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Newest Homes for Sale in Chester, MD

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  • 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
    /9

    $494,900 Open House 3/08

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

    1000 Herons Nest Way Unit 23, Chester, MD 21619

    Welcome to 1000 Herons Nest Way, where you can live the good life at an great price. This immaculate two bedroom condo, with two and a half baths and additional flex space, provides turn key convenience and resort style amenities. This home is a MUST SEE! This FORMER MODEL is like new and includes features that other condos won’t - including decorator upgrades, custom designed closets, plantation

    Nola Meyers EXP Realty, LLC

    1000 Herons Nest Way Unit 23, Chester, MD 21619
  • 1150 Little Creek Rd, Chester, MD 21619
    1150 Little Creek Rd, Chester, MD 21619
    1150 Little Creek Rd, Chester, MD 21619
    /28

    $425,000

    • 3 Beds
    • 1.5 Baths
    • 2,200 Sq Ft

    1150 Little Creek Rd, Chester, MD 21619

    Start living the watermen dream in Dominion! This charming home offers a thoughtfully designed layout with an open, airy flow and spacious rooms throughout. Situated in the Dominion neighborhood on nearly one acre, you’ll enjoy both comfort and room to roam. The oversized living area is filled with natural sunlight streaming through the windows, creating a warm and inviting atmosphere. The first

    Dee Dee McCracken Coldwell Banker Realty

    1150 Little Creek Rd, Chester, MD 21619
  • 54B Queen Caroline Ct, Chester, MD 21619
    54B Queen Caroline Ct, Chester, MD 21619
    /2

    $324,900 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54B Queen Caroline Ct, Chester, MD 21619

    Professional photos will be uploaded! Tucked inside the sought-after Queens Landing community, this beautifully maintained townhome delivers the space, layout, and low-maintenance lifestyle everyone loves, plus a rare private setting with no traffic behind the home. Step inside to an open, airy main level featuring luxury vinyl plank flooring throughout the living area and an easy flow that is

    Julia Stevens Realty Navigator

    54B Queen Caroline Ct, Chester, MD 21619
  • 106 Merganser Ct, Chester, MD 21619
    106 Merganser Ct, Chester, MD 21619
    106 Merganser Ct, Chester, MD 21619
    /7

    $285,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    106 Merganser Ct, Chester, MD 21619

    First floor unit is coming available and those do not come around often! Freshly painted, new hardwood floors, new carpet in bedrooms, new light fixtures in bathrooms, updated kitchen cabinets, fireplace, and the convenience of first floor living! Don't hesitate on this one!

    Crystal Smith RE/MAX Executive

    106 Merganser Ct, Chester, MD 21619
  • 110 Boatswain Way Unit 32, Chester, MD 21619
    110 Boatswain Way Unit 32, Chester, MD 21619
    110 Boatswain Way Unit 32, Chester, MD 21619
    /31

    $769,990 New Construction

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

    110 Boatswain Way Unit 32, Chester, MD 21619

    Gourmet kitchen with central island for prep & dining. Home office with double doors adds privacy & style. Dining area enhanced by a convenient dry bar. Great room centered around an electric fireplace. Balcony extends living space off the great room. Owner’s suite with private balcony access for relaxation. Spa-like owner’s bath with dual sinks & sleek finishes.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 32, Chester, MD 21619
  • 141 Redstart Dr, Chester, MD 21619
    141 Redstart Dr, Chester, MD 21619
    141 Redstart Dr, Chester, MD 21619
    /25

    $899,990 New Construction

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    141 Redstart Dr, Chester, MD 21619

    First-floor Extra Suite offers flexible guest accommodations. Home office with sliding barn doors adds charm. Kitchen with white stacked cabinetry & glass-front uppers. Fireplace anchors the great room as a warm focal point. Screened patio off the great room for relaxed outdoor living. Primary suite with decorative feature wall & ceiling treatment. Primary bath with dual freestanding vanities.

    K. Hovnanian Homes Builder
    141 Redstart Dr, Chester, MD 21619
  • 110 Boatswain Way Unit 31, Chester, MD 21619
    110 Boatswain Way Unit 31, Chester, MD 21619
    110 Boatswain Way Unit 31, Chester, MD 21619
    /18

    $899,990 New Construction

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

    110 Boatswain Way Unit 31, Chester, MD 21619

    Home office with double doors for privacy. Great room with an electric fireplace for warmth & charm. Large central island anchors the gourmet kitchen. Dry bar in dining area creates a perfect hosting space. Owner’s suite with a serene sitting room & balcony access. Dual walk-in closets for organized living. Owner’s bath with sleek dual sinks & spacious layout.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 31, Chester, MD 21619
  • 110 Kinglet Ct, Chester, MD 21619
    110 Kinglet Ct, Chester, MD 21619
    110 Kinglet Ct, Chester, MD 21619
    /38

    $899,990 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    110 Kinglet Ct, Chester, MD 21619

    First-floor Extra Suite with private bath for guest comfort. Home office with sliding barn doors adds character. Kitchen, dining area & great room share a vaulted ceiling with beams. Kitchen with central island highlighted by matte black pendant lighting. Shiplap fireplace with hearth anchors the great room. Screened patio off the great room for relaxed outdoor living. Primary suite with ceiling

    K. Hovnanian Homes Builder
    110 Kinglet Ct, Chester, MD 21619
  • 110 Boatswain Way Unit 33, Chester, MD 21619
    110 Boatswain Way Unit 33, Chester, MD 21619
    110 Boatswain Way Unit 33, Chester, MD 21619
    /31

    $769,990 New Construction

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

    110 Boatswain Way Unit 33, Chester, MD 21619

    Private home office with elegant French doors. Chef-worthy gourmet kitchen with sprawling island. Exquisite 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
    110 Boatswain Way Unit 33, Chester, MD 21619
  • 110 Boatswain Way Unit 21, Chester, MD 21619
    110 Boatswain Way Unit 21, Chester, MD 21619
    110 Boatswain Way Unit 21, Chester, MD 21619
    /18

    $799,990 New Construction

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

    110 Boatswain Way Unit 21, Chester, MD 21619

    Gourmet kitchen with spacious central island. Dining area includes a convenient dry bar. Great room features an electric fireplace. Beautiful balcony extends off of the great room. Owner’s suite with dual walk-in closets. Private sitting room with balcony access. Luxurious owner’s bath with dual sinks.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 21, Chester, MD 21619
  • 176 Flagstaff Way Unit 11, Chester, MD 21619
    176 Flagstaff Way Unit 11, Chester, MD 21619
    176 Flagstaff Way Unit 11, Chester, MD 21619
    /9

    $599,990 New Construction

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

    176 Flagstaff Way Unit 11, Chester, MD 21619

    Gourmet kitchen featuring designer cabinetry & center island. Spacious great room with electric fireplace. Inviting dining area featuring lovely dry bar. Pristine owner's suite & spa bath with walk-in closet. Versatile outdoor patio, perfect for spending time with friends. Productive home office with lited double doors. Functional laundry room for added convenience.

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 11, Chester, MD 21619
  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /2

    $769,500 Open Sat 1PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1868 Roberta Dr, Chester, MD 21619

    This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning room transitions seamlessly into a

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 446-2477

    1868 Roberta Dr, Chester, MD 21619
  • 27 Queen Mary Ct Unit F, Chester, MD 21619
    27 Queen Mary Ct Unit F, Chester, MD 21619
    27 Queen Mary Ct Unit F, Chester, MD 21619
    /16

    $419,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 2 Baths
    • 1,380 Sq Ft

    27 Queen Mary Ct Unit F, Chester, MD 21619

    Fabulous Adriatic Grande unit ( largest end unit and 1 of 4) in the desirable Queens Landing community. With 1,380 sq. ft. of meticulously maintained space, this home features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. FIRST FLOOR BEDROOM suite features a private patio while second floor owner suite has an adjoining loft with a

    Agent Photo

    Deborah Shiley

    Long & Foster Real Estate, Inc.

    (667) 249-7796

    27 Queen Mary Ct Unit F, Chester, MD 21619
  • 230 Switchgrass Way Unit 21, Chester, MD 21619
    230 Switchgrass Way Unit 21, Chester, MD 21619
    230 Switchgrass Way Unit 21, Chester, MD 21619
    /14

    $694,500 Open House 3/08

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

    230 Switchgrass Way Unit 21, Chester, MD 21619

    --------------------------------------EXCEPTIONAL PANORAMIC VIEWS -------------------------------------Nature, water and sunshine abound in this beautifully situated, stunning 3BR corner unit at Four Seasons. Flexible closing available. South, west and north exposures through 17 windows and two sets of sliding doors assure that this condo is drenched in sunshine, water and the natural seasons in

    Lawrence Doyle Long & Foster Real Estate, Inc.

    230 Switchgrass Way Unit 21, Chester, MD 21619
  • 129 Sailcloth Way, Chester, MD 21619
    129 Sailcloth Way, Chester, MD 21619
    129 Sailcloth Way, Chester, MD 21619
    /34

    $764,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 2,303 Sq Ft

    129 Sailcloth Way, Chester, MD 21619

    *** Coming Soon*** Professional Photos will be uploaded 2/24 .

    Catherine Watson - Bye RE/MAX Executive

    129 Sailcloth Way, Chester, MD 21619
  • 311 Kingfisher Ln, Chester, MD 21619
    311 Kingfisher Ln, Chester, MD 21619
    311 Kingfisher Ln, Chester, MD 21619
    /37

    $949,990 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    311 Kingfisher Ln, Chester, MD 21619

    Beautiful kitchen with white cabinetry & pendant lighting. Open concept living spaces with vaulted ceiling & elegant fireplace. Private primary suite & bath with generous walk-in closet. Productive home office for working remotely. Secluded Extra Suite, ideal for overnight guests. Lovely screened patio for outdoor meals or activities. Attached 3-car tandem garage for vehicles & storage.

    K. Hovnanian Homes Builder
    311 Kingfisher Ln, Chester, MD 21619
  • 266 Peregrine Dr, Stevensville, MD 21666
    266 Peregrine Dr, Stevensville, MD 21666
    266 Peregrine Dr, Stevensville, MD 21666
    /3

    $750,000 Coming Soon

    • 4 Beds
    • 3 Baths
    • 2,870 Sq Ft

    266 Peregrine Dr, Stevensville, MD 21666

    Coming Soon... Get ready for this beautiful, less than 1 year old home in the sought after community of Four Seasons at Kent Island. This Simone model home with loft features 4 bedrooms and 3 full baths is awaiting it's next owner. With recent improvements including paint and Plantation Shutters, this home is move in ready so that you can enjoy this community and the upcoming Spring and Summer on

    Edward Beres RE/MAX Executive

    266 Peregrine Dr, Stevensville, MD 21666
  • 111 Marshgrass Way Unit 22, Chester, MD 21619
    111 Marshgrass Way Unit 22, Chester, MD 21619
    111 Marshgrass Way Unit 22, Chester, MD 21619
    /100

    $539,000 Coming Soon

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

    111 Marshgrass Way Unit 22, Chester, MD 21619

    Rare resale condo, turnkey! Your dream retreat awaits in this stunning luxury condo, where modern elegance meets breathtaking natural beauty. This exquisite residence features two spacious bedrooms, each with its own en-suite bath, and an additional half bath for guests. The thoughtfully designed office boasts custom built-in cabinets, providing both functionality and style.--Step into the heart

    Dee Dee Miller Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 22, Chester, MD 21619
  • 3 D Queen Victoria Ct, Chester, MD 21619
    3 D Queen Victoria Ct, Chester, MD 21619
    3 D Queen Victoria Ct, Chester, MD 21619
    /8

    $275,000 Open Sun 12PM - 2PM

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    3 D Queen Victoria Ct, Chester, MD 21619

    Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living room. The spacious bedroom has plenty of closet space and access to a gated private courtyard with locked storage area. Laundry closet is conveniently situated off the bedroom. Move in ready with fresh paint throughout, new LVP floors in the living areas, and new carpet in the bedroom. Queens Landing is a

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 888-0022

    3 D Queen Victoria Ct, Chester, MD 21619
  • 9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    /26

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    9B Queen Victoria Way, Chester, MD 21619

    Jennifer Thomas RE/MAX Executive

    9B Queen Victoria Way, Chester, MD 21619
  • 176 Flagstaff Way Unit 33, Chester, MD 21619
    176 Flagstaff Way Unit 33, Chester, MD 21619
    176 Flagstaff Way Unit 33, Chester, MD 21619
    /30

    $849,990 New Construction

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

    176 Flagstaff Way Unit 33, Chester, MD 21619

    Gourmet kitchen with central island for prep & gathering. Home office with French doors for focused work. Dining area with built-in dry bar for easy entertaining. Great room with fireplace as a cozy focal point. Balcony off the great room extends living space outdoors. Owner’s suite with spacious walk-in closet. Owner’s spa bath with dual sinks & glass shower enclosure.

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 33, Chester, MD 21619
  • 176 Flagstaff Way Unit 12, Chester, MD 21619
    176 Flagstaff Way Unit 12, Chester, MD 21619
    176 Flagstaff Way Unit 12, Chester, MD 21619
    /9

    $679,990 New Construction

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

    176 Flagstaff Way Unit 12, Chester, MD 21619

    Welcoming foyer leads to open concept living spaces. Efficient gourmet kitchen featuring designer cabinetry & wall oven. Vast center island overlooking dining area with dry bar. Electric fireplace adds warmth & character to great room. Private owner's suite for rest & relaxation. Pristine owner's spa bath featuring framless shower door. Organized home office with lited double doors. Versatile

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 12, Chester, MD 21619
  • 176 Flagstaff Way Unit 43, Chester, MD 21619
    176 Flagstaff Way Unit 43, Chester, MD 21619
    176 Flagstaff Way Unit 43, Chester, MD 21619
    /31

    $999,990 New Construction

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

    176 Flagstaff Way Unit 43, Chester, MD 21619

    Central island anchors the gourmet kitchen for everyday use. Home office with lited French doors add character. Dining area includes a convenient dry bar for hosting. Fireplace highlights the great room’s inviting design. Private balcony off the great room for outdoor relaxation. Owner’s suite features a generous walk-in closet. Spa-inspired owner’s bath with dual sinks & glass-enclosed shower.

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 43, Chester, MD 21619
  • 110 Warbler Way Unit 3032, Chester, MD 21619
    110 Warbler Way Unit 3032, Chester, MD 21619
    110 Warbler Way Unit 3032, Chester, MD 21619
    /52

    $769,990 New Construction

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

    110 Warbler Way Unit 3032, Chester, MD 21619

    The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 baths, and a 1-car garage. The main living area is anchored by an electric fireplace, while a dry bar adds both function and style for entertaining. A dedicated home office with lighted French doors provides a flexible space

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3032, Chester, MD 21619
  • 110 Warbler Way Unit 3033, Chester, MD 21619
    110 Warbler Way Unit 3033, Chester, MD 21619
    110 Warbler Way Unit 3033, Chester, MD 21619
    /52

    $769,990 New Construction

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

    110 Warbler Way Unit 3033, Chester, MD 21619

    The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 baths, and a 1-car garage. The main living area is anchored by an electric fireplace, while a dry bar adds both function and style for entertaining. A dedicated home office with lighted French doors provides a flexible space

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3033, Chester, MD 21619
  • 110 Warbler Way Unit 3031, Chester, MD 21619
    110 Warbler Way Unit 3031, Chester, MD 21619
    110 Warbler Way Unit 3031, Chester, MD 21619
    /44

    $899,990 New Construction

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

    110 Warbler Way Unit 3031, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3031, Chester, MD 21619
  • 110 Warbler Way Unit 3021, Chester, MD 21619
    110 Warbler Way Unit 3021, Chester, MD 21619
    110 Warbler Way Unit 3021, Chester, MD 21619
    /44

    $799,990 New Construction

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

    110 Warbler Way Unit 3021, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3021, Chester, MD 21619
  • 1025 Dundee Ct, Chester, MD 21619
    1025 Dundee Ct, Chester, MD 21619
    1025 Dundee Ct, Chester, MD 21619
    /26

    $350,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,400 Sq Ft

    1025 Dundee Ct, Chester, MD 21619

    Something special is coming to the market on Kent Island! This 3-bedroom, 2.5-bath, 1400 sf. home in Dundee Harbor Condo Townhouse Association offers the perfect blend of comfort and coastal living. Enjoy water privileges with access to Piney Creek Lake, including a private community pier ideal for fishing, kayaking, paddleboarding, and more. Just minutes away, Kent Narrows delivers the full

    Rick Parreco RE/MAX Executive

    1025 Dundee Ct, Chester, MD 21619
  • 204 Ringneck Ct, Chester, MD 21619
    204 Ringneck Ct, Chester, MD 21619
    204 Ringneck Ct, Chester, MD 21619
    /29

    $334,000

    • 3 Beds
    • 3.5 Baths
    • 1,747 Sq Ft

    204 Ringneck Ct, Chester, MD 21619

    Price improvement just in time for the spring market!Come see all of amazing amenities this water privileged community has! Enjoy the boating, pool, restaurants and Cross Island trail all within walking distance of this great home! Lovely 3 level townhome in the water oriented community of Bayside Marina offering 2/3 bedrooms and 3 full and one half baths. This multifunctional unit can be two

    Mary Wagner Cummings & Co. Realtors

    204 Ringneck Ct, Chester, MD 21619
  • 6 G Queen Victoria Way, Chester, MD 21619
    6 G Queen Victoria Way, Chester, MD 21619
    6 G Queen Victoria Way, Chester, MD 21619
    /50

    $299,000

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    6 G Queen Victoria Way, Chester, MD 21619

    Marina front and perfectly sized for easy living or a weekend escape. This one-bedroom one-bath condo offers approximately 724 square feet with an open floor plan. Walk into a bright living area that flows directly into the adjacent kitchen, creating an inviting and functional space for everyday living or entertaining. The kitchen has been updated with granite countertops, stainless steel

    Julia Stevens Realty Navigator

    6 G Queen Victoria Way, Chester, MD 21619
  • 402 Blenny Ln, Chester, MD 21619
    402 Blenny Ln, Chester, MD 21619
    402 Blenny Ln, Chester, MD 21619
    /51

    $399,000

    • 3 Beds
    • 3.5 Baths
    • 1,747 Sq Ft

    402 Blenny Ln, Chester, MD 21619

    End-unit three-level townhome overlooking the pond in Bayside community. Freshly painted, new LVP on lower level. Engineered wood floors on main level. Living room has propane fireplace and built-in bookcases/shelves. Most windows have plantation shutters. Sliding door overlooks rear deck, lower level sliding door overlooks rear patio; both with pond views! Amenity-rich Bayside Community offers

    Thomas Welch Long & Foster Real Estate, Inc.

    402 Blenny Ln, Chester, MD 21619
  • 200 Newtown Rd, Chester, MD 21619
    200 Newtown Rd, Chester, MD 21619
    200 Newtown Rd, Chester, MD 21619
    /30

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 1,296 Sq Ft

    200 Newtown Rd, Chester, MD 21619

    NO HOA! Beautifully maintained 2017-built home offering 3 bedrooms and 2.5 baths. Features a fenced yard for kids and pets, screened porch, large yard with concrete pad, and small storage shed. Temperature-controlled concrete crawl space, new sump pump, and septic contract for easy, worry-free living. Conveniently located near shopping and everything Kent Island has to offer.Make sure you see

    Agent Photo

    Linda Moran

    Berkshire Hathaway HomeServices PenFed Realty-WOC

    (410) 650-8215

    200 Newtown Rd, Chester, MD 21619
  • 176 Flagstaff Way Unit 2433, Chester, MD 21619
    176 Flagstaff Way Unit 2433, Chester, MD 21619
    176 Flagstaff Way Unit 2433, Chester, MD 21619
    /52

    $849,990 New Construction

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

    176 Flagstaff Way Unit 2433, Chester, MD 21619

    The Chester at Lot 2433 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it an excellent opportunity for buyers planning ahead. This home features 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Standout features include a dedicated home office with lighted French doors, a dry bar

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2433, Chester, MD 21619
  • 176 Flagstaff Way Unit 2443, Chester, MD 21619
    176 Flagstaff Way Unit 2443, Chester, MD 21619
    176 Flagstaff Way Unit 2443, Chester, MD 21619
    /52

    $999,900 New Construction

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

    176 Flagstaff Way Unit 2443, Chester, MD 21619

    The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2443, Chester, MD 21619
  • 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

    $560,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    ** New Listing! Four Seasons @ Kent Island - 55+ Community - Turnkey & 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 featuring a beautiful white Kitchen with quartz counters, propane

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 390-0346

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    /44

    $489,900

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1906 Harbor Dr, Chester, MD 21619

    Experience the epitome of luxury living in this stunning ranch-style home located in the prestigious Harbor View subdivision. This meticulously renovated residence boasts an impressive 1,750 square feet of thoughtfully designed space, perfect for those who appreciate both elegance and functionality. Step inside to discover a harmonious blend of modern sophistication and timeless charm. The

    Gregory Bennett Jr. Five Star Real Estate

    1906 Harbor Dr, Chester, MD 21619
  • 15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    /18

    $465,000

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    15 Queen Anne Way Unit E, Chester, MD 21619

    PRICE DROP! Motivated Seller! Escape to the water — without the waterfront price. This Chester River–front townhome in Queens Landing is the perfect second home or low-maintenance retreat, all for under $500K. Enjoy sunrise water views from your private patio and balcony, and lock-and-leave peace of mind when you head back home. Inside, the layout is easy and functional with luxury vinyl plank

    Jennifer Thomas RE/MAX Executive

    15 Queen Anne Way Unit E, Chester, MD 21619
  • 176 Flagstaff Way Unit 2412, Chester, MD 21619
    176 Flagstaff Way Unit 2412, Chester, MD 21619
    176 Flagstaff Way Unit 2412, Chester, MD 21619
    /63

    $679,990 New Construction

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

    176 Flagstaff Way Unit 2412, Chester, MD 21619

    The Magothy at Lot 2412 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting home features 2 bedrooms, 2.5 baths, and a 1-car garage, making it an ideal blend of style and functionality. Standout features include a dedicated home office with lighted French doors, a stylish dry bar perfect for entertaining,

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2412, Chester, MD 21619
  • 176 Flagstaff Way Unit 2411, Chester, MD 21619
    176 Flagstaff Way Unit 2411, Chester, MD 21619
    176 Flagstaff Way Unit 2411, Chester, MD 21619
    /63

    $599,990 New Construction

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

    176 Flagstaff Way Unit 2411, Chester, MD 21619

    The Magothy at Lot 2411 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting home features 2 bedrooms, 2.5 baths, and a 1-car garage, making it an ideal blend of style and functionality. Standout features include a dedicated home office with lighted French doors, a stylish dry bar perfect for entertaining,

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2411, Chester, MD 21619
  • 54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    /40

    $349,000

    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54H Queen Caroline Ct, Chester, MD 21619

    OPEN HOUSE 2/21, 11:00 to 1:00... Nothing to do but move in! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout the living areas and new vinyl flooring in the kitchen. A propane fireplace highlights the great room for cozy chilly nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside.

    Mary Stevens Long & Foster Real Estate, Inc.

    54H Queen Caroline Ct, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Annes County Chester

Newest Listings for Sale in Chester, MD

Frequently Asked Questions

What is the average home price in Chester, MD?
Homes for sale in Chester, MD have an average home price of $643,978.
How many homes have sold over the last 12 months in Chester, MD?
202 homes have sold in Chester, MD over the last 12 months.
Is Chester, MD a safe city?
In general, the safest neighborhood in Chester, MD with lower crime scores is Kent Narrows.
What are the most popular zip codes in Chester, MD?
The most popular zip codes in Chester, MD include 21619, 21666, 21638, 21658 and 21409.
What are the most popular neighborhoods in Chester, MD?
The most popular neighborhood in Chester, MD with the most homes for sale is Kent Narrows.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $650,000. If you put a 20% down payment of $130,000 and had a 30-year fixed mortgage with an interest rate of 6.01%, your estimated principal and interest payment would be $3,120 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $134K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chester, MD?
Chester, MD has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Bayside Elementary School, Matapeake Middle School and Kent Island Elementary School. The neighborhood in Chester with the highest rated schools is Kent Narrows. Browse all the schools in Chester, MD to learn more.

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 156 days on the market compared to the national average of 54 days. The median sale price for homes in Chester, MD over the last 12 months is $629,950, up 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$629,950
Median Single Family Sale Price
$675,976
Median Townhouse Sale Price
$365,000
Median 2 Bedroom Sale Price
$549,900
Median 1 Bedroom Sale Price
$297,500
Average Price Per Sq Ft
$293
Number of Homes for Sale
66
Last 12 months Home Sales
202
Months of Supply
3.90
Median List Price
$650,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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