Chester Condos for Sale

Welcome to Chester, Maryland—a hidden gem nestled in the heart of Queen Anne's County. Known for its picturesque landscapes and charming small-town vibe, Chester offers a unique blend of serene waterfront living and vibrant community life. With its close proximity to the Chesapeake Bay, residents can enjoy a plethora of outdoor activities, from boating and fishing to hiking and biking along scenic trails. The town's rich history is reflected in its well-preserved architecture and friendly neighborhoods, making it a delightful place to call home.

For those seeking a low-maintenance lifestyle without sacrificing comfort, Chester boasts an array of stunning condos for sale. These modern residences offer spacious layouts, contemporary designs, and breathtaking views of the surrounding natural beauty. Whether you’re a first-time homebuyer, a retiree looking to downsize, or a busy professional seeking convenience, Chester’s condo options cater to a variety of lifestyles.

Imagine waking up to the gentle sounds of nature, sipping your morning coffee on a private balcony, or taking a leisurely stroll along the waterfront. With easy access to local amenities, including shops, restaurants, and recreational facilities, your days can be filled with both relaxation and adventure.

Chester is not just a place to live; it’s a community where neighbors become friends and memories are made. Explore the available condos for sale and discover the perfect sanctuary that combines modern living with the charm of this delightful town. Your dream home awaits in Chester, Maryland!

Newest Chester Condos for Sale

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

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

201 Switchgrass Way Unit #34, Chester image

201 Switchgrass Way Unit #34, Chester $835,000 ▼

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

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 $919,990 ▼

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 $819,990 ▼

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 #2911, Chester image

102 Boatswain Way Unit #2911, Chester $619,990 ▼

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 $819,990 ▼

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 $719,990 ▼

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 $524,999 ▼

NEW INCENTIVE — THE OWNERS WILL COVER YOUR $8,000 COMMUNITY BUY-IN WITH ACCEPTABLE OFFER! Move-in ready condo with zero wait! This meticulously maintained, first-floor Ma...

2 Beds
3 Baths

Courtesy of Real Broker, LLC - Chester

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

1000 Herons Nest Way Unit #43, Chester image

1000 Herons Nest Way Unit #43, Chester $595,000 ▼

Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun ...

2 Beds
3 Baths

Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

2000 Herons Nest Way Unit #401, Chester image

2000 Herons Nest Way Unit #401, Chester $700,000 ▼

Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resor...

3 Beds
3 Baths

Courtesy of Real Broker, LLC

Listing courtesy of Real Broker, LLC. Contact: 8504500442

132 Wheelhouse Way Unit #11, Chester image

132 Wheelhouse Way Unit #11, Chester $699,000 ▼

Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its repl...