16

Homes in 21620 under $400,000

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  • 21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    /26

    $339,900

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft

    21125 Iowa Ave, Chestertown, MD 21620

    Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to call home. Inside, you’ll find a bright and inviting layout featuring a Florida Room, a spacious dining room with a cozy fireplace, and two comfortable bedrooms. The large living room is filled with natural light and showcases

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 405-2192

    21125 Iowa Ave, Chestertown, MD 21620
  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /24

    $320,000

    • 3 Beds
    • 1.5 Baths
    • 1,096 Sq Ft

    222 Dutchess Rd, Chestertown, MD 21620

    Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 927-1169

    222 Dutchess Rd, Chestertown, MD 21620
  • 202 Waldo Dr, Chestertown, MD 21620
    202 Waldo Dr, Chestertown, MD 21620
    202 Waldo Dr, Chestertown, MD 21620
    /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
  • 104 Flying Cloud Dr, Chestertown, MD 21620
    104 Flying Cloud Dr, Chestertown, MD 21620
    104 Flying Cloud Dr, Chestertown, MD 21620
    /31

    $399,900

    • 5 Beds
    • 3.5 Baths
    • 2,535 Sq Ft

    104 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to The Verona, a spacious three-story, move-in ready home offering over 2,500 square feet of thoughtfully designed living space. With five bedrooms and three and a half bathrooms, this home provides the perfect balance of comfort, functionality, and flexibility for modern living.Step inside to an inviting foyer that leads to the bright and open main living area, where the family room

    David Moore Real Broker, LLC

    104 Flying Cloud Dr, Chestertown, MD 21620
  • 217 Philosophers Terrace, Chestertown, MD 21620
    217 Philosophers Terrace, Chestertown, MD 21620
    217 Philosophers Terrace, Chestertown, MD 21620
    /25

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 1,404 Sq Ft

    217 Philosophers Terrace, Chestertown, MD 21620

    Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Chestertown location with thoughtful updates already in place. New roof (December 2025), central air unit (2022), and new carpet upstairs provide peace of mind, while classic features like hardwood floors, abundant natural light, and a wood-burning fireplace add warmth and character. The flexible layout

    Courtney Chipouras TTR Sotheby's International Realty

    217 Philosophers Terrace, Chestertown, MD 21620
  • 1517 Dudley Corners Rd, Millington, MD 21651
    1517 Dudley Corners Rd, Millington, MD 21651
    1517 Dudley Corners Rd, Millington, MD 21651
    /40

    $335,000

    • 6 Beds
    • 3 Baths
    • 2,948 Sq Ft

    1517 Dudley Corners Rd, Millington, MD 21651

    Take advantage of this irresistible opportunity to purchase 12 acres with 2 houses, a few outbuildings and a ton of potential. The property is located just off of Route 301, the Eastern Shore's main thoroughfare. The location is perfect for commuters looking to improve their quality of life or someone looking for a homestead close to Chestertown's waterfront historic district. The property is

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    1517 Dudley Corners Rd, Millington, MD 21651
  • 301 Lincoln Dr, Chestertown, MD 21620
    301 Lincoln Dr, Chestertown, MD 21620
    301 Lincoln Dr, Chestertown, MD 21620
    /40

    $309,900

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    301 Lincoln Dr, Chestertown, MD 21620

    Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of thoughtfully updated living space. The open floor plan creates a seamless flow between the living, dining, and kitchen areas — ideal for both everyday living and entertaining.The spacious kitchen features a central island, stainless steel appliances, and ample cabinetry, making it as functional as it is

    Heather Dolan Chesapeake Real Estate Associates, LLC

    301 Lincoln Dr, Chestertown, MD 21620
  • 154 Longfellow Dr, Chestertown, MD 21620
    154 Longfellow Dr, Chestertown, MD 21620
    154 Longfellow Dr, Chestertown, MD 21620
    /26

    $315,000

    • 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
  • 109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    /31

    $344,900

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    109 Wilton Rd, Chestertown, MD 21620

    Charming 3-bedroom, 2-bath rancher in the desirable Chester Harbor community. Situated on a spacious 0.76-acre lot, this home offers comfortable one-level living with a bright layout, private primary suite, and plenty of outdoor space to enjoy. Detached two-car garage provides ample storage and parking. Conveniently located just minutes from historic downtown Chestertown, marinas, shops, and

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • 117 N Water St Unit 2B, Chestertown, MD 21620
    117 N Water St Unit 2B, Chestertown, MD 21620
    117 N Water St Unit 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
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, 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
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /44

    $339,000

    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a

    Gregory Morris Cummings & Co. Realtors

    304 Hadaway Dr, Chestertown, MD 21620
  • 6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    /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
  • 720 Deep Landing Rd, Chestertown, MD 21620
    720 Deep Landing Rd, Chestertown, MD 21620
    /2

    $369,999 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,271 Sq Ft

    720 Deep Landing Rd, Chestertown, MD 21620

    Welcome to Pine Cove . A small enclave of homes close to the Chester River and the Deep Landing Boat Launch. This beautifully maintained home is just 9 years young. Boasting an open concept layout with soaring cathedral ceilings in the main living areas, a gourmet kitchen with granite counters and stainless-steel appliances, and hardwood floors throughout, you will fall in love with this idyllic

    Cornelia Fallon Coldwell Banker Waterman Realty

    720 Deep Landing Rd, Chestertown, MD 21620
  • 2032 Pondtown Rd, Chestertown, MD 21620
    2032 Pondtown Rd, Chestertown, MD 21620
    /2

    $325,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    2032 Pondtown Rd, Chestertown, MD 21620

    Coming Soon!

    Joie White Northrop Realty

    2032 Pondtown Rd, Chestertown, MD 21620
  • 10584 Klamath Rd, Chestertown, MD 21620
    10584 Klamath Rd, Chestertown, MD 21620
    /2

    $319,900 New Construction

    • 2 Beds
    • 2 Baths

    10584 Klamath Rd, Chestertown, MD 21620

    David Moore Real Broker, LLC

    10584 Klamath Rd, Chestertown, MD 21620
Maryland Kent County Chestertown 21620

Real Estate & Homes in 21620 under $400,000

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