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Chester, MD Homes for Sale with Garage

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  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /42

    $744,500

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

    1868 Roberta Dr, Chester, MD 21619

    Price improvement! Motivated sellers. 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

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 446-2477

    1868 Roberta Dr, Chester, MD 21619
  • 126 Watermans Cove Ln, Chester, MD 21619
    126 Watermans Cove Ln, Chester, MD 21619
    126 Watermans Cove Ln, Chester, MD 21619
    /44

    $579,000

    • 3 Beds
    • 3 Baths
    • 1,536 Sq Ft

    126 Watermans Cove Ln, Chester, MD 21619

    Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman’s Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience. An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite deck, built

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 222-1760

    126 Watermans Cove Ln, Chester, MD 21619
  • 134 Mchenny Ct, Chester, MD 21619
    134 Mchenny Ct, Chester, MD 21619
    134 Mchenny Ct, Chester, MD 21619
    /31

    $599,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 1,839 Sq Ft

    134 Mchenny Ct, Chester, MD 21619

    Welcome home to this beautifully maintained three-bedroom, two-and-a-half-bath home in the sought-after waterfront community of Gibson’s Grant, where lifestyle and a prime Kent Island location come together effortlessly. A welcoming front porch sets the tone, leading into an open-concept main level designed for both everyday living and entertaining. The spacious living room with propane fireplace

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 771-2810

    134 Mchenny Ct, 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

    Four Seasons @ Kent Island - 55+ Community - 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 with quartz counters, propane gas cooktop

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 390-0346

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 190 Harrier Way Unit 21, Chester, MD 21619
    190 Harrier Way Unit 21, Chester, MD 21619
    190 Harrier Way Unit 21, Chester, MD 21619
    /73

    $649,900 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 2,639 Sq Ft

    190 Harrier Way Unit 21, Chester, MD 21619

    Impeccably finished and immediately available, this corner residence provides the ease and comfort of luxury condo living surrounded by the natural beauty of the Chesapeake Bay landscape. Windows on three sides fill more than 2600 square feet with natural light, while the peaceful pond-to-river setting creates a backdrop of fountains, wildlife, and winter water views beyond. Secure building

    Agent Photo

    Timothy McIntyre

    The KW Collective

    (667) 290-8908

    190 Harrier Way Unit 21, Chester, MD 21619
  • 135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    /81

    $799,999

    • 3 Beds
    • 3 Baths
    • 2,795 Sq Ft

    135 Nauset Ln, Chester, MD 21619

    If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style amenities.

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 226-9287

    135 Nauset Ln, 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 K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, 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 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    /12

    $886,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    Mykonos Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36477689, 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

    $752,990 New Construction

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

    Taylor Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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

    $504,990 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    /27

    $819,990 New Construction

    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    Kerr Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Extra Suite perfect for overnight guests. Private home office off foyer for working from home. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing primary bath with split vanities and walk-in closet. Convenient 3-car tandem garage for additional storage space.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
  • 131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    /40

    $848,990 New Construction

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

    Tuscaloosa Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Extra Suite with full bath for overnight guests. Private home office off foyer for working from home. Spacious great room with adjacent dining area. Beautiful kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
  • 2855 Cox Neck Rd, Chester, MD 21619
    2855 Cox Neck Rd, Chester, MD 21619
    2855 Cox Neck Rd, Chester, MD 21619
    /79

    $1,250,000

    • 3 Beds
    • 4.5 Baths
    • 4,413 Sq Ft

    2855 Cox Neck Rd, Chester, MD 21619

    Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring

    Tricia Wilson Wilson Realty & Staging LLC

    2855 Cox Neck Rd, Chester, MD 21619
  • 2000 Herons Nest Way Unit 401, Chester, MD 21619
    2000 Herons Nest Way Unit 401, Chester, MD 21619
    2000 Herons Nest Way Unit 401, Chester, MD 21619
    /93

    $750,000

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

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    This rare, luxurious Severn penthouse in Four Seasons at Kent Island is available immediately and offers a lifestyle that blends comfort, elegance, and natural beauty. Built in 2020 and beautifully maintained, the residence features an open floor plan with abundant windows that fill the home with natural light, creating a warm, inviting atmosphere. At the heart of the home is a stunning kitchen

    Veronica Lawson Real Broker, LLC

    2000 Herons Nest Way Unit 401, Chester, MD 21619
  • 121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    /48

    $999,990 New Construction

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

    121 Kinglet Ct, Chester, MD 21619

    Efficient kitchen featuring white cabinetry & quartz countertops. Open concept living area with vaulted ceiling & cozy fireplace. Pristine primary suite with stylish feature wall & ceiling treatment. Refreshing primary bath featuring a freestanding tub & brushed nickel finishes. Private Extra Suite & home office off foyer. Inviting screened patio for relaxing with friends. Attached 3-car tandem

    K. Hovnanian Homes Builder
    121 Kinglet Ct, Chester, MD 21619
  • 215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    /44

    $1,049,500

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

    215 Kingfisher Ln, Stevensville, MD 21666

    Price Reduced $50K – Open House Sunday May 3rd 1-3pm Please come see this beautiful home. Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent IslandWhy wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from

    Jennifer Thomas RE/MAX Executive

    215 Kingfisher Ln, Stevensville, MD 21666
  • 307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    /35

    $929,990 New Construction

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

    307 Kingfisher Ln, Chester, MD 21619

    Welcoming foyer leads to beautiful open concept floorplan. Inviting kitchen featuring white cabinetry, quartz countertops, & center island. Spacious great room with cozy fireplace, perfect for spending time with family. Tranquil primary suite featuring detailed ceiling treatment. Polished primary bath with brushed nickel finishes & generous walk-in closet. Convenient Extra Suite & home office off

    K. Hovnanian Homes Builder
    307 Kingfisher Ln, 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

    $689,990 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
  • 132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    /74

    $799,900

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

    132 Wheelhouse Way Unit 11, Chester, MD 21619

    Experience refined coastal living at 132 Wheelhouse Way #11, where the highly desirable Magothy floor plan offers sweeping water views and an unparalleled setting just steps from the clubhouse and Eastern Shore-inspired amenities. Perfectly positioned in one of the community’s most sought-after buildings, this residence has been meticulously maintained and reflects true pride of ownership

    Veronica Lawson Real Broker, LLC

    132 Wheelhouse Way Unit 11, Chester, MD 21619
  • 132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    /45

    $945,000

    • 4 Beds
    • 3.5 Baths
    • 3,634 Sq Ft

    132 Kestrel Ln, Chester, MD 21619

    Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully designed living space, this residence combines elegant design, modern functionality, and a lifestyle centered around comfort, connection, and the natural beauty of the Chesapeake Bay. From the moment you arrive, the covered front

    Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, 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

    $649,900

    • 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 tile

    shannon Gompers Long & Foster Real Estate, Inc.

    200 Harrier Way Unit 21, Chester, MD 21619
  • 190 Harrier Way Unit 24, Chester, MD 21619
    190 Harrier Way Unit 24, Chester, MD 21619
    190 Harrier Way Unit 24, Chester, MD 21619
    /81

    $650,000

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

    190 Harrier Way Unit 24, Chester, MD 21619

    Built for low-maintenance living, this beautiful 3-bedroom, 2.5-bath condo offers 2,600 square feet of comfort, space, and resort-style amenities. The open living, dining, and kitchen layout is ideal for everyday living and entertaining.Enjoy peaceful views of three ponds from the beautiful porch, with limited views of the Chester River. The kitchen features 42-inch cabinets, white quartz

    Dee Dee McCracken Coldwell Banker Realty

    190 Harrier Way Unit 24, Chester, MD 21619
  • 111 Marshgrass Way Unit 21, Chester, MD 21619
    111 Marshgrass Way Unit 21, Chester, MD 21619
    111 Marshgrass Way Unit 21, Chester, MD 21619
    /55

    $680,000 Open Sun 1PM - 3PM

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

    111 Marshgrass Way Unit 21, Chester, MD 21619

    A rare blend of coastal proximity and refined living unfolds within this beautifully appointed corner residence in the sought-after 55+ waterfront community of Four Seasons at Kent Island. Built in 2024 and impeccably maintained , this like-new residence offers the comfort of immediate enjoinment without the wait for new construction. Positioned near a tranquil creek leading to the Chesapeake

    Marisol Cardona Samson Properties

    111 Marshgrass Way Unit 21, Chester, MD 21619
  • 131 Flycatcher Way Unit 36455262, Chester, MD 21619
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
    /16

    $883,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,601 Sq Ft

    Munich ESP Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Extra Suite Plus for multi-generational living. Striking kitchen with large center island and corner pantry. Spacious great room with tons of windows for natural sun light. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities and optional freestanding tub. Private home office off foyer for working from home. Large covered patio for enjoying the outdoors.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
  • 1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    /23

    $455,000

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft

    1872 Harbor Dr, Chester, MD 21619

    Harbor View Community | Corner Lot | Renovated Rancher with Room to GrowIf you’ve been searching for a home where the work is already done and you can move in without worrying about repairs or updates, this one deserves your attention. This fully renovated home in Harbor View offers exactly what so many first-time buyers are looking for—low maintenance living now, with room to grow later. One

    Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
  • 102 Warbler Way Unit 2912, Chester, MD 21619
    102 Warbler Way Unit 2912, Chester, MD 21619
    102 Warbler Way Unit 2912, Chester, MD 21619
    /63

    $629,990 New Construction

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

    102 Warbler Way Unit 2912, Chester, MD 21619

    Welcome to the Magothy, 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

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2912, 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

    $504,990 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
  • 1719 Harbor Dr, Chester, MD 21619
    1719 Harbor Dr, Chester, MD 21619
    1719 Harbor Dr, Chester, MD 21619
    /87

    $1,495,000

    • 3 Beds
    • 5 Baths
    • 4,208 Sq Ft

    1719 Harbor Dr, Chester, MD 21619

    Escape the ordinary in this one-of-a-kind waterfront masterpiece on Cox Creek. Designed for those who refuse to settle for "cookie-cutter," this residence seamlessly blends sophisticated daily living with an unparalleled entertaining layout. The ground-level "Party Zone" is a showstopper, featuring a full bar and lounge with dual garage doors that open directly to a private oasis complete with a

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    1719 Harbor Dr, Chester, MD 21619
  • 102 Warbler Way Unit 2934, Chester, MD 21619
    102 Warbler Way Unit 2934, Chester, MD 21619
    102 Warbler Way Unit 2934, Chester, MD 21619
    /44

    $969,990 New Construction

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

    102 Warbler Way Unit 2934, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, 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

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2934, Chester, MD 21619
  • 111 Flycatcher Way, Chester, MD 21619
    111 Flycatcher Way, Chester, MD 21619
    111 Flycatcher Way, Chester, MD 21619
    /37

    $1,300,000 New Construction

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

    111 Flycatcher Way, Chester, MD 21619

    Beautiful kitchen with wood-stained 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. Stunning screened patio for outdoor entertaining. Attached 3-car tandem garage for vehicles & storage.

    K. Hovnanian Homes Builder
    111 Flycatcher Way, Chester, MD 21619
  • 330 Serenity Ln, Chester, MD 21619
    330 Serenity Ln, Chester, MD 21619
    330 Serenity Ln, Chester, MD 21619
    /50

    $5,900,000

    • 7 Beds
    • 9 Baths
    • 9,974 Sq Ft

    330 Serenity Ln, Chester, MD 21619

    Designed to rival a private resort, the outdoor spaces were made for celebrating with family and friends. Sweeping water views set the stage for unforgettable gatherings. The waterfront pool features a cascading natural rock waterfall with a bench tucked underneath and a generous shallow sun shelf. A beautifully appointed pool house offers a covered summer kitchen, bar, seating area and full bath

    Brad Kappel TTR Sotheby's International Realty

    330 Serenity Ln, Chester, MD 21619
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /47

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    807 Auckland Way, Chester, MD 21619

    Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades.Welcome to Bayside living at its finest. This meticulously maintained

    David Moore Real Broker, LLC

    807 Auckland Way, Chester, MD 21619
  • 126 Claiborne St, Chester, MD 21619
    126 Claiborne St, Chester, MD 21619
    126 Claiborne St, Chester, MD 21619
    /44

    $787,900

    • 3 Beds
    • 2.5 Baths
    • 2,276 Sq Ft

    126 Claiborne St, Chester, MD 21619

    Welcome to 126 Claiborne Street in the sought-after Gibson's Grant community on Kent Island — a beautifully crafted Covell-built Sawgrass model offering the perfect blend of coastal charm and comfortable with peaceful pond and park views right outside your door This thoughtfully designed home features 3 bedrooms, 2.5 baths, and a desirable main-level primary suite complete with a private en suite

    Tara Trout Samson Properties

    126 Claiborne St, 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
    /56

    $488,000

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

    1000 Herons Nest Way Unit 22, Chester, MD 21619

    BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE.This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 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

    Ralph Kennedy RE/MAX Executive

    1000 Herons Nest Way Unit 22, Chester, MD 21619
  • 1000 Herons Nest Way Unit 402, Chester, MD 21619
    1000 Herons Nest Way Unit 402, Chester, MD 21619
    1000 Herons Nest Way Unit 402, Chester, MD 21619
    /54

    $599,000

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

    1000 Herons Nest Way Unit 402, Chester, MD 21619

    Rarely on the market Penthouse level Chester model available immediately! Balcony views from the top floor leftside provide view of the Chester River, Macum Creek and the Community Kayak's. Located within the serene and vibrant community of Four Seasons at Kent Island, this exquisite 2-bedroom, 2.5 bath Built in 2020, this elegant unit combines modern design with high-end finishes, creating a

    Dan Judge RE/MAX United Real Estate

    1000 Herons Nest Way Unit 402, Chester, MD 21619
  • 102 Warbler Way Unit 2921, Chester, MD 21619
    102 Warbler Way Unit 2921, Chester, MD 21619
    102 Warbler Way Unit 2921, Chester, MD 21619
    /44

    $869,990 New Construction

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

    102 Warbler Way Unit 2921, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, 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

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2921, Chester, MD 21619
  • 131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    /13

    $701,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    Simone Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, Chester, MD 21619

    Private bedroom 2 located off foyer for overnight guests. Striking kitchen with large island and plenty of counter space. Open and airy great room with slider to covered patio. Convenient covered patio with screened patio option. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities. Versatile loft on second floor with 2 secondary bedrooms and full bath.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • 127 Flycatcher Way, Chester, MD 21619
    127 Flycatcher Way, Chester, MD 21619
    127 Flycatcher Way, Chester, MD 21619
    /49

    $1,000,000 New Construction

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft

    127 Flycatcher Way, Chester, MD 21619

    The Jenkins Model Home offers a beautifully crafted open-concept layout paired with high-end designer finishes throughout—now available for immediate settlement with a rent-back opportunity. Thoughtfully designed with 2 bedrooms, 2 baths, and a 2-car garage, this home blends comfort, sophistication, and convenience. Standout features include a dedicated home office, a cozy fireplace, and a

    Mary Anne Kowalewski KOVO Realty

    127 Flycatcher Way, Chester, MD 21619
  • 117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    /24

    $1,400,000 New Construction

    • 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
  • 212 Switchgrass Way Unit 34, Chester, MD 21619
    212 Switchgrass Way Unit 34, Chester, MD 21619
    212 Switchgrass Way Unit 34, Chester, MD 21619
    /13

    $770,000 Coming Soon

    • 3 Beds
    • 2.5 Baths

    212 Switchgrass Way Unit 34, Chester, MD 21619

    Professional photos coming! Experience elevated Eastern Shore living in this beautifully appointed corner residence overlooking the Chester River in the sought-after 55+ waterfront community of K. Hovnanian’s Four Seasons at Kent Island. Just one year old and impeccably maintained, this spacious three-bedroom, two-and-a-half-bath home offers more than 2,600 square feet of upscale living with the

    Jennifer Thomas RE/MAX Executive

    212 Switchgrass Way Unit 34, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Anne's County Chester

Homes for Sale with Garage in Chester, MD

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 252 days on the market compared to the national average of 58 days. The median sale price for homes in Chester, MD over the last 12 months is $640,000, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$640,000
Median Single Family Sale Price
$698,518
Median Townhouse Sale Price
$365,000
Median 2 Bedroom Sale Price
$553,450
Median 1 Bedroom Sale Price
$294,500
Average Price Per Sq Ft
$300
Number of Homes for Sale
79
Last 12 months Home Sales
217
Months of Supply
4.40
Median List Price
$663,917
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 56 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Chester, MD and find the perfect place to call home.

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