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Chester, MD 1-Story Homes 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 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    /27

    $858,990

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    Franklin Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Formal dining room off foyer for entertaining guests. Stylish kitchen with plenty of cabinet space and large island. Open and airy great room with slider to covered patio. Luxurious primary suite with triple windows. Private primary bath with optional freestanding tub. Convenient 2-car garage with storage space.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
  • 131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    /10

    $699,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    Taylor Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Secluded bedroom 2 and bath off foyer for overnight guests.Stylish home office off foyer for working from home.Open & airy great room with adjacent dining area.Striking kitchen with island & tons of cabinet space.Luxurious primary suite with oversized walk-in closet.Palatial primary bath with roomy shower.Convenient 3-car tandem garage for additional storage.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36474700, 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
  • 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
  • 118 Kinglet Ct, Chester, MD 21619
    118 Kinglet Ct, Chester, MD 21619
    118 Kinglet Ct, Chester, MD 21619
    /8

    $969,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    118 Kinglet Ct, Chester, MD 21619

    Home office with sliding doors for added privacy.Vaulted ceiling with stunning beams spans the great room, dining area & kitchen.Fireplace adds a warm focal point to the great room.Screened patio extends directly from the great room.Spacious central island anchors the kitchen.Walk-in closet provides generous storage in the primary suite.Dual freestanding vanities & Plus

    K. Hovnanian Homes Builder
    118 Kinglet Ct, 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
  • 8F Queen Victoria Way, Chester, MD 21619
    8F Queen Victoria Way, Chester, MD 21619
    8F Queen Victoria Way, Chester, MD 21619
    /30

    $240,000

    $9K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    8F Queen Victoria Way, Chester, MD 21619

    Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertaining. Private patio off bedroom with secured storage. Laundry is stackable located in bedroom. You will enjoy the Queen's Landing community clubhouse, marina, tennis court and pool and well as the trails in the community.Call today for your private showing.

    Linda Austin Long & Foster Real Estate, Inc.

    8F Queen Victoria Way, 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
  • 118 Broadwater Dr, Chester, MD 21619
    118 Broadwater Dr, Chester, MD 21619
    /2

    $660,000

    Coming Soon
    • 2 Beds
    • 2 Baths
    • 2,473 Sq Ft

    118 Broadwater Dr, Chester, MD 21619

    Welcome to Resort-Style Living at Four Seasons at Kent Island! Why wait for new construction when you can move right into this beautifully upgraded Donegal model with the sought-after Great Room extension? Offering exceptional value, this is currently the lowest-priced single-family home in the community, making it an outstanding opportunity to enjoy one of Maryland’s premier 55+ active adult

    Ralph Kennedy RE/MAX Executive

    118 Broadwater Dr, 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
  • 108 Price Rd, Chester, MD 21619
    108 Price Rd, Chester, MD 21619
    108 Price Rd, Chester, MD 21619
    /10

    $216,000

    $24K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    108 Price Rd, Chester, MD 21619

    You wouldn't think it but the property offers 3 bedroom and 2 full baths. Patio right off kitchen for the summer cookouts! Easy yard maintenance here, not much grass to manage, leaves plenty of time for those cookouts. Close to Route 8 for easy east/west access. Property sold as is, no repairs will be made by seller. HUD CASE 244-032645, reach out for more information on this unique buying

    Dana Byrd Thurston Wyatt Real Estate, LLC

    108 Price Rd, Chester, MD 21619
  • 117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    /24

    $1,200,000

    New Construction $200K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    117 Flycatcher Way, Chester, MD 21619

    Formal dining room off the foyer for hosting celebrations. Breathtaking kitchen with stacked grey cabinetry & glass uppers. Sprawling quartz island perfect for prep & dining. Vaulted ceiling with ceiling beams connects dining area and great room. Elegant fireplace and sliding door to screened patio in great room. Private home office for working remotely. Primary suite & bath with dual vanities

    K. Hovnanian Homes Builder
    117 Flycatcher Way, 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
  • 121 Merlin Dr, Chester, MD 21619
    121 Merlin Dr, Chester, MD 21619
    121 Merlin Dr, Chester, MD 21619
    /84

    $719,900

    • 2 Beds
    • 2 Baths
    • 2,118 Sq Ft

    121 Merlin Dr, Chester, MD 21619

    Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay.Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful

    Yael Beckman Coldwell Banker Realty

    121 Merlin Dr, 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
  • 1340 Queen Anne Dr, Chester, MD 21619
    1340 Queen Anne Dr, Chester, MD 21619
    1340 Queen Anne Dr, Chester, MD 21619
    /27

    $439,900

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1340 Queen Anne Dr, Chester, MD 21619

    PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, 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
  • 315 Bentons Pleasure Rd, Chester, MD 21619
    315 Bentons Pleasure Rd, Chester, MD 21619
    315 Bentons Pleasure Rd, Chester, MD 21619
    /63

    $629,900

    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft

    315 Bentons Pleasure Rd, Chester, MD 21619

    This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

    Douglas Kayhoe Douglas Realty LLC

    315 Bentons Pleasure Rd, 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
  • 1609 Crab Alley Dr, Chester, MD 21619
    1609 Crab Alley Dr, Chester, MD 21619
    /2

    $345,000

    Coming Soon
    • 3 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    1609 Crab Alley Dr, Chester, MD 21619

    Welcome to 1609 Crab Alley Drive, a charming three-bedroom, one-and-a-half-bath rancher offering comfortable one-level living and lovely water views. Inside, hardwood flooring adds warmth and character, while the oversized picture window fills the front living room with natural light. The spacious backyard is made for summertime enjoyment, featuring an above-ground pool with plenty of additional

    Dee Dee Miller Paul Wesley Real Estate

    1609 Crab Alley Dr, 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
  • 131 Flycatcher Way Unit 36471203, Chester, MD 21619
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
    /11

    $709,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    Kelly Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private home office for working from home. Spacious great room with slider to covered patio. Beautiful kitchen with large island and roomy pantry. Luxurious primary suite with triple windows. Relaxing primary bath with spacious shower and walk-in closet. Convenient covered patio with screen patio option.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36471203, 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
  • 205 Riverside Dr, Chester, MD 21619
    205 Riverside Dr, Chester, MD 21619
    205 Riverside Dr, Chester, MD 21619
    /38

    $749,000

    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    205 Riverside Dr, Chester, MD 21619

    Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This

    Melissa Chick Engel & Völkers Annapolis

    205 Riverside Dr, 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

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Anne's County

1-Story Homes for Sale in Chester, MD

Home Prices in Chester, MD

The median home sale price in Chester, MD is $669,900, up 17% year-over-year. Homes in Chester sell in 371 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$669,900
Median Single Family Sale Price
$744,500
Median Townhouse Sale Price
$369,950
Median 2 Bedroom Sale Price
$618,750
Median 1 Bedroom Sale Price
$289,000
Average Price Per Sq Ft
$306
Number of Homes for Sale
95
Last 12 months Home Sales
216
Months of Supply
5.30
Median List Price
$699,995
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
17%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 45 one-story homes for sale, catering to individuals and families who value the simplicity and accessibility of single-level living. Whether you're entering the real estate market for the first time, transitioning to a downsized lifestyle, or simply prioritizing the convenience of a single-story layout, these homes offer a variety of options to explore. From cozy bungalows to spacious ranch-style houses, the one-story homes for sale in Chester, MD come in various architectural styles and sizes, ensuring there's something to accommodate every preference and lifestyle.

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