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

July 2026 Market Snapshot

Median Sold Price

+26% vs. 2025

Homes Sold

+4% vs. 2025

Average Days on Market

+77% vs. 2025

Active Listings

+5% vs. 2025

Current Properties by Courtney in Queen Anne's County

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

Front view of 246 Upland Lane in Centreville, Maryland, buyer represented sale for Courtney Chipouras

246 Upland Lane Centreville, MD 21617

4 BD | 3 BA | 2,909 SQFT | 1.25 ACRES

Front of 2812 Harvest Ct, buyer represented sale by Courtney Chipouras

2812 Harvest Ct. Chester, MD

4 BD | 3BA | 3,017 SQFT | 1.21 ACRES

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

5135 Crosby Road, Rock Hall, MD 21661

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

2800 Bennett Point Rd. Queenstown, MD 21658

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

Aerial view of Waterman's Crab House in Rock Hall, Maryland

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

Aerial view of 21321 Rock Hall Ave in Rock Hall, Maryland

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

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