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Chester Condos for Sale

Chester Condos for Sale

Welcome to Chester, Maryland, a charming town nestled in the heart of Queen Anne's County. Known for its picturesque landscapes and tight-knit community, Chester offers a perfect blend of small-town charm and modern conveniences. With its stunning waterfront views along the Chester River and close proximity to the Chesapeake Bay, residents enjoy a lifestyle rich in outdoor activities, including boating, fishing, and hiking.

Chester is not just about natural beauty; it boasts a vibrant local culture, complete with inviting shops, delightful eateries, and friendly neighbors. The town is also conveniently located near major highways, making it easy to access nearby attractions and amenities in larger cities like Annapolis and Easton. Families will appreciate the excellent schools and community services that contribute to the area's reputation as a wonderful place to raise children.

If you're considering a move to this idyllic town, you'll be pleased to know that there are beautiful condos for sale in Chester. These modern residences offer a variety of styles and layouts, catering to diverse lifestyles and preferences. Enjoy the convenience of maintenance-free living, with amenities that often include pools, fitness centers, and scenic walking paths. Whether you're a first-time homebuyer, looking to downsize, or seeking a serene getaway, Chester's condos provide the perfect opportunity to embrace a relaxed yet vibrant lifestyle.

Explore the possibilities that await you in Chester, MD, and discover why this charming town is the perfect place to call home!

Newest Chester Condos for Sale

201 Switchgrass Way Unit #34, Chester image
201 Switchgrass Way Unit #34, Chester $859,500

Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking...

  • 3 Beds
  • 3 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

509 Teal Ct Unit #E, Chester image
509 Teal Ct Unit #E, Chester — Bayside $300,000

Welcome to your perfect island retreat in the sought-after waterfront community of Bayside! This beautifully positioned end-unit condominium offers the ideal blend of com...

  • 2 Beds
  • 2 Baths
Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact: 4432741900

102 Boatswain Way Unit #2912, Chester image
102 Boatswain Way Unit #2912, Chester $609,990

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
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

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
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

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
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

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
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

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
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

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
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

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
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

102 Boatswain Way Unit #2933, Chester image
102 Boatswain Way Unit #2933, 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
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

110 Boatswain Way Unit #3042, Chester image
110 Boatswain Way Unit #3042, Chester $749,990

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

  • 2 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

230 Switchgrass Way Unit #12, Chester image
230 Switchgrass Way Unit #12, Chester $525,000 ▼

Welcome to resort-style living at K. Hovnanian's Four Seasons at Kent Island — one of the Eastern Shore's premier 55+ waterfront communities on the Chesapeake Bay. This ...

  • 2 Beds
  • 3 Baths
Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

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