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Chester, MD Homes for Sale with AC

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  • /52

    $799,990 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

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3042, Chester, MD 21619
  • /52

    $699,990 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
  • /44

    $849,990 New Construction

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

    110 Warbler Way Unit 3031, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3031, Chester, MD 21619
  • /44

    $749,990 New Construction

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

    110 Warbler Way Unit 3021, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3021, Chester, MD 21619
  • /40

    $899,990 New Construction

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

    311 Kingfisher Ln, Chester, MD 21619

    The Tuscaloosa, located on Lot 588, is scheduled for an April 2026 settlement and offers generous space with 5 bedrooms, 4.5 baths, and a 3-car garage—ideal for growing households and effortless entertaining. Designed with both comfort and function in mind, this home includes a private home office, a screened patio for relaxed outdoor living, and a striking stone fireplace complemented by ceiling

    Mary Anne Kowalewski KOVO Realty

    311 Kingfisher Ln, Chester, MD 21619
  • /40

    $889,990 New Construction

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

    110 Kinglet Ct, Chester, MD 21619

    The Tuscaloosa home offers a thoughtfully designed layout with elevated finishes throughout, with a projected settlement of April 2026. Featuring 2 bedrooms, 2.5 baths, and a 3-car garage, this home blends everyday functionality with timeless style. Standout features include a dedicated home office, a screened patio perfect for outdoor relaxation, and a shiplap-accented fireplace paired with

    Mary Anne Kowalewski KOVO Realty

    110 Kinglet Ct, Chester, MD 21619
  • /48

    $1,400,000 New Construction

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

    111 Flycatcher Way, Chester, MD 21619

    The Tuscaloosa Model Home offers an exceptional open-concept design enriched with high-end finishes and thoughtful upgrades throughout. Available for immediate settlement with a rent-back opportunity, this expansive home features 5 bedrooms, 4.5 baths, and a 3-car garage, delivering both space and sophistication. Standout features include a dedicated home office, an inviting fireplace, and a

    Mary Anne Kowalewski KOVO Realty

    111 Flycatcher Way, Chester, MD 21619
  • /49

    $1,100,000 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
  • /47

    $1,300,000 New Construction

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

    123 Flycatcher Way, Chester, MD 21619

    The Kerr Model Home offers a beautifully crafted layout enhanced with elevated designer finishes throughout—available now for immediate settlement with a rent-back opportunity. Thoughtfully designed with 3 bedrooms, 3 baths, and a 3-car garage, this home blends spacious living, refined styling, and everyday functionality. Standout features include a dedicated home office, an inviting fireplace,

    Mary Anne Kowalewski KOVO Realty

    123 Flycatcher Way, Chester, MD 21619
  • /49

    $1,400,000 New Construction

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

    117 Flycatcher Way, Chester, MD 21619

    The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio

    Mary Anne Kowalewski KOVO Realty

    117 Flycatcher Way, Chester, MD 21619
  • /12

    $519,900 New Construction

    • 1,250 Sq Ft

    0 Harbor Dr, Chester, MD 21619

    House is now substantially constructed. Builder has finished the lower level and included a bathroom! Lots of extra space and upgrades at this new home! Settle in 30-60 days. LVP floors, granite countertops, stainless steel appliances, etc.

    DJ Dauses Coldwell Banker Waterman Realty

    0 Harbor Dr, Chester, MD 21619
  • /64

    $1,167,890 Open Sat 12PM - 3PM

    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

    *****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, Chester, MD 21619
  • /13

    $950,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 2,940 Sq Ft

    102 Carriage Heath, Chester, MD 21619

    This stunning, truly one of a kind coastal-style home in Gibsons Grant offers a perfect blend of comfort and community. With a total of 4 spacious bedrooms and 3.5 baths (1 bed and bath is over garage), the open floor plan invites natural light, showcasing a modern kitchen with an island and a dining area and cozy living room. The main level primary suite features a luxurious bath and walk-in

    Tricia Wilson Wilson Realty & Staging LLC

    102 Carriage Heath, Chester, MD 21619
  • /33

    $765,000 Coming Soon

    • 2 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 43, Chester, MD 21619

    Rare penthouse unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for ever builder upgrade that was offered, over $60,000.00 in options. The open concept design seamlessly connects the living room, dining area, and kitchen areas, all enhanced by

    John Freeman Coldwell Banker Realty

    111 Marshgrass Way Unit 43, Chester, MD 21619
  • /6

    $380,000 Open House 4/11

    • 2 Beds
    • 2 Baths
    • 1,804 Sq Ft

    2008 Bridgepointe Dr, Chester, MD 21619

    Coming Soon - Gorgeous End Unit Townhouse. 2 Bedrooms and 2 Full Bathrooms with a converted garage that has the potential for a 3rd Bedroom option, den or change back into a garage space! Long Kitchen that leads to an Open Floor Plan Living Area PLUS Bonus Sunroom and Large Rear Deck add additional backyard privacy. Kick back, relax and enjoy the pond and fountain views. More details and photos

    Crystal Smith RE/MAX Executive

    2008 Bridgepointe Dr, Chester, MD 21619
  • /29

    $400,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft

    1803 Chester Dr, Chester, MD 21619

    Adorable rancher on Kent Island in the community of Harbor View! Featuring 3 beds, 2 baths, and private driveway. Enjoy the large fenced yard with deck, shed, and firepit. The living room has a cozy fireplace with wood stove insert. The primary bedroom has a private bath with tile and stand up shower. Updates include both bathrooms, updated windows, roof 2020. Close to Route 50 for easy access to

    Jennifer Kramer-Dela Cruz Keller Williams Legacy

    1803 Chester Dr, Chester, MD 21619
  • /12

    $300,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    102 Merganser Ct, Chester, MD 21619

    Come see this spacious, coastal inspired condo at Bayside on Kent Island. This 2 BR/2 Bath home offers all the benefits of first floor,one level living. A welcoming entrance whispers, " stay awhile" with a sunny patio area overlooking a lush lawn and water views. Inside you will notice plenty of windows, light, and an open-concept design that creates the perfect mood for that "laid back" Kent

    Carol Delayo Chaney Homes, LLC

    102 Merganser Ct, Chester, MD 21619
  • /8

    $445,000 Coming Soon

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

    23F Queen Victoria Way, Chester, MD 21619

    Offered for the first time in over 30 years, this lovingly maintained 2-bedroom, 2-bath residence is filled with warmth, history, and memories that have been cherished by the same family for decades. Perfectly positioned in sought-after Queen’s Landing, the home captures truly exceptional, direct views of the marina basin, marina fairway, and the Chester River—an ever-changing waterfront backdrop

    Jennifer Thomas RE/MAX Executive

    23F Queen Victoria Way, Chester, MD 21619
  • /2

    $1,100,000 Open House 4/18

    • 5 Beds
    • 4 Baths
    • 3,914 Sq Ft

    215 Kingfisher Ln, Stevensville, MD 21666

    COMING SOON! Professional Pictures coming...... Why wait to build? This less-than-one-year-old Tusculusa model on sought-after Kingfisher Lane sits just across from the Chester River, offering peekaboo water views from the covered front porch. You can see the clubhouse from the home! Loaded with over $70k in premium upgrades—owned solar, custom closets, and designer window treatments—all done for

    Jennifer Thomas RE/MAX Executive

    215 Kingfisher Ln, Stevensville, MD 21666

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