172

Homes for Sale near Kent County High School

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  • 21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    /26

    $339,900

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft

    21125 Iowa Ave, Chestertown, MD 21620

    Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to call home. Inside, you’ll find a bright and inviting layout featuring a Florida Room, a spacious dining room with a cozy fireplace, and two comfortable bedrooms. The large living room is filled with natural light and showcases

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 405-2192

    21125 Iowa Ave, Chestertown, MD 21620
  • 110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    /26

    $465,000 Open Sun 2PM - 4PM

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

    110 Trafford Dr, Chestertown, MD 21620

    Here’s the opportunity buyers wait for. A classic Colonial in sought-after Coventry Farms, priced where this neighborhood rarely plays, offering space, comfort, and the chance to build equity while you live well. Step inside and you’re welcomed by a warm, traditional layout that just feels right. Accent walls add personality, the formal dining room sets the stage for holidays and celebrations,

    Agent Photo

    Debbi Rivero

    RE/MAX Advantage Realty

    (410) 406-7422

    110 Trafford Dr, Chestertown, MD 21620
  • 7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    /51

    $695,000 Open Sat 12PM - 2PM

    • 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
  • 116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    /21

    $509,000

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

    116 Harlan Loop, Chestertown, MD 21620

    Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office setup Curb

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • 21305 Haven Rd, Rock Hall, MD 21661
    21305 Haven Rd, Rock Hall, MD 21661
    21305 Haven Rd, Rock Hall, MD 21661
    /53

    $350,000

    • 4 Beds
    • 2 Baths
    • 1,499 Sq Ft

    21305 Haven Rd, Rock Hall, MD 21661

    Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod located in the heart of Rock Hall, MD! Completely updated from top to bottom, this home features a brand-new roof, HVAC system, water heater, flooring, paint, upgraded bathrooms, interior doors, and stylish recessed lighting as well as ceiling fans throughout. Enjoy mornings and evenings on the charming screened-in front porch,

    Agent Photo

    Anthony Borleis

    RE/MAX Point Realty

    (410) 213-3053

    21305 Haven Rd, Rock Hall, MD 21661
  • 24204 Drayton Landing Dr, Worton, MD 21678
    24204 Drayton Landing Dr, Worton, MD 21678
    24204 Drayton Landing Dr, Worton, MD 21678
    /47

    $725,000 Open Sat 12PM - 2PM

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

    24204 Drayton Landing Dr, Worton, MD 21678

    Set on two peaceful acres in the highly regarded Kinnaird’s Point community, this beautifully renovated home offers modern comfort, privacy, and access to the best of Eastern Shore living. Thoughtfully updated inside and out, the property delivers a rare combination of quality upgrades, flexible space, and community water access just minutes from Chestertown. Step inside to a bright, open

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 594-6295

    24204 Drayton Landing Dr, Worton, MD 21678
  • 202 Waldo Dr, Chestertown, MD 21620
    202 Waldo Dr, Chestertown, MD 21620
    202 Waldo Dr, Chestertown, MD 21620
    /3

    $389,000

    • 3 Beds
    • 1.5 Baths
    • 2,055 Sq Ft

    202 Waldo Dr, Chestertown, MD 21620

    A Place Full of Possibility in Byford Development Tucked in the heart of the Byford community, just minutes from everything Chestertown has to offer, this welcoming rancher is ready for its next chapter. Step inside and feel the charm of traditional hardwood floors, the glow of a wood-burning fireplace in the spacious family room, and the comfort of a home that’s been well-loved. The layout flows

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 971-7157

    202 Waldo Dr, Chestertown, MD 21620
  • 14183 Roberts Dr, Galena, MD 21635
    14183 Roberts Dr, Galena, MD 21635
    14183 Roberts Dr, Galena, MD 21635
    /51

    $1,975,000

    • 5 Beds
    • 3 Baths
    • 3,915 Sq Ft

    14183 Roberts Dr, Galena, MD 21635

    Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 609-5094

    14183 Roberts Dr, Galena, MD 21635
  • 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
  • 107 Boxwood Ln, Galena, MD 21635
    107 Boxwood Ln, Galena, MD 21635
    107 Boxwood Ln, Galena, MD 21635
    /28

    $398,000 Open Sat 12PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,798 Sq Ft

    107 Boxwood Ln, Galena, MD 21635

    Welcome to 107 Boxwood Lane in the Dogwood Village community. This home is nicely situated at the end of a cul-de-sac with a spacious triangular lot. The backyard is nicely edged with foliage, making a private oasis. The home offers convenient one-floor living. Large open living space, stainless steel appliances, wood floors and natural light. A bonus sunroom is just steps away from the dining

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 724-1207

    107 Boxwood Ln, Galena, MD 21635
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /32

    $898,000

    • 3 Beds
    • 3.5 Baths
    • 2,172 Sq Ft

    226 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring 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. You'll love the warm hardwood floors throughout the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-3661

    226 S Water St, Chestertown, MD 21620
  • 10 Ericsson Ave Unit 37, Betterton, MD 21610
    10 Ericsson Ave Unit 37, Betterton, MD 21610
    10 Ericsson Ave Unit 37, Betterton, MD 21610
    /40

    $315,000 Open Sun 11AM - 1PM

    • 2 Beds
    • 2 Baths
    • 1,520 Sq Ft

    10 Ericsson Ave Unit 37, Betterton, MD 21610

    Beach day... or boat day.......maybe pool day? Welcome to the “Jewel of the Chesapeake” in charming Betterton—where the Eastern Shore of Maryland living meets effortless waterfront luxury.This is a rare opportunity to own the ONLY condo currently available in Betterton, perfectly positioned with breathtaking, views of Betterton Beach and the expansive Chesapeake Bay, right at the mouth of the

    Agent Photo

    Julie Strickler

    Remax Vision

    (410) 339-8749

    10 Ericsson Ave Unit 37, Betterton, MD 21610
  • 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
  • 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
  • 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
  • 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!** **To be built! 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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, 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
  • 5979 Lawton Ave, Rock Hall, MD 21661
    5979 Lawton Ave, Rock Hall, MD 21661
    5979 Lawton Ave, Rock Hall, MD 21661
    /39

    $1,250,000

    • 4 Beds
    • 5.5 Baths
    • 3,527 Sq Ft

    5979 Lawton Ave, Rock Hall, MD 21661

    This spectacular waterfront retreat offers over 3,500 square feet of living space on 0.76 acres, ideally located within the town limits of Rock Hall. With an elevator, five bedrooms an office and four and a half baths, there is abundant space for family, guests, and effortless entertaining.The ground level welcomes you with a spacious game room, sitting area, exercise space, and an oversized

    Cindy Genther Rock Hall Properties Real Estate

    5979 Lawton Ave, Rock Hall, MD 21661
  • 21610 Hidden Creek Dr, Rock Hall, MD 21661
    21610 Hidden Creek Dr, Rock Hall, MD 21661
    21610 Hidden Creek Dr, Rock Hall, MD 21661
    /22

    $749,900

    • Land
    • 7.9 Acres
    • $94,924 per Acre

    21610 Hidden Creek Dr, Rock Hall, MD 21661

    Enjoy a long, secluded driveway to 2,185 sq ft home sitting on 7.9 acres of mature, heavily-forested woods with waterfront views of Greys Inn Creek. The home features vaulted ceilings and has access to a private pier and dock; its perfect for boating, fishing, crabbing, or just enjoying the outdoors. Located in Rock Hall, Maryland, known for hunting, fishing, and Chesapeake Bay boating, this

    Mike Arajakis Whitetail Properties Real Estate

    21610 Hidden Creek Dr, Rock Hall, MD 21661
  • 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
  • 12400 Woods Rd, Worton, MD 21678
    12400 Woods Rd, Worton, MD 21678
    12400 Woods Rd, Worton, MD 21678
    /9

    $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

    Stacy Kendall Cross Street Realtors LLC

    12400 Woods Rd, Worton, MD 21678
  • 31729 W Edge Rd, Millington, MD 21651
    31729 W Edge Rd, Millington, MD 21651
    31729 W Edge Rd, Millington, MD 21651
    /60

    $534,000

    • 3 Beds
    • 2.5 Baths
    • 1,821 Sq Ft

    31729 W Edge Rd, Millington, MD 21651

    Spacious 3-bedroom, 2.5-bath rancher with pole barn on the upper Chester River!Step inside this private waterfront retreat to a welcoming living room featuring a cozy propane fireplace with a beautiful stone surround. The spacious primary suite offers an oversized bathroom with a garden tub beside a second gas fireplace, a walk-in shower, and a separate water closet. The dining room opens to

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    31729 W Edge Rd, Millington, MD 21651
  • 10087 John Carvill Rd, Chestertown, MD 21620
    10087 John Carvill Rd, Chestertown, MD 21620
    10087 John Carvill Rd, Chestertown, MD 21620
    /63

    $695,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft

    10087 John Carvill Rd, Chestertown, MD 21620

    Toad Hall, as the current owners affectionately call it, is located in a natural wooded setting on Fairlee Creek in Great Oak Estates just minutes from the Chesapeake Bay. Peaceful water views from almost every room in the home create the feeling of living in a tree house, and the dock is just steps away down the hillside - no flood insurance needed. Enter the house through a split foyer with a

    Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    10087 John Carvill Rd, Chestertown, MD 21620
  • 21186 Chesapeake Ave, Rock Hall, MD 21661
    21186 Chesapeake Ave, Rock Hall, MD 21661
    21186 Chesapeake Ave, Rock Hall, MD 21661
    /46

    $540,000 Open Sat 12:30PM - 3:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,760 Sq Ft

    21186 Chesapeake Ave, Rock Hall, MD 21661

    Built in 2018, this custom coastal raised home is ideally located just one block from the Chesapeake Bay, offering the perfect blend of relaxation, recreation, and investment potential. Enjoy easy access to Rock Hall’s 12 marinas, Ferry Park Beach, local restaurants, shops, and charming downtown—all just a short walk, bike ride, or drive away. Nature lovers will appreciate the close proximity to

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    21186 Chesapeake Ave, Rock Hall, MD 21661
  • 13840 Mill Creek Ln, Galena, MD 21635
    13840 Mill Creek Ln, Galena, MD 21635
    13840 Mill Creek Ln, Galena, MD 21635
    /41

    $1,300,000

    • 3 Beds
    • 2 Baths
    • 2,987 Sq Ft

    13840 Mill Creek Ln, Galena, MD 21635

    Do you crave peace, privacy and waterfront? Escape to your own slice of paradise in this meticulously maintained 3-bedroom, 2-bathroom estate, where luxury meets sustainability. Nestled on a beautifully wooded and private 1.58 acre lot, this home is a true sanctuary for nature lovers and water enthusiasts alike. The interior features a thoughtful layout designed for comfort, but the true magic

    Mary Binns EXP Realty, LLC

    13840 Mill Creek Ln, Galena, MD 21635
  • 6374 Rock Hall Rd, Rock Hall, MD 21661
    6374 Rock Hall Rd, Rock Hall, MD 21661
    6374 Rock Hall Rd, Rock Hall, MD 21661
    /34

    $295,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,000 Sq Ft

    6374 Rock Hall Rd, Rock Hall, MD 21661

    Welcome to life in Rock Hall — a charming waterfront town where the pace is slower, the people are friendlier, and the Chesapeake Bay lifestyle is part of everyday living. This lovingly renovated home was thoughtfully updated by owners who cared about the details—not a quick flip—resulting in a property full of character and quality improvements throughout. Inside, you’ll find beautiful LVP

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    6374 Rock Hall Rd, Rock Hall, MD 21661
  • 21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    /20

    $265,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    21217 Texas Ave, Chestertown, MD 21620

    MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head

    Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620
  • 21447 E Sharp St, Rock Hall, MD 21661
    21447 E Sharp St, Rock Hall, MD 21661
    21447 E Sharp St, Rock Hall, MD 21661
    /14

    $115,000

    • 3 Beds
    • 1 Bath
    • 1,258 Sq Ft

    21447 E Sharp St, Rock Hall, MD 21661

    Major Rehab or Tear Down - bring your ideas

    Chris Kendall Cross Street Realtors LLC

    21447 E Sharp St, Rock Hall, MD 21661
  • 5883 Williams St, Rock Hall, MD 21661
    5883 Williams St, Rock Hall, MD 21661
    5883 Williams St, Rock Hall, MD 21661
    /20

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,358 Sq Ft

    5883 Williams St, Rock Hall, MD 21661

    Tucked just off Rock Hall’s Main Street, this 3-bedroom, 2-bath rancher offers easy, single-level living in one of the Eastern Shore’s most beloved waterfront towns. Lovingly cared for by its original owner, the home features a comfortable, open-concept layout connecting the living, dining, and kitchen areas. The primary suite includes an en-suite bathroom and walk-in closet, while two additional

    Courtney Chipouras TTR Sotheby's International Realty

    5883 Williams St, Rock Hall, MD 21661
  • 103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    /53

    $550,000

    • 4 Beds
    • 3.5 Baths
    • 3,816 Sq Ft

    103 Sutton Way, Chestertown, MD 21620

    103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and

    Liddy Campbell TTR Sotheby's International Realty

    103 Sutton Way, Chestertown, MD 21620
  • 104 Flying Cloud Dr, Chestertown, MD 21620
    104 Flying Cloud Dr, Chestertown, MD 21620
    104 Flying Cloud Dr, Chestertown, MD 21620
    /31

    $399,900

    • 5 Beds
    • 3.5 Baths
    • 2,535 Sq Ft

    104 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to The Verona, a spacious three-story, move-in ready home offering over 2,500 square feet of thoughtfully designed living space. With five bedrooms and three and a half bathrooms, this home provides the perfect balance of comfort, functionality, and flexibility for modern living.Step inside to an inviting foyer that leads to the bright and open main living area, where the family room

    David Moore Real Broker, LLC

    104 Flying Cloud Dr, Chestertown, MD 21620
  • 106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    /70

    $865,000

    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    106 S Queen St, Chestertown, MD 21620

    *Open House Friday April 3rd 5-7pm and Saturday April 4th 10am-12pm *The Bedingfield Hands House, circa 1750, traces its routes back to pre-revolutionary times and has a story to tell. One of the few downtown homes to offer a large front courtyard, the property features beautifully landscaped gardens and a mature magnolia tree creating a private and welcoming outdoor retreat. Offering

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    106 S Queen St, Chestertown, MD 21620
  • 201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    /24

    $435,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    201 Birch Run Rd, Chestertown, MD 21620

    *****PRICED $30,000 UNDER THE RECENT APPRAISED VALUE***** One floor living, a wood burning fireplace, and hardwood floors help this represent the cozy but elevated Eastern Shore lifestyle. The Mile Tree Village community is tucked on a quiet cul-de-sac with views of the Chester River. The home has been thoughtfully improved with major 2021 updates including joist replacement, flooring, crawl

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    201 Birch Run Rd, Chestertown, MD 21620
  • 139 Prospect St, Chestertown, MD 21620
    139 Prospect St, Chestertown, MD 21620
    139 Prospect St, Chestertown, MD 21620
    /28

    $225,000

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

    139 Prospect St, Chestertown, MD 21620

    Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in

    Barbara McCaffrey Redfin Corp

    139 Prospect St, Chestertown, MD 21620
  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    /4

    $250,000

    • Land
    • 0.85 Acre
    • $294,118 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /7

    $225,000

    • Land
    • 0.87 Acre
    • $258,621 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.87± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic.There is also

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • 5980 Lawton Ave, Rock Hall, MD 21661
    5980 Lawton Ave, Rock Hall, MD 21661
    5980 Lawton Ave, Rock Hall, MD 21661
    /32

    $1,100,000

    • 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
  • 12733 Still Pond Rd, Still Pond, MD 21667
    12733 Still Pond Rd, Still Pond, MD 21667
    12733 Still Pond Rd, Still Pond, MD 21667
    /21

    $349,900

    • 6 Beds
    • 2 Baths
    • 3,270 Sq Ft

    12733 Still Pond Rd, Still Pond, MD 21667

    NEW TO MARKET !!!!! Step back in time with this spacious 1920 Colonial offering over 3,200+ sq ft and room for everyone. With 6 bedrooms, 1.5 Bath, two large living rooms, and a formal dining room, this home provides incredible flexibility for large households, multi-generational living, or anyone needing extra space to spread out. The home features generously sized rooms, classic character, and

    Jeff Guthrie Taylor Properties

    12733 Still Pond Rd, Still Pond, MD 21667
  • 11944 Augustine Herman Hwy, Kennedyville, MD 21645
    11944 Augustine Herman Hwy, Kennedyville, MD 21645
    11944 Augustine Herman Hwy, Kennedyville, MD 21645
    /21

    $480,000

    • 4 Beds
    • 2 Baths
    • 2,156 Sq Ft

    11944 Augustine Herman Hwy, Kennedyville, MD 21645

    Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences. From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying small-town

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    11944 Augustine Herman Hwy, Kennedyville, MD 21645
  • 1 Idlewhile Ave Unit 4, Betterton, MD 21610
    1 Idlewhile Ave Unit 4, Betterton, MD 21610
    1 Idlewhile Ave Unit 4, Betterton, MD 21610
    /43

    $449,000 Open Sun 11AM - 1:15PM

    • 3 Beds
    • 2.5 Baths

    1 Idlewhile Ave Unit 4, Betterton, MD 21610

    Crew's Landing 3 bedroom Townhouse, located in Betterton, The Jewel of the Chesapeake. This 12 unit complex has become a premier waterfront community on the upper Bay. Located on a 5 acre setting of beautiful landscape offering carefree living. It includes a community dock and a great private sandy beach. The unit has had upgrades with wood plank tile floors, kitchen with granite countertops, and

    Ashton Kelley Gunther-McClary Real Estate

    1 Idlewhile Ave Unit 4, Betterton, MD 21610

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