170

Kent County MD Homes for Sale

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  • 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
  • 356 Cypress St, Millington, MD 21651
    356 Cypress St, Millington, MD 21651
    /2

    $270,000 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,508 Sq Ft

    356 Cypress St, Millington, MD 21651

    Coming soon! Looking for a 3 bed farmhouse in Millington with classic charm and modern updates? This warm and friendly 1920 single family home offers 1508 square feet on a 0.17 acre lot with a 2021 roof, vinyl siding, three second floor bedrooms, one full bath, and a half bath off the kitchen. A wrapped front and side porch sets the tone, while a rear wooden deck opens to the yard for easy

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    356 Cypress St, Millington, MD 21651
  • 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
  • 22537 Shipyard Ln, Rock Hall, MD 21661
    22537 Shipyard Ln, Rock Hall, MD 21661
    22537 Shipyard Ln, Rock Hall, MD 21661
    /6

    $3,665,000

    • Land
    • 113 Acres
    • $32,434 per Acre

    22537 Shipyard Ln, Rock Hall, MD 21661

    Located along Shipyard Creek just outside Rock Hall, this 113-acre farm offers a strong combination of productive soils, waterfront access, and long-term investment value. The property includes approximately 100 tillable acres with primarily Mattapex soils moderately well-drained and highly rated for grain and forage production. The balance consists of woodland providing natural buffers between

    Sue Hudson National Land Realty

    22537 Shipyard Ln, Rock Hall, MD 21661
  • 186 Birchwood Ln, Galena, MD 21635
    186 Birchwood Ln, Galena, MD 21635
    186 Birchwood Ln, Galena, MD 21635
    /26

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 1,780 Sq Ft

    186 Birchwood Ln, Galena, MD 21635

    Welcome to this charming and well-maintained 3-bedroom, 2.5-bath home offering a cozy layout and desirable amenities throughout. This home features multiple living spaces—including a bright sunroom and a separate dining area providing comfort and versatility for everyday living. The spacious primary bedroom features vaulted ceilings, an en suite bath, and a large walk-in closet. Cozy up by one of

    Heather Carrow Crown Homes Real Estate

    186 Birchwood Ln, Galena, MD 21635
  • 0 Lot 30 Hagy Rd, Rock Hall, MD 21661
    0 Lot 30 Hagy Rd, Rock Hall, MD 21661
    0 Lot 30 Hagy Rd, Rock Hall, MD 21661
    /46

    $155,000

    • Land
    • 1 Acre
    • $155,000 per Acre

    0 Lot 30 Hagy Rd, Rock Hall, MD 21661

    Welcome to Little Neck Farm - this waterfront community has 30 homesites within a 354 acre farm with 4 miles of protected shoreline and plenty of open space where getting back to nature is possible. Lot 30 is available for sale - it is a generous level one acre lot with plenty of room to build your dream or getaway home. The lot has evergreens and crape myrtle plantings outlining a portion of the

    Cindy DelZoppo Northrop Realty

    0 Lot 30 Hagy Rd, Rock Hall, MD 21661
  • 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
  • 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
  • 21745 Centennial Ln, Rock Hall, MD 21661
    21745 Centennial Ln, Rock Hall, MD 21661
    21745 Centennial Ln, Rock Hall, MD 21661
    /5

    $379,500

    • 3 Beds
    • 2 Baths
    • 1,413 Sq Ft

    21745 Centennial Ln, Rock Hall, MD 21661

    COMING SOON!Welcome to 21745 Centennial Lane, Rock Hall, MD — a brand-new 1,415 SF coastal-style rancher perfectly situated just minutes from local marinas, waterfront dining, and unforgettable sunsets.Crafted by JAC Homes, this thoughtfully designed 3-bedroom, 2-bath home combines modern comfort with timeless coastal charm. Step inside to discover an open concept living space filled with

    Pamela Geib Long & Foster Real Estate, Inc.

    21745 Centennial Ln, Rock Hall, MD 21661
  • 21133 Striper Run, Rock Hall, MD 21661
    21133 Striper Run, Rock Hall, MD 21661
    21133 Striper Run, Rock Hall, MD 21661
    /7

    $364,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft

    21133 Striper Run, Rock Hall, MD 21661

    New Construction Alert! The last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates are now for sale. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the 1st and 2nd levels is included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious

    Cindy Genther Rock Hall Properties Real Estate

    21133 Striper Run, Rock Hall, MD 21661
  • 21131 Striper Run, Rock Hall, MD 21661
    21131 Striper Run, Rock Hall, MD 21661
    21131 Striper Run, Rock Hall, MD 21661
    /8

    $364,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft

    21131 Striper Run, Rock Hall, MD 21661

    New Construction Alert! Last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring on 1st and 2nd floors, quartz counter tops and stainless appliances are included. Upstairs, there's a primary suite with walk-in closet, full

    Cindy Genther Rock Hall Properties Real Estate

    21131 Striper Run, Rock Hall, MD 21661
  • 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
  • 24204 Drayton Landing Dr, Worton, MD 21678
    24204 Drayton Landing Dr, Worton, MD 21678
    24204 Drayton Landing Dr, Worton, MD 21678
    /34

    $799,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft

    24204 Drayton Landing Dr, Worton, MD 21678

    Welcome to 24204 Drayton Landing Drive — a beautifully renovated 3-bedroom, 2-bath home set on 2 peaceful acres in the heart of Kent County on Maryland’s Eastern Shore.Nestled within the desirable Kinnairds Point community, residents enjoy a warm neighborhood setting along with exclusive access to two waterfront common areas: a boat launch and a swim beach. These shared spaces provide the

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 594-6295

    24204 Drayton Landing Dr, Worton, MD 21678
  • 32287 Quinn Rd, Massey, MD 21650
    32287 Quinn Rd, Massey, MD 21650
    32287 Quinn Rd, Massey, MD 21650
    /30

    $429,000

    • 4 Beds
    • 2 Baths
    • 1,794 Sq Ft

    32287 Quinn Rd, Massey, MD 21650

    Just off Route 301 for commuters, but located in the country with privacy, space for animals, hobbies, and entertaining. Large detached garage with storage space above, full unfinished basement, fenced pasture area, and inground pool. So much potential here, come with vision and make it your own!

    John Carroll Village Real Estate Company LLC

    32287 Quinn Rd, Massey, MD 21650
  • 206 Virginia Ave, Galena, MD 21635
    206 Virginia Ave, Galena, MD 21635
    206 Virginia Ave, Galena, MD 21635
    /31

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,406 Sq Ft

    206 Virginia Ave, Galena, MD 21635

    Are you looking for a classic home with a ton of charm? Do you love original wood floors? Not afraid of some updating? This could just be the home for you! Screened in porch welcomes you to a beautiful foyer, and a classic living room with a fireplace that has been closed up but still provides a nice focal point. Owner is not sure if it could become a working wood-burning fireplace or not, but a

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (667) 843-7243

    206 Virginia Ave, Galena, MD 21635
  • 21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    /16

    $370,000 Coming Soon

    • 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
  • 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
  • 12400 Woods Rd, Worton, MD 21678
    12400 Woods Rd, Worton, MD 21678
    12400 Woods Rd, Worton, MD 21678
    /29

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    12400 Woods Rd, Worton, MD 21678

    Tucked away along the quiet shores of Still Pond Creek, this cedar cabin offers a rare blend of privacy, comfort, and natural beauty. Surrounded by mature woods and set on a peaceful stretch of waterfront, this 1,944 square foot home features 3 bedrooms, 2 bathrooms, a spacious screened-in porch perfect for crab feasts, a private beach and pier with 2'+ MLW improved with bilk head installed by

    Jack Boniface Cross Street Realtors LLC

    12400 Woods Rd, Worton, MD 21678
  • 0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661
    0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661
    0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661
    /10

    $995,000

    • Land
    • 18.62 Acres
    • $53,437 per Acre

    0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661

    Discover 18.62 acres of waterfront land on Tavern Creek, offering 1,086 feet of shoreline and stunning natural surroundings. Zoned Resource Conservation and currently tilled, this property provides a rare opportunity for those seeking space, privacy, and water access. A small portion of the shoreline lies within the flood zone; buyer to confirm buildability.

    Sarah Ulrick Rock Hall Properties Real Estate

    0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661
  • 5980 Lawton Ave, Rock Hall, MD 21661
    5980 Lawton Ave, Rock Hall, MD 21661
    5980 Lawton Ave, Rock Hall, MD 21661
    /15

    $1,100,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    5980 Lawton Ave, Rock Hall, MD 21661

    Welcome to Silly Manor, a Chesapeake Bay-front property with an abundance of coastal charm and panoramic views. This home is perfectly situated on the coveted Lawton Avenue, one of Kent County's most sought-after neighborhoods. Enjoy stunning sunsets all year-round and direct access to the dynamic waters of the Chesapeake Bay. The open living and dining space offer spectacular views of the

    Julia Hilfiker Gunther-McClary Real Estate

    5980 Lawton Ave, Rock Hall, MD 21661
  • 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

    $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
  • 0 Still Pond Creek Rd Unit MDKE2005888, Worton, MD 21678
    0 Still Pond Creek Rd Unit MDKE2005888, Worton, MD 21678
    0 Still Pond Creek Rd Unit MDKE2005888, Worton, MD 21678
    /9

    $95,000

    • Land
    • 1.2 Acres
    • $79,167 per Acre

    0 Still Pond Creek Rd Unit MDKE2005888, Worton, MD 21678

    The last buildable lot in the Cheerful Echoes neighborhood is perc approved and ready for improvement. NO HOA! With a gentle slope and plenty of room for the backyard of your dreams, a walkout lower level can open to a patio, gardens, etc... you name it! Just a few miles from the Worton Community Center and the walking trails at Worton Park, and a convenient drive to Chestertown, Middletown, and

    Liddy Campbell TTR Sotheby's International Realty

    0 Still Pond Creek Rd Unit MDKE2005888, Worton, MD 21678
  • 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
  • 21163 Chesapeake Ave, Rock Hall, MD 21661
    21163 Chesapeake Ave, Rock Hall, MD 21661
    21163 Chesapeake Ave, Rock Hall, MD 21661
    /50

    $649,900

    • 4 Beds
    • 3.5 Baths
    • 2,944 Sq Ft

    21163 Chesapeake Ave, Rock Hall, MD 21661

    This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the beginning of the surprise you will find in this special, 2,900+/- square foot, home. There are 4 bedrooms, 3.5 baths, a large living room with cathedral ceiling, 2 bedrooms upstairs and 2 bedrooms down, heat pump and mini-split

    Doug Ashley Doug Ashley Realtors, LLC

    21163 Chesapeake Ave, Rock Hall, MD 21661
  • 31695 Olivet Cir, Galena, MD 21635
    31695 Olivet Cir, Galena, MD 21635
    31695 Olivet Cir, Galena, MD 21635
    /18

    $269,900

    • 3 Beds
    • 2 Baths
    • 1,701 Sq Ft

    31695 Olivet Cir, Galena, MD 21635

    Welcome Home to 31695 Olivet Circle, this 3 bedroom 2 bath home is a great started home! Beautiful property with lots of possibilities! Off the beaten path & surrounded by nature with a detached garage.

    Donnie Horton RE/MAX Chesapeake

    31695 Olivet Cir, Galena, MD 21635
  • 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

Showing Results 1 - 40, Page 1 of 5

Maryland Kent County

Real Estate & Homes for Sale in Kent County, MD

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