18

Chester, MD Condos for Sale

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

    $469,000

    • 2 Beds
    • 2.5 Baths
    • 1,104 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    Price Improvement on this CHESTER RIVER WATERFRONT 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,

    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

    $499,000

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

    170 Harrier Way Unit 11, Chester, MD 21619

    ***Redfin powered by Rocket Mortgage Preferred Pricing*** Enjoy with a 1% lower interest rate for your initial year or potential savings of up to $6,000 on your closing costs when you finance with Rocket Mortgage*** 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

    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

    $795,000

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

    170 Harrier Way Unit 34, Chester, MD 21619

    New improved price of $795,000 and immediate occupancy! No need to wait five months for a new condo to be built. 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

    Barry Davis Long & Foster Real Estate, Inc.

    170 Harrier Way Unit 34, Chester, MD 21619
  • Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    /32

    $779,900 New Construction

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

    121 Wheelhouse Way, Chester, MD 21619

    Charming gourmet kitchen featuring designer cabinets & center island.Connected dining area & great room for seamless flow.Convenient dry bar & electric firepelace in main living spaces.Peaceful owner's suite & bath with walk-in closet.Organized home office for leisure activities.Versatile balcony for outdoor enjoyment.

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • Severn, Chester, MD 21619
    Severn, Chester, MD 21619
    Severn, Chester, MD 21619
    /18

    $719,900 New Construction

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

    121 Wheelhouse Way, Chester, MD 21619

    Beautiful gourmet kitchen overlooks open concept living spaces.Spacious great room with warm fireplace.Sun-lit dining area with drybar, perfect for hosting dinner parties.Lavish owner's suite & bath featuring dual walk-in closets & sitting room.Convenient laundry room located near secondary bedrooms.Lovely balcony for outdoor relaxation.

    K Hovnanian's Four Seasons

    Severn, 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
  • 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
  • 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

    $540,000

    • 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

    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

    For a limited time, $4000 credit towards Capital Contribution Fee for full price offer.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 !!

    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

    $498,000

    • 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
  • 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

    $499,950

    • 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
    /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
Maryland Chester

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

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 45 days on the market compared to the national average of 69 days. The median sale price for homes in Chester, MD over the last 12 months is $649,900, down 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$649,900
Median Single Family Sale Price
$685,450
Median Townhouse Sale Price
$469,000
Median 2 Bedroom Sale Price
$540,000
Average Price Per Sq Ft
$347
Number of Homes for Sale
17
Last 12 months Home Sales
122
Months of Supply
1.70
Median List Price
$649,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-12%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 18 condos for sale, providing a variety of options for potential buyers. With condos priced between $469,000 to $795,000, there's a range to accomodate every budget. As of July, 2025 the median home price in Chester is $649,900, while the average sale price is $605,859, offering insights into the local housing market. On average, condos spend 45 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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