For centuries, sailors and landlubbers alike have extolled the virtues of living on the Chesapeake. Today, homebuyers are lured to its shores by myriad choices. Following is a sampling of communities—and lifestyles—to consider when buying near the bay.

Urban Living
Annapolis, the capital of Maryland and home to the U.S. Naval Academy, boasts a picturesque downtown of cobbled streets and vintage row houses fanning out from the grand Maryland State House. A plethora of galleries, shops, restaurants and music venues means that on a night out in this historic town, dinner at a crab house or chic eatery might be followed by music at Rams Head Tavern or a night at the Annapolis Opera.

It’s the perfect locale for those looking to enjoy urban living on the bay. And buyers seeking city amenities in a natural setting will find that elusive combination at Parkeside Preserve, a new townhouse community by Lennar situated just three miles from the Annapolis City Dock. The enclave, parts of which are still under development, is adjacent to the 340-acre waterfront Quiet Waters Park, where a boat launch creates easy access to Harness Creek and the South River. More than a dozen marinas are located within two and a half miles. There’s also quick access to Washington, DC, the Chesapeake Bay Bridge and points east. 

When complete, Parkeside Preserve will encompass 86 townhomes and 34 single-family homes. Townhomes are currently available with open floor plans, three bedrooms, two bathrooms and a garage; they’re priced from the mid $600s. Single-family-home lots will soon be available. lennar.com

55 and Up
K. Hovnanian’s Four Seasons at Kent Island in Maryland is a resort-style community steps from the Chester River and northeast Chesapeake Bay and minutes from Annapolis. The enclave offers myriad amenities in a bucolic setting with small-town charm. Dining and shopping opportunities are nearby, but residents may be content to stay home and take advantage of the community’s spoils.

Restricted to homeowners with at least one resident age 55 or older, Four Seasons at Kent Island has an on-site activities director who plans wine tastings, chef demonstrations, club meetings and field trips. The 24,000-square-foot clubhouse is outfitted with an exercise room, a game room, a yoga studio and a ballroom; indoor and outdoor swimming pools each have their own spa. Other communal gathering spots include an outdoor bar and patio; a covered patio; a beach; pickleball and tennis courts; an amphitheater for concerts; a dog park; and a playground for visiting grandchildren. 

Now beginning the third of four development phases, the community will eventually encompass 1,079 residences, including condos starting at $494,900 and single-family homes priced from $609,900. The latter offers 10 floor plans that can be personalized with different styles and color palettes. khov.com

Golf, Anyone?
Perched on the southern tip of Virginia’s Eastern Shore, the Bay Creek Cape Charles community enjoys access to sandy beaches and a 350-acre nature preserve. But for many residents, its two golf courses, which meander along the Chesapeake Bay and Old Plantation Creek through sand dunes and woodlands, are the prime draw. The nine-hole Jack Nicklaus Signature Golf Course complements the community’s renowned 18-hole Arnold Palmer Signature Golf Course, which has been winning national awards since it opened in 2001. 

Bay Creek offers activities for non-golfers, too, especially those who want to fish, catch crabs or get on the water by kayak or canoe. Residents can keep boats and yachts at several nearby marinas. Two miles of sand beaches are part of the community, which also boasts two outdoor pools, a fitness center, a yoga lawn, a splash zone and a giant kids’ slide. Wellness and nutrition experts are available for consultations. 

About 1,200 families now live in Bay Creek, which will include approximately 2,000 homes when complete. Homesites with views of the water, golf course or lake are priced from the $100s. Residences are priced from the $400s to more than $1 million. Multiple builders belong to the Bay Creek Builder Guild; see baycreeklife.com for information.

Health + Wellness
An active lifestyle with plenty of opportunities for healthy pursuits—both indoors and out—is a goal for many homebuyers. At Brookfield Residential’s Lakeside at Trappe, an array of recreational activities gives residents loads of options for staying fit. Trails for biking, running and walking wind through the community; dog parks accommodate pets and their owners; and multipurpose courts provide places to play basketball and other games. An outdoor swimming pool, playgrounds and parks with picnic areas all offer further ways to enjoy the outdoors. New community features in the works include pickleball and tennis courts and lakeside amenities such as a café and a beach.

Lakeside at Trappe is located in Trappe, Maryland, 10 or 15 minutes from Easton and Cambridge. The Atlantic beaches are less than 90 minutes away. 

There are currently 60 homes in the community, which will include 2,500 homes when complete. Single-family abodes are priced from the upper $300s to the mid $500s. Multiple floor plans are available, some with a first-floor primary suite and some designed for multigenerational living. Buyers can choose among layouts ranging from two to six bedrooms with a two- or three-car garage. lakesideattrappe.com

Boaters’ Delight
Buyers looking to house their boats as well as themselves will find newly built townhomes and a marina at Deep Harbour on Cambridge Creek. This tributary flows into the Choptank River—which in turn leads into the Chesapeake Bay, making for easy access to numerous destinations along the Eastern Shore by boat, as well as sailing and fishing opportunities.

Located in Cambridge, Maryland, the gated community of Deep Harbour was conceived by Beazer Homes in 2006 as two five-story condos. A few years ago, the company began an expansion with 93 three-level, three-bedroom townhouses now in the second phase of development. 

Deep Harbour is within easy distance of downtown Cambridge via a riverwalk along Cambridge Creek that takes in marina views, restaurants and one of the oldest crab processing plants in the world. It meanders through the revitalized Cambridge Waterfront, with its restaurants, shops and public green space, and picturesque Long Wharf Park.

Townhomes, some with marina or water views, start at $250,000; move-in ready models featuring upgrades are priced at $283,000. Deep Harbour’s marina contains 26 deeded 25- to 30-foot boat slips that will soon be available for sale. beazer.com

Back to Nature
Most homebuyers will choose a view if they can get one. Some may prefer a water vista, some may want a city skyline—and some may be drawn to the panorama of green trees and rolling hills. At Robinson’s Reserve in Severna Park, buyers will find privacy and a connection to nature. Built by Wagner Homes, the enclave of 19 single-family abodes is nestled within several forest conservation areas; interiors have open floor plans with oversized windows intended to capture the surrounding forested vistas, plus covered porches and landscaped rear yards. 

Despite its wooded location, Robinson’s Reserve is situated just 20 minutes from downtown Annapolis. And for those who crave even more time communing with nature, the development is also just minutes from Yantz and Cedar Creeks, which flow into the Severn River. The Kinder Farm Park, with hands-on activities for families, and Lake Waterford Park are also nearby. 

The final five lots in Robinson’s Reserve in Severna Park were recently released for sale, with prices starting around $850,000 for a four- or five-bedroom house. Each includes an eight-foot kitchen island anchoring a dwelling designed for entertaining. Wagner Homes; 410-987-3777.