9 Best Places To Call Home on the Chesapeake Bay In 2025
The Chesapeake Bay region spans multiple states, primarily Maryland and Virginia, and is one of the East Coast’s most captivating natural landscapes. Known for its scenic shorelines, laid-back pace, and thriving fishing culture, the watershed has long drawn those seeking a slower, more peaceful way of life. Dotted with charming small towns, it’s an ideal destination for anyone drawn by the prospect of coastal living amid a welcoming community with mild weather and rich local traditions.
But finding the right spot means balancing charm with affordability. Whether you're after waterfront views, outdoor recreation, a simple way of life, or new employment opportunities, here are the best places to call home in the Chesapeake Bay region in 2025.
Chesapeake Beach, Maryland
Laid-back seaside living and small-town flair attract people to this unassuming community in Calvert County. The weather is mild throughout the year, encouraging residents to step outside and discover the open spaces during a leisurely hike along the Chesapeake Beach Railway Trail. Several local outfitters provide thrilling tours on the water, and those interested can book a trip with Katherine Charter Fishing to bond with family and friends while trying their hand at angling.
The Chesapeake Beach Railway Museum reminds citizens of the community's railroading heritage with a collection of resourceful exhibits inside a late 19th-century railway station. Meanwhile, the Northeast Community Center is where townsfolk gather to participate in recreational activities and other events that foster social cohesion. As of September 2025, Chesapeake Beach's median home listing price is $452,500, a bit below Maryland's state average.
Rock Hall, Maryland
This unpretentious bayside town on the National Chesapeake Scenic Byway charms potential movers with its thriving seafood culture, wide open spaces, and an unbeatable sense of privacy. A little over 1,000 people call this tiny coastal village home, leaving adequate room to roam serene natural areas for your outdoor recreation, including Eastern Neck National Wildlife Refuge. This secluded island escape straddles over 2,000 acres of hiking trails, wildlife habitats, and undiscovered beaches. The Waterman's Museum preserves Rock Hall's seafood heritage with rare historical exhibits about crabbing and oystering in the region.
Elsewhere, locals can always venture into the open sea for unforgettable sightseeing excursions courtesy of Blue Crab Chesapeake Sailing Charters. Retirees in Rock Hall are well taken care of, thanks to senior facilities like Golden Rule Assisted Living. Also, homes in the area have a median listing price of $435,000, making this an affordable town to settle down in.
Deltaville, Virginia
Deltaville lies directly along the Chesapeake Bay on the eastern end of Middlesex County, and is known for its relaxed small-town flair and fun water adventures. The vast waters surrounding the town are a platform for exciting aquatic recreation, with numerous vessels docked at Fishing Bay Marina available to anyone who wishes to head out to sea. Nature lovers and history buffs find mutual interest at the Deltaville Maritime Museum & Holly Point Nature Park. This 36-acre waterfront property features a mix of woodlands, gardens, and parks where locals can relax, and there’s also an on-site museum chronicling the region's nautical past.
Several beachside taverns treat townsfolk to a delectable dining experience, and one of the trendiest in the area is Deltaville Tap & Raw Bar, which serves fresh seafood, craft beer, and cocktails in an upbeat atmosphere. Meanwhile, Deltaville's median listing home price is $449,500, making it a good deal by Virginia standards.
Crisfield, Maryland
Crisfield boasts a median home listing price of $200,000, making it one of the most affordable places to call home in the Chesapeake Bay in 2025. But beyond its affordability, the community maintains a lively arts and culture scene throughout the Crisfield Arts and Entertainment District. The neighborhood is always buzzing with high-spirited performers, musicians, artists, and creators plying their trade. A blend of fine weather and sprawling waters around Crisfield cultivates easygoing tours at sea courtesy of Tangier Island Cruises.
Those curious to learn the area's past can always stop by the Crisfield Heritage Foundation to browse interesting historical exhibits. Meanwhile, TidalHealth Primary Care stays on hand to render medical services whenever necessary.
Mathews, Virginia
Established in the 1700s, this Chesapeake Bay community tells a unique story of the past, especially for anyone exploring its historic village. The town's lively Main Street is lined with historic structures, highlighted by Sibley's General Store. This rustic building has been a local mainstay since it was constructed in the late 1800s and provides a unique glimpse into the period. The Mathews Maritime Museum is a notable stop along the main thoroughfare, with documents, photographs, and artifacts preserving the legacy of the region.
Residents also get to constantly connect with the arts at the Bay School Community Arts Center, which provides classes, workshops, exhibitions, and other programs curated for enthusiasts of all ages. The presence of Riverside Mathews Medical Center ensures there is reliable healthcare provision locally. With a median home listing price of $349,900, Mathews is a great place to make your home.
Irvington, Virginia
This unassuming village on the Rappahannock River impresses with its relaxed rural feel and immersive historical heritage. It boasts a rich maritime heritage thanks to its waterfront setting, and displays a collection of related artifacts, relics, dioramas, and other exhibits inside the Steamboat Era Museum. Several studios and galleries in the town offer proof of the town's active arts community. You can browse a beautiful catalog of paintings, jewelry, sculptures, and other art forms at Objects Art and More.
The Compass Entertainment Complex provides a state-of-the-art amusement venue where residents of all ages can access all-around recreation. From climbing walls and go-karts to arcade games and mini golf, it is the perfect getaway for family fun. Irvington's median home listing price is $525,000, with good deals to be found below that price point.
Havre De Grace, Maryland
The Chesapeake Bay peacefully collides with the Susquehanna River in this historic town of Harford County, known for its sublime waterfront scenery, fascinating museums, and idyllic green spaces. There is adequate room for outdoor recreation, and families often flock to the Millard Tydings Memorial Park for a quiet picnic. From the park, you can easily notice the imposing Friends-Concord Point Lighthouse. This, alongside the Havre de Grace Maritime Museum, tells a unique story about nautical expeditions in the region through the years.
The Havre de Grace Promenade provides the perfect setting for those seeking alone time to meditate, while losing themselves in terrific views of the Susquehanna River. Locals find time to come together and participate in various social programs at the Havre de Grace Community Center, while the median home listing price here is $430,000.
Chestertown, Maryland
This rustic colonial town on the Chester River banks is known for its intact historic district, vibrant arts and culture, and enduring maritime heritage in Maryland. A walk through the old town square reveals an assemblage of old-world structures, and newcomers can learn all about Chestertown's dynamic history while visiting the Historical Society of Kent County. The year-round Chestertown Farmers Market enhances a sense of camaraderie in the community as townsfolk constantly come together to sell and buy fresh produce, crafts, and other wares.
Another popular social spot is the Garfield Center for the Arts, where live theatrical productions are staged to support the local arts community. Chestertown also houses the University of Maryland Shore Medical Center, assuring new residents of readily accessible and reliable healthcare. Lastly, its median home listing price is $475,000, with the median sold price falling lower at $354,500.
Colonial Beach, Virginia
Historical lore meets waterside charm in this scenic town in northwest Westmoreland County. Colonial Beach is steeped in history and hosts several attractions that take you back in time. The George Washington Birthplace National Monument is a fine example, providing a glimpse of the founding father's birthplace and 1700s plantation life. Meanwhile, the Colonial Beach Municipal Pier is one of the best outdoor spots in town, providing a serene setting to walk, run, fish, or sit down and admire gorgeous water views.
Residents enjoy easygoing cruises on the calm waters of the Potomac River by chartering a tour at the Colonial Beach Yacht Center. Furthermore, vital social amenities like Westmoreland Rehabilitation & Healthcare enhance the overall well-being of the community in Colonial Beach. With a median home listing price of $369,000, prices in the town are below Virginia's average.
Charming Hometowns on the Chesapeake Bay
If you are searching for the best places to call home on the Chesapeake Bay in 2025, these are only a fraction of the numerous options that offer charm, affordability, and a high quality of life. Whether you're drawn to waterfront views, historic streets, or tight-knit communities, the Bay has something for everyone. Take the time to explore, visit, and connect with locals because you just might find your perfect forever home nestled along the scenic Eastern shores of the United States.
