although the builders do not have plans for a clubhouse or shared amenities, residents can enjoy the parks and natural space around the neighborhood. The Stumpy Lake Country Club and Greenbrier Country Club are also just a short drive from the community, as are large shopping centers.

Monarch Walk

Mid $100s – High $100s

Monarch Walk is the smallest of Chesapeake’s age-restricted communities, with just 62 homes. McQ Builders completed construction on the community in 2014, and the attached homes are now offered for resale.

The homes range from about 1,250 to 1,650 square feet but can include attics or lofts, first-floor master bedrooms, stainless steel appliances, fireplaces, granite countertops, and a privacy fence.

Although small, Monarch Walk does have a community clubhouse where residents can use a fitness center and multipurpose room. A putting green and walking trails allow residents to enjoy the community’s outdoor space. The community members come together for events during the year like holiday parties and special events.

Can you spot the $207,744 difference between these identical homes?

Financing is the difference!

Get the details in The 62+ Loan Homebuyers Guide.

55places Mortgage is a joint venture between Mutual of Omaha Mortgage and 55places.com.
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We’re changing the way people 55 and older are searching for their perfect next place. With a national network of hand-selected real estate experts, plus comprehensive information, unbiased content, and on-the-go insight about thousands of communities across the country, we’re a trusted resource paving the way from here to home. Whether you’re interested in a low-maintenance single-level residence, an active lifestyle or age-qualified community, an intimate enclave, or anything in between, we can help you make your next move the best one yet.

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