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Chestertown, MD Houses 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

    $519,000

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

    116 Harlan Loop, Chestertown, MD 21620

    $$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$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

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • 247 Blakefield Dr, Chestertown, MD 21620
    247 Blakefield Dr, Chestertown, MD 21620
    247 Blakefield Dr, Chestertown, MD 21620
    /17

    $425,000

    • 3 Beds
    • 3 Baths
    • 2,572 Sq Ft

    247 Blakefield Dr, Chestertown, MD 21620

    Unlock the door to your future with an exclusive offer: Qualify for an exceptional 5.05% financing rate and $2,300 per month payment for one year. $7,000 lender-specific grant available on this property OR $21,250 in down payment assistance meaning no down payment is required. ARM financing also available at 5.25% rate for 5 years. Purchase this home and receive a FREE, 1-year home warranty plus

    Agent Photo

    Vinny Steo

    Your Home Sold Guaranteed Realty

    (443) 706-8420

    247 Blakefield Dr, 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
  • 7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    /51

    $770,000

    • 4 Beds
    • 2.5 Baths
    • 3,248 Sq Ft

    7844 Chester Ct, Chestertown, MD 21620

    Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 648-9684

    7844 Chester Ct, Chestertown, MD 21620
  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /24

    $320,000

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

    222 Dutchess Rd, Chestertown, MD 21620

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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 927-1169

    222 Dutchess Rd, Chestertown, MD 21620
  • 107 Malone Ave, Chestertown, MD 21620
    107 Malone Ave, Chestertown, MD 21620
    107 Malone Ave, Chestertown, MD 21620
    /27

    $290,000

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft

    107 Malone Ave, Chestertown, MD 21620

    Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bedroom, 1 Bath home is ready for you to make new memories, grow your family or downsize while enjoying single level living. Hardwood Floors throughout the living room and bedrooms have recently all been refinished. Through the front door is the well-lit family room with a large bay

    Agent Photo

    Barbara McPhail

    Douglas Realty LLC

    (410) 705-2953

    107 Malone Ave, 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

    $285,000

    • 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
  • 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
    /29

    $1,800,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

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

    **Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    /25

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    0 Little Harbor Way Unit 1, Chestertown, MD 21620

    Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath,

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 835-9021

    0 Little Harbor Way Unit 1, 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

    $2,500,000

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

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Price Improvement! 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

    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 Cross Street Realtors LLC

    23620 Land's End Rd, Chestertown, MD 21620
  • 311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    /40

    $598,000

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

    311 Devon Dr, Chestertown, MD 21620

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

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • 121 Primrose Rd, Chestertown, MD 21620
    121 Primrose Rd, Chestertown, MD 21620
    121 Primrose Rd, Chestertown, MD 21620
    /22

    $399,000 Open House 12/06

    • 3 Beds
    • 2.5 Baths
    • 2,034 Sq Ft

    121 Primrose Rd, Chestertown, MD 21620

    Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a .345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown. Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright living area, a classic

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    121 Primrose Rd, Chestertown, MD 21620
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /44

    $425,000

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

    304 Hadaway Dr, Chestertown, MD 21620

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

    Gregory Morris Cummings & Co. Realtors

    304 Hadaway Dr, Chestertown, MD 21620
  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /29

    $470,000

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

    222 Mount Vernon Ave, Chestertown, MD 21620

    Motivated sellers - bring us an offer! This historic 1916 home is charming inside and out. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and a short stroll to downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests. Gorgeous original heart-pine hardwood

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • 10230 John Carvill Rd, Chestertown, MD 21620
    10230 John Carvill Rd, Chestertown, MD 21620
    10230 John Carvill Rd, Chestertown, MD 21620
    /41

    $750,000

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft

    10230 John Carvill Rd, Chestertown, MD 21620

    Tremendously charming historic house, sensitively restored, a short distance from Great Oak Marina. Beautiful original 18th century pine floors, mantel pieces, six-panel doors and built-in cupboard. House was originally two small historic houses located in the village of Church Creek, Dorchester County, Maryland, moved to current location ca.1980. Private yard and garden. Chestertown and Rock

    Robert G. Shannahan Shoreline Realty

    10230 John Carvill Rd, Chestertown, MD 21620
  • 109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    /26

    $449,900 Open Sat 11AM - 1PM

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

    109 S College Ave, Chestertown, MD 21620

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

    Jeff Guthrie Cross Street Realtors LLC

    109 S College Ave, Chestertown, MD 21620
  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /53

    $499,900

    • 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. 1⁄2 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

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • 206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    /46

    $619,000

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

    206 S Water St, Chestertown, MD 21620

    Live in the heart of Chestertown’s Historic District—see your boat from your front porch!Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story waterview deck—built

    Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    /38

    $499,999

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

    101 Birch Run Rd, Chestertown, MD 21620

    Welcome to 101 Birch Run Rd., Chestertown, MD! 3 Bedrooms | 2 Full Baths | Oversized 2-Car Garage | .42 AcresDiscover this stunning full-brick rancher located in the heart of historic Chestertown! Every inch of this 3-bedroom, 2-bath home has been completely updated with a sophisticated modern flair while maintaining an inviting, boutique-style warmth throughout.Step inside to find a

    Julie Strickler Remax Vision

    101 Birch Run Rd, Chestertown, MD 21620
  • 100 Adela Way, Chestertown, MD 21620
    100 Adela Way, Chestertown, MD 21620
    100 Adela Way, Chestertown, MD 21620
    /71

    $515,000

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

    100 Adela Way, Chestertown, MD 21620

    *Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn.Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    100 Adela Way, 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

    $499,900

    • 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

    $695,000 Open House 12/06

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

    200 Washington Ave, Chestertown, MD 21620

    Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of a traditional "Four Square". This prominent STAND-OUT RESIDENCE, crafted by acclaimed master builder Walter Pippin, extends a warm welcome to anyone driving (only 25mph please!) or strolling from the college campus to town, along the historically scenic Washington Avenue. The gracious flow of its' first

    Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, 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

    NO HOA OR FRONT FEES: 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

    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
    /67

    $429,999

    • 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
  • 204 Rolling Rd, Chestertown, MD 21620
    204 Rolling Rd, Chestertown, MD 21620
    204 Rolling Rd, Chestertown, MD 21620
    /40

    $370,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 2 Baths
    • 2,296 Sq Ft

    204 Rolling Rd, Chestertown, MD 21620

    Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    204 Rolling Rd, Chestertown, MD 21620
  • 108 Flying Cloud Dr, Chestertown, MD 21620
    108 Flying Cloud Dr, Chestertown, MD 21620
    108 Flying Cloud Dr, Chestertown, MD 21620
    /21

    $375,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    108 Flying Cloud Dr, Chestertown, MD 21620

    Simply, beautifully done! A MUST see! UPGRADED 2023-built Smart Home, tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living spaces, while the laundry room offers added

    Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
  • 611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    /18

    $299,000

    • 2 Beds
    • 1.5 Baths
    • 920 Sq Ft

    611 Cannon St, Chestertown, MD 21620

    This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing

    Hayley Norris Select Land & Homes, LLC

    611 Cannon St, Chestertown, MD 21620
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /59

    $1,395,500 Open Sat 11AM - 1PM

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

    105 High St, Chestertown, MD 21620

    This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House. Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 112 Silver Heel Dr, Chestertown, MD 21620
    112 Silver Heel Dr, Chestertown, MD 21620
    112 Silver Heel Dr, Chestertown, MD 21620
    /43

    $369,900

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft

    112 Silver Heel Dr, Chestertown, MD 21620

    Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space. The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level also includes a convenient first-floor laundry and a powder room. The kitchen is equipped with

    Federico Busacca EXP Realty, LLC

    112 Silver Heel Dr, Chestertown, MD 21620
  • 318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    /21

    $269,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    318 Lincoln Dr, Chestertown, MD 21620

    Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    318 Lincoln Dr, Chestertown, MD 21620
  • 10121 Fairlee Rd, Chestertown, MD 21620
    10121 Fairlee Rd, Chestertown, MD 21620
    10121 Fairlee Rd, Chestertown, MD 21620
    /67

    $2,350,000

    • 6 Beds
    • 5 Baths
    • 4,954 Sq Ft

    10121 Fairlee Rd, Chestertown, MD 21620

    Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers,

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    10121 Fairlee Rd, Chestertown, MD 21620
  • 8833 Georgetown Rd, Chestertown, MD 21620
    8833 Georgetown Rd, Chestertown, MD 21620
    8833 Georgetown Rd, Chestertown, MD 21620
    /47

    $314,000

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft

    8833 Georgetown Rd, Chestertown, MD 21620

    Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on a .387-acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located just

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    8833 Georgetown 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

    $359,900

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

    23110 Old Fairlee Rd, Chestertown, MD 21620

    Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impressed by this stunning ranch home that has undergone a complete, top-to-bottom renovation! Offering 1800 sq. ft. of newly renovated finished interior space, this property is much bigger than it looks and provides true move-in ready convenience with zero deferred maintenance. Upgrades Inside & Out! Enjoy peace

    Thomas Huston Real Broker LLC

    23110 Old Fairlee 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
  • 23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    /27

    $325,000

    • 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
  • 5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    /7

    $110,000

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft

    5700 Johnsontown Rd, Chestertown, MD 21620

    Serene 2-acre partially cleared wooded lot with existing 1900-built home, in need of major repair or possible tear-down. Value is in the land. No interior access – partial roof and floor collapse. Sellers accept no liability and are held harmless.Property includes well and septic (buyer to verify), detached building and shed. Close to water and surrounded by peace and privacy. Sold as-is;

    Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
  • 108 S Kent St, Chestertown, MD 21620
    108 S Kent St, Chestertown, MD 21620
    108 S Kent St, Chestertown, MD 21620
    /19

    $315,000

    • 1 Bed
    • 1.5 Baths
    • 936 Sq Ft

    108 S Kent St, Chestertown, MD 21620

    Price improvement! Cute as a button in the historic district on South Kent St. This 1-bedroom, 1.5 bath home is in the center of town, within walking distance to the farmers market and all the shops and restaurants. Just 4 blocks from Chestertown's waterfront promenade. Upstairs is a large, sun-filled room with a spacious closet that serves as an office. It could also be a den or sitting room.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    108 S Kent St, 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

Showing Results 1 - 40, Page 1 of 2

Maryland Kent County Chestertown

Houses for Sale in Chestertown, MD

Why Live in Chestertown

Chestertown, Maryland, is a historic community on the Chester River, known for its maritime heritage and charming downtown. Founded in 1706, Chestertown was once a bustling port and remains a popular destination for homebuyers seeking a quieter lifestyle away from larger cities like Washington or Philadelphia. The town features a mix of Victorian homes downtown and waterfront properties, with river access being a significant draw. Residents enjoy boating on the river, and many homes feature private docks. The private Chester River Yacht & Country Club offers additional amenities such as an 18-hole golf course and a marina. Local parks like Wilmer Park provide walking trails and playgrounds, while the Wayne Gilchrest Trail caters to bikers and joggers. Downtown Chestertown is pedestrian-friendly, hosting boutiques, galleries and locally owned restaurants. Annual events like the Chestertown Tea Party Festival and the Sultana Downrigging Festival celebrate the town's rich history. Washington College, a small liberal arts institution, adds to the vibrant atmosphere. The University of Maryland Shore Medical Center provides health care services, including an emergency room. Chestertown is within driving distance of Baltimore, 75 miles away, and Baltimore/Washington International Airport. With its blend of historic charm, riverfront recreation and local amenities, Chestertown offers a unique living experience.

Learn more about living in Chestertown

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 51 days on the market compared to the national average of 53 days. The median sale price for homes in Chestertown, MD over the last 12 months is $365,000, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$365,000
Median Single Family Sale Price
$385,000
Median Townhouse Sale Price
$289,500
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$215
Number of Homes for Sale
35
Last 12 months Home Sales
91
Months of Supply
4.60
Median List Price
$372,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 49 houses for sale, offering an array of options for potential buyers. With houses priced between $62,400 to $4,850,000, there's a range to accomodate every budget. As of November, 2025 the median home price in Chestertown is $372,500, while the average sale price is $425,247, offering insights into the local housing market. On average, houses spend 51 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale 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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