25

Chester, MD Condos for Sale

Section Image Section Image
  • 34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    /57

    $499,000

    • 2 Beds
    • 2.5 Baths
    • 1,586 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    CHESTER RIVER WATERFRONT on the Eastern Shore! Nestled within the water-privileged resort-style community of Queen's Landing, along the scenic Chester River and Macum Creek off the Chesapeake Bay. Step into the light-filled foyer and head up the stairs to the main level, you will find this lovely 2 bedroom, 2.5 bath condominium is move in ready. Just bring your patio chairs, sit back and enjoy

    Agent Photo

    Lona Todd

    Taylor Properties

    (667) 291-8898

    34 Queen Anne Way, 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
    /62

    $530,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - $10,000 Closing Cost Assistance Available - 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 featuring a beautiful white Kitchen

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 936-3917

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    /74

    $545,000

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

    170 Harrier Way Unit 11, Chester, MD 21619

    Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island!Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent Island! Completely move-in ready, this home boasts a gourmet kitchen, a formal dining area, and a cozy family room, all enhanced by luxurious finishes throughout.The spacious primary bedroom features a full ensuite bath, while the

    Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
  • Magothy, Chester, MD 21619
    Magothy, Chester, MD 21619
    Magothy, Chester, MD 21619
    /12

    $474,990 New Construction

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

    Magothy, 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

    K Hovnanian's Four Seasons

    Magothy, Chester, MD 21619
  • 170 Harrier Way Unit 34, Chester, MD 21619
    170 Harrier Way Unit 34, Chester, MD 21619
    170 Harrier Way Unit 34, Chester, MD 21619
    /81

    $825,000

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

    170 Harrier Way Unit 34, Chester, MD 21619

    Immediate Occupancy! No need to wait five months for a new condo to be built. And price just reduced! Welcome to luxury condo living at Four Seasons at Kent Island, an active 55+ community packed with amenities. No need to wait for a new condo to be built – you can move in now to 170 Harrier Way #34. This third floor Severn model (3 BR / 2 1⁄2 Bath / 2,602 sqft) offers beautiful views of the

    Barry Davis Long & Foster Real Estate, Inc.

    170 Harrier Way Unit 34, Chester, MD 21619
  • 201 Switchgrass Way Unit 1443, Chester, MD 21619
    201 Switchgrass Way Unit 1443, Chester, MD 21619
    201 Switchgrass Way Unit 1443, Chester, MD 21619
    /58

    $784,900 New Construction

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

    201 Switchgrass Way Unit 1443, Chester, MD 21619

    Welcome home to the Chester, a beautifully crafted 2-bedroom, 2.5-bath residence with a 1-car garage, offering low-maintenance luxury and stylish finishes throughout. Ideal for full-time living or a lock-and-leave lifestyle, this home delivers comfort, flexibility, and charm in every room.Inside, you’ll find a dedicated home office with lighted French doors, perfect for remote work or a

    Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1443, Chester, MD 21619
  • 201 Switchgrass Way Unit 1442, Chester, MD 21619
    201 Switchgrass Way Unit 1442, Chester, MD 21619
    201 Switchgrass Way Unit 1442, Chester, MD 21619
    /58

    $784,900 New Construction

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

    201 Switchgrass Way Unit 1442, Chester, MD 21619

    Experience the perfect balance of function and finesse in the Chester, a 2-bedroom, 2.5-bath home with a 1-car garage, designed for effortless living and elevated comfort.Thoughtfully laid out, this home includes a stylish home office with lighted French doors, a dry bar for entertaining, and a welcoming electric fireplace to anchor the living space. Elegant tray ceilings in both the great room

    Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1442, Chester, MD 21619
  • 201 Switchgrass Way Unit 1433, Chester, MD 21619
    201 Switchgrass Way Unit 1433, Chester, MD 21619
    201 Switchgrass Way Unit 1433, Chester, MD 21619
    /58

    $684,900 New Construction

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

    201 Switchgrass Way Unit 1433, Chester, MD 21619

    Welcome home to the Chester, a beautifully crafted 2-bedroom, 2.5-bath residence with a 1-car garage, offering low-maintenance luxury and stylish finishes throughout. Ideal for full-time living or a lock-and-leave lifestyle, this home delivers comfort, flexibility, and charm in every room.Inside, you’ll find a dedicated home office with lighted French doors, perfect for remote work or a

    Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1433, Chester, MD 21619
  • 211 Switchgrass Way Unit 1531, Chester, MD 21619
    211 Switchgrass Way Unit 1531, Chester, MD 21619
    211 Switchgrass Way Unit 1531, Chester, MD 21619
    /88

    $739,900 New Construction

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

    211 Switchgrass Way Unit 1531, Chester, MD 21619

    Discover effortless living in the Chester, a well-appointed 3-bedroom, 2.5-bath home with a 1-car garage, thoughtfully designed for both everyday comfort and style. This home blends clean lines with upgraded finishes to create a welcoming and functional retreat.Enjoy cozy evenings by the electric fireplace, or entertain with ease thanks to a built-in dry bar—perfect for hosting or relaxing at

    Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1531, Chester, MD 21619
  • 218 Switchgrass Way Unit 1732, Chester, MD 21619
    218 Switchgrass Way Unit 1732, Chester, MD 21619
    218 Switchgrass Way Unit 1732, Chester, MD 21619
    /55

    $899,900 New Construction

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

    218 Switchgrass Way Unit 1732, Chester, MD 21619

    Experience the perfect blend of form and function in the Chester, a thoughtfully designed 2-bedroom, 2.5-bath home with a 1-car garage and smart upgrades throughout. Whether you're looking for a comfortable everyday retreat or a low-maintenance second home, this property offers it all.Enjoy the warmth of an electric fireplace, the convenience of a built-in dry bar, and the flexibility of

    Mary Anne Kowalewski KOVO Realty

    218 Switchgrass Way Unit 1732, Chester, MD 21619
  • Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    /24

    $684,900 New Construction

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

    201 Switchgrass Way, Chester, MD 21619

    Gourmet kitchen with wall oven & spacious central island.Dry bar in the dining area adds a stylish touch.Great room features an electric fireplace for cozy evenings.Sliding doors open to a private balcony off the great room.Owner’s suite with direct balcony access for fresh air.Dual vanities in the spa-inspired owner’s bath.Thoughtfully designed layout with

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • Severn, Chester, MD 21619
    Severn, Chester, MD 21619
    Severn, Chester, MD 21619
    /21

    $559,990 New Construction

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

    Severn, 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's Four Seasons

    Severn, Chester, MD 21619
  • Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    /33

    $474,990 New Construction

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

    Chester, 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

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • 132 Wheelhouse Way Unit 21, Chester, MD 21619
    132 Wheelhouse Way Unit 21, Chester, MD 21619
    132 Wheelhouse Way Unit 21, Chester, MD 21619
    /86

    $1,099,000

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

    132 Wheelhouse Way Unit 21, Chester, MD 21619

    Open Saturday 12-2pm Welcome to 132 Wheelhouse Way Unit 21, an extraordinary residence where elegance meets ease. This impeccably designed 3-bedroom, 2.5-bath corner unit in the coveted Four Seasons at Kent Island offers over 2,600 square feet of refined single-level living with unparalleled panoramic views of the Chester River. From the moment you enter, you’ll fall in love with the attention to

    Kathleen Higginbotham Keller Williams Flagship

    132 Wheelhouse Way Unit 21, Chester, MD 21619
  • 204 Teal Ct Unit B, Chester, MD 21619
    204 Teal Ct Unit B, Chester, MD 21619
    204 Teal Ct Unit B, Chester, MD 21619
    /25

    $295,000

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    204 Teal Ct Unit B, Chester, MD 21619

    Lakefront Condo in Premier Community! Don’t miss your chance to own this stunning ground-floor condo with serene lake views from every room—including the soothing sights and sounds of a peaceful fountain just outside your window. Located in an amenity-rich, highly desirable community offering:• Clubhouse• Fitness Center• Sparkling Pool• Tennis Courts• Restaurants &

    Thomas Hennerty NetRealtyNow.com, LLC

    204 Teal Ct Unit B, Chester, MD 21619
  • 190 Harrier Way Unit 11, Chester, MD 21619
    190 Harrier Way Unit 11, Chester, MD 21619
    190 Harrier Way Unit 11, Chester, MD 21619
    /32

    $560,000

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

    190 Harrier Way Unit 11, Chester, MD 21619

    Luxury 55+ Living at Four Seasons on Kent Island – Move-In Ready & Priced to Sell!Welcome to the resort-style lifestyle of Four Seasons on Kent Island, an amenity-rich 55+ waterfront community where luxury, comfort, and convenience meet. Inside, you'll find open-concept layouts filled with natural light, gourmet kitchens with quartz countertops, GE Profile stainless steel appliances, custom

    Jennifer Thomas RE/MAX Executive

    190 Harrier Way Unit 11, Chester, MD 21619
  • 170 Harrier Way Unit 22, Chester, MD 21619
    170 Harrier Way Unit 22, Chester, MD 21619
    170 Harrier Way Unit 22, Chester, MD 21619
    /73

    $510,000

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

    170 Harrier Way Unit 22, Chester, MD 21619

    When I asked the seller what is the best part of living here, she said......"the best things about my place is the balcony and view !! Unobstructed. No buildings directly between my unit and the river". Easy place to live !! Lock the door and leave everything to someone else !! Stunning condo with breathtaking views of the Chester River! This turnkey unit features two

    Vic Pascoe Keller Williams Select Realtors of Annapolis

    170 Harrier Way Unit 22, Chester, MD 21619
  • 1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    /26

    $499,000

    • 2 Beds
    • 2 Baths

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Priced to Sell! Seller is ready for their next adventure! Move in, in May! Enjoy low-maintenance living in the amenity-rich, 55+ community of Four Seasons on Kent Island. This 2-bedroom, 2-bath home offers comfortable one-level living with an open layout, perfect for entertaining or relaxing. The property includes a 1-car garage with additional storage units—ideal for keeping your home organized

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • 1000 Herons Nest Way Unit 22, Chester, MD 21619
    1000 Herons Nest Way Unit 22, Chester, MD 21619
    1000 Herons Nest Way Unit 22, Chester, MD 21619
    /59

    $515,000

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

    1000 Herons Nest Way Unit 22, Chester, MD 21619

    Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. With 1900 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet

    Ralph Kennedy RE/MAX Executive

    1000 Herons Nest Way Unit 22, Chester, MD 21619
  • 7C Queen Victoria Way, Chester, MD 21619
    7C Queen Victoria Way, Chester, MD 21619
    7C Queen Victoria Way, Chester, MD 21619
    /68

    $254,750

    • Studio
    • 1 Bath
    • 724 Sq Ft

    7C Queen Victoria Way, Chester, MD 21619

    Price Improvement!! Discover the charm of waterfront living with this unique studio condominium in the sought-after community of Queen’s Landing. Priced attractively, this open-floor-plan oasis offers no ordinary view – gaze out from a generous patio as boats drift by and the sun sets in a spectacular display, arguably one of the best on Kent Island.Perfect as a year-round vacation retreat, this

    Julia Stevens Realty Navigator

    7C Queen Victoria Way, Chester, MD 21619
  • 170 Harrier Way Unit 33, Chester, MD 21619
    170 Harrier Way Unit 33, Chester, MD 21619
    170 Harrier Way Unit 33, Chester, MD 21619
    /41

    $514,950

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

    170 Harrier Way Unit 33, Chester, MD 21619

    This Chester model has scenic views of the river, beautiful sunrises, and an incredible display of wildlife in all seasons. Upgraded lighting package, dry bar, and fireplace are just a few of the features of this award winning condominium. With nearly 2000 square feet of open living space on one floor, this home has a great layout for entertaining friends and family. Spacious Great Room,

    Ralph Kennedy RE/MAX Executive

    170 Harrier Way Unit 33, Chester, MD 21619
  • Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    /26

    $919,900 New Construction

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

    218 Switchgrass Way, Chester, MD 21619

    Private home office offers a quiet & functional workspace.Gourmet kitchen features a center island & built-in wall oven.Dining area with a dry bar adds convenience for hosting.Great room includes an electric fireplace & balcony access.Sliding glass doors connect indoor & outdoor living spaces.Owner's suite with private balcony creates a serene

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    /25

    $784,900 New Construction

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

    201 Switchgrass Way, Chester, MD 21619

    Private home office with double doors for a quiet workspace.Central island anchors the gourmet kitchen with wall oven.Great room with a warm electric fireplace & balcony access.Dining area includes a dry bar, perfect for hosting.Owner’s suite offers a retreat with private balcony entry.Spa-like owner’s bath with dual vanities & modern

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    /25

    $784,900 New Construction

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

    201 Switchgrass Way, Chester, MD 21619

    Home office with elegant double-door entry.Gourmet kitchen with wall oven & oversized island.Dining area includes a built-in dry bar for entertaining.Great room with an electric fireplace & natural light.Access to the balcony from both the great room & owner’s suite.Dual vanities in the owner’s spa bath for a luxe feel.Smartly designed floorplan

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • Severn, Chester, MD 21619
    Severn, Chester, MD 21619
    Severn, Chester, MD 21619
    /19

    $739,900 New Construction

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

    211 Switchgrass Way, 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's Four Seasons

    Severn, Chester, MD 21619
Maryland Chester

Condos for Sale in Chester, MD

Why Live in Chester

Chester features a diverse housing market with single-family homes, condos, and townhouses. The neighborhood includes ranch-style homes, colonials, and New Traditional builds. Properties south of Highway 50 date back to the mid-to-late 20th century, while newer communities in the northern sector have been developed over the past decade. Chester's parks and recreational activities are abundant, with Terrapin Nature Park offering walking paths and Chesapeake Bay views, and the Cross Island Trail providing a paved walkway for hikers and cyclists. Castle Marina is a hub for boating activities, and Club One Fitness and Aerobics offers gym facilities and an aquatic center. Shopping and dining are concentrated in plazas off Highway 50, with big-box stores like Safeway, Walgreens, and Target, and a variety of restaurants ranging from fast food to local favorites. Notable dining spots include The Jetty, Bridges, and Fisherman’s Inn in nearby Kent Narrows. Annual events such as the Kent Island Day parade and the Annapolis Baygrass Music Festival bring the community together. Highway 50 is the main thoroughfare, connecting Chester to Annapolis, 17 miles away, and the Chesapeake Bay Bridge provides access to Baltimore and Washington, D.C. Public transportation is available via Queen Anne’s County buses, and BWI International Airport is about 30 miles away. Schools in Chester are highly rated, with Bayside Elementary, Stevensville Middle, and Kent Island High all receiving strong ratings.
Learn more about living in Chester

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 51 days on the market compared to the national average of 50 days. The median sale price for homes in Chester, MD over the last 12 months is $569,450, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$569,450
Median Single Family Sale Price
$616,900
Median Townhouse Sale Price
$400,000
Median 2 Bedroom Sale Price
$514,950
Median 1 Bedroom Sale Price
$293,000
Average Price Per Sq Ft
$295
Number of Homes for Sale
87
Last 12 months Home Sales
172
Months of Supply
6.10
Median List Price
$569,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 25 condos for sale, providing a variety of options for potential buyers. With condos priced between $254,750 to $1,099,000, there's a range to accomodate every budget. As of June, 2025 the median home price in Chester is $569,500, while the average sale price is $586,201, offering insights into the local housing market. On average, condos spend 51 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.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group