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Chestertown, MD Homes for Sale with Garage

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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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    /39

    $949,900

    • 3 Beds
    • 2 Baths
    • 2,600 Sq Ft

    492 Pear Tree Point Rd, Chestertown, MD 21620

    Great opportunity to own a waterfront property on the scenic Chester River! This beautifully landscaped 3 bedroom, 2 bath home with a wraparound porch offers stunning views. There is an additional partially finished 700+/- sq ft space over the garage, filled with natural light and river views, ideal for extra bedrooms with bath, master bedroom or an in-law suite. Tucked away in a peaceful,

    Leo Kuneman Meredith Fine Properties

    492 Pear Tree Point Rd, 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
  • 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
  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    /22

    $549,000

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    101 Birch Run Rd, Chestertown, MD 21620

    A sleek, thoughtfully executed renovation with clean lines and a minimalist aesthetic—sure to impress even the most discerning buyer... Located in Chestertown's coveted Mile Tree Village community, this newly updated 3-bedroom, 2-bath rancher with oversized 2-car garage features a New Encapsulated Crawl Space, New Roof with 50-year shingles and a transferable warranty, new water and sewer lines

    Stacy Kendall Cross Street Realtors LLC

    101 Birch Run Rd, Chestertown, MD 21620
  • 26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    /32

    $699,000

    • 2 Beds
    • 2 Baths
    • 1,966 Sq Ft

    26889 Morgnec Rd, Chestertown, MD 21620

    This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
  • 11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    /67

    $659,000 Open House 10/05

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft

    11040 Kylie Ln, Chestertown, MD 21620

    Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, 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
  • 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
  • 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
  • 10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    /50

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,942 Sq Ft

    10751 Millbrook Dr, Chestertown, MD 21620

    Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another

    Linda Austin Long & Foster Real Estate, Inc.

    10751 Millbrook Dr, 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
  • 23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    /27

    $375,000

    • 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
  • 907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    /33

    $440,000 Open House 10/05

    • 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
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    /16

    $167,000

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft

    141 Prospect St, Chestertown, MD 21620

    INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find!Located just minutes from Chestertown and Washington College. Plenty of space and character, it’s a rare opportunity to create something

    Jeff Guthrie Cross Street Realtors LLC

    141 Prospect St, 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
  • 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
  • 10674 Kasota Rd, Chestertown, MD 21620
    10674 Kasota Rd, Chestertown, MD 21620
    10674 Kasota Rd, Chestertown, MD 21620
    /34

    $309,999

    • 2 Beds
    • 1 Bath
    • 1,350 Sq Ft

    10674 Kasota Rd, Chestertown, MD 21620

    Welcome to 10674 Kasota Rd – Your Tranquil Masterpiece on the Chesapeake's Edge. Nestled in the serene enclave of Chesapeake Landing near Chestertown, this charming 2-bed, 1-bath ranch-style home invites you to reimagine rural living on nearly 0.6 acres of lush landscape. With 1,350 sq ft of one–level living, the brick exterior and detached 2–car garage offers timeless appeal and solid bones with

    Andrew Kruzienski Long & Foster Real Estate, Inc.

    10674 Kasota Rd, Chestertown, MD 21620
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /52

    $1,395,500

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

    105 High St, Chestertown, MD 21620

    ***Photos reflect the progress as of 3 months ago. The property is now nearly completed and is simply awaiting a finishing coat of paint and a layer of sod on the newly fenced in rear yard. A superb level of craftsmanship and scope of work not to be missed.***Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored legacy

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /59

    $415,000

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft

    128 Edmore Rd, Chestertown, MD 21620

    Your Dream Eastern Shore Retreat Awaits!Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting.Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
  • 23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    /77

    $4,850,000

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

    23620 Lands End Rd, Chestertown, MD 21620

    Hartwell Estate features 80 private acres with pristine, panoramic views on the mouth of the Langford and Chester River. This light filled custom built home and property captures the essence of serene living on Maryland's Eastern Shore. One of only 4 premiere properties at the end of Quaker Neck, often called "Kent County's Gold Coast" is sited to take advantage of the natural landscape with

    Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
  • 109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    /31

    $349,900

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

    109 Wilton Rd, Chestertown, MD 21620

    Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike.The home boasts a

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • 23393 Cacaway Farm Ln, Chestertown, MD 21620
    23393 Cacaway Farm Ln, Chestertown, MD 21620
    23393 Cacaway Farm Ln, Chestertown, MD 21620
    /45

    $1,195,000

    • 3 Beds
    • 3.5 Baths
    • 4,446 Sq Ft

    23393 Cacaway Farm Ln, Chestertown, MD 21620

    **Exclusive Waterfront Craftsman Home with Sandy Beach – A Rare Opportunity**Nestled on the serene East Fork of Langford Creek/Bay, this stunning 3-bedroom Craftsman-style home offers the perfect blend of comfort, privacy, and natural beauty. With approximately150 feet of shoreline and a sandy beach, this property is a true waterfront gem.**Key Features:**- **Spacious Great

    Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, 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
  • 221 Richard Dr, Chestertown, MD 21620
    221 Richard Dr, Chestertown, MD 21620
    221 Richard Dr, Chestertown, MD 21620
    /41

    $385,000 Coming Soon

    • 2 Beds
    • 2.5 Baths
    • 1,711 Sq Ft

    221 Richard Dr, Chestertown, MD 21620

    With almost every inch updated since 2012 - from the roof to the floors - this adorable two bedroom, two and half bath cottage is turnkey. The luxury primary suite, added in 2014 by a sought-after custom contractor, has tall ceilings, a cozy bay window seat, walk-in closet, en-suite bath with heated tile flooring, and spa shower. The cozy family room with wood-burning fireplace opens to the

    Liddy Campbell TTR Sotheby's International Realty

    221 Richard Dr, Chestertown, MD 21620
  • 126 Char Nor Manor Blvd, Chestertown, MD 21620
    126 Char Nor Manor Blvd, Chestertown, MD 21620
    126 Char Nor Manor Blvd, Chestertown, MD 21620
    /4

    $349,000 Open Sat 1:30PM - 3:30PM

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft

    126 Char Nor Manor Blvd, Chestertown, MD 21620

    *Please join us for our Open House Saturday, September 20th from 1:30pm-3:30pm*This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience, and functionality that has major upgrades including Fresh Paint throughout, Renovated Primary Bath and New carpet. The bonus office room is an essential for remote work! The property also features a large 2-car

    Crystal Smith RE/MAX Executive

    126 Char Nor Manor Blvd, Chestertown, MD 21620
  • 110 Tuxedo Rd, Chestertown, MD 21620
    110 Tuxedo Rd, Chestertown, MD 21620
    /2

    $275,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    110 Tuxedo Rd, Chestertown, MD 21620

    YOUR DIAMOND IN ROUGH.........Home is original and needs updating through out....Priced to sell. Good bones, will need a buyer with vision. Main level has a large eat in kitchen, living room area and laundry room. Upper level has 3 bedrooms, 2 full bath; including master on suite. Large deck and fenced in back yard. Minutes from The Chester Bridge.

    Vince Stonesifer Cummings & Co. Realtors

    110 Tuxedo Rd, Chestertown, MD 21620
Maryland Kent County Chestertown

Homes for Sale with Garage in Chestertown, MD

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

In Chestertown, there are currently 40 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Chestertown, MD and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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