Chesapeake 55+ Active Adult Retirement Communities

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Chesapeake is a coastal city near the Atlantic Ocean in Eastern Virginia. Retirees enjoy experiencing all four seasons without extreme temperatures, plenty of water and outdoor recreation, and local festivals and events throughout the year. With its rich history and tax-friendliness, Chesapeake is a popular destination for active adults looking to retire near the ocean.

Climate & Geography 

Chesapeake is just south of Norfolk on the border of Virginia and North Carolina. Its summers are hot and humid, and winters are cool and mild. There is more rainfall than average, but less snowfall. The land is low and level throughout the city, and the nearby Atlantic seabreezes help moderate the long warm summer. Residents have 211 days of sunshine each year. 

The northern border of the city follows several forks of the Elizabeth River, and much of the southwest contains part of the Great Dismal Swamp. Due to these geographical features, expansion of the city is difficult, but Chesapeake remains the third most populous city in Virginia.

Recreation, Culture, & Entertainment 

Though there is no traditional downtown in Chesapeake, it does have several central shopping centers throughout its various neighborhoods. Greenbrier Mall has name brands, while Towne Place at the Greenbrier is an open-air mall with boutiques, outdoor entertainment, and a free summer concert series. 

Hikers have abundant options in Chesapeake. The Dismal Swamp Canal Trail is open year round for biking and hiking in the historic land preserve. Oak Grove Lake Park has wide, flat trails as well as beach and picnic areas, and the Northwest River Park has paddleboating, canoeing, and fishing options. Another popular hiking and jogging destination, the Chesapeake Arboretum, has over 3.5 miles of trails.

Residents can also enjoy the annual Chesapeake Virginia Wine Festival, Tap Tap Craft Beer Festival, and BikeFest, as well as the Chesapeake Farmers Market on Saturdays and Wednesdays during the summer.

Cost of Living & Taxes 

Chesapeake’s cost of living hovers just above the national average. Housing is the biggest cost, followed by health and transportation. Utilities and groceries are below the national average. Though the overall cost of living is higher than the U.S. average, it is on par with Virginia’s average.

Virginia is somewhat tax-friendly for retirees. Social Security is not taxed, and while other retirement incomes like pensions and 401(k)s are taxed, there are substantial deductions available. Property taxes are fairly low, and sales taxes are some of the lowest in the country. Prescription medication is exempt from Chesapeake’s 6 percent sales tax, and groceries are taxed at a lower rate of 2.5 percent.

Health Care

Chesapeake is part of the Virginia Beach-Norfolk-Newport News metropolitan area. Most recently, this region ranked in the top 90 communities in Gallup’s annual Well-Being Index.

The Chesapeake Regional Medical Center is a high performing hospital in the city, according to U.S. News, and is ranked for is treatment of heart failure and chronic obstructive pulmonary disorder (COPD). In nearby Norfolk, Sentara Norfolk General Hospital is nationally ranked and the No. 1 hospital in the metro area and the No. 2 hospital in Virginia. Sentara Leigh Hospital is also high performing and the No. 2 hospital in the region.

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