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Explore Similar Homes Within 10 Miles of 21628, MD

  • /21

    $509,000

    • 5 Beds
    • 3.5 Baths
    • 4,067 Sq Ft

    116 Harlan Loop, Chestertown, MD 21620

    Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office setup Curb

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • /26

    $465,000

    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    110 Trafford Dr, Chestertown, MD 21620

    Here’s the opportunity buyers wait for. A classic Colonial in sought-after Coventry Farms, priced where this neighborhood rarely plays, offering space, comfort, and the chance to build equity while you live well. Step inside and you’re welcomed by a warm, traditional layout that just feels right. Accent walls add personality, the formal dining room sets the stage for holidays and celebrations,

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    Debbi Rivero

    RE/MAX Advantage Realty

    (410) 406-7422

    110 Trafford Dr, Chestertown, MD 21620
  • /2

    $250,000

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft

    113 Pear Tree Point Rd, Chestertown, MD 21620

    OPPORTUNITY KNOCKS!! This home is being sold as-is and is ready for someone with vision and plenty of elbow grease. Located in Queen Anne's County on Pear Tree Point Rd, the property sits on a generous 2.08-acre lot bordered by farmland on one side of the road, offering peaceful views, and room to breathe. With wood floors, a spacious living room and a living/dining area, the bones are here --

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    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 373-5178

    113 Pear Tree Point Rd, Chestertown, MD 21620
  • /28

    $398,000 Open Sat 12PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,798 Sq Ft

    107 Boxwood Ln, Galena, MD 21635

    Welcome to 107 Boxwood Lane in the Dogwood Village community. This home is nicely situated at the end of a cul-de-sac with a spacious triangular lot. The backyard is nicely edged with foliage, making a private oasis. The home offers convenient one-floor living. Large open living space, stainless steel appliances, wood floors and natural light. A bonus sunroom is just steps away from the dining

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    John Burke

    Gunther-McClary Real Estate

    (410) 724-1207

    107 Boxwood Ln, Galena, MD 21635
  • /12

    $3,395,000 Coming Soon

    • 8 Beds
    • 6.5 Baths
    • 5,947 Sq Ft

    148 Vernick Ln, Church Hill, MD 21623

    With approximately 2,650 feet of private waterfront along Southeast Creek and sweeping views toward the Chester River, this exceptional 13.2-acre estate in the desirable Kennersley Farm community offers the rare combination of protected water, expansive acreage, and extraordinary privacy — complemented by a beautifully crafted main residence and detached carriage house.Originally constructed

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    Biana Arentz

    Coldwell Banker Realty

    (667) 303-1013

    148 Vernick Ln, Church Hill, MD 21623
  • /32

    $985,000

    • 4 Beds
    • 3.5 Baths
    • 3,803 Sq Ft

    115 Scott Rd, Warwick, MD 21912

    Nestled on 5 acres and overlooking 60 acres of beautiful community land, this 4 bedroom home offers a unique blend of privacy and access to nature. Enjoy the community dock on the Sassafras River, a deeded boat slip, and a jet ski lift, making it perfect for water enthusiasts. The partially finished basement features a walkout, providing extra living space and convenient access to the outdoors.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-7135

    115 Scott Rd, Warwick, MD 21912
  • /40

    $315,000

    • 2 Beds
    • 2 Baths
    • 1,520 Sq Ft

    10 Ericsson Ave Unit 37, Betterton, MD 21610

    Beach day... or boat day.......maybe pool day? Welcome to the “Jewel of the Chesapeake” in charming Betterton—where the Eastern Shore of Maryland living meets effortless waterfront luxury.This is a rare opportunity to own the ONLY condo currently available in Betterton, perfectly positioned with breathtaking, views of Betterton Beach and the expansive Chesapeake Bay, right at the mouth of the

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    Julie Strickler

    Remax Vision

    (410) 339-8749

    10 Ericsson Ave Unit 37, Betterton, MD 21610
  • /77

    $545,000

    • 4 Beds
    • 3.5 Baths
    • 3,300 Sq Ft

    226 Ash Wood Dr, Church Hill, MD 21623

    Amazing price on this beautifully upgraded, nearly-new home in Church Hill Hunt! Welcome to 226 Ash Wood Drive, a thoughtfully designed home built less than two years ago that offers all the benefits of new construction—without the wait. Located in the desirable Church Hill Hunt community, this move-in ready home combines modern finishes, smart home features, and comfortable everyday living. Step

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    Gretchen Wichlinski

    Compass

    (410) 705-7075

    226 Ash Wood Dr, Church Hill, MD 21623
  • /3

    $389,000

    • 3 Beds
    • 1.5 Baths
    • 2,055 Sq Ft

    202 Waldo Dr, Chestertown, MD 21620

    A Place Full of Possibility in Byford Development Tucked in the heart of the Byford community, just minutes from everything Chestertown has to offer, this welcoming rancher is ready for its next chapter. Step inside and feel the charm of traditional hardwood floors, the glow of a wood-burning fireplace in the spacious family room, and the comfort of a home that’s been well-loved. The layout flows

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 971-7157

    202 Waldo Dr, Chestertown, MD 21620
  • /9

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    12400 Woods Rd, Worton, MD 21678

    Tucked away along the quiet shores of Still Pond Creek, this cedar cabin offers a rare blend of privacy, comfort, and natural beauty. Surrounded by mature woods and set on a peaceful stretch of waterfront, this 1,944 square foot home features 3 bedrooms, 2 bathrooms, a spacious screened-in porch perfect for crab feasts, a private beach and pier with 2'+ MLW improved with bilk head installed by

    Stacy Kendall Cross Street Realtors LLC

    12400 Woods Rd, Worton, MD 21678
  • /117

    $799,000

    • 4 Beds
    • 3 Baths
    • 3,388 Sq Ft

    14540 Stirrup Ln, Galena, MD 21635

    Tucked away in the exclusive waterfront enclave of Fox Hole Estates, this serene retreat offers an exceptional blend of luxury, privacy, and natural beauty. Overlooking the beautiful Sassafras River, this beautifully renovated residence is designed to impress the discerning buyer seeking peace without compromise. The home’s inviting interior features rich hardwood floors, vaulted ceilings, and

    Ben Esh Astoria Realty Advisors LLC

    14540 Stirrup Ln, Galena, MD 21635
  • /70

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 2,941 Sq Ft

    721 Knight Island Rd, Earleville, MD 21919

    Exquisite 10 acre waterfront estate offering the perfect blend of broad lawns contrasted by a beautiful woodland glade. With over 500' frontage on Dowdel Creek this is a rare gem waiting to be explored. In addition to the stunning residence, there is an oversized 3 car garage plus a work studio complete with hvac and a powder room. Overall building size is 32' x 60'. This includes 36' for the

    Steve Parker L. C. Parker Real Estate

    721 Knight Island Rd, Earleville, MD 21919
  • /40

    $894,900

    • 5 Beds
    • 5 Baths
    • 5,256 Sq Ft

    850 Arthursville Rd, Hartly, DE 19953

    Thirteen acres of privacy, a 40x64 drive-through pole barn, owned solar, and a 5-bedroom Cape Cod with over 5,200 square feet of finished living space. Properties like this rarely come to market.The home delivers exceptional flexibility across multiple levels. Above grade, five bedrooms and five full bathrooms are spread across thoughtfully separated wings, giving every occupant genuine

    Scott Kompa EXP Realty, LLC

    850 Arthursville Rd, Hartly, DE 19953
  • /53

    $550,000

    • 4 Beds
    • 3.5 Baths
    • 3,816 Sq Ft

    103 Sutton Way, Chestertown, MD 21620

    103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and

    Liddy Campbell TTR Sotheby's International Realty

    103 Sutton Way, Chestertown, MD 21620
  • /37

    $295,000

    • 3 Beds
    • 1 Bath

    107 Longfellow Dr, Chestertown, MD 21620

    There is so much potential for this 3 bedroom, 1 bath ranch, in need of a little updating, with attached carport located in Chester Harbor. There is a full unfinished basement and a 3 car detached garage all situated on 2 parcels that include 5 lots. Chester harbor offers water access to Rosin Creek.

    Doug Ashley Doug Ashley Realtors, LLC

    107 Longfellow Dr, Chestertown, MD 21620
  • /21

    $480,000 Open House 5/07

    • 4 Beds
    • 2 Baths
    • 2,156 Sq Ft

    11944 Augustine Herman Hwy, Kennedyville, MD 21645

    Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences. From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying small-town

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    11944 Augustine Herman Hwy, Kennedyville, MD 21645
  • /43

    $449,000

    • 3 Beds
    • 2.5 Baths

    1 Idlewhile Ave Unit 4, Betterton, MD 21610

    Crew's Landing 3 bedroom Townhouse, located in Betterton, The Jewel of the Chesapeake. This 12 unit complex has become a premier waterfront community on the upper Bay. Located on a 5 acre setting of beautiful landscape offering carefree living. It includes a community dock and a great private sandy beach. The unit has had upgrades with wood plank tile floors, kitchen with granite countertops, and

    Ashton Kelley Gunther-McClary Real Estate

    1 Idlewhile Ave Unit 4, Betterton, MD 21610
  • /24

    $419,900

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft

    109 S College Ave, Chestertown, MD 21620

    Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors,

    Jeff Guthrie Taylor Properties

    109 S College Ave, Chestertown, MD 21620
  • /27

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft

    154 Longfellow Dr, Chestertown, MD 21620

    Located in the water-oriented community of Chester Harbor just outside of historic Chestertown, 154 Longfellow Drive offers the ideal blend of convenience and Eastern Shore living. This single-level home is situated on a cleared and fenced 0.34 acre-parcel and a voluntary HOA fee provides access to the community boat ramp and waterfront park. Less than a mile and a half from Route 213, enjoy

    Katie Stecklair Cross Street Realtors LLC

    154 Longfellow Dr, Chestertown, MD 21620
  • /51

    $1,279,000

    • 5 Beds
    • 3 Baths
    • 2,956 Sq Ft

    231 Richard Dr, Chestertown, MD 21620

    Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town

    Liddy Campbell TTR Sotheby's International Realty

    231 Richard Dr, Chestertown, MD 21620
  • /45

    $489,900

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    201 Ericsson Ave, Betterton, MD 21610

    Phenomenal 3.75 acres+- in sought after Betterton. The hidden bay front town retreat from the past.Rolling pasture like setting with specimen trees. Farmhouse style home with pinewood floors perched up high overlooking the property. Detached garage and 2 other large sheds on the property. Craftsman's dream. Deer and all other creatures abound. Short walk to town beach, gazebo and boat ramp.

    Jonathan Olsavsky Coldwell Banker Waterman Realty

    201 Ericsson Ave, Betterton, MD 21610
  • /73

    $1,600,000

    • 7 Beds
    • 6 Baths
    • 5,400 Sq Ft

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620

    **Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
  • /23

    $350,000

    • 7 Beds
    • 6 Baths
    • 850 Sq Ft

    117 N Water St Unit 2B, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 2B, Chestertown, MD 21620
  • /24

    $375,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 2A, Chestertown, MD 21620
  • /46

    $685,000

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft

    117 N Water St Unit 1A, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, Chestertown, MD 21620
  • /20

    $200,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    117 N Water St Unit 1B, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1B, Chestertown, MD 21620
  • /76

    $750,000

    • 6 Beds
    • 4 Baths
    • 5,277 Sq Ft

    118 Dabbling Ct, Church Hill, MD 21623

    Stunning, custom built beauty boasting over 5,200 SF of customized three-level living on 1.27 private acres at the end of a cul-de-sac, offering space, flexibility, and thoughtful design throughout.This newly listed 6-bedroom, 5-bath home features an airy, open floor-plan with a dramatic two-story foyer, formal dining room, private office, and main-level bedroom with full bath. The spacious

    Jennifer Chaney Chaney Homes, LLC

    118 Dabbling Ct, Church Hill, MD 21623
  • /38

    $385,000

    • 3 Beds
    • 2.5 Baths
    • 1,270 Sq Ft

    11981 Dewees Ln, Kennedyville, MD 21645

    Come see this home in the sought after community of Village at Kennedyville. This beautiful, updated 3 bedroom 2 and 1/2 bath home is awaiting it's next owner. As you enter this home you immediately feel the pride in ownership and notice the updates. From the bright open feel of the home and gourmet kitchen featuring stainless appliances with the refrigerator replaced in 2023, the dishwasher

    Edward Beres RE/MAX Executive

    11981 Dewees Ln, Kennedyville, MD 21645
  • /45

    $525,000

    • 5 Beds
    • 3.5 Baths
    • 3,932 Sq Ft

    218 Camelot Dr, Chestertown, MD 21620

    Picture Perfect Colonial in Coventry Farms – Chestertown, MarylandWelcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates

    Dee Dee McCracken Coldwell Banker Realty

    218 Camelot Dr, Chestertown, MD 21620
  • /51

    $949,500

    • 5 Beds
    • 3 Baths
    • 2,352 Sq Ft

    530 Kennersley Farm Ln, Church Hill, MD 21623

    Welcome to 530 Kennersley Farm Lane, nestled in the private waterfront community of Kennersley Farm.Set on 5 private acres along Island Creek, this property offers lots of privacy and nature. A long, tree-lined driveway leads you past mature landscaping and ample parking, where you can see views of the water. Inside, there is beautiful flooring and a bright, open layout. The kitchen features

    Christina Zerbe Coldwell Banker Realty

    530 Kennersley Farm Ln, Church Hill, MD 21623
  • /30

    $650,000

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

    131 Log Yard Ln, Townsend, DE 19734

    Beautiful 3-bedroom 2.5 bath home on 4.9 acres in the country. updated floors downstairs and landing upstairs. new blacktop driveway. new windows 2022 and new roof in 2012.A new hot water heater being installed. Professional pictures coming soon. Open house coming. Seller is related to the listing agent.

    Mary Ellen Landry Lester Realty

    131 Log Yard Ln, Townsend, DE 19734
  • /40

    $525,000

    • 5 Beds
    • 3.5 Baths
    • 3,504 Sq Ft

    311 Devon Dr, Chestertown, MD 21620

    REDUCED! 311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • /48

    $1,395,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /29

    $439,999

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft

    222 Mount Vernon Ave, Chestertown, MD 21620

    HIGHLY MOTIVATED SELLERS — bring us an offer! This historic 1916 home is comfortable, convenient, and move-in ready. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and walking distance from downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests.

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • /62

    $625,000

    • 2 Beds
    • 2.5 Baths
    • 4,054 Sq Ft

    13983 Turners Point Rd, Kennedyville, MD 21645

    Impeccably kept Kentmore Park home with a white picket fence. Over two acres with private rear yard for relaxation. Adorable brick outbuilding for storage, home office, man cave or she shed. Gazebo for al fresco dining, afternoon card games or just enjoying nature. Two additional sheds for storing just about anything. Habitat for many bird species in season. Owl, Heron and Eagle territory year

    Patricia Kern Gunther-McClary Real Estate

    13983 Turners Point Rd, Kennedyville, MD 21645
  • /29

    $3,200,000

    • 3 Beds
    • 3 Baths
    • 2,412 Sq Ft

    112 Open Meadow Ct, Clayton, DE 19938

    This is an almost 60 acre property with one main residence, one secondary residence, and 3ea 652’x67’, well-maintained chicken houses kept as clean as chicken houses can possibly be! There is still quite a bit of open land for expansion and possible income potential (ask about other opportunities). This would be an amazing multi-generational property or you could also live in the main house, and

    KATE Gleeson EXP Realty, LLC

    112 Open Meadow Ct, Clayton, DE 19938
  • /18

    $355,000

    • 3 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    27279 Jenny Hye Ln, Marydel, MD 21649

    Welcome to Your Peaceful Retreat!This 3-bedroom, 2.5-bath split-foyer home offers 1,488 sq. ft. of comfortable living space, plus a full basement and an attached one-car garage. With its classic brick-and-siding exterior, inviting front patio, and serene surroundings, this property blends warmth, character, and endless potential.Step inside and imagine the possibilities—a bright, open

    Hudson Post Keller Williams Select Realtors of Easton

    27279 Jenny Hye Ln, Marydel, MD 21649
  • /46

    $230,000

    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft

    26670 Maple Ave, Still Pond, MD 21667

    The listing includes 26670 Maple Avenue with a 1920 dwelling of 2024 SF on .54 acre of land as well as 26680 Maple Avenue dwelling of 1680 SF on .624 acre of land and a parcel of land 100 X 160. Both homes are in need of major repair; however, one will find potential. Final perc information for sewage system will be provided by Kent County Health Department when water table is acceptable which

    Debbie Meikle Doug Ashley Realtors, LLC

    26670 Maple Ave, Still Pond, MD 21667
  • /50

    $384,000

    • 5 Beds
    • 2.5 Baths
    • 3,371 Sq Ft

    6746 Quaker Neck Rd, Chestertown, MD 21620

    Michele Palmer Doug Ashley Realtors, LLC

    6746 Quaker Neck Rd, Chestertown, MD 21620
  • /5

    $685,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 3,505 Sq Ft

    441 Eagle Manor Dr, Church Hill, MD 21623

    House in picture is to be built. This floor plan is a 3-bedroom 2.5 bath layout. Finished bonus room upstairs would make great home office or craft room. Unfinished basement for even more space. Upstairs has a separate laundry room with cabinets and countertop. Large pantry alongside the kitchen perfect for all your supplies and storage. Kitchen has been designed to take full advantage of the

    Chris Haddaway Chesapeake Real Estate Associates, LLC

    441 Eagle Manor Dr, Church Hill, MD 21623
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