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Kent County MD Homes for Sale with AC

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  • /23

    $350,000

    • 7 Beds
    • 6 Baths
    • 850 Sq Ft

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

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

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

    $375,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

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

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 2A, Chestertown, MD 21620
  • /46

    $685,000

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

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

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

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

    $200,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

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

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1B, Chestertown, MD 21620
  • /13

    $795,000

    • 2 Baths
    • 2,045 Sq Ft

    201 N Lynchburg St, Chestertown, MD 21620

    Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • /22

    $235,000

    • 3 Beds
    • 1.5 Baths
    • 1,278 Sq Ft

    25044 Travis Trail, Worton, MD 21678

    Welcome to this sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knight’s Landing surrounded by beautiful farmland. It’s the perfect spot if you’re looking for peaceful living without feeling far from everything—just under five minutes to the local high school, community center, and park. Cozy, convenient, and easy on the budget, this home offers small-town

    Jay McCall Coldwell Banker Chesapeake Real Estate Company

    25044 Travis Trail, Worton, MD 21678
  • /44

    $339,000

    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a

    Gregory Morris Cummings & Co. Realtors

    304 Hadaway Dr, Chestertown, MD 21620
  • /56

    $675,000 Open Sat 10AM - 12PM

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

    118 Little Harbor Way Unit 202, Chestertown, MD 21620

    Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the

    Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
  • /20

    $159,900

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft

    132 Prospect St, Chestertown, MD 21620

    Beautifully Remodeled Two-Level Colonial Offering Timeless Charm and Modern Comfort. This home features a Brand New Kitchen with New Cabinets (2026), Quartz Counters, Stainless Steel Appliances (2026), and a Stylish Tile Backsplash. Enjoy Fully Updated Bathrooms, New Flooring Throughout, and Spacious Bedrooms Filled With Natural Light. New Modern Lighting (2026) and Fresh Custom Paint enhance the

    Matthew Altizer ANR Realty, LLC

    132 Prospect St, Chestertown, MD 21620
  • /38

    $399,000

    • 3 Beds
    • 3 Baths
    • 2,200 Sq Ft

    6416 Edesville Rd, Rock Hall, MD 21661

    Completely renovated from the studs up, this beautifully updated 3-story home offers 2,200 square feet of thoughtfully designed living space just outside of Rock Hall. Featuring 3 spacious bedrooms and 3 full bathrooms — one on each level — this home provides flexibility and comfort for everyday living or guests. The open-concept main floor showcases luxury flooring, brand-new stainless steel

    Sarah Ulrick Rock Hall Properties Real Estate

    6416 Edesville Rd, Rock Hall, MD 21661
  • /33

    $510,000

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft

    32135 River Rd, Millington, MD 21651

    Experience true waterfront living on the beautiful Chester River in Millington, just 15 minutes from Middletown, DE. Situated on 0.53 acres, this charming riverfront carriage house captures breathtaking panoramic water views and offers the perfect blend of relaxation, recreation, and convenience. An expansive lighted deck creates the ideal setting for morning coffee, outdoor dining, entertaining

    Christine Catalano Coldwell Banker Realty

    32135 River Rd, Millington, MD 21651
  • /15

    $295,000

    • 3 Beds
    • 1 Bath
    • 952 Sq Ft

    423 Cypress St, Millington, MD 21651

    Turn-key, one-level living in the heart of charming downtown Millington! Welcome to 423 Cypress Street, a beautifully maintained and thoughtfully updated home that is truly move-in ready!! Take advantage of the seller’s option to convey the home fully furnished as they relocate out of state. This stress-free property has been lovingly cared for, and it shows in every detail. Major updates include

    Jenyne Ward Patterson-Schwartz Real Estate

    423 Cypress St, Millington, MD 21651
  • /25

    $275,000

    • 2 Beds
    • 2 Baths
    • 720 Sq Ft

    10971 Bottom Rd, Worton, MD 21678

    Nestled among the farmland and waterways in Kent County is a cul de sac of new homes on Bottom Road just outside of Chestertown. The new 2 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered

    Andy Batch Keller Williams Select Realtors of Annapolis

    10971 Bottom Rd, Worton, MD 21678
  • /62

    $3,500,000

    • 7 Beds
    • 6.5 Baths
    • 12,520 Sq Ft

    6520 Swan Creek Rd, Rock Hall, MD 21661

    All showings require pre screening and financial capability prior to scheduling any showing. Rarely does a property of this sort come available in Kent County Maryland! This incredible 139+/- acre Chesapeake Bay property is available in it's entirety, however the seller may consider selling the primary residence with a reduced amount of acreage under the right conditions, providing the purchaser

    William Norris Select Land & Homes, LLC

    6520 Swan Creek Rd, Rock Hall, MD 21661
  • /38

    $385,000

    • 3 Beds
    • 2.5 Baths
    • 1,270 Sq Ft

    11981 Dewees Ln, Kennedyville, MD 21645

    Come see this home in the sought after community of Village at Kennedyville. This beautiful, updated 3 bedroom 2 and 1/2 bath home is awaiting it's next owner. As you enter this home you immediately feel the pride in ownership and notice the updates. From the bright open feel of the home and gourmet kitchen featuring stainless appliances with the refrigerator replaced in 2023, the dishwasher

    Edward Beres RE/MAX Executive

    11981 Dewees Ln, Kennedyville, MD 21645
  • /45

    $525,000

    • 5 Beds
    • 3.5 Baths
    • 3,932 Sq Ft

    218 Camelot Dr, Chestertown, MD 21620

    Picture Perfect Colonial in Coventry Farms – Chestertown, MarylandWelcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates

    Dee Dee McCracken Coldwell Banker Realty

    218 Camelot Dr, Chestertown, MD 21620
  • /40

    $525,000

    • 5 Beds
    • 3.5 Baths
    • 3,504 Sq Ft

    311 Devon Dr, Chestertown, MD 21620

    REDUCED! 311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • /18

    $275,000

    • 2 Beds
    • 1.5 Baths
    • 920 Sq Ft

    611 Cannon St, Chestertown, MD 21620

    This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing

    Hayley Norris Select Land & Homes, LLC

    611 Cannon St, Chestertown, MD 21620
  • /48

    $1,395,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /29

    $444,999

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft

    222 Mount Vernon Ave, Chestertown, MD 21620

    HIGHLY MOTIVATED SELLERS — bring us an offer! This historic 1916 home is comfortable, convenient, and move-in ready. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and walking distance from downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests.

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • /53

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. 1⁄2 basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • /62

    $625,000

    • 2 Beds
    • 2.5 Baths
    • 4,054 Sq Ft

    13983 Turners Point Rd, Kennedyville, MD 21645

    Impeccably kept Kentmore Park home with a white picket fence. Over two acres with private rear yard for relaxation. Adorable brick outbuilding for storage, home office, man cave or she shed. Gazebo for al fresco dining, afternoon card games or just enjoying nature. Two additional sheds for storing just about anything. Habitat for many bird species in season. Owl, Heron and Eagle territory year

    Patricia Kern Gunther-McClary Real Estate

    13983 Turners Point Rd, Kennedyville, MD 21645
  • /29

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,684 Sq Ft

    21336 Haven Rd, Rock Hall, MD 21661

    UPDATE - New carpet just installed! Convenient one-level living in this 3BR, 2.5 bath rancher. The house has a desirable split bedroom layout with the primary bedroom, bath & closet off the kitchen and two bedrooms and another full bath off the other side of the house. The sun room has a propane stove and exits to a 12' x 15' deck. There's a 10' x 16' shed. Nice quiet, in-town location.

    Cindy Genther Rock Hall Properties Real Estate

    21336 Haven Rd, Rock Hall, MD 21661
  • /90

    $2,400,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • /70

    $519,999 Open House 4/25

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

    103 Landing Ln, Chestertown, MD 21620

    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 rear den or office which could be

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • /28

    $469,000

    • 2 Beds
    • 2 Baths
    • 1,129 Sq Ft

    21090 W Sharp St Unit 112, Rock Hall, MD 21661

    Back on the market. Spectacular Chesapeake Bay waterview condo located in the heart of Rock Hall. Beautiful upgrades include LVP flooring, tile bathrooms, kitchen cabinets, backsplash, granite countertops and appliances, plus new electric fireplace. Relax on the recently refinished Bayview deck or cuddle up next to the fireplace. The convenience of condo living lets you enjoy all the festivals

    Cindy Genther Rock Hall Properties Real Estate

    21090 W Sharp St Unit 112, Rock Hall, MD 21661
  • /40

    $545,000

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    21090 W Sharp St Unit 133, Rock Hall, MD 21661

    Experience the allure of waterfront living with this stunning condominium, perfectly situated to offer breathtaking views of the Chesapeake Bay and the Rock Hall Harbor. Inside, you are greeted by an inviting ambiance, accentuated by updated kitchen and flooring that seamlessly blend style and functionality. Whether you’re an aspiring chef or simply enjoy the art of entertaining, the modern

    Lynn Hilfiker Gunther-McClary Real Estate

    21090 W Sharp St Unit 133, Rock Hall, MD 21661
  • /117

    $819,000

    • 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 beautifully 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

    Ben Esh Astoria Realty Advisors LLC

    14540 Stirrup Ln, Galena, MD 21635
  • /43

    $5,900,000

    • 6 Beds
    • 4.5 Baths
    • 4,214 Sq Ft

    5135 Crosby Rd, Rock Hall, MD 21661

    A true sportsman’s paradise and a family compound, this impressive 212 +/-acre farm offers breathtaking water views and unparalleled outdoor recreation. The solidly built, colonial style home is designed to capture the beauty of Davis Creek from nearly every room. The kitchen and dining area are perfectly positioned for waterfront entertaining, seamlessly flowing into the family room with gas

    Courtney Chipouras TTR Sotheby's International Realty

    5135 Crosby Rd, Rock Hall, MD 21661
  • /50

    $384,000

    • 5 Beds
    • 2.5 Baths
    • 3,371 Sq Ft

    6746 Quaker Neck Rd, Chestertown, MD 21620

    Michele Palmer Doug Ashley Realtors, LLC

    6746 Quaker Neck Rd, Chestertown, MD 21620
  • /32

    $289,900

    • 3 Beds
    • 1 Bath
    • 1,340 Sq Ft

    202 Virginia Ave, Galena, MD 21635

    John Carroll Village Real Estate Company LLC

    202 Virginia Ave, Galena, MD 21635
  • /9

    $110,000 New Construction

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft

    5656 Circle Park Dr Unit 5594, Rock Hall, MD 21661

    Brand new 2025 Clayton Ruby Z located in the Circle Park mobile home community in Rock Hall. This 2-bedroom, 2-bathroom home features a spacious open floor plan with a full bedroom and bathroom on either end, offering privacy and flexibility. The home comes complete with brand-new appliances and is ready for its first owners. Public water and sewer. Financing available through Clayton Homes,

    Sarah Ulrick Rock Hall Properties Real Estate

    5656 Circle Park Dr Unit 5594, Rock Hall, MD 21661
  • /24

    $395,000 New Construction

    • 4 Beds
    • 2 Baths
    • 2,162 Sq Ft

    21733 Centennial Ln, Rock Hall, MD 21661

    Welcome to Crosby Woods, a charming new community located less than a mile from downtown Rock Hall. This thoughtfully designed neighborhood features just ten single-family homes situated on a quiet cul-de-sac with shared open space and no HOA. This brand-new 2,162 sq. ft. rancher offers comfortable one-level living with four bedrooms and two full bathrooms. The home features beautifully finished

    Sarah Ulrick Rock Hall Properties Real Estate

    21733 Centennial Ln, Rock Hall, MD 21661
  • /17

    $259,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    107 Metcalfe Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxuryvinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granitecountertops, 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

    David Moore Real Broker, LLC

    107 Metcalfe Rd, Chestertown, MD 21620
  • /28

    $264,900 Open Sat 11AM - 1PM

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

    109 Metcalfe Rd, Chestertown, MD 21620

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

    David Moore Real Broker, LLC

    109 Metcalfe Rd, Chestertown, MD 21620
  • /24

    $765,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    37 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 bath

    Julia Hilfiker Gunther-McClary Real Estate

    37 Landing Ln, Chestertown, 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
  • /22

    $1,099,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, Chestertown, MD 21620
  • /24

    $369,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,413 Sq Ft

    21745 Centennial Ln, Rock Hall, MD 21661

    “PRICE IMPROVEMENT! Move-in Ready New ConstructionRancher in Rock Hall - Perfect for Retirees or Weekend Getaways at 21745 Centennial Lane, Rock Hall, MD, a brand-new 1,415 sq ft home offering single-story living just minutes from marinas, waterfront dining, and all that Rock Hall has to offer. Built by JAC Homes, this 3-bedroom, 2-bath home features an open-concept layout with abundant

    Pamela Geib Long & Foster Real Estate, Inc.

    21745 Centennial Ln, Rock Hall, MD 21661
  • /9

    $364,900 Open Sat 12PM - 2PM

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

    21133 Striper Run, Rock Hall, MD 21661

    New Construction Alert! The last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates are now for sale. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the 1st and 2nd levels is included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious

    Cindy Genther Rock Hall Properties Real Estate

    21133 Striper Run, Rock Hall, MD 21661

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