197

Kent County MD Homes for Sale

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  • 102 Flying Cloud Dr, Chestertown, MD 21620
    102 Flying Cloud Dr, Chestertown, MD 21620
    102 Flying Cloud Dr, Chestertown, MD 21620
    /41

    $339,900

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    102 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large

    Dan Foster Long & Foster Real Estate, Inc.

    102 Flying Cloud Dr, Chestertown, MD 21620
  • 20694 Mercer Ave, Rock Hall, MD 21661
    20694 Mercer Ave, Rock Hall, MD 21661
    20694 Mercer Ave, Rock Hall, MD 21661
    /34

    $650,000

    • 4 Beds
    • 2 Baths
    • 2,271 Sq Ft

    20694 Mercer Ave, Rock Hall, MD 21661

    Spacious in-town home with coastal charm, just 1 block from the Rock Hall beach on the Chesapeake Bay! This home offers a luxe front porch, as well as a screened-in porch, perfect for meals and entertaining. The large family room boasts a gas fireplace, built-in shelving, wood ceilings, and a sunny balcony featuring a striped awning. The eat-in kitchen has updated appliances and ample room; it

    Julia Hilfiker Gunther-McClary Real Estate

    20694 Mercer Ave, Rock Hall, MD 21661
  • 23683 L Rd, Chestertown, MD 21620
    23683 L Rd, Chestertown, MD 21620
    23683 L Rd, Chestertown, MD 21620
    /4

    $6,000

    • Land
    • 30,056 Sq Ft
    • $8,696 per Acre

    23683 L Rd, Chestertown, MD 21620

    List Price is opening bid at online auction. Auction at or above $6,000. Bidding begins Saturday, June 20th, and ends Thursday, June 25, 2026 at 11:30am. 0.69± Acres of Unimproved Land in Chestertown, Kent County Zoning - Village (V) district. Is intended for:• Small, historic, or traditional rural villages• A mix of residential uses (mostly single-family homes, sometimes limited

    Larry Cooper Alex Cooper Auctioneers, Inc.

    23683 L Rd, Chestertown, MD 21620
  • 121 1st Ave, Betterton, MD 21610
    121 1st Ave, Betterton, MD 21610
    121 1st Ave, Betterton, MD 21610
    /9

    $450,000

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 3,360 Sq Ft

    121 1st Ave, Betterton, MD 21610

    This property truly has a little something for everyone! Spacious 4-bedroom, 2-bath rancher situated on 1.94 private acres in the charming waterfront town of Betterton. Featuring a full walkout basement, attached 2-car garage, and a 30x40' pole building, there’s plenty of room for hobbies, storage, boats, workshops, or recreational toys. Step onto the welcoming screened front porch and into the

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    121 1st Ave, Betterton, MD 21610
  • 107 Flying Cloud Dr, Chestertown, MD 21620
    107 Flying Cloud Dr, Chestertown, MD 21620
    107 Flying Cloud Dr, Chestertown, MD 21620
    /51

    $385,000

    $10K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,534 Sq Ft

    107 Flying Cloud Dr, Chestertown, MD 21620

    NEW PRICE – Exceptional value for over 2,500 square feet of newer construction in the Village of Chestertown! A stunning 2023-built home with well-designed architectural elevations; two tone complimentary shades which beautifully compliment these unique features. The curb appeal captures your attention and the welcoming front porch invites you to slow down and relax.. your home! Step through the

    Cynthia Gardner CENTURY 21 New Millennium

    107 Flying Cloud Dr, Chestertown, MD 21620
  • 0 River Bend Ln, Millington, MD 21651
    0 River Bend Ln, Millington, MD 21651
    0 River Bend Ln, Millington, MD 21651
    /7

    $86,000

    • Land
    • 18,730 Sq Ft
    • $200,000 per Acre

    0 River Bend Ln, Millington, MD 21651

    Located on the upper Chester River in Millington, River Bend Lane offers the perfect blend of convenience and waterfront lifestyle just seconds from Route 301 for easy commuting. Skip the hassle and expense of a perc test — the owners have already secured public water and sewer allocation, making the building process that much easier. Enjoy kayaking, fishing, and peaceful river views right from

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 River Bend Ln, Millington, MD 21651
  • 22300 Frazier Rd, Rock Hall, MD 21661
    22300 Frazier Rd, Rock Hall, MD 21661
    22300 Frazier Rd, Rock Hall, MD 21661
    /38

    $427,000

    Open Sat 11AM - 1PM $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,556 Sq Ft

    22300 Frazier Rd, Rock Hall, MD 21661

    Tucked away on a peaceful 0.47-acre lot surrounded by trees, this custom-built contemporary home offers the kind of privacy and natural beauty that’s hard to find. From the moment you arrive, it feels like your own private retreat.Inside, the open floor plan is filled with warmth and character, featuring exposed beams, rich hickory flooring, and beautiful wood accents throughout. Skylights

    Chris Kendall Cross Street Realtors LLC

    22300 Frazier Rd, Rock Hall, MD 21661
  • 34203 Cypress Rd, Millington, MD 21651
    34203 Cypress Rd, Millington, MD 21651
    34203 Cypress Rd, Millington, MD 21651
    /65

    $760,000

    • 3 Beds
    • 2 Baths
    • 2,058 Sq Ft

    34203 Cypress Rd, Millington, MD 21651

    Two parcels combine for a total of 5.22 acres, offering a rare blend of space, versatility, and opportunity. The separate 3.21-acre parcel is perc-approved and buildable, currently used for hunting, and includes its own right-of-way for private access. The main home sits on 2.012 acres and has been lovingly maintained and thoughtfully updated over the years. Inside, you’ll find a spacious and

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    34203 Cypress Rd, Millington, MD 21651
  • 4819 Eastern Neck Rd, Rock Hall, MD 21661
    4819 Eastern Neck Rd, Rock Hall, MD 21661
    4819 Eastern Neck Rd, Rock Hall, MD 21661
    /74

    $665,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,745 Sq Ft

    4819 Eastern Neck Rd, Rock Hall, MD 21661

    Custom-built and thoughtfully designed, this stunning one-level home offers the perfect blend of privacy, quality, and Eastern Shore charm on 2.5 serene acres just across from the Chester River and only two miles from the quaint waterfront town of Rock Hall. Built to the highest of standards in 2022, this newer home showcases designer touches throughout with an open, airy layout featuring three

    Jennifer Chaney Chaney Homes, LLC

    4819 Eastern Neck Rd, Rock Hall, MD 21661
  • 0 Sandy Bottom Rd, 6, Fairlee, MD 21620
    0 Sandy Bottom Rd, 6, Fairlee, MD 21620
    0 Sandy Bottom Rd, 6, Fairlee, MD 21620
    /6

    $79,000

    • Land
    • 1.95 Acres
    • $40,513 per Acre

    0 Sandy Bottom Rd, 6, Fairlee, MD 21620

    Escape to the peace and quiet of the countryside with this beautiful private wooded 2-acre lot, tucked away down a secluded gravel lane. Offering a perfect blend of mature trees and a partially open entrance area, this property is ideal for camping, hunting, recreation, or simply enjoying nature in a tranquil setting. Bring your RV or pitch a tent and enjoy the great outdoors! Electric is

    John Carroll Village Real Estate Company LLC

    0 Sandy Bottom Rd, 6, Fairlee, MD 21620
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /38

    $314,900

    $15K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town amenities. Enjoy easy one-level living with a functional layout and gorgeous hardwood floors that add warmth and character throughout the home. The beautiful white kitchen features stainless steel appliances, including a gas

    Dawn Kane Redfin Corporation

    304 Hadaway Dr, Chestertown, MD 21620
  • 21190 Green Ln, Rock Hall, MD 21661
    21190 Green Ln, Rock Hall, MD 21661
    21190 Green Ln, Rock Hall, MD 21661
    /8

    $850,000

    • Land
    • 10.4 Acres
    • $81,731 per Acre

    21190 Green Ln, Rock Hall, MD 21661

    Unique opportunity offering two adjoining parcels with exceptional potential in Rock Hall. Parcel 1 consists of approximately 1.4 acres located on Geen Lane and is zoned Critical Area Residential. Improvements include the foundation of a pre-existing structure, an existing well, and a grinder pump connected to public sewer already installed. Buyer to verify well usability and buildability. Parcel

    Cindy Genther Rock Hall Properties Real Estate

    21190 Green Ln, Rock Hall, MD 21661
  • 214 Silver Heel Rd, Chestertown, MD 21620
    214 Silver Heel Rd, Chestertown, MD 21620
    214 Silver Heel Rd, Chestertown, MD 21620
    /26

    $340,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,972 Sq Ft

    214 Silver Heel Rd, Chestertown, MD 21620

    Price Reduction! VERY motivated seller—open to all reasonable offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer construction—major

    Chris Kendall Cross Street Realtors LLC

    214 Silver Heel Rd, Chestertown, MD 21620
  • 21451 E Sharp St, Rock Hall, MD 21661
    21451 E Sharp St, Rock Hall, MD 21661
    /2

    $55,000

    $5K PRICE DROP
    • Land
    • 13,503 Sq Ft
    • $177,419 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
  • 407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    /57

    $798,000

    $30K PRICE DROP
    • 3 Beds
    • 4.5 Baths
    • 3,047 Sq Ft

    407 High St, Chestertown, MD 21620

    Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    407 High St, Chestertown, MD 21620
  • 0 Crosby Rd, Rock Hall, MD 21661
    0 Crosby Rd, Rock Hall, MD 21661
    0 Crosby Rd, Rock Hall, MD 21661
    /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
  • 103 Trafford Dr, Chestertown, MD 21620
    103 Trafford Dr, Chestertown, MD 21620
    103 Trafford Dr, Chestertown, MD 21620
    /65

    $399,900

    Open Sat 11AM - 1PM $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,944 Sq Ft

    103 Trafford Dr, Chestertown, MD 21620

    PRICE IMPROVEMENT: Priced below 2025 Appraisal!! Instant equity! NOTE: Zillow's property taxes are incorrect: correct annual property taxes are $4,338. Welcome to 103 Trafford Drive; an exceptionally maintained 3 bedroom home just minutes from downtown Chestertown. Nestled in family-friendly Coventry Farms Community, this Colonial-style residence has been recently updated in all the right places

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Trafford Dr, Chestertown, MD 21620
  • 116 N Cross St, Chestertown, MD 21620
    116 N Cross St, Chestertown, MD 21620
    116 N Cross St, Chestertown, MD 21620
    /9

    $109,999

    • Land
    • 7,840 Sq Ft
    • $611,106 per Acre

    116 N Cross St, Chestertown, MD 21620

    Great opportunity in the heart of Chestertown. This downtown commercial lot offers incredible potential just steps from established businesses and local amenities. Public sewer is available and accessible, making development that much more convenient. Positioned next to a professional office building, the property benefits from strong daily visibility with both foot and vehicle traffic passing

    Hayley Norris Select Land & Homes, LLC

    116 N Cross St, Chestertown, MD 21620
  • 26765 Dutchtown Rd, Still Pond, MD 21667
    26765 Dutchtown Rd, Still Pond, MD 21667
    26765 Dutchtown Rd, Still Pond, MD 21667
    /15

    $159,999

    $29K PRICE DROP
    • Land
    • 21,780 Sq Ft
    • $319,998 per Acre

    26765 Dutchtown Rd, Still Pond, MD 21667

    Situated at the end of a quiet dead-end street with only a handful of neighboring homes, this private 1/2 acre lot with a 1250 SF Rancher , 3 bedroom, 2 bath offers a serene setting backing to woods, with open farmland across the street. Enjoy the peace of rural living just minutes from the waterfront—only about 3 minutes to Betterton Beach. Location is the ultimate Pet safe environment as you're

    Michael Kelczewski DMV Prime Properties

    26765 Dutchtown Rd, Still Pond, MD 21667
  • 0 Walnut St, Rock Hall, MD 21661
    0 Walnut St, Rock Hall, MD 21661
    0 Walnut St, Rock Hall, MD 21661
    /4

    $50,000

    • Land
    • 37,026 Sq Ft
    • $58,824 per Acre

    0 Walnut St, Rock Hall, MD 21661

    This listing is for the sale of parcel 504, a 0.85 ac property off Walnut St in the town of Rock Hall. A buyer should confirm buildability and availability of public water and sewer.

    Cindy Genther Rock Hall Properties Real Estate

    0 Walnut St, Rock Hall, MD 21661
  • 104 Main St, Betterton, MD 21610
    104 Main St, Betterton, MD 21610
    104 Main St, Betterton, MD 21610
    /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
  • 0 Walnut St, Rock Hall, MD 21661
    0 Walnut St, Rock Hall, MD 21661
    0 Walnut St, Rock Hall, MD 21661
    /4

    $67,000

    • Land
    • 11,325 Sq Ft
    • $257,692 per Acre

    0 Walnut St, Rock Hall, MD 21661

    Nice lot near Rock Hall Harbor. The property is 75 ft x 150 ft. This lot (Parcel 502) is in the 100 year flood plain and in the Intense Development Area of the Chesapeake Bay Critical Area. It is partially cleared. Public water and sewer hook ups are available. Buyer to confirm buildability. There are a total of 3 adjacent vacant land parcels available for sale in this offering, either separately

    Cindy Genther Rock Hall Properties Real Estate

    0 Walnut St, Rock Hall, MD 21661
  • 0 Walnut St, Rock Hall, MD 21661
    0 Walnut St, Rock Hall, MD 21661
    0 Walnut St, Rock Hall, MD 21661
    /4

    $89,000

    • Land
    • 14,810 Sq Ft
    • $261,765 per Acre

    0 Walnut St, Rock Hall, MD 21661

    This listing is for parcel 501 on Walnut Street, a 100 ft x 150 ft vacant lot. The property is in the 100 year flood plain and in the Intense Development Area of the Chesapeake Bay Critical Area. Public water and sewer hook ups could be available. Buyer to confirm buildability. Additional adjacent lots are available separately or as a package.

    Cindy Genther Rock Hall Properties Real Estate

    0 Walnut St, Rock Hall, MD 21661
  • 103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    /22

    $259,900

    New Construction
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    103 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

    103 Metcalf Rd, Chestertown, MD 21620
  • 5666 Walnut St, Rock Hall, MD 21661
    5666 Walnut St, Rock Hall, MD 21661
    5666 Walnut St, Rock Hall, MD 21661
    /18

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    5666 Walnut St, Rock Hall, MD 21661

    Great location for this older manufactured home near Rock Hall harbor. The house needs renovation and repairs, but the site offers a great location with nice views of North Point Marina and Rock Hall harbor. With three bedrooms and 2 baths on one-level living, this 1,200+ sq.ft. home would make a wonderful vacation or retirement home. The property is being sold as-is. Cleared, level lot.

    Cindy Genther Rock Hall Properties Real Estate

    5666 Walnut St, Rock Hall, MD 21661
  • 11060 Plum Dr, Worton, MD 21678
    11060 Plum Dr, Worton, MD 21678
    11060 Plum Dr, Worton, MD 21678
    /14

    $280,000

    $19K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    11060 Plum Dr, Worton, MD 21678

    Discover this beautiful 3-bedroom Cape Cod home in the heart of Worton, Maryland, conveniently located near local amenities and scenic Eastern Shore attractions. Thoughtfully updated with over $20,000 in upgrades, this residence effortlessly blends classic charm with modern comfort. The inviting living spaces feature abundant natural light and elegant finishes throughout. The upgraded kitchen is

    ALICE BENNETT Patterson-Schwartz Real Estate

    11060 Plum Dr, Worton, MD 21678
  • 4020 Eastern Neck Rd, Rock Hall, MD 21661
    4020 Eastern Neck Rd, Rock Hall, MD 21661
    4020 Eastern Neck Rd, Rock Hall, MD 21661
    /26

    $850,000

    • 4 Beds
    • 2 Baths
    • 3,300 Sq Ft

    4020 Eastern Neck Rd, Rock Hall, MD 21661

    This charming traditional home, originally built in 1957 was renovated around 2000. It offers a blend of classic appeal and modern comfort. Spanning about 3,300 square feet, the spacious layout invites you to create lasting memories. Wood and ceramic tile flooring throughout provide a cozy atmosphere. The expansive outdoor space offers endless possibilities. Currently in ag use, the 25 acres at

    Cindy Genther Rock Hall Properties Real Estate

    4020 Eastern Neck Rd, Rock Hall, MD 21661
  • 5120 Eastern Neck Rd, Rock Hall, MD 21661
    5120 Eastern Neck Rd, Rock Hall, MD 21661
    5120 Eastern Neck Rd, Rock Hall, MD 21661
    /5

    $55,000

    • Land
    • 21,780 Sq Ft
    • $110,000 per Acre

    5120 Eastern Neck Rd, Rock Hall, MD 21661

    Welcome to 5120 Eastern Neck Road—an exceptional opportunity to own a .50-acre homesite just outside the charming waterfront town of Rock Hall. Perfectly positioned for both privacy and convenience, this property offers the ideal setting to bring your vision to life in a peaceful, coastal-inspired setting. This lot features an existing public water and sewer allocation already in place, offering

    Angela Demattia Berkshire Hathaway HomeServices PenFed Realty

    5120 Eastern Neck Rd, Rock Hall, MD 21661
  • 8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    /7

    $320,000

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

    8706 Elm Rd, Chestertown, MD 21620

    Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the

    Andrew Meikle Doug Ashley Realtors, LLC

    8706 Elm Rd, Chestertown, MD 21620
  • 11167 Oak Ln, Worton, MD 21678
    11167 Oak Ln, Worton, MD 21678
    11167 Oak Ln, Worton, MD 21678
    /17

    $288,500

    $11K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    11167 Oak Ln, Worton, MD 21678

    Affordable, updated, and close to the water! Welcome to easy Eastern Shore living in this beautifully updated 3-bedroom, 1-bath home that truly feels like new. Recently updated with a new roof, water heater, HVAC system, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, and a vapor barrier and insulation in the crawlspace. This home brings modern

    Marti McGinty Chesapeake Real Estate Associates, LLC

    11167 Oak Ln, Worton, MD 21678
  • 11942 Flour Mill St, Kennedyville, MD 21645
    11942 Flour Mill St, Kennedyville, MD 21645
    11942 Flour Mill St, Kennedyville, MD 21645
    /27

    $350,000

    • 4 Beds
    • 2.5 Baths
    • 1,806 Sq Ft

    11942 Flour Mill St, Kennedyville, MD 21645

    Colonial in Kennedyville overlooking the pond. Situated on a corner lot with a private driveway behind the house. 2 car attached garage, 4 bedrooms and 2.5 baths. Gas fireplace. Large mudroom with laundry. Partially finished basement with new carpeting. Lovely front porch for relaxing and enjoying the view.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    11942 Flour Mill St, Kennedyville, MD 21645
  • 11901 Dairy St, Kennedyville, MD 21645
    11901 Dairy St, Kennedyville, MD 21645
    11901 Dairy St, Kennedyville, MD 21645
    /33

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 2,458 Sq Ft

    11901 Dairy St, Kennedyville, MD 21645

    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 downtown Chestertown.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    11901 Dairy St, Kennedyville, MD 21645
  • 14136 Kentmore Park Rd, Kennedyville, MD 21645
    14136 Kentmore Park Rd, Kennedyville, MD 21645
    14136 Kentmore Park Rd, Kennedyville, MD 21645
    /54

    $525,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,132 Sq Ft

    14136 Kentmore Park Rd, Kennedyville, MD 21645

    Kentmore Park cottage. 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 dryer. Could be returned to full bath when relocating washer and

    Patricia Kern Gunther-McClary Real Estate

    14136 Kentmore Park Rd, Kennedyville, MD 21645
  • 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
  • 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 House 7/02
    • 3 Beds
    • 2.5 Baths
    • 1,760 Sq Ft

    21186 Chesapeake Ave, Rock Hall, MD 21661

    Deck was washed and stained on 5/20/26! 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

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    21186 Chesapeake Ave, Rock Hall, MD 21661
  • 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

    $282,000

    Open House 7/05 $13K PRICE DROP
    • 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. *SELLER ASSISTANCE AVAILABLE TOWARDS CLOSING COSTS* 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

    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

    $244,500

    $21K PRICE DROP
    • 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
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /31

    $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
  • 103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    /53

    $550,000

    • 5 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
    /30

    $394,900

    $5K PRICE DROP
    • 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

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