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Homes for Sale in 21620

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  • 105 Pearl Creek Ln, Chestertown, MD 21620
    105 Pearl Creek Ln, Chestertown, MD 21620
    105 Pearl Creek Ln, Chestertown, MD 21620
    /73

    $449,000 Open Sat 10AM - 12PM

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

    105 Pearl Creek Ln, Chestertown, MD 21620

    (Open House January 31 from 10:00 - 12:00) Welcome to your private Eastern Shore retreat on 1.37 acres. Built in 2018, this beautiful custom one-level home is thoughtfully designed for relaxed, everyday living and effortless entertaining. Sun-filled and inviting, the open layout creates a warm, comfortable atmosphere—perfect for gathering with family and friends or enjoying quiet moments at home.

    Lona Todd Taylor Properties

    105 Pearl Creek 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
    /34

    $675,000 Coming Soon

    • 2 Beds
    • 2.5 Baths
    • 1,600 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 the Chester River. Here, body, mind, and spirit naturally align - it's simply impossible not to feel balance. River House, with only five private residences, occupies the best real estate within this prized, friendly and well managed neighborhood called

    Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, Chestertown, MD 21620
  • 112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    /4

    $249,500 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    112 Metcalf Rd, Chestertown, MD 21620

    Less than three years old, this affordable end-unit townhome is ready for you to call HOME! Offering a spacious 1,280-sq-ft floor plan with durable LVP flooring throughout the first floor. Enjoy a bright, open-concept living area where the living room flows into the kitchen, featuring a large island, stainless steel appliances, granite countertops, and white shaker cabinets. Step outside to a

    April Heim Rosendale Realty

    112 Metcalf Rd, Chestertown, MD 21620
  • 109 S Water St, Chestertown, MD 21620
    109 S Water St, Chestertown, MD 21620
    109 S Water St, Chestertown, MD 21620
    /69

    $650,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 2,064 Sq Ft

    109 S Water St, Chestertown, MD 21620

    109 South Water, along with the historic Custom House, is a bookend to a small, but iconic, cluster of historic (c1900) townhouses that give pause to every passer-by, especially those equipped with a lens. Beautifully designed and maintained block-wide landscaping, individually maintained, provides exceptional street appeal. The smallest (2064 square feet) of the four clapboard houses, all with

    Richard Keaveney Cross Street Realtors LLC

    109 S Water St, Chestertown, MD 21620
  • 23055 Old Fairlee Rd, Chestertown, MD 21620
    23055 Old Fairlee Rd, Chestertown, MD 21620
    /2

    $330,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,628 Sq Ft

    23055 Old Fairlee Rd, Chestertown, MD 21620

    Enjoy easy single-story living in this well-maintained 3-bedroom, 2-bath home situated on a 1⁄2-acre lot backing to peaceful farmland. Offering privacy and scenic views, this property blends comfort, space, and thoughtful upgrades throughout. Recent improvements include vinyl siding, a newer roof, and luxury vinyl plank flooring, with original hardwoods underneath for added value and charm. The

    Deborah Callahan Benson & Mangold, LLC

    23055 Old Fairlee Rd, Chestertown, MD 21620
  • 0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    /11

    $212,000

    • Land
    • 10.05 Acres
    • $21,095 per Acre

    0 Hoffecker Rd, Chestertown, MD 21620

    Discover a rare opportunity to create your future home on this beautiful parcel of land, set in a peaceful and scenic setting. With ample space and flexibility, the property offers endless possibilities for a custom build, from a cozy retreat to a thoughtfully designed estate. Enjoy the tranquility of country living while remaining conveniently close to local shops, dining, and nearby routes for

    Heather Dolan Chesapeake Real Estate Associates, LLC

    0 Hoffecker Rd, Chestertown, MD 21620
  • 129 Parma Rd, Chestertown, MD 21620
    129 Parma Rd, Chestertown, MD 21620
    129 Parma Rd, Chestertown, MD 21620
    /41

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,170 Sq Ft

    129 Parma Rd, Chestertown, MD 21620

    Welcome to Chester Harbor. This one level home offers 3 bedroom 2 baths with LVP flooring in living room, kitchen and dining area. Fenced in backyard and a detached Garage/shop. Currently set up as a "Zen Den" offering electric and heat/air from own mini split. Could be converted back to garage if desired. Photos to be taken 1/13

    Roger Boyce Chesapeake Real Estate Associates, LLC

    129 Parma 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
    /45

    $585,000

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

    206 S Water St, Chestertown, MD 21620

    Significant price reduction!!! Great value!! Live in the heart of Chestertown’s Historic District—see your boat from your front porch!Beautifully rebuilt and expanded, this versatile home offers 4 Bedrooms, 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.

    Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    /16

    $165,000

    • 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 Taylor Properties

    141 Prospect St, Chestertown, MD 21620
  • 22681 Wood Yard Ln, Chestertown, MD 21620
    22681 Wood Yard Ln, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 0.52 Acre
    • $28,846 per Acre

    22681 Wood Yard Ln, Chestertown, MD 21620

    Half acre+ secluded wooded lot. There used to be a house on the property but county does not have well or septic records so buyer would need to perform perc test to build. There appears to be electric run to lot and there is a 16' right of way to access. Buyer to do any due diligence. Could be a great hunting property surrounded by woods and farmland!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22681 Wood Yard Ln, Chestertown, MD 21620
  • 24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    /36

    $319,900

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    24775 Langford Rd, Chestertown, MD 21620

    Welcome to 24775 Langford Rd, a quiet countryside retreat just minutes from downtown Chestertown. This well-maintained three-bedroom, one-bath home sits on 1.27 acres and offers a peaceful setting with ample outdoor space. The property features a generously sized three-car detached garage/workshop and a large Trex deck with hot tub, ideal for relaxing or entertaining. In 2018, the home underwent

    Agent Photo

    Ryan Fitzwater

    RE/MAX Advantage Realty

    (410) 835-4609

    24775 Langford Rd, Chestertown, MD 21620
  • 6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    /50

    $445,000

    • 5 Beds
    • 2.5 Baths
    • 3,371 Sq Ft

    6746 Quaker Neck Rd, Chestertown, MD 21620

    Michele Palmer Doug Ashley Realtors, LLC

    6746 Quaker Neck Rd, Chestertown, MD 21620
  • 110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    /26

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    110 Trafford Dr, Chestertown, MD 21620

    Discover an incredible opportunity in the highly sought-after Coventry Farms community—one of the rare chances to get into this neighborhood for under $500K. This inviting Colonial offers the perfect blend of comfort, charm, and value, with plenty of room to make it your own and build equity over time. Step inside to a warm and welcoming layout featuring thoughtfully designed accent walls, a

    Agent Photo

    Debbi Rivero

    RE/MAX Advantage Realty

    (410) 406-7422

    110 Trafford Dr, Chestertown, MD 21620
  • 22481 Goose Hollow Dr, Chestertown, MD 21620
    22481 Goose Hollow Dr, Chestertown, MD 21620
    22481 Goose Hollow Dr, Chestertown, MD 21620
    /18

    $379,500 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    22481 Goose Hollow Dr, Chestertown, MD 21620

    Welcome to peaceful country living with modern comfort.This beautifully updated 3-bedroom, 2-full-bath home sits on a private 2-acre lot with mature trees lining the property and a cornfield backdrop for exceptional privacy. Thoughtfully designed for everyday living and entertaining, the home features a spacious rear deck, perfect for hosting family and friends in a quiet, serene setting.

    Daryl Huber Realty Mark Cityscape

    22481 Goose Hollow Dr, Chestertown, MD 21620
  • 23698 L Rd, Chestertown, MD 21620
    23698 L Rd, Chestertown, MD 21620
    23698 L Rd, Chestertown, MD 21620
    /5

    $29,000

    • Land
    • 2.6 Acres
    • $11,154 per Acre

    23698 L Rd, Chestertown, MD 21620

    Property record consists of two lots for a total of 2.6 Acres zoned Village. Please notify listing agent if you intend to walk the property.

    Joe Howerton Taylor Properties

    23698 L Rd, Chestertown, MD 21620
  • 218 Camelot Dr, Chestertown, MD 21620
    218 Camelot Dr, Chestertown, MD 21620
    218 Camelot Dr, Chestertown, MD 21620
    /45

    $525,000

    • 5 Beds
    • 3.5 Baths
    • 3,932 Sq Ft

    218 Camelot Dr, Chestertown, MD 21620

    Picture Perfect Colonial in Coventry Farms – Chestertown, MarylandWelcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates

    Dee Dee McCracken Coldwell Banker Realty

    218 Camelot Dr, Chestertown, MD 21620
  • 109 Metcalfe Rd, Chestertown, MD 21620
    109 Metcalfe Rd, Chestertown, MD 21620
    109 Metcalfe Rd, Chestertown, MD 21620
    /27

    $264,900 New Construction

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    109 Metcalfe Rd, Chestertown, MD 21620

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

    David Moore Real Broker, LLC

    109 Metcalfe Rd, Chestertown, MD 21620
  • 0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    /32

    $39,000

    • Land
    • 1.51 Acres
    • $25,828 per Acre

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620

    Largest privately held parcel in Chesapeake Landing. 8 Lots each more than 10,000 sq ft. for a total 1.51 acres. Tax map 27, lots 254-257 & 297-300 (2 contiguous lots). The site is level & wooded. Raw land near Worton's Marina. Community has a boat ramp and offers easy access to the Chesapeake Bay. Chesapeake Landing has a voluntary HOA giving you access to the boat ramp, marina and a slip for an

    Becky Schor Berkshire Hathaway HomeServices Homesale Realty

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
  • 213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    /23

    $314,900

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

    213 Central Dr, Chestertown, MD 21620

    Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached "pole barn" style garage. Fenced back yard. This

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    213 Central Dr, Chestertown, MD 21620
  • 102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    /23

    $839,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 983-3178

    102 Little Harbor Way, Chestertown, MD 21620
  • 37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    /24

    $765,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    37 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 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, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath

    Julia Hilfiker Gunther-McClary Real Estate

    37 Landing Ln, Chestertown, MD 21620
  • 36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    /26

    $753,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    36 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 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, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 819-1523

    36 Landing Ln, Chestertown, MD 21620
  • 35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    /26

    $786,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    35 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 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, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Julia Hilfiker Gunther-McClary Real Estate

    35 Landing Ln, Chestertown, MD 21620
  • 104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    /24

    $813,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 609-5588

    104 Landing Ln, Chestertown, MD 21620
  • 25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    /22

    $1,099,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, 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
  • 216 Blakefield Dr, Chestertown, MD 21620
    216 Blakefield Dr, Chestertown, MD 21620
    216 Blakefield Dr, Chestertown, MD 21620
    /49

    $579,000 New Construction

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

    216 Blakefield Dr, Chestertown, MD 21620

    The wait is over 216 Blakefield Drive is complete, ready for occupancy and you will not be disappointed. This is the last avaiable lot in this community so don't wait! Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    216 Blakefield Dr, Chestertown, MD 21620
  • 121 Primrose Rd, Chestertown, MD 21620
    121 Primrose Rd, Chestertown, MD 21620
    121 Primrose Rd, Chestertown, MD 21620
    /22

    $350,000

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

    121 Primrose Rd, Chestertown, MD 21620

    Motivated Seller. Welcome to 121 Primrose Road, a well-built two-story home offering 2,034 square feet of living space on a .345-acre lot, located just outside downtown Chestertown in a quiet setting. The upper level includes three bedrooms and two full bathrooms, while the main level offers a convenient half bath. The first floor features a bright living area, a traditional dining space, and a

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    121 Primrose 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

    $364,900

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

    108 Flying Cloud Dr, Chestertown, MD 21620

    New Year, new home! No need to worry for years about the roof or mechanics!! Built in 2023 - this Smart Home is 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

    Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    /7

    $89,500

    • Land
    • 3.92 Acres
    • $22,832 per Acre

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

    Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. The rear portion of the property is designated palustrine forested shrub wetlands, though

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • 108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    /5

    $635,000

    • Land
    • 0.09 Acre
    • $7,055,556 per Acre

    108 Little Harbor Way, Chestertown, MD 21620

    Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 335-6192

    108 Little Harbor Way, 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
  • 106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    /24

    $799,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,092 Sq Ft

    106 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Julia Hilfiker Gunther-McClary Real Estate

    106 Landing Ln, 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

    **To be built! 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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 835-9021

    0 Little Harbor Way Unit 1, Chestertown, MD 21620
  • 104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    /23

    $849,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /44

    $350,000

    • 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
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /51

    $1,395,500

    • 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
  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /29

    $455,000

    • 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
  • 109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    /24

    $449,900

    • 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 Taylor Properties

    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

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