207

Kent County MD Homes for Sale

Section Image
  • /2

    $50,000

    $10K PRICE DROP
    • Land
    • 13,503 Sq Ft
    • $161,290 per Acre

    21451 E Sharp St, Rock Hall, MD 21661

    Build your Eastern Shore getaway on this desirable in‐town lot in the heart of Rock Hall, just moments from marinas, waterfront dining, and all the charms of this beloved harbor town.. Rare opportunity to own a cleared, town‐served building lot on East Sharp Street, offering approximately 0.31 acres (about 13,500+ square feet) in Rock Hall’s R‐1 low‐density residential district. With public water

    Dale Hunter Bayside Realty

    21451 E Sharp St, Rock Hall, MD 21661
  • /17

    $663,000

    • Land
    • 18.62 Acres
    • $35,607 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
  • /3

    $125,000

    • Land
    • 32,670 Sq Ft
    • $166,667 per Acre

    13 Wilson Point Rd, Galena, MD 21635

    Build your custom Eastern Shore home at Wilson Point Estates, this intimate 14-lot community minutes from the Sassafras River and local marinas. Homesites feature a builder tie-in with Concierge Homes, offering a fully custom design experience guided by Construction Concierge by Conestoga. Design review and minimum building requirements apply. Pricing varies by lot and home design.

    Aaron Clark Patterson-Schwartz-Middletown

    13 Wilson Point Rd, Galena, MD 21635
  • /2

    $24,000

    $4K PRICE INCREASE
    • Land
    • 21,780 Sq Ft
    • $48,000 per Acre

    23710 L Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    23710 L Rd, Chestertown, MD 21620
  • /46

    $385,000

    $155K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft

    26670 Maple Ave, Still Pond, MD 21667

    The Kent County State Health Department have approved percs for the following three properties: 26670 Maple Avenue Tax Map 13/Parcel 16/Deed Reference 77/422 with the recording of a 1920 dwelling, 26680 Maple Avenue Tax Map 13/Parcel 17/identified as Parcel #1 Deed Reference 249/96 with the recording of a 1940 dwelling and .5 acre parcel of land Tax Map 13/Parcel 9/identified as Parcel #2 Deed

    Debbie Meikle Doug Ashley Realtors, LLC

    26670 Maple Ave, Still Pond, MD 21667
  • /3

    $150,000

    • Land
    • 32,670 Sq Ft
    • $200,000 per Acre

    6 Wilson Point Rd, Galena, MD 21635

    Build your custom Eastern Shore home at Wilson Point Estates, this intimate 14-lot community minutes from the Sassafras River and local marinas. Homesites feature a builder tie-in with Concierge Homes, offering a fully custom design experience guided by Construction Concierge by Conestoga. Design review and minimum building requirements apply. Pricing varies by lot and home design.

    Aaron Clark Patterson-Schwartz-Middletown

    6 Wilson Point Rd, Galena, MD 21635
  • /2

    $75,000

    $20K PRICE DROP
    • Land
    • 16,553 Sq Ft
    • $197,366 per Acre

    11930 Kennedyville Rd, Kennedyville, MD 21645

    Seller Says Bring All Offers! This rural 0.38-acre lot presents a unique investment opportunity in a quaint small-town atmosphere. The property is cleared and ready for your building plans, offering a blank canvas for various residential projects. With road frontage, it ensures easy access and visibility, enhancing its appeal for future buyers or renters. Notably, the lot is not currently in

    Lori Cichocki-Leonardi Remax Vision

    11930 Kennedyville Rd, Kennedyville, MD 21645
  • /14

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,476 Sq Ft

    1010 Twin Ct, Chestertown, MD 21620

    Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but

    Jason Dey Kevin Dey Realty

    1010 Twin Ct, Chestertown, MD 21620
  • /28

    $325,000

    • 3 Beds
    • 2.5 Baths
    • 1,520 Sq Ft

    21128 Striper Run, Rock Hall, MD 21661

    Welcome to 21128 Striper Run, a charming 3-bedroom, 2.5-bath home nestled in the heart of Rock Hall. Offering an exceptional opportunity to own in one of Maryland's most sought-after waterfront communities, this home combines classic charm, quality features, and outstanding value. Step inside to find beautiful real hardwood flooring throughout the main level, creating warmth and character from

    ETHAN HARVEY EXP Realty, LLC

    21128 Striper Run, Rock Hall, MD 21661
  • /50

    $468,000

    Open Sat 11AM - 1PM
    • 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
  • /30

    $415,000

    Open House 8/08 Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft

    189 Birchwood Ln, Galena, MD 21635

    Beautifully updated and maintained Colonial home in Dogwood Village. This spacious home offers nearly 2000 square feet of living plus a basement area. There is an attached 2 car garage and both a screened porch and open deck at the rear of the home. A fireplace in the living room adds warmth to cool fall and winter days. The rear of the home is accented by both spacious screened porch and an open

    Steve Parker L. C. Parker Real Estate

    189 Birchwood Ln, Galena, MD 21635
  • /3

    $300,000

    • Land
    • 4,356 Sq Ft
    • $3,000,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • /10

    $264,900

    New Construction
    • 3 Beds
    • 1.5 Baths

    121 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in 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 walk-in

    David Moore Real Broker, LLC

    121 Metcalf Rd, Chestertown, MD 21620
  • /5

    $48,000

    • Land
    • 20,037 Sq Ft
    • $104,348 per Acre

    0 Sharp St Unit MDKE2005760, Rock Hall, MD 21661

    Come build your dream home. Located right off E Sharp Street on Chesapeake Villa is your .46 acre lot. Location is perfect to everything Rock Hall has to offer, from shops to restaurants to the water. Come check it out today. Lot has water/sewer hookup available, contact town of rock hall to confirm fees.

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    0 Sharp St Unit MDKE2005760, Rock Hall, MD 21661
  • /13

    $364,900

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

    21131 Striper Run, Rock Hall, MD 21661

    New construction duplex in desirable Waterman’s Estates! Move-in ready 3BR, 2.5BA home with quality finishes throughout including luxury vinyl plank flooring on both levels, quartz countertops, and stainless steel appliances. Open-concept first floor offers spacious living, dining, and kitchen areas, plus powder room and separate laundry room. Upstairs features a primary suite with walk-in closet

    Cindy Genther Rock Hall Properties Real Estate

    21131 Striper Run, Rock Hall, MD 21661
  • /2

    $38,000

    $17K PRICE INCREASE
    • Land
    • 24,393 Sq Ft
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Spinnaker Rd, Chestertown, MD 21620
  • /4

    $5,000

    • Land
    • 14,810 Sq Ft
    • $14,706 per Acre

    0 Bunting Rd, 6, Fairlee, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:30 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to all the attractions in Chestertown, Maryland. It offers easy

    Adam Shpritz Ashland Auction Group LLC

    0 Bunting Rd, 6, Fairlee, 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
  • /14

    $129,900

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 800 Sq Ft

    21899 Lovers Ln, Rock Hall, MD 21661

    Charming home nestled on a spacious lot in the Rock Hall area. This property offers comfortable single-level living with a functional layout, generous outdoor space, and plenty of room to enjoy the peaceful surroundings. Conveniently located near local amenities, marinas, and the Chesapeake Bay, this home presents an excellent opportunity for year-round living, a weekend retreat, or investment

    Daniel Demers Sell Your Home Services

    21899 Lovers Ln, Rock Hall, MD 21661
  • /16

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft

    20725 Wilkins Ave, Rock Hall, MD 21661

    Charming 3-bedroom, 2-bath rancher situated on a 0.4-acre lot in Ferry Park, just one block from Rock Hall Beach. This 1,458 sq. ft. home features an open-concept kitchen and dining area, creating a bright and inviting space for everyday living and entertaining. Located on a quiet street, yet within walking distance of local restaurants, marinas, and all that downtown Rock Hall has to offer.

    Robin Fithian Rock Hall Properties Real Estate

    20725 Wilkins Ave, Rock Hall, MD 21661
  • /2

    $205,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,341 Sq Ft

    202 Pine St, Chestertown, MD 21620

    Jay McCall Coldwell Banker Chesapeake Real Estate Company

    202 Pine St, Chestertown, MD 21620
  • /2

    $10,000

    • Land
    • 14,810 Sq Ft
    • $29,412 per Acre

    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620

    Build Your Dream Home on Two Expansive Lots in Chesapeake Landing!15,000 SQFT of prime land combining Lots 191 & 192 on the south side of Clarissa Road, Block 2 of Chesapeake Landing, all under one tax ID. This is a rare opportunity to design and build your custom home in a sought-after community where nearby homes are selling in the high $600Ks!Enjoy the charm of Chestertown living, just

    Rena Champaco EXP Realty, LLC

    0 Clarissa Rd Unit MDKE2005786, Chestertown, MD 21620
  • /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
  • /23

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,326 Sq Ft

    5686 S Main St, Rock Hall, MD 21661

    Sweet corner property in downtown Rock Hall, right on the 4th of July parade route! Just two blocks from the Rock Hall Harbor/ Chesapeake Bay. A welcoming home with a spacious kitchen and formal dining room, or enjoy meals outside in the fenced-in back yard! The large living room has hardwood floors and a wood stove for cozy winter nights. This home features a hard to find first-floor primary

    Julia Hilfiker Gunther-McClary Real Estate

    5686 S Main St, Rock Hall, MD 21661
  • /6

    $10,500

    $2K PRICE DROP
    • Land
    • 1.49 Acres
    • $7,047 per Acre

    23737 Smithville Rd, Worton, MD 21678

    This 1.49-acre wooded lot offers a strong opportunity for buyers seeking flexibility and value. The property provides space for recreational use and the potential for a long-term investment.Ideal for hunting and camping, the land offers a range of outdoor activities. With a location just 5 miles from Worton Creek Marina, this brings you convenient access for boating the Chesapeake Bay and its

    Jack Boniface Cross Street Realtors LLC

    23737 Smithville Rd, Worton, MD 21678
  • /70

    $499,999

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

    103 Landing Ln, Chestertown, MD 21620

    MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • /3

    $135,000

    • Land
    • 32,670 Sq Ft
    • $180,000 per Acre

    5 Wilson Point Rd, Galena, MD 21635

    Welcome to Wilson Point Estates – Nestled in a peaceful, secluded setting, this exclusive community offers 14 generously sized lots with No Builder Tie-In but developer must approve the architectural appearance of the home. With each lot carefully placed to preserve the natural beauty and privacy of the landscape, Every residence will reflect quality craftsmanship, offering both comfort and style

    Aaron Clark Patterson-Schwartz-Middletown

    5 Wilson Point Rd, Galena, MD 21635
  • /54

    $515,000

    $35K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,132 Sq Ft

    14136 Kentmore Park Rd, Kennedyville, MD 21645

    Amazing waterfront community on the Sassafras river. This Kentmore Park cottage was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect get away or primary residence. Well maintained. Four bedrooms and two baths. One bath reconfigured with stack washer and

    Patricia Kern Gunther-McClary Real Estate

    14136 Kentmore Park Rd, Kennedyville, MD 21645
  • /92

    $829,000

    $36K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    106 S Queen St, Chestertown, MD 21620

    Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic DistrictThe Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    106 S Queen St, Chestertown, MD 21620
  • /6

    $128,000

    • Land
    • 1.64 Acres
    • $78,049 per Acre

    0 Crosby Rd, Rock Hall, MD 21661

    This nice wooded lot on Crosby Rd is 0.2 mile to Long Cove Marina and Long Cove County Landing. Rock Hall Yacht Club is just up the road on McKinleyville Rd. With 142 ft of road frontage and a wooded buffer, there's lots of privacy and room to roam. Included in the price is a 2-hour consult with a licensed architect to design your dream home. The property is near navigable water, but not in the

    Cindy Genther Rock Hall Properties Real Estate

    0 Crosby Rd, Rock Hall, MD 21661
  • /74

    $824,900

    Open Sat 11AM - 1PM
    • 5 Beds
    • 3.5 Baths
    • 4,353 Sq Ft

    8999 Orchard Dr, Chestertown, MD 21620

    Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort.Upon arrival, the

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    8999 Orchard Dr, Chestertown, 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
  • /7

    $5,000

    • Land
    • 16,117 Sq Ft
    • $13,514 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:35 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to all the attractions in Chestertown, Maryland. It offers easy

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • /9

    $155,000

    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft

    409 Calvert St, Chestertown, MD 21620

    Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants, parks, and the waterfront. Offering a functional floor plan with spacious living areas, generously sized bedrooms, and a back yard with additional rear parking, this home is ready for its next owner to make it their own. This

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    409 Calvert St, Chestertown, MD 21620
  • /5

    $259,900

    Open House 8/08 Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    6179 Dorlon Dr, Rock Hall, MD 21661

    Coming Soon in Rock Hall! Freshly renovated and ready to welcome you home. This property offers a bright new feel from the moment you step inside. Thoughtful updates and beautiful finishes create an inviting interior, while the spacious yard and mature trees provide plenty of room to enjoy the outdoors. Whether you’re searching for your first home, looking to downsize or low maintenance living,

    Crystal Smith RE/MAX Executive

    6179 Dorlon Dr, Rock Hall, MD 21661
  • /3

    $85,000

    $35K PRICE DROP
    • 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
  • /2

    $9,000

    $3K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $26,471 per Acre

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

    All offers considered! Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
  • /43

    $935,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 3 Baths
    • 2,102 Sq Ft

    24050 Macs Ln, Worton, MD 21678

    This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to serve as base camp for water sports down by the water, dock with direct access to the Chesapeake Bay, barn with a stall for your horse or sheep, and detached 2 car garage with lounge area above. Here you can enjoy the abundance

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    24050 Macs Ln, Worton, MD 21678
  • /33

    $382,500

    $43K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,458 Sq Ft

    11901 Dairy St, Kennedyville, MD 21645

    Buyer's remorse means this house is again available at an amazing price! Spacious home in Kenndyville with lots of amenities. Featuring 4 bedrooms and 2.5 baths with a large kitchen with granite countertops, living room with gas fireplace, 2-car detached garage, and a huge unfinished basement. Plenty of storage. Deck off the living room leads to a partially fenced back yard. Just a short drive to

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    11901 Dairy St, Kennedyville, MD 21645
  • /33

    $379,900

    $40K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,927 Sq Ft

    104 Main St, Betterton, MD 21610

    Sweet Victorian in downtown Betterton, just a short walk to Betterton Beach. Home has been lovingly cared for by the same owners for nearly 50 years. The main floor features the living room, dining room, and kitchen. As well as a laundry room with half bath, an office, an entry room in the front, and mud room in the back. On the second floor you will find 3 bedrooms and a full bath. On the 3rd

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    104 Main St, Betterton, MD 21610

Showing Results 121 - 160, Page 4 of 6

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