44

Chestertown, MD Homes for Sale under $500,000

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  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /25

    $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

    222 Dutchess Rd, Chestertown, MD 21620
  • 7415 Wilkins Ln, Chestertown, MD 21620
    7415 Wilkins Ln, Chestertown, MD 21620
    7415 Wilkins Ln, Chestertown, MD 21620
    /23

    $229,000

    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    7415 Wilkins Ln, Chestertown, MD 21620

    This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    7415 Wilkins Ln, Chestertown, MD 21620
  • 117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    /18

    $295,000

    • 1 Bed
    • 1 Bath

    117 N Water St Unit 3B, Chestertown, MD 21620

    Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with river views, spend shaded afternoons beneath the trees, or retreat to the floating dock for sunbathing and quiet reflection. With an updated kitchen and bath, kayak storage, off-street parking, and downtown Chestertown’s shops

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    117 N Water St Unit 3B, Chestertown, MD 21620
  • 8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    /10

    $315,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    8706 Elm Rd, Chestertown, MD 21620

    * SELLER IS OFFERING A 1 YEAR HOME WARRANTY WITH ACCEPTABLE OFFER * Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large

    Andrew Meikle Doug Ashley Realtors, LLC

    8706 Elm Rd, Chestertown, MD 21620
  • 533 Round Top Rd, Chestertown, MD 21620
    533 Round Top Rd, Chestertown, MD 21620
    533 Round Top Rd, Chestertown, MD 21620
    /17

    $225,000

    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    533 Round Top Rd, Chestertown, MD 21620

    Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan ready for your personal updates and vision. Whether you’re looking for your

    Chris Craddock EXP Realty, LLC

    533 Round Top Rd, Chestertown, MD 21620
  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    /4

    $250,000

    • Land
    • 37,026 Sq Ft
    • $294,118 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • 10781 Fermoy Rd, Chestertown, MD 21620
    10781 Fermoy Rd, Chestertown, MD 21620
    10781 Fermoy Rd, Chestertown, MD 21620
    /54

    $429,900

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    10781 Fermoy Rd, Chestertown, MD 21620

    Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country

    David Moore Real Broker, LLC

    10781 Fermoy Rd, Chestertown, MD 21620
  • 109 Parma Rd, Chestertown, MD 21620
    109 Parma Rd, Chestertown, MD 21620
    109 Parma Rd, Chestertown, MD 21620
    /55

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    109 Parma Rd, Chestertown, MD 21620

    Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    109 Parma Rd, Chestertown, MD 21620
  • 24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    /25

    $315,000

    Coming Soon Sep 18
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    24775 Langford Rd, Chestertown, MD 21620

    Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space.The home

    Joseph A Zang III RE/MAX Chesapeake

    24775 Langford Rd, Chestertown, MD 21620
  • 123 Trafford Dr, Chestertown, MD 21620
    123 Trafford Dr, Chestertown, MD 21620
    123 Trafford Dr, Chestertown, MD 21620
    /45

    $375,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 2,504 Sq Ft

    123 Trafford Dr, Chestertown, MD 21620

    Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience.The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    123 Trafford Dr, Chestertown, MD 21620
  • 101 S College Ave, Chestertown, MD 21620
    101 S College Ave, Chestertown, MD 21620
    101 S College Ave, Chestertown, MD 21620
    /35

    $359,000

    $10K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,036 Sq Ft

    101 S College Ave, Chestertown, MD 21620

    This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space.Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled

    Michele Palmer Doug Ashley Realtors, LLC

    101 S College Ave, Chestertown, MD 21620
  • 7982 Radcliffe Rd, Chestertown, MD 21620
    7982 Radcliffe Rd, Chestertown, MD 21620
    7982 Radcliffe Rd, Chestertown, MD 21620
    /37

    $455,000

    $23K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,904 Sq Ft

    7982 Radcliffe Rd, Chestertown, MD 21620

    Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed

    Abigail Usilton Doug Ashley Realtors, LLC

    7982 Radcliffe Rd, Chestertown, MD 21620
  • 104 Conley Dr, Chestertown, MD 21620
    104 Conley Dr, Chestertown, MD 21620
    104 Conley Dr, Chestertown, MD 21620
    /26

    $239,900

    $7K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    104 Conley Dr, Chestertown, MD 21620

    Price Improvement! Now offered at $239,900Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a

    Heather Kooser Cummings & Co. Realtors

    104 Conley Dr, Chestertown, MD 21620
  • 956 Washington Ave, Chestertown, MD 21620
    956 Washington Ave, Chestertown, MD 21620
    956 Washington Ave, Chestertown, MD 21620
    /29

    $275,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    956 Washington Ave, Chestertown, MD 21620

    Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in

    Grace Crockett Doug Ashley Realtors, LLC

    956 Washington Ave, Chestertown, MD 21620
  • 129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    /15

    $480,000

    • 3 Beds
    • 2.5 Baths
    • 3,176 Sq Ft

    129 Trafford Dr, Chestertown, MD 21620

    PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light.The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space

    Teresa Queen Elevated Real Estate Solutions

    129 Trafford Dr, Chestertown, MD 21620
  • 104 Acorn Dr, Chestertown, MD 21620
    104 Acorn Dr, Chestertown, MD 21620
    104 Acorn Dr, Chestertown, MD 21620
    /26

    $275,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    104 Acorn Dr, Chestertown, MD 21620

    Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCA—blending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car

    Sarah King Cross Street Realtors LLC

    104 Acorn Dr, Chestertown, MD 21620
  • 115 Metcalf Rd, Chestertown, MD 21620
    115 Metcalf Rd, Chestertown, MD 21620
    115 Metcalf Rd, Chestertown, MD 21620
    /10

    $259,900

    New Construction Open Thu 6PM - 7PM
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    115 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with

    David Moore Real Broker, LLC

    115 Metcalf Rd, Chestertown, MD 21620
  • 23208 Buck Neck Rd, Chestertown, MD 21620
    23208 Buck Neck Rd, Chestertown, MD 21620
    23208 Buck Neck Rd, Chestertown, MD 21620
    /35

    $349,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    23208 Buck Neck Rd, Chestertown, MD 21620

    Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price.Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and

    David Moore Real Broker, LLC

    23208 Buck Neck Rd, Chestertown, MD 21620
  • 23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    /27

    $385,000

    • 4 Beds
    • 3 Baths
    • 2,630 Sq Ft

    23043 Bay Shore Spur, Chestertown, MD 21620

    Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural

    Robin Fithian Rock Hall Properties Real Estate

    23043 Bay Shore Spur, Chestertown, MD 21620
  • 10540 Tonopah Rd, Chestertown, MD 21620
    10540 Tonopah Rd, Chestertown, MD 21620
    10540 Tonopah Rd, Chestertown, MD 21620
    /21

    $269,000

    Open House 9/19 $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    10540 Tonopah Rd, Chestertown, MD 21620

    Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

    Michele Palmer Doug Ashley Realtors, LLC

    10540 Tonopah Rd, Chestertown, MD 21620
  • 8630 Elm Rd, Chestertown, MD 21620
    8630 Elm Rd, Chestertown, MD 21620
    8630 Elm Rd, Chestertown, MD 21620
    /45

    $424,900

    $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    8630 Elm Rd, Chestertown, MD 21620

    Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore.The home offers five generously sized bedrooms, providing comfortable space for family,

    Lawrence Lessin Save 6, Incorporated

    8630 Elm Rd, Chestertown, MD 21620
  • 115 Chester Arms Dr, Chestertown, MD 21620
    115 Chester Arms Dr, Chestertown, MD 21620
    /2

    $263,000

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft

    115 Chester Arms Dr, Chestertown, MD 21620

    Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own.The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown

    Jarnell Foster Samson Properties

    115 Chester Arms Dr, 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

    • 1 Bed
    • 1 Bath
    • 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
  • 104 Lincoln Dr, Chestertown, MD 21620
    104 Lincoln Dr, Chestertown, MD 21620
    104 Lincoln Dr, Chestertown, MD 21620
    /5

    $300,000

    Open Sun 11AM - 1PM Coming Soon Sep 11
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    104 Lincoln Dr, Chestertown, MD 21620

    Coming Soon to Chestertown! This adorable rancher will soon be at the top of your "favorites" list, with a welcoming interior and plenty to love outside. Set on a spacious corner lot, you'll find a long driveway, new paver patio, vinyl privacy fencing, playset and room to roam, while the inside features a beautiful kitchen, spacious living room and updated bathroom. Cute, low maintenance and just

    Crystal Smith RE/MAX Executive

    104 Lincoln Dr, Chestertown, MD 21620
  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /7

    $225,000

    • Land
    • 37,897 Sq Ft
    • $258,621 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.87± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic.There is also

    Hayley Norris Select Land & Homes, LLC

    3 Haacke 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

    $339,000

    $106K PRICE DROP
    • 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
  • 217 Edmore Rd, Chestertown, MD 21620
    217 Edmore Rd, Chestertown, MD 21620
    217 Edmore Rd, Chestertown, MD 21620
    /36

    $345,000

    • 3 Beds
    • 1.5 Baths
    • 1,398 Sq Ft

    217 Edmore Rd, Chestertown, MD 21620

    Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then.Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings.

    Michele Palmer Doug Ashley Realtors, LLC

    217 Edmore Rd, Chestertown, MD 21620
  • 1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    /25

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,476 Sq Ft

    1010 Twin Ct, Chestertown, MD 21620

    Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but

    Jason Dey Kevin Dey Realty

    1010 Twin Ct, Chestertown, MD 21620
  • 201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    /3

    $300,000

    • Land
    • 4,356 Sq Ft
    • $3,000,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • 121 Metcalf Rd, Chestertown, MD 21620
    121 Metcalf Rd, Chestertown, MD 21620
    121 Metcalf Rd, Chestertown, MD 21620
    /10

    $264,900

    New Construction
    • 3 Beds
    • 1.5 Baths

    121 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in

    David Moore Real Broker, LLC

    121 Metcalf Rd, Chestertown, MD 21620
  • 0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    /9

    $450,000

    • Land
    • 12,477 Sq Ft
    • $1,570,925 per Acre

    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620

    Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /70

    $499,999

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • 213 Byford Dr, Chestertown, MD 21620
    213 Byford Dr, Chestertown, MD 21620
    213 Byford Dr, Chestertown, MD 21620
    /39

    $372,000

    $8K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,277 Sq Ft

    213 Byford Dr, Chestertown, MD 21620

    Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other

    Grace Crockett Doug Ashley Realtors, LLC

    213 Byford Dr, Chestertown, MD 21620
  • 7464 Shortall St, Chestertown, MD 21620
    7464 Shortall St, Chestertown, MD 21620
    7464 Shortall St, Chestertown, MD 21620
    /32

    $304,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    7464 Shortall St, Chestertown, MD 21620

    Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy.The laundry room is conveniently located just off the kitchen and includes a separate exterior entrance. Step

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    7464 Shortall St, 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
  • 0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    /9

    $350,000

    • Land
    • 9,380 Sq Ft
    • $1,625,200 per Acre

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620

    Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops,

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
  • 0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    /23

    $200,000

    • Land
    • 5.81 Acres
    • $34,423 per Acre

    0 Round Top Rd, Chestertown, MD 21620

    This is a unique opportunity to invest in cleared and level acreage just off one of the Eastern Shore's commercial corridors and a few minutes from Downtown Chestertown. Suburban Commercial Zoning allows for a variety of possible uses.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 Round Top Rd, Chestertown, MD 21620
  • 200 Manor Ave, Chestertown, MD 21620
    200 Manor Ave, Chestertown, MD 21620
    200 Manor Ave, Chestertown, MD 21620
    /34

    $325,000

    • 4 Beds
    • 2 Baths
    • 2,198 Sq Ft

    200 Manor Ave, Chestertown, MD 21620

    A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and

    Liddy Campbell TTR Sotheby's International Realty

    200 Manor Ave, Chestertown, MD 21620
  • 7482 Poplar Ave, Chestertown, MD 21620
    7482 Poplar Ave, Chestertown, MD 21620
    7482 Poplar Ave, Chestertown, MD 21620
    /40

    $275,000

    • 3 Beds
    • 1 Bath
    • 975 Sq Ft

    7482 Poplar Ave, Chestertown, MD 21620

    Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite

    Lona Todd Taylor Properties

    7482 Poplar Ave, Chestertown, MD 21620
  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /66

    $489,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors.Forced

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 2

Maryland Kent County

Real Estate & Homes in Chestertown, MD under $500,000

Home Prices in Chestertown, MD

The median home sale price in Chestertown, MD is $367,500, up 2% year-over-year. Homes in Chestertown sell in 48 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$367,500
Median Single Family Sale Price
$379,900
Median Townhouse Sale Price
$264,900
Median 2 Bedroom Sale Price
$359,000
Median 1 Bedroom Sale Price
$295,000
Average Price Per Sq Ft
$218
Number of Homes for Sale
34
Last 12 months Home Sales
104
Months of Supply
3.90
Median List Price
$372,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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