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Homes for Sale in 21620

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  • 21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    /16

    $370,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    21111 Texas Ave, Chestertown, MD 21620

    COMING SOON in Tolchester Estates!Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up

    Glory Bee Costa Keller Williams Select Realtors of Easton

    21111 Texas Ave, 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
  • 676 Deep Landing Rd, Chestertown, MD 21620
    676 Deep Landing Rd, Chestertown, MD 21620
    676 Deep Landing Rd, Chestertown, MD 21620
    /24

    $315,000

    • 3 Beds
    • 2.5 Baths
    • 1,468 Sq Ft

    676 Deep Landing Rd, Chestertown, MD 21620

    Situated on an open .59 acre lot in Queen Anne’s County, this charming 3 bedroom, 2.5 bath built home in 2014 offers buyers the perfect blend of modern comfort with spacious living. This property features a beautiful kitchen with granite countertops and a new range, a finished basement with a half bath that can be used for anything from an office to a playroom, and an attached front-loading

    Katie Stecklair Cross Street Realtors LLC

    676 Deep Landing 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
  • 110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    /2

    $475,000 Open House 1/03

    • 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
  • 213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    /23

    $319,900

    • 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
  • 7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    /24

    $250,000

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    7521 Pine Ave, Chestertown, MD 21620

    Priced to sell! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. Bring your vision for this home to life and add instant equity with cosmetic updates! It has been lovingly maintained with a newer roof and

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    7521 Pine Ave, 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
  • 204 Rolling Rd, Chestertown, MD 21620
    204 Rolling Rd, Chestertown, MD 21620
    204 Rolling Rd, Chestertown, MD 21620
    /31

    $370,000 Open Sat 11AM - 1PM

    • 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
  • 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
    /2

    $579,000 New Construction

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

    216 Blakefield Dr, Chestertown, MD 21620

    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 space for relaxation and entertainment. The kitchen is a chef's dream, featuring an island, eat-in space, and modern appliances including a built-in microwave,

    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

    $399,000

    • 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
  • 108 Flying Cloud Dr, Chestertown, MD 21620
    108 Flying Cloud Dr, Chestertown, MD 21620
    108 Flying Cloud Dr, Chestertown, MD 21620
    /21

    $375,000

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

    108 Flying Cloud Dr, Chestertown, MD 21620

    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 function

    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
  • 0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    /8

    $88,900

    • Land
    • 0.48 Acre
    • $185,208 per Acre

    0 East St, Chestertown, MD 21620

    This corner lot offers a rare opportunity to build just minutes from Downtown Chestertown. Located on a quiet street and close to the Chester River, this property combines a peaceful setting with everyday convenience.The lot is perc approved and has site plans—see documents for details. With close proximity to Chestertown’s shops, galleries, and restaurants, it’s the perfect setting for those

    William Norris Select Land & Homes, LLC

    0 East St, 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

    $399,000

    • 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

    $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
  • 318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    /21

    $269,000 Open Sat 12PM - 3PM

    • 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
  • 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 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
  • 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. Taxes and insurance not included. Buy direct and received a free,

    Agent Photo

    Vinny Steo

    Your Home Sold Guaranteed Realty

    (443) 706-8420

    247 Blakefield Dr, 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
  • 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
  • 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
  • 8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    /30

    $339,000

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    8750 Georgetown Rd, Chestertown, MD 21620

    Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bed, 2-bathroom home situated on 1 acre with public water/sewer, no HOA, and a detached garage with electric. Whether you're dreaming of a workshop, a hobby space, extra storage, or room for your equipment, this property delivers flexibility that’s hard to find at this price point. Inside, you’ll love the

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    8750 Georgetown Rd, Chestertown, MD 21620
  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /32

    $878,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft

    228 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with all the desired attributes. Fantastic water views from the living level and bedrooms! Spacious open living space with warm hardwood floors and a gourmet kitchen. 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. On the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 647-9404

    228 S Water St, Chestertown, MD 21620
  • 127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    /26

    $215,000

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft

    127 Wood Duck Ln, Chestertown, MD 21620

    Tom Riccio RE/MAX Point Realty

    127 Wood Duck Ln, 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

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