Waterfront property remains the most sought after in the Chesapeake Bay region but “affordable upscale” also is trending, along with the riches of residential amenities, natural environs, and urban proximity…if you know where to look
Home is where the heart is, and in the greater Chesapeake Bay region, our hearts are full. We like to think we’ve got things pretty well in the Land of Pleasant Living. And we’re right. Our local economy is humming, anchored by federal government and contractors, national cyber defense, a number of private global companies, and a wealth of residential, professional, and leisure driven industries. So much so, that home construction and development has also soared in an attempt to fulfill an ever-growing workforce’s housing needs.
We’re also fortunate to have a high number of state, county, and municipal business chambers, job development programs, and robust small business resources, enabling our communities to thrive on the shoulders of independent entrepreneurs.
Our schools—both public and private—are healthy, many of which rank well in state and national standards of performance excellence. Our local hospitals are supported by research and academic medical institutions anchored in the Baltimore-Washington corridor. Infrastructure continues to adapt and improve, as evidenced by the recent broadband connectivity across the Eastern Shore, or transit enhancements (MARC and Metro networks) and future considerations (high-speed ferries, anyone?). Crime statistics could always be rosier, but in general remain at stable averages that should keep those living in suburban communities at ease.
All of this to say that choosing to live in Anne Arundel and the Mid-Shore counties is a pretty safe bet in terms of one’s ability to find the ideal property and lifestyle, and in a range of demographics (e.g. first-time buyers, urban professionals, suburban families, plus-55, seniors, etc.).
We’ll help guide the decision-making with the following guide, Attractive Places to Live!
Offering a mix of regional real estate and demographic data with select community, neighborhood, and new development profiles, this guide showcases myriad places and reasons to locate/relocate here…which may be just around the corner.

The Big Real Estate Picture
If the buzzwords you’ve heard around the picnic table this summer about the local real estate market have been “difficult,” “slowing down,” or “sellers’ market,” you’d have reason to be cautious as a buyer. But these sentiments don’t paint the full picture of our unique region, which boasts a high number of elite properties (waterfront), specialized developments (mixed-use urban, active adult), and attracts buyers from across the globe. True, competition is strong among buyers. Prices remain elevated on limited inventory. But, with a companion realtor to walk one through the buying (or selling) process, dreams are still becoming reality…and often.
Statistics help tell the story. According to the most recent data available from Maryland REALTORS® (April 2023 compared to April 2024), the average home sales price increased year-over-year in almost every county of Maryland. Interestingly, Garrett County in the west led all with a 40.1 percent increase ($568K up to $796K). Calvert County saw the next highest increase at 22 percent. Anne Arundel County held “middle of the pack” status at 12.3 percent ($540K to $606K), while Talbot County’s saw a 10.5 percent increase ($723K to $799K). Nearby Dorchester County came in at a 21.7 percent increase ($238K to $290K) and Kent County slightly more at 21.8 percent ($369K to $450K).
This makes sense, given that the active inventory during this same period of comparison decreased in most counties. (If you’re considering selling your property, now could be a very good time to do so.) Some counties, however, experienced the opposite—Queen Anne’s County has seen an increase in inventory and slightly lower home prices than the year before.
Regardless of inventory or price, homes are selling lightning fast! The State average for median days on market is just eight days. Eight. In Anne Arundel County, six days on market is the median, while Talbot County takes 12 days to sell. Overall, the number of homes sold in Maryland increased year-over-year, an encouraging sign for the market.
“Seeing the increase in sales is good news for all of us: the homeowner, the community, the local governments,” said Chris Hill, 2024 President, Maryland REALTORS®, “but inventory and interest rates remain huge issues. In April, months of inventory grew to 1.7 months, but a balanced market would have about six months of inventory available.”
Teach the Children
For many, the decision of where to live is driven by education options for their children. Public education systems in Anne Arundel and Mid-Shore counties remain challenged by high student enrollment coupled with staffing inadequacies. Though the most recent data available (2023) from the Maryland State Department of Education suggests shortcomings in meeting annual targets at all three levels of education (elementary, middle, and high) in terms of the indicators of academic achievement, academic progress, English language proficiency, and school quality/student success, overall graduation rates remain optimistic. Talbot County Public Schools graduated 97.34 percent of its enrolled students in 2023; Queen Anne’s County, 94.21 percent; Kent County, 92.65 percent; Anne Arundel County, 87.68 percent; and Dorchester County, 81.57 percent.
Among Anne Arundel County’s 14 public high schools, Severna Park boasts a 78 percent performance rank, Broadneck at 67.2, and South River at 65.7. On the Eastern Shore, both Queen Anne’s County high schools (Kent Island High and Queen Anne’s County High) were the best performing among the Mid-Shore counties in 2023.
Across all counties, private school options are plentiful from pre-K education through high school and their proximity to neighborhoods, developments, towns, and cities have made them attractive options for many families. According to Niche, a “market leader in connecting colleges and schools with students and families” with over 140 million school reviews and ratings, the top eight private schools in Anne Arundel County are: Key School (Annapolis), Severn School (Severna Park), Indian Creek School (Crownsville), Rockbridge Academy (Crownsville), Archbishop Spalding High School (Severn), Annapolis Area Christian Upper School (Severn), St. Mary’s School (Annapolis), and Odenton Christian School (Odenton). And there are at least 11 additional private high schools from which to consider, with two new elite private schools having opened in the county within the past couple years: Divine Mercy Academy and the Chesterton Academy.
On the Shore, top tier private schools include: The Gunston School (Centreville), Wye River Upper School (Centerville), Lighthouse Christian Academy (Stevensville), Chestertown Christian Academy (Chestertown), Kent School (Chestertown), Radcliffe Creek School (Chestertown), Saints Peter & Paul Elementary and High Schools (Easton), The Country School (Easton), and Chesapeake Christian School (Easton).
For the most complete listings of all private schools, including pre-K through high school options and data points such as tuition costs, student-teacher ratios, religious/philosophical affiliations, and more, read What’s Up? Media’s 2024 Private School Guide.
Safe Streets
It can seem that we’re living in a scary society, given how often the news cycle attends to recent crime. If we hear of a gun-shooting or carjacking in a nearby neighborhood, not only are we put on alert, but we wonder if our lifestyle and safety are compromised. You may think back to “the good old days” when front-doors and cars were left unlocked, and children played freely in neighborhoods well past sunset on summer days. The good news is that those days can still, somewhat, be had. Overall, real crime statistics paint a much better picture than daily news reporting.
Since 1975—the first year of tracked data available from the Maryland Statistical Analysis Center of the Governor’s Office of Crime Prevention, Youth, and Victim Services—overall crime has dropped in most Maryland counties. Take Anne Arundel County, for example. In 1975, more than 22,000 crimes were reported. By 2020 (the most recent year of available consolidated data), that number more than halved to about 10,000 crimes. In Talbot County, just 879 crimes were reported in 1975 and reduced to 477 in 2020.
Nationally, overall crime saw a 15 percent decline between 2015 and 2020. This is not all to say that we’re living our best lives in terms of crime (violent crime, like murder, has seen an increase, especially in large cities), but there are ways to make good decisions about where to live safely.
For complete, county-by-county and city/zip code crime data sets, visit Maryland’s Crime Dashboard.
Leisure & Lifestyle
The Chesapeake Bay region is wondrous in many ways. It’s an environmental gem with protected tributaries and swaths of land. But it’s also an infrastructure behemoth—a region with at least three major airports (Baltimore-Washington International, Reagan National, and Dulles International) within an hour’s drive for many; plus, ground transportation systems that rival some of the best in the nation. We check the box as a hotbed of world-class medical research facilities and elite healthcare providers. And the Bay region is a leisure paradise of boundless water recreation, State and local parks to explore, museums that explain our collective history, thrilling attractions, and all the fixings of stylish urban living and shopping. The four-season weather is also attractive for those that enjoy the uniqueness of summer, fall, winter, and spring!
In addition to the romance of the region, here’s a quick and very random list of how Maryland ranks nationally in a number of recent surveys conducted by various interest groups:
- Maryland ranks #4 nationally in “highest paying jobs in SEO” (source: Ahrefs)
- Maryland ranks #5 nationally in “states with the best school systems” (source: Teach Simple)
- Maryland ranks #6 among all 50 states for “natural environment” (source: US News & World Report)
- Maryland ranks #7 nationally in “healthcare” (source: US News & World Report)
- Maryland ranks #7 among “cleanest states in America” (source: IT Asset Management Group)
- Maryland ranks #8 nationally among “the happiest states” (source: MentalHealthRehabs.com)
- Maryland ranks #9 in “safest states for cyclists” (source: Sweeney Merrigan Law LLP)
- Among all 50 states, Maryland showed the biggest increase in homeownership over the past 10 years, with an increase of 12.15 percent (source: Agent Advice)
And if you’re wondering what interior design trend to outfit your newly settled home with, try the “Boho” look. According to real estate research group Palm Paradise Realty, the most popular home aesthetic in Maryland is currently “Boho,” followed by “Steampunk” and “Farmhouse.”

Murray Hill, Annapolis
Where Exactly We’re Looking to Buy
The following local profiles cover a range of community styles and interests in Anne Arundel and the Mid-Shore counties, from historic to modern, urban to the ’burbs, and family to plus-55. This list doesn’t represent every amazing community; but, rather, a sampling of longtime and emerging favorites among homeowners, realtors, and the editors of this magazine.
Murray Hill, Annapolis The walkable neighborhood with centuries-old roots epitomizes best-in-class Annapolitan living with a mix of colonial, craftsman, and modern homes. With the Spa Creek waterfront on its southern side and the bustling shopping/dining district along West Street to its north, Murray Hill is perfectly situated to enjoy the Chesapeake lifestyle with an antiquey sort of charm. Homes prices here usually eclipse $1M—anything less would be considered an extreme bargain.
Kent Island Depending on your travels, Kent Island is either the first or last destination of Maryland’s Eastern Shore. Either way, it definitely has a unique character that romanticizes nautical, island living…Chesapeake style. Life centers around Stevensville and Kent Narrows with its many marinas, dockside restaurants, shopping plazas, and water accesses. But the entire island features various properties, including classic Shore homes (Bay City, Romancoke, Marling Farms), remote waterfronts (Love Point, Turkey Point), townhouses for boaters (Bayside), and newer developments such as Four Seasons—an amenity-rich community ideal for retirees. Finding your ideal property at a matching price point should be possible within a short amount of time.
Severn River Watershed Along the northern and southern shorelines of the renowned Severn River are unique waterfront communities, many of which date to the early-20th century. Many began as summer cottage enclaves and have grown into premier communities, each with its own waterfront amenities, associations, and character. Winchester on the Severn, Pines on the Severn, Round Bay, Linstead on the Severn, Ben Oaks, Arden on the Severn, Herald Harbor, Sherwood Forest, Epping Forest, and many more communities are highly sought after today, with price points to match. Waterfronts easily eclipse $1.5M with some hitting eight figures, and off-water/in-community parcels usually slot between $500K and $1M.
Davidsonville/Harwood The contiguous 21035 and 20776 zip codes are synonymous with rolling foothills, vast farmland, and plenty of acreage—the Davidsonville and Harwood dynamic is country-living. If space is what you seek or horse tacking your thing, look no further. Large lots with large homes are common, but there are a number of well-developed neighborhoods (Foxhall Estates, Cheval/Lavall, Harbor Hills, Spring Lakes, Ashley, Lake of the Pines to name a few), too, that offer a more uniform, community vibe. A scan of homes—mostly single-family in the plus-5,000-square-foot range—are selling for $1M and up. The road arteries running through the area include Routes 2, 4, and 214, which directly connect to the more urban centers of Edgewater and Annapolis to the east, and Upper Marlboro and Washington, D.C., to the west.
Prospect Bay You’d be hard-pressed to find a more complete and amenity-rich community on Maryland’s Eastern Shore than Prospect Bay in Grasonville. Boasting an 18-hole golf course, country club, dining, pool, tennis/pickleball courts, boat ramp/slips/docking, and, of course, direct water access to Prospect Bay sanctuary, which feeds into Eastern Bay and the greater Chesapeake, the Prospect Bay community epitomizes upscale Shore living. Built in the mid-80s through the early-2000s, most homes now command prices north of $800K.
Two Rivers in Odenton One of the newer community developments, located in southern Odenton, is Two Rivers. Its age shows in a very good way in that it represents the latest in design, amenities, and residential resort trends, catering to two distinct, but adjacent, buyers—families and plus-55. Nestled between the Patuxent and Little Patuxent rivers, this modern, 1500-acre community (700 of which is green space, with the central Cattail Lake) is divided into an active adult community, “55 & Better,” and the all-ages “The Hamlets” with about 1,000 single-family homes. Each has its own clubhouse, pools, gardens, tennis courts (pickleball, too), and other recreational amenities. With eight active builders still developing the community, buying new means you can have the pick of plans—there are several styles of homes from which to choose. As of press time, we’re seeing pricing begin at about $799K in 55 & Better, and $790–945K in The Hamlets.

Easton to Tilghman
Easton to Tilghman It’s perhaps one of the most iconic and authentic inhabited stretches of the Eastern Shore. From the heartbeat of the Shore, the Town of Easton, and moving westward along the rural peninsula sandwiched between the Choptank River on the south and the Miles River to the north, you’ll bob and weave through the enclaves of Royal Oak, St. Michaels, Bozman, McDaniel, Claiborne, Whitman, Sherwood, Deep Harbor, and eventually arrive at the point of Tilghman Island. It’s a smorgasbord of property types and price points with ranchers, waterfront estates, cute craftsmans, Colonials, farmettes, and even waterfront resort-style marinas mixed in. Charming St. Michaels, itself, has become a small-town culinary hotbed attracting retirees and second-home vacationers.
Parole, Annapolis One needn’t look any further than the Parole area of greater Annapolis for evidence of urban growth and a changing skyline. Built more than 15 years ago, the Annapolis Town Center took the concept of mixed-use development and went skyward with 10-plus stories of luxury apartments and condominiums, upscale dining and shopping, recreational spaces, on-site parking, security, and much more. Today, the area continues to evolve with the new Beacon Square development nearing completion just across the street (Riva Road) from the ATC. It, too, will feature state-of-the-art upscale residences, retail, restaurants, and anchor stores to round out the nouveau-urban residential experience…Annapolitan style, of course.