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Chester, MD Condos for Sale

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  • 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

    $474,990 New Construction

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

    Magothy Plan at K. Hovnanian’s® 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36493007, 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
    /71

    $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
  • 141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    /61

    $684,950

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    141 Switchgrass Way Unit 34, Chester, MD 21619

    K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesapeake Bay, offering island resort-style and maintenance-free living at its finest! Shows Like a Model!!! The Severn design is a spacious and airy 3 bedroom, 2.5 bath end-unit boasting an expansive open floor plan with over 2600 square feet of luxurious living space. This home features a lavish gourmet kitchen

    Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
  • 200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    /44

    $699,900 Open Sun 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    200 Harrier Way Unit 21, Chester, MD 21619

    Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with plenty of natural light with "Perfect Fit" planation shutters and ample privacy on all windows and doors. The kitchen has a gourmet package including quartz countertops and a large island with space for barstool eating, subway

    shannon Gompers Long & Foster Real Estate, Inc.

    200 Harrier Way Unit 21, Chester, MD 21619
  • 630 Warbler Way Unit 22, Chester, MD 21619
    630 Warbler Way Unit 22, Chester, MD 21619
    630 Warbler Way Unit 22, Chester, MD 21619
    /21

    $603,156 New Construction

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

    630 Warbler Way Unit 22, Chester, MD 21619

    Functional home office with elegant French doors. Beautiful gourmet kitchen with pendant lighting. Spacious dining area and great room with electric fireplace. Palatial owner's suite with triple windows & balcony access. Glamorous owner's spa bath featuring split vanities. Beautiful balcony for outdoor enjoyment.

    Builder Photo

    K. Hovnanian Homes

    Builder

    630 Warbler Way Unit 22, Chester, MD 21619
  • 630 Warbler Way Unit 21, Chester, MD 21619
    630 Warbler Way Unit 21, Chester, MD 21619
    630 Warbler Way Unit 21, Chester, MD 21619
    /17

    $751,168 New Construction

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

    630 Warbler Way Unit 21, Chester, MD 21619

    Kitchen with large island & wall oven for gourmet meal prep. Dining area with a built-in dry bar perfect for hosting and entertaining. Great room includes a fireplace & opens to the balcony. Owner's suite features a sitting area with tranquil balcony views. Dual walk-in closets offer exceptional organization options. Luxe spa bath with dual vanities creates a relaxing retreat.

    Builder Photo

    K. Hovnanian Homes

    Builder

    630 Warbler Way Unit 21, Chester, MD 21619
  • 630 Warbler Way Unit 12, Chester, MD 21619
    630 Warbler Way Unit 12, Chester, MD 21619
    630 Warbler Way Unit 12, Chester, MD 21619
    /8

    $569,900 New Construction

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

    630 Warbler Way Unit 12, Chester, MD 21619

    Charming gourmet kitchen featuring center island & ample counter space. Electric fireplace adds warmth to spacious great room. Refined dining area with dry bar. Functional home office for studying or reading. Private owner's suite & spa bath with walk-in closet. Versatile covered patio for outdoor relaxation.

    Builder Photo

    K. Hovnanian Homes

    Builder

    630 Warbler Way Unit 12, Chester, MD 21619
  • 630 Warbler Way Unit 2222, Chester, MD 21619
    630 Warbler Way Unit 2222, Chester, MD 21619
    630 Warbler Way Unit 2222, Chester, MD 21619
    /48

    $594,900 New Construction

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

    630 Warbler Way Unit 2222, Chester, MD 21619

    Chester|| Available May 2026This home offers 2 bedrooms, 2.5 baths, and a 1-car garage. Standout features include a dry bar, an electric fireplace, and a dedicated home office with lited French doors. The kitchen is thoughtfully designed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lights, and a tile backsplash, all accented by quartz countertops.The

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2222, Chester, MD 21619
  • 630 Warbler Way Unit 2221, Chester, MD 21619
    630 Warbler Way Unit 2221, Chester, MD 21619
    630 Warbler Way Unit 2221, Chester, MD 21619
    /62

    $744,900 New Construction

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

    630 Warbler Way Unit 2221, Chester, MD 21619

    Magothy || Available May 2026This thoughtfully designed home features 3 bedrooms, 2.5 baths, and a 1-car garage. Inside, you’ll find an open layout complemented by a dry bar, electric fireplace, and an owner’s suite with a sitting room and large walk-in closets. The kitchen is beautifully appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lights, and a

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2221, Chester, MD 21619
  • 121 Wheelhouse Way Unit 32, Chester, MD 21619
    121 Wheelhouse Way Unit 32, Chester, MD 21619
    121 Wheelhouse Way Unit 32, Chester, MD 21619
    /26

    $679,900 New Construction

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

    121 Wheelhouse 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

    Builder Photo

    K. Hovnanian Homes

    Builder

    121 Wheelhouse Way Unit 32, Chester, MD 21619
  • 630 Warbler Way Unit 11, Chester, MD 21619
    630 Warbler Way Unit 11, Chester, MD 21619
    630 Warbler Way Unit 11, Chester, MD 21619
    /10

    $573,365 New Construction

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

    630 Warbler Way Unit 11, Chester, MD 21619

    Efficient gourmet kitchen featuring designer cabinets & vast center island.Open concept living areas featuring electric fireplace & dry bar.Spacious owner's suite & spa bath for relaxation.Organized home office, perfect for working remotely.Inviting outdoor patio for spending time with friends.

    Builder Photo

    K. Hovnanian Homes

    Builder

    630 Warbler Way Unit 11, 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

    $559,990 New Construction

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

    Severn Plan at K. Hovnanian’s® 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36503530, Chester, MD 21619
  • 312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    /42

    $305,000

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

    312 Teal Ct Unit F, Chester, MD 21619

    This is a highly sought-after location on Kent Island, known for its limited availability.Sellers have updated shiplap in the living room, paint throughout the house. This second-floor condo offers breathtaking views of the pond. You will enjoy an updated backsplash in the kitchen, featuring granite countertops and stainless steel appliances. Hardwood flooring is throughout the house. The

    Mary Rice Engel & Völkers Ocean City

    312 Teal Ct Unit F, Chester, MD 21619
  • 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,

    Lona Todd Taylor Properties

    34 Queen Anne Way, 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
  • 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 Open Sun 12PM - 2PM

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

    170 Harrier Way Unit 34, Chester, MD 21619

    Open House this Sunday 9/14 from 12-2. New improved price of $795,000 and immediate occupancy! This is the only 3 bedroom condo on the market in Four Seasons with the immediate availability. The other two will not be ready until February 2026. 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 –

    Barry Davis Long & Foster Real Estate, Inc.

    170 Harrier Way Unit 34, 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

    $488,000

    • 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
  • 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

    $474,990 New Construction

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

    Chester Plan at K. Hovnanian’s® 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36493320, Chester, MD 21619
Maryland Queen Annes County 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 42 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, MD over the last 12 months is $599,900, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$599,900
Median Single Family Sale Price
$639,900
Median Townhouse Sale Price
$420,000
Median 2 Bedroom Sale Price
$519,500
Median 1 Bedroom Sale Price
$306,500
Average Price Per Sq Ft
$295
Number of Homes for Sale
64
Last 12 months Home Sales
177
Months of Supply
4.30
Median List Price
$598,950
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 20 condos for sale, providing a variety of options for potential buyers. With condos priced between $305,000 to $795,000, there's a range to accomodate every budget. As of September, 2025 the median home price in Chester is $598,950, while the average sale price is $599,538, offering insights into the local housing market. On average, condos spend 42 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.

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