Newest Property Listings In Chester

Professional Photos Coming Soon! Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This though...

3 Beds
3 Baths
MDQA2018418 MLS

6005 Bridgepointe Dr, Chester $349,000

Low maintenance island living at its best! 6005 Bridgepointe Dr is freshly painted, deep cleaned, and ready for its new owners! All appliances new within the last two yea...

3 Beds
3 Baths
MDQA2018634 MLS

326 Castle Marina Rd, Chester $550,000

Discover the charm of this beautiful home in the desirable Castle Marina community. With five spacious bedrooms (including one on the main level) and 3.5 bathrooms, this ...

5 Beds
4 Baths
MDQA2018594 MLS

641 Warbler Way, Chester $649,990 ▼

Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful desig...

2 Beds
2 Baths
MDQA2018602 MLS

200 Church St, Chester $350,000

None

2 Beds
2 Baths
MDQA2018584 MLS

275 Warbler Way, Chester $944,900

Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and a...

3 Beds
3 Baths
MDQA2018566 MLS

1868 Roberta Dr, Chester $400,000

List price is Opening Bid at the Online auction to be conducted on Auctioneers website. - Auction ends Tuesday, September 29, 2026 at 11:00 AM. Discover the space and ver...

5 Beds
4 Baths
MDQA2018570 MLS

1717 Harbor Dr, Chester $1,250,000

Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with ...

3 Beds
3 Baths
MDQA2018534 MLS

736 Warbler Way Unit #2733, Chester image

736 Warbler Way Unit #2733, Chester $719,990

Welcome to Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in May 2027, this home combines comfort, fun...

2 Beds
3 Baths
MDQA2018548 MLS

41 Queen Catherine Ct, Chester $439,000

Set along scenic Lake Amletto in the waterfront resort-style community of Queen’s Landing, this three-level garage townhome pairs updated interiors with relaxing water vi...

3 Beds
4 Baths
MDQA2018508 MLS

233 Cross Creek Ct, Chester $569,900

Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of...

4 Beds
3 Baths
MDQA2018296 MLS

2513 Cecil Dr, Chester $1,290,000 ▼

Waterfront homes are common on Kent Island. Waterfront acreage is not. The difference is the land -- and at 1.65 acres with 205 feet of protected shoreline, this property...

5 Beds
2 Baths
MDQA2018504 MLS

43 Queen Neva Ct, Chester $459,000

Welcome to 43-A Queen Neva Court, a pristine 3-bedroom, 2.5-bath contemporary condo in the sought-after Queens Landing community. Offering more than 2,000 square feet of ...

3 Beds
3 Baths
MDQA2018494 MLS

148 Elinor St, Chester $899,000

Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedr...

3 Beds
3 Baths
MDQA2018244 MLS

207 Thomas White Blvd, Chester $819,900

Located in the sought-after waterfront community of Gibson’s Grant, this beautiful Koch Homes property features the popular Ashford model, with a first-floor Primary Bedr...

3 Beds
3 Baths
MDQA2018222 MLS

Homes In Chester Maryland

Homes in the Chester Area are great for anyone who loves the water. Some of the many activities include, fishing, boating, kayaking, Dock Bar Restaurants and night life. The Kent Island Narrows offers great casual and Fine dinning all along the beautiful shore lines. Places include, The Narrows, Big Owls, The Jetty, Red Eyes, Bridges and Annie's.