109

Chestertown, MD Homes for Sale

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  • 116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    /21

    $529,000

    • 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

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /41

    $569,000

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

    103 Landing Ln, Chestertown, MD 21620

    Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 981-2534

    103 Landing Ln, Chestertown, MD 21620
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /28

    $725,000

    • 3 Beds
    • 3 Baths

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

    Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

    117 N Water St Unit 1A, Chestertown, MD 21620
  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /20

    $185,000

    • Land
    • 1.95 Acres
    • $94,872 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, 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
    /28

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

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

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, Chestertown, MD 21620
  • 206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    /9

    $1,150,000

    • Land
    • 1.56 Acres
    • $737,179 per Acre

    206 Cannon St, Chestertown, MD 21620

    Extraordinary development opportunity in downtown historic Chestertown. Large parcel of land (1.56+/- acres) zoned C-2 (half R1 and half R5 zoning) many permitted uses such as Muliple-Family dwelling, Townhouses, professional and business offices, non-profit museums, and others. Includes 1 building (Warehouse) and property fronts on three streets. Excellent location-- just a few blocks to the

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 419-7633

    206 Cannon St, Chestertown, MD 21620
  • 21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    /25

    $179,000

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    21316 Persimmon Dr, Chestertown, MD 21620

    Two bedroom & one bath townhome with a nice view from the living room/patio area. Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio area and the back patio area. New carpet and fresh paint will update this property nicely. Covered storage for bikes/yard toys and more. The townhouse is all

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 708-2172

    21316 Persimmon Dr, Chestertown, MD 21620
  • 110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    /40

    $745,000

    • Studio
    • 2,492 Sq Ft

    110 S Mill St, Chestertown, MD 21620

    Beautiful home in historic Chestertown. This property can be a single family home, or two separate units. The larger apartment features a gourmet kitchen with a beautiful wood-top island and stainless steel appliances. The kitchen leads to the large formal dining room, featuring the original stone fireplace, updated with a gas insert. The living space is designed for both comfortable living

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 514-3490

    110 S Mill St, Chestertown, MD 21620
  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    /42

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Charm: Your Gateway toEastern Shore LivingCompletely Renovated Cottage with River Views & Endless PossibilitiesDiscover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifullytransformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristineChester River. Whether you're seeking a weekend escape, investment

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 282-1137

    134 Char Nor Manor Blvd, Chestertown, MD 21620
  • 300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    /30

    $1,198,000

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    300 Hickory Ln, Chestertown, MD 21620

    Welcome to Pheasantfield Farm, a 21- acre equestrian estate beautifully nestled on the Chester River. Fantastic location, ample privacy, and yet only a short drive, or boat ride, to historic Chestertown. The main home boasts 4 bedrooms and two and a half baths. The primary bedroom has a lovely view of the river, two walk-in closets and a large attached full bath. The spacious

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-6289

    300 Hickory Ln, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    /9

    $65,000

    • Land
    • 3 Acres
    • $21,667 per Acre

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620

    E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Call listing agent for more information regarding this offering. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 909-1378

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
  • 7961 Quaker Neck Rd, Chestertown, MD 21620
    7961 Quaker Neck Rd, Chestertown, MD 21620
    7961 Quaker Neck Rd, Chestertown, MD 21620
    /93

    $1,550,000

    • 5 Beds
    • 4 Baths
    • 4,167 Sq Ft

    7961 Quaker Neck Rd, Chestertown, MD 21620

    **Exquisite Waterfront Retreat on Chester River**Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre

    Agent Photo

    Gretchen Wichlinski

    Compass

    (443) 320-6559

    7961 Quaker Neck Rd, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    /22

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,315 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and second floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /22

    $998,000 New Construction

    • 3 Beds
    • 3.5 Baths

    226 S Water St, Chestertown, MD 21620

    Newly finished 3 Bedroom townhouses with nearly all the desired attributes of town living, with harbor and marina views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. No short term rental restrictions.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 376-5375

    226 S Water St, Chestertown, MD 21620
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $759,000 New Construction

    • 3 Beds
    • 3.5 Baths

    212 Landing Ln, Chestertown, MD 21620

    Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm.This elegant 3-bedroom, 2.5-bath residence is designed to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 883-7032

    212 Landing Ln, Chestertown, MD 21620
  • 724 Aldora Dr Unit 111, Chestertown, MD 21620
    724 Aldora Dr Unit 111, Chestertown, MD 21620
    724 Aldora Dr Unit 111, Chestertown, MD 21620
    /38

    $559,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    724 Aldora Dr Unit 111, Chestertown, MD 21620

    PRICE IMPROVEMENT ON THE HOME OF THE MONTHLuxury, End of Group, 4 Bedroom Villa with a walk-out lower level. The layout is welcoming and very functional. The main level boasts an oversized family room which is open to the kitchen and dining area. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 883-7905

    724 Aldora Dr Unit 111, Chestertown, MD 21620
  • 7514 Muirfield Dr, Chestertown, MD 21620
    7514 Muirfield Dr, Chestertown, MD 21620
    7514 Muirfield Dr, Chestertown, MD 21620
    /33

    $797,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,522 Sq Ft

    7514 Muirfield Dr, Chestertown, MD 21620

    Beautiful home in a prime location! Prestwick offers ample privacy while only a short distance from Historic District Chestertown and just off of the Chester River Yacht and Country Club's 10th tee. Recently constructed in 2023, the house offers three bedrooms, oak floors throughout, a gourmet kitchen, and ample room for entertaining, all on one floor! The kitchen was completed with stainless

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 206-3727

    7514 Muirfield Dr, Chestertown, MD 21620
  • 728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    /38

    $509,990 Open Sat 12PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    728 Aldora Dr Unit 113, Chestertown, MD 21620

    PRICE IMPROVEMENT ON THIS QUICK MOVE IN. Luxury 4 Bedroom Villa. The layout is welcoming and very functional. The main level boasts an oversized family room which is open to the kitchen and dining area. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 517-7657

    728 Aldora Dr Unit 113, Chestertown, MD 21620
  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    /90

    $2,750,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper,

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • 23620 Land's End Rd, Chestertown, MD 21620
    23620 Land's End Rd, Chestertown, MD 21620
    23620 Land's End Rd, Chestertown, MD 21620
    /30

    $4,850,000

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft

    23620 Land's End Rd, Chestertown, MD 21620

    80 private acres beautifully situated on the highly prized Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. One of only 4 properties on Orchard Point and sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to

    Stacy Kendall

    23620 Land's End Rd, Chestertown, MD 21620
  • 25800 Collins Ave, Chestertown, MD 21620
    25800 Collins Ave, Chestertown, MD 21620
    25800 Collins Ave, Chestertown, MD 21620
    /31

    $485,000

    • 3 Beds
    • 2 Baths
    • 2,162 Sq Ft

    25800 Collins Ave, Chestertown, MD 21620

    Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick rancher with good bones. 3 bedrooms, 2 full baths. The basement has a workshop space and garage. Hardwood floors. Spacious family room with woodstove. Nice screened-in porch and outdoor patio with a fire pit. Home is ready for your finishing touches. Near the Chester River Yacht and Country Club and just a

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    25800 Collins Ave, Chestertown, MD 21620
  • 515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    /37

    $509,900

    • 4 Beds
    • 2 Baths
    • 2,220 Sq Ft

    515 N Kent St, Chestertown, MD 21620

    Welcome to 515 N Kent Street in the heart of Chestertown! This charming two story home features a half-circle driveway, 1-car attached garage, and inviting brick patio leading to the front door. Step inside and you’ll love the gorgeous hardwood floors throughout the main level (2022). The formal living room showcases a wood-burning fireplace with a brick mantel, creating a warm and welcoming

    Jody Baker Cross Street Realtors LLC

    515 N Kent St, Chestertown, MD 21620
  • 200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    /35

    $745,000

    • 4 Beds
    • 3.5 Baths
    • 2,917 Sq Ft

    200 Washington Ave, Chestertown, MD 21620

    Every initial showing stated “what a great house but it is priced a little high!”. The house is still GREAT! This early 20th C gem of a traditional "Four Square" has been a Chestertown STAND-OUT RESIDENCE since originally crafted by acclaimed master builder Walter Pippin. The flawless flow of its' first floor, with discreet powder room, and the abundance of windows throughout make this corner

    Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, Chestertown, MD 21620
  • 103 Adela Way, Chestertown, MD 21620
    103 Adela Way, Chestertown, MD 21620
    103 Adela Way, Chestertown, MD 21620
    /90

    $595,000

    • 4 Beds
    • 3.5 Baths
    • 5,576 Sq Ft

    103 Adela Way, Chestertown, MD 21620

    Looking for a large spacious home in a lovely neighborhood that is close to downtown & shopping, then look no further! 3 Floors of living space, 4 - possibly 5 Bedrooms, 3 Full & 1 -1/2 Baths. As you enter into the foyer with space up to the top floor, brightly lit with a chandelier and oak wood flooring you can access the formal dining room and the formal living room on each side. Moving

    Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
  • 907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    /33

    $440,000

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft

    907 N Meadowview Dr, Chestertown, MD 21620

    Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space.Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly evenings. The eat-in kitchen provides plenty

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
  • 201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    /46

    $449,000

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

    201 Boundary Ave, Chestertown, MD 21620

    Discover this spacious home offering 3,100 sq ft of living space on a 1⁄2 acre lot with deeded access to the Chester River. Generously sized rooms and an inviting floor plan create an ideal setting for both everyday living and entertaining. The main level bedroom features a recently remodeled bath and large walk in closet. Enjoy the natural light and tranquil views from the sunroom, perfect for

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
  • 600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    /36

    $424,000

    • 3 Beds
    • 3 Baths
    • 1,300 Sq Ft

    600 Rosin Dr, Chestertown, MD 21620

    Nestled along the peaceful shores of Rosin Creek, this charming 3-bedroom, 2-bathroom waterfront cottage combines classic character with modern updates. Inside, the open floor plan creates a warm, inviting flow—perfect for everyday living or entertaining. The renovated kitchen features stylish finishes and connects seamlessly to the dining and living areas, all enhanced by updated flooring and

    Sarah King Cross Street Realtors LLC

    600 Rosin Dr, Chestertown, MD 21620
  • 251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    /54

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 3,935 Sq Ft

    251 Devon Dr, Chestertown, MD 21620

    Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that features a peninsula

    Debbie Meikle Doug Ashley Realtors, LLC

    251 Devon Dr, Chestertown, MD 21620
  • 165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    /59

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft

    165 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Views from Every Angle!Welcome to this stunning Colonial located on the Queen Anne’s County side of Chestertown, offering unmatched views of the Chester River and serene waterfront living.This spacious home features 4 large bedrooms, 2.5 bathrooms, and gorgeous hardwood floors throughout. Enjoy cozy nights by the wood-burning fireplace in the living room and enjoy

    Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
  • 26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, Chestertown, MD 21620
    /15

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    26933 Mallard Rd, Chestertown, MD 21620

    Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    26933 Mallard Rd, Chestertown, MD 21620
  • 206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    /54

    $648,750

    • 4 Beds
    • 3.5 Baths
    • 2,008 Sq Ft

    206 S Water St, Chestertown, MD 21620

    Just in time for the annual Downrigging Festival! See tall ships sailing the Chester River from your front porch and live in the heart of Chestertown's thriving Historic District! This versatile home has over 2,000 square feet of finished living space and was rebuilt and expanded with future customizations in mind!* The rear addition includes a sunroom/mudroom with a separate entrance connecting

    Beth Ostrander Doug Ashley Realtors, LLC

    206 S Water St, Chestertown, MD 21620
  • 201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    /23

    $470,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    201 Birch Run Rd, Chestertown, MD 21620

    This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted neighborhoods. One floor living makes things a breeze with this open and easy floor plan. Serious structural updates have been performed on the home, the crawl space has been encapsulated, and the kitchen and bathrooms have been remodeled. The home was also recently had the entire exterior painted and much

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    201 Birch Run Rd, Chestertown, MD 21620
  • 116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    /35

    $475,000

    • 3 Beds
    • 1.5 Baths
    • 2,767 Sq Ft

    116 Pine Chip Rd, Chestertown, MD 21620

    Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    116 Pine Chip Rd, Chestertown, MD 21620
  • 100 Adela Way, Chestertown, MD 21620
    100 Adela Way, Chestertown, MD 21620
    /2

    $515,000

    • 4 Beds
    • 3.5 Baths
    • 3,799 Sq Ft

    100 Adela Way, Chestertown, MD 21620

    Preparing for Market- Don't miss this. Stunning and well maintained home on a corner lot with fenced yard, finished basement, sauna room, private office and 2 car garage. Recently replaced: HVAC, Roof and Water Heater. More details to come- On Market by Sept 15, 2025.

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    100 Adela Way, Chestertown, MD 21620
  • 118 Little Harbor Way Unit 201, Chestertown, MD 21620
    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    /35

    $695,000

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft

    118 Little Harbor Way Unit 201, Chestertown, MD 21620

    An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and Chester River. It is nearly impossible for the body, mind and spirit of its residents and guests not to be "in a good place" on the cloudiest or most challenging of days. River House, with only five private residences, occupies the best real estate within

    Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, Chestertown, MD 21620
  • 23628 Canvasback Rd, Chestertown, MD 21620
    23628 Canvasback Rd, Chestertown, MD 21620
    23628 Canvasback Rd, Chestertown, MD 21620
    /5

    $15,000

    • Land
    • 0.34 Acre
    • $44,118 per Acre

    23628 Canvasback Rd, Chestertown, MD 21620

    Waterfront lot in the community of Chesapeake Landing, just outside of Chestertown. This lot has failed previous perc tests and is most likely not buildable.

    Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
  • 119 Darden Rd, Chestertown, MD 21620
    119 Darden Rd, Chestertown, MD 21620
    /2

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft

    119 Darden Rd, Chestertown, MD 21620

    Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by

    Solomon Zaldivar Compass

    119 Darden Rd, Chestertown, MD 21620
  • 23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    /30

    $379,900

    • 3 Beds
    • 1 Bath
    • 1,805 Sq Ft

    23110 Old Fairlee Rd, Chestertown, MD 21620

    Renovated Ranch Home in Fairlee. This home has been updated top to bottom. Recent updates include a new roof, new windows, new siding, new electrical service, new hot water heater, new air conditioner, new heater, updated kitchen with new cabinets, new appliances, granite countertops, updated bathroom with new tub, new vanity, new tile, new fixtures, new flooring, and paint throughout the house.

    Thomas Huston Real Broker LLC

    23110 Old Fairlee Rd, Chestertown, MD 21620
  • 111 Cee Jay Rd, Chestertown, MD 21620
    111 Cee Jay Rd, Chestertown, MD 21620
    111 Cee Jay Rd, Chestertown, MD 21620
    /38

    $359,900 Open Sat 1:30PM - 3:30PM

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft

    111 Cee Jay Rd, Chestertown, MD 21620

    Beautiful, like new rancher built in 2021 offers 4 bedrooms and 2 baths. Luxury vinyl tile throughout much of the house including the primary bedroom. Seller has upgraded all plumbing fixtures, added kitchen backsplash, added shiplap, fully fenced rear yard with vinyl fencing, and more. Open kitchen, dining and living area. Located 45 minutes from Bay Bridge with a short easy commute to

    Michelle Abplanalp Rosendale Realty

    111 Cee Jay Rd, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /69

    $559,000 Open Sat 10AM - 12PM

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

    103 Landing Ln, Chestertown, MD 21620

    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 rear den or office which could be

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 3

Maryland Kent County Chestertown

Real Estate & Homes for Sale in Chestertown, MD

Frequently Asked Questions Why Live in Chestertown

What is the average home price in Chestertown, MD?
Homes for sale in Chestertown, MD have an average home price of $446,711.
How many homes have sold over the last 12 months in Chestertown, MD?
93 homes have sold in Chestertown, MD over the last 12 months.
What are the most popular zip codes in Chestertown, MD?
The most popular zip codes in Chestertown, MD include 21620, 21678, 21623, 21645 and 21668.
What are the most popular neighborhoods in Chestertown, MD?
The most popular neighborhood in Chestertown, MD with the most homes for sale is Kingstown.
How much do you need to make to afford a house in Chestertown?
The median home price in Chestertown is $377,500. If you put a 20% down payment of $75,500 and had a 30-year fixed mortgage with an interest rate of 6.35%, your estimated principal and interest payment would be $1,880 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $81K a year to afford the median home price in Chestertown.
How are the schools in Chestertown, MD?
Chestertown, MD has highly rated public and private schools. Some of the best schools in Chestertown based on Niche Grades are H.H. Garnett Elementary School, Kent County High School and Chestertown Christian Academy. The neighborhood in Chestertown with the highest rated schools is Kingstown. Browse all the schools in Chestertown, MD to learn more.
Learn more about living in Chestertown

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 52 days on the market compared to the national average of 52 days. The median sale price for homes in Chestertown, MD over the last 12 months is $359,000, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$359,000
Median Single Family Sale Price
$385,000
Median Townhouse Sale Price
$289,500
Median 2 Bedroom Sale Price
$482,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$217
Number of Homes for Sale
35
Last 12 months Home Sales
93
Months of Supply
4.50
Median List Price
$377,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
How to Buy a Home How to Finance a Home How to Sell a Home

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