Homes for Sale in Kent County, Maryland
Explore homes for sale in Kent County, Maryland, and discover one of the Eastern Shore’s most distinctive places to call home. From historic Chestertown to waterfront communities like Rock Hall and Betterton, Kent County offers a blend of small-town charm, scenic beauty, and a slower pace that continues to attract buyers looking for character, community, and access to the water.
Why Buy in Kent County?
Kent County offers buyers a quieter kind of Eastern Shore living, where historic towns, waterfront access, and scenic backroads create a lifestyle that feels both grounded and beautiful. From the charm of Chestertown to the boating culture of Rock Hall and the peaceful Bay views in Betterton, the county appeals to buyers who want character, community, and a little more breathing room in everyday life.
Area Highlights
- Historic towns with distinct personality, including Chestertown, Rock Hall, Betterton, Galena, and Millington
- Boating, fishing, kayaking, and outdoor recreation woven into the local lifestyle
- Waterfront access and Chesapeake Bay influence that shapes daily life across the county
- A strong sense of history and place, especially in and around Chestertown
- Peaceful open space, farmland, and scenic drives that give the area its relaxed character
Kent County, Maryland
July 2026 Market Snapshot
Median Sold Price
-8% vs. 2025
Homes Sold
-20% vs. 2025
Average Days on Market
+54% vs. 2025
Active Listings
+90% vs. 2025
Current Properties by Courtney in Kent County
Recent Homes Sold by Courtney in Kent County
20658 Wilkins Avenue, Rock Hall, MD 21661
BLUE HERON OYSTER HOUSE & INN
5742 & 5746 N. Main Street, Rock Hall, MD 21661
MIXED USE | ZONING C-3 | 2,880 SQFT
5135 Crosby Road, Rock Hall, MD 21661
6 BD | 4 1/2 BA | 4,214 SQFT | 212.88 ACRES
5786 S Hawthorne Avenue, Rock Hall, MD 21661
3 BD | 2 BA | 1,803 SQF | .92 ACRES
4511 Piney Neck Road, Rock Hall, Maryland
5 BD | 4 BA | 4,050 SQFT | 31.99 ACRES
21053 W Sharp St, Rock Hall, MD 21661
MDW | 9,437 SQFT
1026 Long Point Road, Grasonville, MD 21638
6 BD | 5.5 BA | 4,016 SQFT | 0.35 ACRES
21321 Rock Hall Avenue, Rock Hall, MD 21661
C-3 | 6,100 SQFT | .48 ACRES
136 Governors Way S. Queenstown, MD 21658
3 BD | 2.5 BA | 2,445 SQFT | 1.6 ACRES
25871 Gosling Lane Royal Oak, MD
4 BD | 3 BA | 3,024 SQFT | 5.24 ACRES
About Courtney Chipouras, Realtor
As a local real estate agent with deep roots in the Chesapeake Bay area, Courtney Chipouras brings professionalism, integrity, and insider knowledge to every transaction. Whether buying, selling, or investing in Queenstown real estate, she's your go-to guide.
