38

Chester, MD Condos for Sale

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  • 4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    /70

    $515,000

    $45K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 towards Capital Contribution Fee * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    /12

    $544,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    Magothy Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owner’s suite with spa bath . Fantastic great room with large windows for your viewing pleasure. Large secondary bedroom with opt. door to access patio. Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 830 Warbler Way Unit 24, Chester, MD 21619
    830 Warbler Way Unit 24, Chester, MD 21619
    830 Warbler Way Unit 24, Chester, MD 21619
    /19

    $749,990

    New Construction $27K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    830 Warbler Way Unit 24, Chester, MD 21619

    Charming gourmet kitchen with designer cabinetry & sprawling island.Elegant dining area with dry bar perfect for hosting.Beautiful great room with electric fireplace for cozy evenings.Private owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish frameless shower.Serene balcony for relaxing outdoors.

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 24, Chester, MD 21619
  • 131 Flycatcher Way Unit 36493320, Chester, MD 21619
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
    /33

    $544,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    Chester Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owner’s suite with spa bath and access to balcony. Large secondary bedroom with access to balcony. Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
  • 110 Boatswain Way Unit 42, Chester, MD 21619
    110 Boatswain Way Unit 42, Chester, MD 21619
    110 Boatswain Way Unit 42, Chester, MD 21619
    /32

    $749,990

    New Construction $110K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 42, Chester, MD 21619

    Gourmet kitchen with designer cabinetry & vast center island.Inviting great room featuring a cozy electric fireplace.Dry bar creates a polished space for serving & entertaining.Peaceful owner's suite with stylish tray ceiling & private bath.Home office with double doors offers a quiet, flexible workspace.Balcony extends the living space outdoors for relaxing or unwinding.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 42, Chester, MD 21619
  • 830 Warbler Way Unit 21, Chester, MD 21619
    830 Warbler Way Unit 21, Chester, MD 21619
    830 Warbler Way Unit 21, Chester, MD 21619
    /18

    $749,990

    New Construction $27K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    830 Warbler Way Unit 21, Chester, MD 21619

    Spacious great room with electric fireplace & seamless flow to the dining area.Private balcony off the main living area, ideal for outdoor relaxation.Gourmet kitchen with large island, ample cabinetry & pantry for extra storage.Included dry bar adds convenience for hosting & everyday use.Owner’s suite with direct access to a cozy sitting room.Luxurious owner’s spa bath with

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 21, Chester, MD 21619
  • 509 Teal Ct, Chester, MD 21619
    509 Teal Ct, Chester, MD 21619
    509 Teal Ct, Chester, MD 21619
    /25

    $300,000

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    509 Teal Ct, Chester, MD 21619

    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 comfort, convenience, and breathtaking scenery. Enjoy tranquil pond views with a charming fountain, along with glimpses of the Chester River and marina—all from the privacy of your own deck. Whether you're sipping your morning

    Darlene Winegardner RE/MAX Executive

    509 Teal Ct, Chester, MD 21619
  • 114 Merganser Ct, Chester, MD 21619
    114 Merganser Ct, Chester, MD 21619
    114 Merganser Ct, Chester, MD 21619
    /27

    $287,500

    $12K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    114 Merganser Ct, Chester, MD 21619

    Experience the ease of resort-style, maintenance-free living in this beautifully updated upper-level condominium featuring open views, abundant natural light, and the privacy of having no neighbors above. Hardwood floors, soaring vaulted ceilings, and a cozy gas fireplace create a warm and inviting atmosphere throughout the main living area.The spacious primary suite offers a peaceful retreat

    Beverly Sloane Benson & Mangold, LLC

    114 Merganser Ct, Chester, MD 21619
  • 830 Warbler Way Unit 31, Chester, MD 21619
    830 Warbler Way Unit 31, Chester, MD 21619
    830 Warbler Way Unit 31, Chester, MD 21619
    /17

    $849,990

    New Construction $27K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    830 Warbler Way Unit 31, Chester, MD 21619

    Beautiful great room with electric fireplace & acccess to balcony.Serene balcony off the main living area, ideal for outdoor relaxation.Gourmet kitchen with large island, ample cabinetry & pantry.Included dry bar adds convenience for hosting & everyday use.Owner’s suite with direct access to a cozy sitting room.Polished owner’s spa bath with dual sinks & frameless shower door.

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 31, Chester, MD 21619
  • 34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    /52

    $515,000

    $34K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,586 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    WATERFRONT Condo! Open House dates scheduled. Beautifully renovated 2BR/2.5BA waterfront condominium located in the sought-after Queen’s Landing resort-style community on the scenic Chester River, just off the Chesapeake Bay. This move-in-ready home showcases a stunning top-to-bottom remodel, including new luxury vinyl plank flooring, new carpet, fresh paint throughout (ceilings, walls, trim, and

    Lona Todd Taylor Properties

    34 Queen Anne Way, Chester, MD 21619
  • 1000 Herons Nest Way Unit 23, Chester, MD 21619
    1000 Herons Nest Way Unit 23, Chester, MD 21619
    1000 Herons Nest Way Unit 23, Chester, MD 21619
    /39

    $490,000

    • 2 Beds
    • 2.5 Baths

    1000 Herons Nest Way Unit 23, Chester, MD 21619

    Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright,

    Tara Trout Samson Properties

    1000 Herons Nest Way Unit 23, Chester, MD 21619
  • 102 Boatswain Way Unit 2943, Chester, MD 21619
    102 Boatswain Way Unit 2943, Chester, MD 21619
    102 Boatswain Way Unit 2943, Chester, MD 21619
    /47

    $929,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 2943, Chester, MD 21619

    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 modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2943, Chester, MD 21619
  • 110 Boatswain Way Unit 3042, Chester, MD 21619
    110 Boatswain Way Unit 3042, Chester, MD 21619
    110 Boatswain Way Unit 3042, Chester, MD 21619
    /47

    $749,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 3042, Chester, MD 21619

    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 modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    110 Boatswain Way Unit 3042, Chester, MD 21619
  • 230 Switchgrass Way Unit 12, Chester, MD 21619
    230 Switchgrass Way Unit 12, Chester, MD 21619
    230 Switchgrass Way Unit 12, Chester, MD 21619
    /23

    $525,000

    $25K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    230 Switchgrass Way Unit 12, Chester, MD 21619

    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 Magothy model condo offers approximately 2003 sq. ft. of thoughtfully designed single-level living, featuring 2 bedrooms — each with its own attached bathroom — plus a powder room for guests, a private home office with French

    David Moore Real Broker, LLC

    230 Switchgrass Way Unit 12, Chester, MD 21619
  • 211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    /19

    $739,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    211 Switchgrass Way Unit 31, Chester, MD 21619

    Striking gourmet kitchen with designer cabinets & chef-worthy island.Elegant dining area featuring fancy dry bar.Refined great room featuring stunning fireplace.Serene owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish shower.Wonderful balcony for relaxing outdoors.

    K. Hovnanian Homes Builder
    211 Switchgrass Way Unit 31, Chester, MD 21619
  • 102 Boatswain Way Unit 2911, Chester, MD 21619
    102 Boatswain Way Unit 2911, Chester, MD 21619
    102 Boatswain Way Unit 2911, Chester, MD 21619
    /56

    $629,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 2911, Chester, MD 21619

    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. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2911, Chester, MD 21619
  • 111 Marshgrass Way Unit 41, Chester, MD 21619
    111 Marshgrass Way Unit 41, Chester, MD 21619
    111 Marshgrass Way Unit 41, Chester, MD 21619
    /56

    $998,000

    • 3 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 41, Chester, MD 21619

    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 fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional

    Meg Moran Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 41, Chester, MD 21619
  • 830 Warbler Way Unit 42, Chester, MD 21619
    830 Warbler Way Unit 42, Chester, MD 21619
    830 Warbler Way Unit 42, Chester, MD 21619
    /30

    $789,990

    New Construction $28K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    830 Warbler Way Unit 42, Chester, MD 21619

    Charming gourmet kitchen featuring designer cabinetry & wall oven.Open concept living spaces with electric fireplace & dry bar.Private owner's suite for rest & relaxation.Refreshing primary bath featuring split vanities & frameless shower door.Functional home office with French double doors for added privacy.Lovely balcony for spending time with friends.

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 42, Chester, MD 21619
  • 102 Boatswain Way Unit 11, Chester, MD 21619
    102 Boatswain Way Unit 11, Chester, MD 21619
    102 Boatswain Way Unit 11, Chester, MD 21619
    /14

    $629,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 11, Chester, MD 21619

    Open home office just off the main living space.Gourmet kitchen with central island for everyday cooking & gathering.Dining area with dry bar for easy entertaining.Electric fireplace adds warmth to the great room.Patio connects seamlessly to the great room & owner’s suite.Owner’s suite with dual closets for added storage.Owner’s bath with dual sinks & glass shower

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 11, Chester, MD 21619
  • 1000 Herons Nest Way Unit 43, Chester, MD 21619
    1000 Herons Nest Way Unit 43, Chester, MD 21619
    1000 Herons Nest Way Unit 43, Chester, MD 21619
    /50

    $595,000

    Open Fri 2PM - 4PM $5K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    1000 Herons Nest Way Unit 43, Chester, MD 21619

    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 from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment.Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center

    Dee Dee McCracken Coldwell Banker Realty

    1000 Herons Nest Way Unit 43, Chester, MD 21619
  • 830 Warbler Way Unit 43, Chester, MD 21619
    830 Warbler Way Unit 43, Chester, MD 21619
    830 Warbler Way Unit 43, Chester, MD 21619
    /22

    $789,990

    New Construction $30K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    830 Warbler Way Unit 43, Chester, MD 21619

    Private home office with French doors, perfect for leisure activities.Gorgeous gourment kitchen with designer cabinets & vast island.Elegant dining area featuring lovely dry bar.Beautiful great room with sleek electric fireplace.Serene owner's suite featuring access to balcony & large walk-in closet.Lavish owner's spa bath featuring dual sinks.Fabulous balcony for

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 43, Chester, MD 21619
  • 102 Boatswain Way Unit 12, Chester, MD 21619
    102 Boatswain Way Unit 12, Chester, MD 21619
    102 Boatswain Way Unit 12, Chester, MD 21619
    /13

    $599,990

    New Construction $64K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 12, Chester, MD 21619

    Open home office for flexible work or study.Gourmet kitchen with central island at the heart of the home.Dining area with dry bar for easy entertaining.Great room with electric fireplace for a cozy focal point.Patio off the great room with direct access to the owner's suite.Owner's suite with dual closets for added storage.Owner's bath with dual sinks & glass shower

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 12, Chester, MD 21619
  • 102 Boatswain Way Unit 2933, Chester, MD 21619
    102 Boatswain Way Unit 2933, Chester, MD 21619
    102 Boatswain Way Unit 2933, Chester, MD 21619
    /47

    $829,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 2933, Chester, MD 21619

    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 modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2933, Chester, MD 21619
  • 201 Switchgrass Way Unit 34, Chester, MD 21619
    201 Switchgrass Way Unit 34, Chester, MD 21619
    201 Switchgrass Way Unit 34, Chester, MD 21619
    /35

    $859,500

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    201 Switchgrass Way Unit 34, Chester, MD 21619

    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, unobstructed water views and exceptional community amenities, this beautifully appointed three-bedroom, two-and-a-half-bath condominium is designed for those who appreciate comfort, elegance, and low-maintenance living. The

    Brad Kappel TTR Sotheby's International Realty

    201 Switchgrass Way Unit 34, Chester, MD 21619
  • 102 Boatswain Way Unit 34, Chester, MD 21619
    102 Boatswain Way Unit 34, Chester, MD 21619
    102 Boatswain Way Unit 34, Chester, MD 21619
    /21

    $969,990

    New Construction $34K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 34, Chester, MD 21619

    Stylish gourmet kitchen centered around a large island. Dining space with convenient dry bar for hosting. Open great room featuring an electric fireplace. Balcony extending from the main living area. Owner’s suite with two spacious walk-in closets. Private sitting area in owner’s suite with balcony connection. Owner’s bath with dual sinks & glass shower enclosure.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 34, Chester, MD 21619
  • 102 Boatswain Way Unit 32, Chester, MD 21619
    102 Boatswain Way Unit 32, Chester, MD 21619
    102 Boatswain Way Unit 32, Chester, MD 21619
    /33

    $829,990

    New Construction $35K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 32, Chester, MD 21619

    Elegant gourmet kitchen with designer cabinetry & center island. Spacious great room featuring electric fireplace. Charming dining area with dry bar for efficient serving. Serene owner's suite & spa bath with frameless shower door. Convenient home office for working remotely. Peaceful balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 32, Chester, MD 21619
  • 830 Warbler Way Unit 34, Chester, MD 21619
    830 Warbler Way Unit 34, Chester, MD 21619
    830 Warbler Way Unit 34, Chester, MD 21619
    /18

    $849,990

    New Construction $29K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    830 Warbler Way Unit 34, Chester, MD 21619

    Gourmet kitchen with large island & built-in wall oven.Bright dining area includes a convenient dry bar.Great room features an electric fireplace.Balcony offers a perfect space for outdoor entertaining.Owner's suite includes a sitting room & balcony access.Two walk-in closets provide ample storage in the suite.Spa bath features dual vanities for added convenience.

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 34, Chester, MD 21619
  • 302 Merganser Ct Unit A, Chester, MD 21619
    302 Merganser Ct Unit A, Chester, MD 21619
    302 Merganser Ct Unit A, Chester, MD 21619
    /21

    $299,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    302 Merganser Ct Unit A, Chester, MD 21619

    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 of Kent Island's most sought-after communities. With no stairs to navigate and handicap-accessible features, this home provides effortless everyday living while enjoying the added privacy and abundant natural light that only an

    Jen Kenney Keller Williams Flagship

    302 Merganser Ct Unit A, Chester, MD 21619
  • 102 Boatswain Way Unit 2932, Chester, MD 21619
    102 Boatswain Way Unit 2932, Chester, MD 21619
    102 Boatswain Way Unit 2932, Chester, MD 21619
    /47

    $829,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 2932, Chester, MD 21619

    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 modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2932, Chester, MD 21619
  • 132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    /29

    $700,000

    $80K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    132 Wheelhouse Way Unit 11, Chester, MD 21619

    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 replacement value. Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four

    Matthew Arnold Real Broker, LLC

    132 Wheelhouse Way Unit 11, Chester, MD 21619
  • 111 Marshgrass Way Unit 43, Chester, MD 21619
    111 Marshgrass Way Unit 43, Chester, MD 21619
    111 Marshgrass Way Unit 43, Chester, MD 21619
    /65

    $765,000

    • 2 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 43, Chester, MD 21619

    Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floor unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design

    John Freeman Coldwell Banker Realty

    111 Marshgrass Way Unit 43, Chester, MD 21619
  • 2000 Herons Nest Way Unit 401, Chester, MD 21619
    2000 Herons Nest Way Unit 401, Chester, MD 21619
    2000 Herons Nest Way Unit 401, Chester, MD 21619
    /36

    $700,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River.The gourmet kitchen is the heart of the home,

    Matthew Arnold Real Broker, LLC

    2000 Herons Nest Way Unit 401, Chester, MD 21619
  • 830 Warbler Way Unit 33, Chester, MD 21619
    830 Warbler Way Unit 33, Chester, MD 21619
    830 Warbler Way Unit 33, Chester, MD 21619
    /25

    $689,990

    New Construction $28K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    830 Warbler Way Unit 33, Chester, MD 21619

    Private home office with elegant French double doors.Gourmet kitchen features a center island & built-in wall oven.Dining area includes a dry bar for added convenience.Great room with an electric fireplace opens to the balcony.Owner's suite offers balcony access for a relaxing retreat.Spa bath provides comfort with dual vanities & modern design.Laundry room includes

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 33, Chester, MD 21619
  • 131 Flycatcher Way Unit 36503530, Chester, MD 21619
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
    /21

    $629,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    Severn Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms.Lavish gourmet kitchen and formal dining area.Huge great room with large corner balcony.Fantastic owner’s suite and sitting room with access to balcony.Extravagant owner’s spa bath with two walk-in closets.Large secondary bedrooms for all of your company.Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
  • 102 Boatswain Way Unit 43, Chester, MD 21619
    102 Boatswain Way Unit 43, Chester, MD 21619
    102 Boatswain Way Unit 43, Chester, MD 21619
    /31

    $929,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 43, Chester, MD 21619

    Beautiful gourmet kitchen featuring designer cabinetry & an efficient layout for everyday living.Bright great room with an electric fireplace adding warmth & character.Dining area complemented by a convenient dry bar for easy entertaining.Private owner’s suite with walk-in closet & direct access to the spa bath.Home office with double doors ideal for work or quiet

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 43, Chester, MD 21619
  • 111 Marshgrass Way Unit 21, Chester, MD 21619
    111 Marshgrass Way Unit 21, Chester, MD 21619
    111 Marshgrass Way Unit 21, Chester, MD 21619
    /57

    $680,000

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    111 Marshgrass Way Unit 21, Chester, MD 21619

    A rare blend of coastal proximity and refined living unfolds within this beautifully appointed corner residence in the sought-after 55+ waterfront community of Four Seasons at Kent Island. Built in 2024 and impeccably maintained , this like-new residence offers the comfort of immediate enjoinment without the wait for new construction. Positioned near a tranquil creek leading to the Chesapeake

    Marisol Cardona Samson Properties

    111 Marshgrass Way Unit 21, Chester, MD 21619
  • 102 Boatswain Way Unit 33, Chester, MD 21619
    102 Boatswain Way Unit 33, Chester, MD 21619
    102 Boatswain Way Unit 33, Chester, MD 21619
    /32

    $829,990

    New Construction $33K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 33, Chester, MD 21619

    Private home office with elegant French doors. Chef-worthy gourmet kitchen with sprawling island. Formal dining area with dry bar, perfect for entertaining. Gorgeous great room with cozy electric fireplace. Sophisticated owner's suite with triple windows. Stunning owner's spa bath featuring split vanities. Beautiful balcony has access through primary suite & great room.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 33, Chester, MD 21619
  • 3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    /66

    $479,000

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    3000 Herons Nest Way Unit 11, Chester, MD 21619

    A price improvement has been made, making this unit the best value in the entire community. This home shows like a model with approximately $55,000.00 in upgrades. No need to wait for new construction this unit is ready for immediate occupancy. Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings

    John Freeman Coldwell Banker Realty

    3000 Herons Nest Way Unit 11, Chester, MD 21619
Maryland Queen Anne's County

Condos for Sale in Chester, MD

Why Live in Chester

Chester, MD, located on Kent Island between the Chester River and Chesapeake Bay, offers a blend of coastal charm and modern convenience. The area is known for its maritime atmosphere, with numerous marinas and waterfront views. Chester is 17 miles from Annapolis, home to the United States Naval Academy. Outdoor enthusiasts can enjoy Terrapin Nature Park's walking paths and tidal marshes, or the Cross Island Trail for hiking and cycling. Castle Marina provides opportunities for boating and fishing. Indoor fitness options include Club One Fitness and Aerobics. Housing in Chester ranges from ranch-style homes and colonials to New Traditional builds, with properties south of Highway 50 dating back to the mid-20th century and newer developments in the north. The area features a mix of single-family homes, condos, and townhouses, with some waterfront estates requiring additional flood insurance. Annual events like the Kent Island Crab Feast and the Annapolis Baygrass Music Festival foster community spirit. Shopping and dining are centered around Highway 50, with big-box stores like Safeway and Target, and bayside dining options in nearby Kent Narrows, including The Jetty and Bridges. Chester's schools are highly rated, with Bayside Elementary, Stevensville Middle, and Kent Island High all receiving commendable scores. Highway 50 is the main transportation route, connecting Chester to Annapolis, Baltimore, and Washington, D.C., while BWI International Airport is about 30 miles away.

Learn more about living in Chester

Condo Prices in Chester, MD

The median price for condos in Chester is $684,950, and there are 38 condo listings available for sale.

Condo Price Trends

Median Condo Price
$684,950
Median 1-Bedroom Condo Price
$338,000
Median 2-Bedroom Condo Price
$606,245
Median 3-Bedroom Condo Price
$749,990
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 38 condos for sale, providing a variety of options for potential buyers. With condos priced between $287,500 to $998,000, there's a range to accomodate every budget. As of August, 2026 the median home price in Chester is $700,995, while the average sale price is $672,563, offering insights into the local housing market. On average, condos spend 371 days listed before being sold. Whether you're considering condominiums, apartments for sale, or modern condos, there are options to cater to different lifestyles. Browse the range of condos for sale in Chester, MD, and discover your ideal residence.

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