Chester Real Estate Search
Address Search
Chester Homes For Sale
Chester, Maryland is the second town you will come to after crossing the Chesapeake Bay Bridge into Queen Anne’s County. This town is also a part of Kent Island and is a seven square mile area. The town of Chester has a wide variety of housing choices to meet any real estate need you may have. There are lovely waterfront condos, townhomes, single family homes and luxury waterfront estates. This area also has all of the conveniences to meet all of your shopping, dining, retail and entertainment needs. There are several public boat launches and marinas for the boating and water sport enthusiast.
Latest Listings In Chester
Nestled within the water-privileged enclave of Queen's Landing, along the scenic Chester River off the Chesapeake Bay, this resort-style community unveils a beautiful res...
- 2 Beds
- 3 Baths
- MDQA2008254 MLS
Professional Photos will be uploaded on the 23rd. Completely updated Cape Cod near the water! Wood flooring throughout the home. White kitchen cabinets with granite cou...
- 3 Beds
- 2 Baths
- MDQA2008258 MLS
Why wait for new construction? Luxurious and Spacious 1st floor condo in highly sought-after Four Seasons at Kent Island-a vibrant, amenity filled 55+ community on the C...
- 2 Beds
- 3 Baths
- MDQA2008234 MLS
This is your chance to own a beautiful waterfront home on Kent Island on the scenic Eastern Shore of Maryland. A short drive to the Bay Bridge, Historic Annapolis and the...
- 2 Beds
- 2 Baths
- MDQA2008168 MLS
Ranch style home with cozy front porch located in the waterfront community of Harbor View. Tree lined lot offers backyard privacy. Laminate wood floors throughout. Open f...
- 3 Beds
- 2 Baths
- MDQA2007870 MLS
WELCOME HOME TO OUR 55+ Four Seasons Community At Kent Island! This Exquisite and Spacious Condominium combines Luxury, Comfort, and Convenience with an Elevator, Atta...
- 2 Beds
- 3 Baths
- MDQA2008204 MLS
- Chester Bldg.
Welcome Home to 1409 Queen Anne Drive offering some of the best Eastern Shore Sunsets off of Crab Alley Bay. This Beautifully updated single family home located in the s...
- 4 Beds
- 3 Baths
- MDQA2008176 MLS
Embrace serenity on Kent Island with this inviting 3-bedroom, 1-bathroom rancher, offering potential for further enhancements. Newly refreshed with fresh paint, plush car...
- 3 Beds
- 1 Baths
- MDQA2008114 MLS
This is an amazing opportunity for anyone looking for a peaceful escape to idyllic island living this summer. This stunning and meticulously maintained condo is located i...
- 3 Beds
- 3 Baths
- MDQA2008104 MLS
The Windermere combines all of the home design elements our purchasers love the most. On the main level is an open plan design with a huge kitchen, breakfast/sunroom and ...
- 4 Beds
- 3 Baths
- MDQA2008126 MLS
This gorgeous Santorini with Loft is Move In Ready and located in the amenity rich 55+ community of Four Seasons. Built in 2019, this home provides a spacious floor plan ...
- 3 Beds
- 4 Baths
- MDQA2008096 MLS
Located in the water privileged community of Queens Landing, this end unit is a rare find and provides a main level owners bedroom with full upgraded bath complete with w...
- 3 Beds
- 3 Baths
- MDQA2008080 MLS
Be the first to see this beautiful 2 story house that has been tastefully renovated & upgraded. You will love open concept of living and dining area with a charming elect...
- 4 Beds
- 3 Baths
- MDQA2007996 MLS
Elegance abounds in this fabulous 3 bedroom, 3 full bath home. Coastal inspired vibes resonate throughout the home with many upgrades that include but are not limited t...
- 3 Beds
- 3 Baths
- MDQA2007974 MLS
The Simone model is a show stopper! This home includes a screened patio, fireplace, upgraded primary bath shower and more. For a full list of features please see a sale...
- 4 Beds
- 3 Baths
- MDQA2007902 MLS
The Kerr model is a show stopper! This home includes a covered patio, fireplace, upgraded primary bath shower and more. For a full list of features please see a sales r...
- 3 Beds
- 3 Baths
- MDQA2007896 MLS
The Taylor model is a show stopper! This home includes a covered patio, fireplace, upgraded primary bath shower and more. For a full list of features please see a sales...
- 2 Beds
- 3 Baths
- MDQA2007892 MLS
Coastal Colonial with pond views. Many recent updates and upgrades. Open kitchen design with large island and gourmet stainless appliances. Adjacent to the kitchen is the...
- 4 Beds
- 3 Baths
- MDQA2007730 MLS
This beautiful townhouse in Bayside is ready for its new owners! Featuring 3 spacious bedrooms, 2 full bathrooms and 2 half baths (on first and second level), attached g...
- 3 Beds
- 4 Baths
- MDQA2007696 MLS
Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does ...
- MDQA2007678 MLS
Welcome to Eastern Shore living at Bayside! This meticulously cared for three level water-view townhome overlooks Northeast Bay and the Chester River. Amazing open-conc...
- 3 Beds
- 4 Baths
- MDQA2007596 MLS
Welcome to Queens Landing in charming Chester, MD! This wonderful 3-level townhome boasts elegant Spanish-style architecture and is one of the most spacious models within...
- 3 Beds
- 3 Baths
- MDQA2007280 MLS
The Kelly model is first floor living at its finest. This home features a screened patio, fireplace, upgraded shower and detailed trim in the foyer and primary bedroom. ....
- 2 Beds
- 2 Baths
- MDQA2007418 MLS
TO BE BUILT. This two-story, two-car garage center hall design is a great multi-generational home option for families looking to accommodate lots of varying needs under ...
- 4 Beds
- 3 Baths
- MDQA2006890 MLS
One of our most popular designs, the Doral offers formal ( office space) and informal living areas with lots of room for the whole family to spread out. Your main level f...
- 4 Beds
- 3 Baths
- MDQA2006888 MLS
To be built. The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great ro...
- 4 Beds
- 4 Baths
- MDQA2006790 MLS
One of our most popular designs, the Doral offers formal ( office space) and informal living areas with lots of room for the whole family to spread out. Your main level f...
- 4 Beds
- 3 Baths
- MDQA2006788 MLS
You little slice of Cox Creek heaven! This 3/4+ acre lot will support a narrow design up to 28' in width. The Seller reports a 6' water depth at 170' from the shoreline. ...
- MDQA2006810 MLS
This beautiful 3/4+ acre waterfront lot is READY to ROLL for you to secure a grading permit and building permit. The sewer tap fee is PAID. The Sellers are working to rem...
- MDQA2006808 MLS
REDUCED $100k!! A deep-water Cox Creek fixer with great "bones" isn't a home that comes up very often, but here it is! Do a little, or do a lot, as this is a true 1968 t...
- 4 Beds
- 3 Baths
- MDQA2006806 MLS