152

Homes for Sale near Kent County Middle School

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  • /41

    $569,000

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the spacious

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 981-2534

    103 Landing Ln, Chestertown, MD 21620
  • /28

    $725,000

    • 3 Beds
    • 3 Baths

    117 N Water St Unit 1A, Chestertown, MD 21620

    Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

    117 N Water St Unit 1A, Chestertown, MD 21620
  • /20

    $212,000

    • Land
    • 1.95 Acres
    • $108,718 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • /28

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, Chestertown, MD 21620
  • /24

    $299,900

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft

    117 N Water St Unit 3B, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 453-1375

    117 N Water St Unit 3B, Chestertown, MD 21620
  • /29

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    10670 Tintah Rd, Chestertown, MD 21620

    Agent Photo

    Bronwyn Scott

    Samson Properties

    (443) 767-4153

    10670 Tintah Rd, Chestertown, MD 21620
  • /2

    $260,000 Coming Soon

    • 2 Beds
    • 1.5 Baths
    • 850 Sq Ft

    5810 Judefind Ave, Rock Hall, MD 21661

    Coming Soon! 2BR/1.5BA, just over a quarter acre of land! Built in 2010, cute as a button, large porch and another on the back to match. Large attic (potential for expansion), on-demand water heater, gutter filters, HVAC, shed in back for storage/lawn mower, mature asparagus bed in front yard! Stay tuned for professional pictures! Living space is open with a nicely appointed kitchen and the

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (667) 222-2354

    5810 Judefind Ave, Rock Hall, MD 21661
  • /26

    $299,000

    • 3 Beds
    • 1.5 Baths
    • 1,482 Sq Ft

    11636 Lynch Rd, Worton, MD 21678

    Classic farmhouse on half an acre! Three spacious bedrooms, central air and updated LVT flooring in the living area. Enjoy mornings on the front porch and dinners on the spacious back deck. There is more than enough room in the yard for a garden or other outdoor activities. The large pole barn could be used as a workshop and has plenty of space for additional storage. Plus, there are two smaller

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 412-8908

    11636 Lynch Rd, Worton, MD 21678
  • /9

    $100,000

    • Land
    • 3.00 Acres
    • $33,333 per Acre

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620

    E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Call listing agent for more information regarding this offering. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 909-1378

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
  • /63

    $1,550,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft

    21082 Wyoming Ave, Chestertown, MD 21620

    Charming Chesapeake Bay Home with Stunning Water Views and Incredible Sunsets! Living space is 2699 and the unfinished basement is 1948. Additional guest house adds additional square footage, a kitchen/bath/sleeping area and living room. Discover the beauty of waterfront living in this exquisite home featuring panoramic views of the Chesapeake Bay. Having undergone a comprehensive renovation

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 883-5429

    21082 Wyoming Ave, Chestertown, MD 21620
  • /45

    $310,000

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    24095 Chestertown Rd, Chestertown, MD 21620

    Motivated Seller! This GEM just outside of Chestertown is back on the market at no fault of her own (buyer remorse prior to inspections) Are you ready to make this lovely well-maintained home yours? It has new HVAC, a new roof, new flooring and other upgrades! Great living space with a front porch and back patio. Large backyard that overlooks beautiful farm fields. There is a one car detached

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 724-1462

    24095 Chestertown Rd, Chestertown, MD 21620
  • /22

    $998,000 New Construction

    • 3 Beds
    • 3.5 Baths

    226 S Water St, Chestertown, MD 21620

    Newly finished 3 Bedroom townhouses with nearly all the desired attributes of town living, with harbor and marina views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. No short term rental restrictions.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 376-5375

    226 S Water St, Chestertown, MD 21620
  • /36

    $759,000 New Construction

    • 3 Beds
    • 3.5 Baths

    212 Landing Ln, Chestertown, MD 21620

    Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm.This elegant 3-bedroom, 2.5-bath residence is designed to maximize

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 883-7032

    212 Landing Ln, Chestertown, MD 21620
  • /23

    $898,000 New Construction

    • 3 Beds
    • 3.5 Baths

    228 S Water St, Chestertown, MD 21620

    Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 230-5332

    228 S Water St, Chestertown, MD 21620
  • /22

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,315 Sq Ft

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

    Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and second floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • /8

    Call for Price

    • Land
    • 0.28 Acre

    21172 Wyoming Ave, Chestertown, MD 21620

    Single family residence in highly desirable Tolchester Estates neighborhood in Kent County, Maryland. Home is 2,920 SF with 4 bedrooms and 3 bathrooms. This home sits just down the street from the Chesapeake Bay. This is an as-is, where-is sale. Home will need a renovation.Property Account No.: 06-011128Please see auction page to view this property and place your bids!

    21172 Wyoming Ave, Chestertown, MD 21620
  • /49

    $638,750

    • 2 Beds
    • 2.5 Baths
    • 1,945 Sq Ft

    213 N Queen St, Chestertown, MD 21620

    A 3 car garage in the Historic District! With a rare combination of desirable features including comfortable modern amenities, this historic home will likely find its new owner quickly! Highlights of the interior include a roomy Family Room between the open concept Kitchen and the Courtyard, a formal Dining Room with a bay window, a front Living Room with gas fireplace, a formal Entry Hall, two

    Beth Ostrander Doug Ashley Realtors, LLC

    213 N Queen St, Chestertown, MD 21620
  • /117

    $879,000

    • 4 Beds
    • 3 Baths
    • 3,388 Sq Ft

    14540 Stirrup Ln, Galena, MD 21635

    Tucked away in the exclusive waterfront enclave of Fox Hole Estates, this serene retreat offers an exceptional blend of luxury, privacy, and natural beauty. Overlooking the beautiful Sassafras River, this finely renovated residence is designed to impress the discerning buyer seeking peace without compromise.The home’s inviting interior features rich hardwood floors, vaulted ceilings, and

    Benuel Esh Keller Williams Elite

    14540 Stirrup Ln, Galena, MD 21635
  • /44

    $989,000

    • 3 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    6119 New St Unit 2, Rock Hall, MD 21661

    Nestled on the tranquil shores of Swan Creek, this 3,000+/- sq ft waterfront home offers a rare blend of elegance, comfort and Chesapeake charm. Featuring 3-4 bedrooms, 3.5 baths, and a desirable first-floor primary suite, this thoughtfully designed home invites relaxed coastal living. The great room is a showstopper with its dramatic two-story windows and cozy fireplace, framing picture-perfect

    Cindy Genther Rock Hall Properties Real Estate

    6119 New St Unit 2, Rock Hall, MD 21661
  • /33

    $549,000

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

    20565 Rock Hall Ave Unit 5, Rock Hall, MD 21661

    Luxurious water view condo by the bay with high-end kitchen and baths. You'll feel pampered with the Chesapeake Bay views from every level. Exceptional view from the kitchen and dining area provides a beautiful space for entertaining. Truly a chef's gourmet kitchen, with granite countertops, a Wolf stove and Sub-Zero refrigerator. beautiful cherry floors in the kitchen. Decks on two levels- one

    Julia Hilfiker Gunther-McClary Real Estate

    20565 Rock Hall Ave Unit 5, Rock Hall, MD 21661
  • /32

    $865,000

    • 2 Beds
    • 2 Baths
    • 1,966 Sq Ft

    26889 Morgnec Rd, Chestertown, MD 21620

    This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
  • /48

    $579,900

    • 1 Bath
    • 1,148 Sq Ft

    5179 Quaker Neck Rd, Chestertown, MD 21620

    BACK ON THE MARKET due to financing. A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized,

    Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
  • /72

    $475,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    1 Bayview Rd, Betterton, MD 21610

    Rigbie Bluff is the perfect maintenance-free community in the quiet waterfront town of Betterton; known as the Jewel of the Chesapeake. Located at the confluence of the Sassafras River and Chesapeake Bay, Betterton got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This 3 bedroom, 2 bathroom

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    1 Bayview Rd, Betterton, MD 21610
  • /47

    $499,900

    • 4 Beds
    • 3.5 Baths
    • 3,420 Sq Ft

    314 Devon Dr, Chestertown, MD 21620

    Welcome to 314 Devon Drive in Chestertown—a beautifully designed 4-bedroom, 3.5-bath home where comfort meets style in every room. From the moment you step into the grand foyer, you’ll feel the openness and care that’s gone into every detail.The heart of the home is the spacious kitchen, featuring a large island that’s perfect for prepping meals, gathering with friends, or simply enjoying your

    Heather Branham The Parker Group

    314 Devon Dr, Chestertown, MD 21620
  • /26

    $449,000

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    5703 Watermans Way, Rock Hall, MD 21661

    Beautifully maintained home in the heart of Rock Hall. Take in the Rock Hall Harbor views from the spacious lower and upper porches! Entertain with ease, generous open living space with wood floors and a cozy gas fireplace. first level laundry room, pantry storage, half bath and attached large storage room with indoor and outdoor access. Back porch and patio are the perfect spots for dinners

    Lynn Hilfiker Gunther-McClary Real Estate

    5703 Watermans Way, Rock Hall, MD 21661
  • /26

    $439,000

    • 4 Beds
    • 2 Baths
    • 1,247 Sq Ft

    21424 Catholic Ave, Rock Hall, MD 21661

    Welcoming to the newly renovated 21424 Catholic Ave! Situated on a large in-town parcel, the largest residential lot on Catholic Ave. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT and engineered hardwood flooring. The welcoming living space contains original wood accents, adding much charm to this newly updated home. There are three bedrooms,

    Lynn Hilfiker Gunther-McClary Real Estate

    21424 Catholic Ave, Rock Hall, MD 21661
  • /53

    $539,000

    • 7 Beds
    • 5 Baths
    • 3,136 Sq Ft

    11960 Flour Mill St, Kennedyville, MD 21645

    Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    11960 Flour Mill St, Kennedyville, MD 21645
  • /2

    $490,000 New Construction

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

    21739 Centennial Ln, Rock Hall, MD 21661

    Charming New Construction in Historic Rock Hall! Welcome to your brand-new home near Rock Hall, a historic harbor town known for its Chesapeake Bay shoreline, boating opportunities, and vibrant local charm. This thoughtfully designed 4-bedroom, 2-bathroom home offers 2,000 sq. ft. (estimated) of modern living space with high-quality craftsmanship and stylish upgrades throughout. Nestled on a

    James Schaecher Keller Williams Flagship

    21739 Centennial Ln, Rock Hall, MD 21661
  • /2

    $490,000 New Construction

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

    21733 Centennial Ln, Rock Hall, MD 21661

    Charming New Construction in Historic Rock Hall! Welcome to your brand-new home near Rock Hall, a historic harbor town known for its Chesapeake Bay shoreline, boating opportunities, and vibrant local charm. This thoughtfully designed 4-bedroom, 2-bathroom home offers 2,000 sq. ft. (estimated) of modern living space with high-quality craftsmanship and stylish upgrades throughout. Nestled on a

    James Schaecher Keller Williams Flagship

    21733 Centennial Ln, Rock Hall, MD 21661
  • /2

    $450,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    22570 Bay Shore Rd, Chestertown, MD 21620

    Lovely countryside Cape Cod on over 3 private acres. Sit on the front porch and enjoy the summer breeze or grill off the back deck and watch the deer in the woods. This home has been meticulously cared for and features a first floor primary bedroom with walk-in closet and ensuite bath with a massive ceramic tile shower. Large formal living room with brick fireplace flows into the kitchen /

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
  • /5

    $565,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft

    11307 Urieville Ln, Worton, MD 21678

    Gorgeous renovated cape cop that is MOVE IN READY! Sitting on over 3 acres with a HUGE detached garage/shop, this is one you DON'T want to miss!!!

    Crystal Smith RE/MAX Executive

    11307 Urieville Ln, Worton, MD 21678
  • /9

    $585,950 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 2,892 Sq Ft

    31667 W Edge Rd, Millington, MD 21651

    Professional photos, floor plan and tour on the way!!Riverfront relaxation with 75ft on the Chester River. Very cozy spot to experience nature's beauty. Beautiful custom-built home waiting to show you just how to relax. Huge flowing space indoors with gorgeous Bella wood flooring into the open kitchen and entertaining space. Primary suite located on the main floor with a private door out to river

    David Crider Berkshire Hathaway HomeServices PenFed Realty

    31667 W Edge Rd, Millington, MD 21651
  • /2

    $549,000 Coming Soon

    • 5 Beds
    • 2.5 Baths
    • 2,476 Sq Ft

    305 Washington Ave, Chestertown, MD 21620

    Wonderful Chestertown home with many endearing features including spacious rooms, hardwood floors, full dry basement, off street parking and more. More info and pictures soon!

    William Norris Select Land & Homes, LLC

    305 Washington Ave, Chestertown, MD 21620
  • /2

    $495,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 2,696 Sq Ft

    207 Lee Ave, Galena, MD 21635

    Irresistible Cedar Retreat in Charming Galena, MD . Nestled on an acre. This is a must- see!Tucked away at the end of a quiet cul-de-sac in the picturesque town of Galena, this beautifullyupdated cedar home is the kind of property that buyers dream about, but rarely find. With itsinviting wood-burning fireplace, and sun-drenched open floor plan, every inch of this home radiates warmth, space,

    Kim Simpson Thyme Real Estate Co LLC

    207 Lee Ave, Galena, MD 21635
  • /38

    $1,495,000

    • 3 Beds
    • 3.5 Baths
    • 3,789 Sq Ft

    26875 Mallard Rd, Chestertown, MD 21620

    Discover the luxury of coastal living with this masterpiece waterfront property located in a much sought-after location on the Chester River. When entering the home, you’re immediately greeted in the elegant foyer that opens to a formal dining room to the right, and an office to the left that could easily be converted to a first floor bedroom.The fully renovated chef’s kitchen features

    Lynn Hilfiker Gunther-McClary Real Estate

    26875 Mallard Rd, Chestertown, MD 21620
  • /37

    $285,000

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

    7483 Shortall St, Chestertown, MD 21620

    Discover this delightful, move-in-ready ranch-style home in a peaceful Chestertown setting. Featuring three bedrooms and two bathrooms, this residence boasts recent updates including fresh paint, new flooring, modern stainless steel appliances, and stunning Beechwood butcher block countertops. Enjoy abundant natural light through the beautiful front door and Anderson windows, relax on the back

    David Moore RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
  • /28

    $375,000 Open House 6/14

    • 3 Beds
    • 2.5 Baths
    • 2,294 Sq Ft

    24607 Chestertown Rd, Chestertown, MD 21620

    Situated on a generous 0.653-acre lot just outside of Chestertown, this property offers the best of both worlds—proximity to town amenities with the added benefit of space and privacy. This well-maintained home features 3 bedrooms and 2.5 bathrooms, including two recently updated baths. The interior boasts a welcoming entryway, formal dining room, and a spacious kitchen equipped with an island,

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    24607 Chestertown Rd, Chestertown, MD 21620
  • /14

    $100,000

    • 3 Beds
    • 1 Bath
    • 1,686 Sq Ft

    25350 Worton Lynch Rd, Worton, MD 21678

    ***INVESTOR ALERT!*** LOCATED IN THE TOWN OF WORTON WITH PUBLIC WATER AND SEWER! This two story, farm house style home is in need of a renovation. Three bedrooms and one second floor bathroom. Bring your tools and give this home the makeover it is waiting for! Roof is 4 years old with a 10 year transferable warranty. CASH/HARD MONEY LOAN.

    Sheila Tome Empower Real Estate, LLC

    25350 Worton Lynch Rd, Worton, MD 21678
  • /18

    $205,000

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

    310 Hilltop Ln, Chestertown, MD 21620

    Super clean, well-maintained and move-in ready! This charming 3-bedroom, 2.5-bath townhouse offers affordable, low-maintenance living. The main level features a bright kitchen, convenient half bath, in-unit laundry, a spacious living room, and an open dining area with sliding doors leading to a private patio and beautifully maintained common grounds. High Speed internet available. HOA covers lawn

    Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, Chestertown, MD 21620
  • /74

    $825,000

    • Studio
    • 7,376 Sq Ft

    3 Howell Point Rd, Betterton, MD 21610

    Charming Beachside Restaurant & Mixed-Use Property in Betterton, MD. Welcome to an exceptional opportunity to own a thriving restaurant and mixed-use building located in the heart of Betterton, a charming waterfront town in Kent County, Maryland. This property is not just a place to dine, but a hub of community life, offering both a bustling restaurant business and multiple income-generating

    Amber Durand Patterson-Schwartz Real Estate

    3 Howell Point Rd, Betterton, MD 21610

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