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Newest Property Listings In Chester

302 Merganser Ct Unit #A, Chester image
302 Merganser Ct Unit #A, Chester — Bayside Condominium $309,900

Welcome to coastal living in this beautifully updated first-floor, end-unit condo, offering the perfect blend of comfort, convenience, and resort-style amenities in one o...

  • 2 Beds
  • 2 Baths
  • MDQA2018076 MLS
  • Bayside Condominium Bldg.
26 Queen Anne Way, Chester image
26 Queen Anne Way, Chester $225,000

Bring your vision to one of the most affordable condos currently available in Queen’s Landing. This one-bedroom, one-bath unit offers approximately 640 square feet and is...

  • 1 Beds
  • 1 Baths
  • MDQA2018040 MLS
111 Marshgrass Way Unit #41, Chester image
111 Marshgrass Way Unit #41, Chester $998,000

Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabul...

  • 3 Beds
  • 3 Baths
  • MDQA2017940 MLS
203 Riverside Dr, Chester image
203 Riverside Dr, Chester $989,800

Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water...

  • 5 Beds
  • 4 Baths
  • MDQA2018004 MLS
102 Boatswain Way Unit #2943, Chester image
102 Boatswain Way Unit #2943, Chester $929,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines mod...

  • 2 Beds
  • 3 Baths
  • MDQA2018010 MLS
102 Boatswain Way Unit #2932, Chester image
102 Boatswain Way Unit #2932, Chester $829,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines mod...

  • 2 Beds
  • 3 Baths
  • MDQA2018008 MLS
134 Richard Ingle Way, Chester image
134 Richard Ingle Way, Chester $749,000

Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Bu...

  • 4 Beds
  • 4 Baths
  • MDQA2017930 MLS
2810 Harvest Ct, Chester image
2810 Harvest Ct, Chester $895,000

Welcome to Southwind, one of Kent Island's most desirable waterfront communities, where peaceful surroundings and an exceptional lifestyle come together. Perfectly positi...

  • 3 Beds
  • 3 Baths
  • MDQA2017934 MLS
1609 Crab Alley Dr, Chester image
1609 Crab Alley Dr, Chester $345,000

Welcome to 1609 Crab Alley Drive, a charming three-bedroom, one-and-a-half-bath rancher offering comfortable one-level living and lovely water views. Inside, hardwood flo...

  • 3 Beds
  • 2 Baths
  • MDQA2017988 MLS
2004 Bridgepointe Dr, Chester image
2004 Bridgepointe Dr, Chester — Bridge Pointe $382,750

OPEN HOUSE this Saturday 7/25 - 9am to 11am! ALL NEW Carpet & flooring, fresh custom paint, granite countertops and newer appliances! Welcome to one of the most desirabl...

  • 3 Beds
  • 2 Baths
  • MDQA2017932 MLS
  • Bridge Pointe Bldg.
2702 Sherman Dr, Chester image
2702 Sherman Dr, Chester $989,000

Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has u...

  • 5 Beds
  • 4 Baths
  • MDQA2017858 MLS
110 Boatswain Way Unit #3044, Chester image
110 Boatswain Way Unit #3044, Chester $999,990

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern c...

  • 3 Beds
  • 3 Baths
  • MDQA2017984 MLS
102 Boatswain Way Unit #2911, Chester image
102 Boatswain Way Unit #2911, Chester $629,990

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. T...

  • 2 Beds
  • 3 Baths
  • MDQA2017980 MLS
323 Kingfisher Ln, Chester image
323 Kingfisher Ln, Chester $974,990

Welcome to the Tuscaloosa, a beautifully designed home that blends an open-concept floorplan with warm Farmhouse-inspired style, creating the perfect balance of comfort a...

  • 5 Beds
  • 5 Baths
  • MDQA2017978 MLS
723 Warbler Way, Chester image
723 Warbler Way, Chester $789,990 ▼

Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces i...

  • 4 Beds
  • 3 Baths
  • MDQA2017962 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.  

Along with great food there is plenty of Shopping on Kent Island as well as the Premiere Queenstown outlets loaded with great stores.

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Centerville Communities

  • Bridgetown Estates
  • Claiborne Fields
  • North Brook
  • Providence Farms
  • Symphony Village
  • Three Creeks
  • Willow Branch

Stevensville / Kent Island Communities

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Easton Communities

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Chestertown Communities

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Grasonville Communities

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Queenstown Communities

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Chester Communities

  • Gibson’s Grant

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