Homes for Sale in Queen Anne's, Maryland

Explore homes for sale in Queen Anne’s County, Maryland, and discover a part of the Eastern Shore known for its waterfront lifestyle, scenic beauty, and convenient access to both Shore living and the western side of the Bay. From Kent Island, Stevensville, and Chester to Centreville, Queenstown, and Grasonville, Queen Anne’s County appeals to buyers looking for a blend of small-town character, boating access, open space, and everyday convenience.

Why Buy in Queen Anne's County?

Queen Anne’s County offers buyers a blend of Eastern Shore beauty, waterfront living, and everyday convenience. With communities like Kent Island, Stevensville, Chester, Grasonville, Queenstown, and Centreville, it appeals to those who want scenic surroundings, access to the water, and an easy connection across the Bay Bridge.

Area Highlights

  • Waterfront communities and Chesapeake Bay access
  • Kent Island, Stevensville, Chester, Grasonville, and Centreville
  • Boating, fishing, marinas, and waterfront dining
  • Cross Island Trail and outdoor recreation
  • Easy access to both the Eastern Shore and the western shore
  • Historic charm with a relaxed coastal feel

Queen Anne's County, Maryland

May 2026 Market Snapshot

Median Sold Price

+4% vs. 2025

Homes Sold

+23% vs. 2025

Average Days on Market

+6% vs. 2025

Active Listings

+14% vs. 2025

Current Properties by Courtney in Queen Anne's County

2800 Bennett Point Rd. Queenstown, MD

2800 Bennett Point Rd. Queenstown, MD

5 BD | 4.5 BA | 6,156 SQFT | 17.97 ACRES

$5,400,000

232 Evelyne St. Chester, MD

232 Evelyne St. Chester, MD

4 BD | 4 BA | 3,312 SQFT

$865,000

There are currently no properties for sale by Courtney Chipouras in Queen Anne's County.

Recent Homes Sold by Courtney in Queen Anne's County

Aerial view of waterfront farm estate 5135 Crosby Road Rock Hall home and farm

5135 Crosby Road Rock Hall, Maryland

6 BD | 4 1/2 BA | 4,214 SQFT | 212.88 ACRES

2800 Bennett Point Rd. Queenstown, MD

5 BD | 4.5 BA | 6,156 SQFT | 17.97 ACRES

The front of 232 Evelyn St. In Chester, MD Listed by Courtney Chipouras

232 Evelyne St. Chester, MD

4 BD | 4 BA | 3,312 SQFT

4511 Piney Neck Road, Rock Hall, Maryland

5 BD | 4 BA | 4,050 SQFT | 31.99 ACRES

1026 Long Point Road, Grasonville Maryland

6 BD | 5.5 BA | 4,016 SQFT | 0.35 ACRES

136 Governors Way S. Queenstown, Maryland

3 BD | 2.5 BA | 2,445 SQFT | 1.6 ACRES

Front of 25871 Gosling Lane in Royal Oak, MD

25871 Gosling Lane Royal Oak, MD

4 BD | 3 BA | 3,024 SQFT | 5.24 ACRES

38 Greenwood Shoals, Grasonville, Maryland

3 BD | 3 BA | 2,879 SQFT | 1.05 ACRES

4938 Huntingfield Road, Rock Hall, Maryland

5 BD | 3.5 BA | 2,174 SQFT | 0.83 ACRES

336 Nottinghman Lane, Queenstown, Maryland

3 BD | 3 BA | 3,651 SQFT | 1.25 ACRES

Courtney Chipouras, Eastern Shore Realtor

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.

 

Courtney Chipouras at her annual Pie Party event