197

Kent County MD Homes for Sale

Section Image Section Image
  • /25

    $325,000

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

    10572 Watonga Rd, Chestertown, MD 21620

    Welcome home to 10572 Watonga Road, a charming Cape Cod nestled on a beautifully wooded corner lot in the desirable Chesapeake Landing community. Built in 2007 and meticulously maintained, this 3-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and Eastern Shore charm. The spacious .35-acre property is surrounded by mature trees, creating peaceful wooded views from both the

    Samantha Zarnes Serhant

    10572 Watonga Rd, Chestertown, MD 21620
  • /64

    $575,000

    • 1 Bed
    • 1.5 Baths
    • 1,724 Sq Ft

    25133 Wymont Park Rd, Worton, MD 21678

    Welcome to Wymont Park, a sought-after waterfront community on picturesque Still Pond Creek, where every day feels like a vacation on Maryland's Eastern Shore. From sipping your morning coffee while watching the sunrise over the water to enjoying breathtaking waterfront sunsets from your private floating dock, this unique property offers the lifestyle you dream about. Nestled on a beautiful

    Agent Photo

    Brittany Fox

    RE/MAX Chesapeake

    (443) 332-9941

    25133 Wymont Park Rd, Worton, MD 21678
  • /7

    $75,000

    • Land
    • 2.2 Acres
    • $34,091 per Acre

    0 Fairlee Rd, Chestertown, MD 21620

    Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Engineered plans are in place as well as architect plans for a 3 bedroom, 2 bath home. Buyer welcome to use these plans if it fits their needs. Lots of wildlife in the area. Perfect location

    Lori Sample RE/MAX Chesapeake

    0 Fairlee Rd, Chestertown, MD 21620
  • /26

    $284,900

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

    104 Acorn Dr, Chestertown, MD 21620

    Welcome to this three-level, interior-unit townhome in the desirable Oak Hollow community of Chestertown. Conveniently located near shopping, schools, the YMCA, and historic downtown, this home offers comfortable living and low-maintenance convenience. The entry level features a one-car garage and a flexible bonus room ideal for a home office, gym, or recreation space with walk-out access to the

    Sarah King Cross Street Realtors LLC

    104 Acorn Dr, Chestertown, MD 21620
  • /30

    $365,000

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    23264 Clarissa Rd, Chestertown, MD 21620

    Tucked neatly on a corner in Chesapeake Landing, this three-quarter acre parcel is among one of the largest in the neighborhood. The 2020 custom built home exudes simple luxury. Offering three bedrooms and two full baths in a simple and efficient floorplan, is has flow and comfort in mind. It features a modern kitchen with tall quiet close cabinets, granite counter tops and a tile backsplash,

    Liddy Campbell TTR Sotheby's International Realty

    23264 Clarissa Rd, Chestertown, MD 21620
  • /48

    $765,000

    • 4 Beds
    • 3.5 Baths
    • 3,006 Sq Ft

    24274 Waterview Dr, Worton, MD 21678

    Country elegance at its finest with this recently updated and spacious Cape Cod in the water oriented community of Clearview, just minutes from historic Chestertown. The amenities here are a major plus with Franklin pond and community access directly to Churn Creek. The home has had a transformation in the last 2 years with updated bathrooms, floors, kitchen, landscaping, and a new HVAC unit. The

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    24274 Waterview Dr, Worton, MD 21678
  • /39

    $515,000

    Open Sat 11AM - 1PM Coming Soon
    • 2 Beds
    • 2.5 Baths
    • 1,476 Sq Ft

    101 S Mill St, Chestertown, MD 21620

    This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
  • /50

    $468,000

    Open House 6/27 Coming Soon
    • 3 Beds
    • 2 Baths
    • 3,262 Sq Ft

    25750 Collins Ave, Chestertown, MD 21620

    Charming Brick Rancher Near the Chester RiverThis custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home...Living Room: Walk

    Grace Crockett Doug Ashley Realtors, LLC

    25750 Collins Ave, Chestertown, MD 21620
  • /3

    $120,000

    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft

    234 N College Ave, Chestertown, MD 21620

    Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or

    Anastasia Zivkovic Palmer Cummings & Co. Realtors

    234 N College Ave, Chestertown, MD 21620
  • /4

    $25,000

    • Land
    • 1.03 Acres
    • $24,272 per Acre

    0 3rd Ave, Betterton, MD 21610

    One acre in Betterton with the beach and boat ramp just a few blocks away! While this lot could be buildable, one would have to build a bridge across a stream to access by vehicle and public utilities while available would need to be run out there as well. Priced as recreational land for the nature enthusiast, occasional tent camper, or hunter.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 3rd Ave, Betterton, MD 21610
  • /6

    $119,900

    • 3 Beds
    • 1.5 Baths
    • 2,210 Sq Ft

    110 Prospect St, Chestertown, MD 21620

    Investor Alert - Classic 2-Story Colonial Packed with Potential! Welcome to this Charming Colonial Offering the Space, Layout, and Bones that Savvy Buyers Dream of. The Spacious Kitchen, Living Areas and Bedrooms Provide Room to Breathe and Personalize. Head Out Back to Enjoy the Enclosed Rear Porch, Yard and a Convenient Storage Shed that offers Ample Space for Tools, Equipment, and More. This

    Matthew Altizer ANR Realty, LLC

    110 Prospect St, Chestertown, MD 21620
  • /16

    $2,800,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    33658 Golts Rd, Massey, MD 21650

    Investment Opportunity is here! Kent County, Md farm offered with 207+/- acres total. The property is unencumbered by any preservation or similar easements such as MALPF or other conservation groups. A quality 1344 square foot rancher home with attached 728 square foot garage with a 216 square foot deck overlooking the pond and fields. The home was built around 1988 and a very substantial

    BRIAN MORRIS The Land Group

    33658 Golts Rd, Massey, MD 21650
  • /60

    $1,650,000

    • 9 Beds
    • 6.5 Baths
    • 4,776 Sq Ft

    8796 Maryland Pkwy, Chestertown, MD 21620

    Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8796 Maryland Pkwy, Chestertown, MD 21620
  • /87

    $1,195,000

    • 4 Beds
    • 2.5 Baths
    • 2,872 Sq Ft

    10672 Worton Rd, Worton, MD 21678

    This property has an amazing amount to offer! There are 3 parcels included with a total of just over 5.5 acres. The complex includes a 4 bedroom, 2.5 baths extremely well built home on 2.68+/- acres, a .35 acre lot and a commercially zoned 2.6+/- parcel with several large outbuildings. The house also offers a spacious kitchen with center island and granite counters, a family area, laminate

    Doug Ashley Doug Ashley Realtors, LLC

    10672 Worton Rd, Worton, MD 21678
  • /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
  • /28

    $279,000

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

    11106 Plum Dr, Worton, MD 21678

    Good as New. Renovated from top to bottom. Pictures say it all. On the outside we have a new roof, windows, and siding . Inside you will not have to do a thing except make it your own. We have all updated painting and flooring throughout the house . You will find Tile and HVLP flooring which are all heated with propane. Kitchen has been updated and freshened up and ready for a new owner. For all

    Grace Crockett Doug Ashley Realtors, LLC

    11106 Plum Dr, Worton, MD 21678
  • /54

    $449,900

    • 4 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    10781 Fermoy Rd, Chestertown, MD 21620

    Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country

    David Moore Real Broker, LLC

    10781 Fermoy Rd, Chestertown, MD 21620
  • /2

    $85,000

    • Land
    • 4.03 Acres
    • $21,092 per Acre

    8886 Georgetown Rd, Georgetown, MD 21620

    Discover the possibilities on this beautiful 4+ acre parcel. Recently surveyed, with water and sewer allocations paid, a value exceeding $16,000! This property offers a rare combination of privacy, recreation, and convenience. Whether you're seeking a peaceful retreat, hunting property, or camping getaway, this versatile parcel offers endless opportunities. Enjoy the tranquility of nature,

    TAMMY GREEN Samson Properties

    8886 Georgetown Rd, Georgetown, MD 21620
  • /39

    $380,000

    • 4 Beds
    • 2 Baths
    • 1,277 Sq Ft

    213 Byford Dr, Chestertown, MD 21620

    Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other

    Grace Crockett Doug Ashley Realtors, LLC

    213 Byford Dr, Chestertown, MD 21620
  • /2

    $200,000

    • 4 Beds
    • 1 Bath
    • 2,920 Sq Ft

    21172 Wyoming Ave, Chestertown, MD 21620

    Great area and lot walking distance to the Chesapeake bay and Tolchester Marina. House is in need of rehab but offers quite a bit of upside in the lot and location. Buyer to verify all info

    Keith French Blue Star Real Estate, LLC

    21172 Wyoming Ave, Chestertown, MD 21620
  • /70

    $3,000,000

    • 3 Beds
    • 4 Baths
    • 3,142 Sq Ft

    25440 Learman Rd, Chestertown, MD 21620

    Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, featuring 560 feet of prime water frontage on the Chester River and a private 140-foot dock with 7 feet of mean low water, perfect for all your adventures. ** The heart of this property is the beautifully renovated 3-bedroom, 2

    Liddy Campbell TTR Sotheby's International Realty

    25440 Learman Rd, Chestertown, MD 21620
  • /49

    $1,450,000

    • 4 Beds
    • 5 Baths
    • 4,257 Sq Ft

    22470 Fairgale Farm Ln, Chestertown, MD 21620

    Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away.The home features 4 bedrooms and 5 full

    Ashton Kelley Gunther-McClary Real Estate

    22470 Fairgale Farm Ln, Chestertown, MD 21620
  • /15

    $425,000

    $25K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 1,518 Sq Ft

    522 High St, Chestertown, MD 21620

    Historic Charm in the Heart of Downtown Chestertown Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3

    Taylor Leaverton Benson & Mangold, LLC

    522 High St, Chestertown, MD 21620
  • /40

    $395,000

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    31673 W Edge Rd, Millington, MD 21651

    Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gently sloped backyard to the updated bulkhead at the water's edge. Launch your kayak and explore the river and allow the tide to take you as you explore the river. When done relax indoors to an updated home that offers an open floor

    Doug Ashley Doug Ashley Realtors, LLC

    31673 W Edge Rd, Millington, MD 21651
  • /2

    $15,000

    • Land
    • 1 Acre
    • $15,000 per Acre

    23741 L Rd, Chestertown, MD 21620

    Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all due diligence regarding perc testing, building suitability, zoning, utilities, and intended use.

    Taylor Leaverton Benson & Mangold, LLC

    23741 L Rd, Chestertown, MD 21620
  • /36

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    21123 Striper Run, Rock Hall, MD 21661

    Beautiful 2,040 sq ft Richland Builders end-unit situated on a premium oversized lot in the heart of Rock Hall. This spacious coastal home offers a flexible and highly desirable floor plan featuring 4 bedrooms, including an expansive rear sunroom/4th bedroom that is larger than the primary suite. With private exterior access and direct kitchen entry, the space is ideal for a guest suite, home

    susan taylor Chaney Homes, LLC

    21123 Striper Run, Rock Hall, MD 21661
  • /28

    $320,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,376 Sq Ft

    11054 Austin Ln, Worton, MD 21678

    The one you’ve been waiting for! This extensively updated 3 bedroom, 2 full bath ranch boasts 1,376 square feet of open living space and a roomy 2 car garage. The property sits at the end of a quiet street and lies adjacent to farm land and a pond with a seasonal view. Enjoy serene privacy from your spacious 20 x 16 deck! The home is beautifully remodeled and updated with a new stone driveway and

    Donnie Horton RE/MAX Chesapeake

    11054 Austin Ln, Worton, MD 21678
  • /48

    $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
  • /30

    $390,000

    • 3 Beds
    • 1.5 Baths
    • 1,386 Sq Ft

    5989 N Main St, Rock Hall, MD 21661

    Beautifully updated and move-in ready, this charming one-level home offers the perfect blend of comfort, style, and convenience! Recent improvements include a newly added full bath off the living area and a beautifully remodeled half bath featuring a gorgeous walk-in shower and all new finishes The inviting kitchen includes an eat-in dining area, breakfast bar, wine cooler, and brand-new

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (667) 660-4966

    5989 N Main St, Rock Hall, MD 21661
  • /28

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft

    11976 Flour Mill St, Kennedyville, MD 21645

    Welcome to 11976 Flour Mill Street in the charming Village at Kennedyville! Nestled in the heart of this small-town community, this well-maintained 3-bedroom, 2-bath rancher offers comfortable one-level living with an inviting open floor plan perfect for everyday living and entertaining alike. Enjoy relaxing mornings on the welcoming front porch or unwind on the spacious back deck overlooking the

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    11976 Flour Mill St, Kennedyville, MD 21645
  • /69

    $384,900

    • 3 Beds
    • 2.5 Baths
    • 1,712 Sq Ft

    21124 Striper Run, Rock Hall, MD 21661

    Location is EVERYTHING. Upgrades are EVERYTHING. And this stunning Rock Hall home offers BOTH. Perfectly positioned in the heart of Rock Hall, Maryland, this beautifully upgraded home delivers the coastal lifestyle buyers are searching for on Maryland’s Eastern Shore. Imagine hopping on your golf cart or bike and being just minutes from waterfront restaurants, marinas, local shops, live music,

    Crystal Smith RE/MAX Executive

    21124 Striper Run, Rock Hall, MD 21661
  • /19

    $399,000

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

    21424 Catholic Ave, Rock Hall, MD 21661

    Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, the largest residential lot on Catholic Avenue. This 4-bedroom home was redone from the inside out in 2024. The welcoming living space contains original wood accents, adding much charm to this newly updated home. Spacious open

    Julia Hilfiker Gunther-McClary Real Estate

    21424 Catholic Ave, Rock Hall, MD 21661
  • /29

    $285,000

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    956 Washington Ave, Chestertown, MD 21620

    Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in

    Grace Crockett Doug Ashley Realtors, LLC

    956 Washington Ave, Chestertown, MD 21620
  • /33

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,381 Sq Ft

    5862 N Main St, Rock Hall, MD 21661

    Adorable 3BR/2BA expanded Farm style home located on a spacious lot in the desirable neighborhood of the Town of Rock Hall. Make your way to the country style covered front porch and the door to your forever home. Step inside a home filled with original charm and character throughout offering an abundance of natural light, crown moldings, luxury flooring, and an open main floor plan. The main

    Jordan Larigan LPT Realty, LLC

    5862 N Main St, Rock Hall, MD 21661
  • /89

    $2,500,000

    • 3 Beds
    • 3.5 Baths
    • 5,236 Sq Ft

    31436 Sassafras River Ave, Galena, MD 21635

    Sassafras Riverfront Retreat | Log cabin custom built home with Deep Water Pier, (seller had their 70 ft boat docked there for 10 years) with space for several boats to be docked as well. Indoor Pool looking to the outdoors with a glass enclosure and loads of space to entertain! There are 2 separate upper-level quarters, one for guests which includes a family room, sitting room and full bath. So

    Tammy Studebaker EXP Realty, LLC

    31436 Sassafras River Ave, Galena, MD 21635
  • /62

    $549,000

    • 6 Beds
    • 6 Baths
    • 4,305 Sq Ft

    12714 Still Pond Rd, Still Pond, MD 21667

    Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    12714 Still Pond Rd, Still Pond, MD 21667
  • /62

    $549,000

    • Studio
    • 4,305 Sq Ft

    12714 Still Pond Rd, Still Pond, MD 21667

    Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    12714 Still Pond Rd, Still Pond, MD 21667
  • /73

    $430,000

    $15K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,857 Sq Ft

    24295 Langford Rd, Chestertown, MD 21620

    Welcome to 24295 Langford Road in Chestertown, Maryland—a rare opportunity to own a peaceful slice of the countryside on 2 beautiful acres surrounded by farmland. Just minutes from downtown Chestertown, this property offers the perfect balance of privacy and convenience. If you’ve been searching for a home away from the hustle and bustle, this is the one. The classic brick rancher features over

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    24295 Langford Rd, Chestertown, MD 21620
  • /49

    $419,900

    • 4 Beds
    • 2.5 Baths
    • 1,684 Sq Ft

    122 S Main St, Galena, MD 21635

    WOW! What a transformation of this sturdy Four Square Colonial nestled in a peaceful small-town setting. Enjoy the convenience of being within walking distance to parks, schools, the post office, and local markets while still having the space and privacy of an oversized nearly half-acre lot. The exterior features a detached oversized two-car garage with pull-through access to the HUGE backyard —

    John Carroll Village Real Estate Company LLC

    122 S Main St, Galena, MD 21635
  • /3

    $55,000

    • Land
    • 30,492 Sq Ft
    • $78,571 per Acre

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620

    Discover the potential of this open .69-acre lot in Fairlee! Whether you’re looking to build your dream home, create a weekend retreat, or invest in future development, this property offers endless possibilities. Zoned Village, this lot could potentially allow for a duplex or multiple dwellings, making it an excellent opportunity for builders, investors, or buyers seeking additional flexibility.

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 5

How to Buy a Home How to Finance a Home How to Sell a Home