76

Kent County MD Houses for Sale

Section Image
  • /34

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,224 Sq Ft

    866 Washington Ave, Chestertown, MD 21620

    This duplex is a prime investment located on Washington Avenue in historic Chestertown, Maryland, offering many amenities. It is within walking distance of shopping, entertainment, schools, and medical facilities. Unit A is freshly updated with a spacious living room and dining room. The kitchen offers lots of storage and a stackable washer/dryer. It is a 2-bedroom apartment with a full bath. The

    Kathleen Brenton Brenton Realty Group

    866 Washington Ave, Chestertown, MD 21620
  • /10

    $995,000

    • 2 Beds
    • 1.5 Baths
    • 1,566 Sq Ft

    29341 Glencoe Rd, Kennedyville, MD 21645

    Nestled along the tranquil banks of the Sassafras River, this charming brick fixer-upper presents a rare opportunity to own a waterfront paradise. Imagine waking up to sweeping river views and sipping coffee from the expansive enclosed porch as the sun rises.Though the home requires renovating, its potential is undeniable. Offering over 1,500 sq ft of functional space, this 2-bedroom

    Christine Catalano Coldwell Banker Realty

    29341 Glencoe Rd, Kennedyville, MD 21645
  • /54

    $648,750

    • 4 Beds
    • 3.5 Baths
    • 2,008 Sq Ft

    206 S Water St, Chestertown, MD 21620

    Just in time for the annual Downrigging Festival! See tall ships sailing the Chester River from your front porch and live in the heart of Chestertown's thriving Historic District! This versatile home has over 2,000 square feet of finished living space and was rebuilt and expanded with future customizations in mind!* The rear addition includes a sunroom/mudroom with a separate entrance connecting

    Beth Ostrander Doug Ashley Realtors, LLC

    206 S Water St, Chestertown, MD 21620
  • /34

    $309,999

    • 2 Beds
    • 1 Bath
    • 1,350 Sq Ft

    10674 Kasota Rd, Chestertown, MD 21620

    Welcome to 10674 Kasota Rd – Your Tranquil Masterpiece on the Chesapeake's Edge. Nestled in the serene enclave of Chesapeake Landing near Chestertown, this charming 2-bed, 1-bath ranch-style home invites you to reimagine rural living on nearly 0.6 acres of lush landscape. With 1,350 sq ft of one–level living, the brick exterior and detached 2–car garage offers timeless appeal and solid bones with

    Andrew Kruzienski Long & Foster Real Estate, Inc.

    10674 Kasota Rd, Chestertown, MD 21620
  • /106

    $350,000

    • 3 Beds
    • 2 Baths
    • 2,762 Sq Ft

    396 Cypress St, Millington, MD 21651

    Investment Opportunity and Motivated Seller! If you are searching for an opportunity to start or relocate your business with rental potential to offset your mortgage, your search is over. Live in one area and rent out the other two!! This income producer is located in the heart of Millington at the main intersection. With its flexible zoning, the property is well-suited for a blend of

    Lona Todd Taylor Properties

    396 Cypress St, Millington, MD 21651
  • /31

    $350,000

    • 4 Beds
    • 2 Baths
    • 1,499 Sq Ft

    21305 Haven Rd, Rock Hall, MD 21661

    This beautiful home is updated and ideally located near marinas and downtown, offering both convenience and tranquility. Key features include:Location: Within town limits, close to marinas and downtown, with easy access to Swan Creek and public boat ramp 4 bedrooms, 2 bathroomsMain Floor: Features Three spacious bedrooms, updated kitchen with granite countertops and stainless steel

    Anthony Borleis RE/MAX Point Realty

    21305 Haven Rd, Rock Hall, MD 21661
  • /67

    $585,950

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

    31667 W Edge Rd, Millington, MD 21651

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

    David Crider Berkshire Hathaway HomeServices PenFed Realty

    31667 W Edge Rd, Millington, MD 21651
  • /31

    $306,000

    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft

    26959 Branchtown Rd, Worton, MD 21678

    Updated in 2024 by a loving family member & their licensed professional! This charming 3-bedroom, 2-bath home offers a perfect blend of modern updates and country serenity. The main level features a convenient first-floor bedroom and full bath, ideal for aging in place. Enjoy stylish & durable vinyl plank flooring throughout and soaring cathedral ceilings upstairs that create an airy, open feel.

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    26959 Branchtown Rd, Worton, MD 21678
  • /3

    $240,000

    • 2 Beds
    • 1 Bath
    • 1,290 Sq Ft

    624 High St, Chestertown, MD 21620

    Step into the charm of historic Chestertown with this 2BR/1BA home full of potential. Featuring a screened front porch, spacious layout, and rear alley access, this property is perfect for investors or visionary buyers. Located just blocks from Washington College, the Chester River, downtown shopping, and restaurants, this home offers the ideal setting for a full-time residence, Airbnb, or

    Nicole Stephens Tesla Realty Group, LLC

    624 High St, Chestertown, MD 21620
  • /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,

    Benuel Esh Keller Williams Elite

    14540 Stirrup Ln, Galena, MD 21635
  • /44

    $950,000

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

    6119 New St Unit 2, Rock Hall, MD 21661

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

    Cindy Genther Rock Hall Properties Real Estate

    6119 New St Unit 2, Rock Hall, MD 21661
  • /68

    $319,000

    • 3 Beds
    • 1.5 Baths
    • 1,735 Sq Ft

    12776 Still Pond Rd, Still Pond, MD 21667

    Welcome to 12776 Still Pond Road: an endearing early 20th Century Victorian in the quiet town of Still Pond. This could be the perfect Eastern Shore retreat or full time residence. Historic Charm abounds with pocket doors, bay windows, 9 foot ceilings, hardwood floors, bullseye corner moldings, mahogany front porch, oak mantels, custom built-ins, and so much more. Enjoy rolling farmland views

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    12776 Still Pond Rd, Still Pond, MD 21667
  • /22

    $549,000

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    101 Birch Run Rd, Chestertown, MD 21620

    A sleek, thoughtfully executed renovation with clean lines and a minimalist aesthetic—sure to impress even the most discerning buyer... Located in Chestertown's coveted Mile Tree Village community, this newly updated 3-bedroom, 2-bath rancher with oversized 2-car garage features a New Encapsulated Crawl Space, New Roof with 50-year shingles and a transferable warranty, new water and sewer lines

    Stacy Kendall Cross Street Realtors LLC

    101 Birch Run Rd, Chestertown, MD 21620
  • /32

    $799,000

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

    26889 Morgnec Rd, Chestertown, MD 21620

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

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
  • /32

    $295,000

    • 4 Beds
    • 2 Baths
    • 1,000 Sq Ft

    6374 Rock Hall Rd, Rock Hall, MD 21661

    Looking for your first place or a weekend stay to enjoy Marylands beautiful eastern shore, look no more! Located just outside of Rock Hall, this charming ranch-style residence offers the convenience of one-level living, perfectly situated on a spacious, treed lot just minutes from downtown. Recently remodeled from top to bottom, this home features sleek stainless steel appliances, stunning

    Dee Dee Miller Long & Foster Real Estate, Inc.

    6374 Rock Hall Rd, Rock Hall, MD 21661
  • /48

    $559,900

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft

    5179 Quaker Neck Rd, Chestertown, MD 21620

    $20,000 Price Reduction!A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly

    Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
  • /48

    $235,000

    • 3 Beds
    • 3 Baths
    • 2,050 Sq Ft

    14 3rd Ave, Betterton, MD 21610

    A home finished your way with what could be over 3,078 square feet of living space! Complete your new Victorian style home with the finishes & colors you enjoy! Located within a .3 mile walk to Betterton Beach and the Town Dock! Public showers, rest rooms and transient boat slips are all at your disposal! The interior of the home is a blank slate and has been protected from the elements. The

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    14 3rd Ave, Betterton, MD 21610
  • /52

    $1,395,500

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

    105 High St, Chestertown, MD 21620

    ***Photos reflect the progress as of 3 months ago. The property is now nearly completed and is simply awaiting a finishing coat of paint and a layer of sod on the newly fenced in rear yard. A superb level of craftsmanship and scope of work not to be missed.***Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored legacy

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /41

    $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
  • /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
  • /17

    $334,900

    • 3 Beds
    • 2.5 Baths
    • 1,856 Sq Ft

    110 Flying Cloud Dr, Chestertown, MD 21620

    SINGLE FAMILY HOME built just 2 years ago at this price! This beautiful home is ready for immediate occupancy. Clean lines and neutral tones make this an easy move-in with nothing to do! Just across the Vintage Chester River Bridge, you will enter a charming little town that surrounds Washington College that has all sorts of new centers and places to go and things to do! The home offers a

    Sandy Savani Berkshire Hathaway HomeServices Homesale Realty

    110 Flying Cloud Dr, Chestertown, MD 21620
  • /6

    $1,800,000

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

    6520 Swan Creek Rd, Rock Hall, MD 21661

    The owner is offering a rare opportunity to subdivide and purchase a spectacular 20-acre waterfront parcel. Renovate the 12,520-square-foot residence, designed by renowned architect Paul Rudolph, and create a breathtaking waterfront estate with panoramic views—just steps from the Chesapeake Bay. An acceptable offer will be contingent upon completion of the subdivision at the buyer's expense. The

    Deborah Laggini Long & Foster Real Estate, Inc.

    6520 Swan Creek Rd, Rock Hall, MD 21661
  • /77

    $4,850,000

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft

    23620 Lands End Rd, Chestertown, MD 21620

    80 private acres beautifully situated on the highly prized Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. One of only 4 properties on Orchard Point and sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to

    Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
  • /67

    $659,000

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft

    11040 Kylie Ln, Chestertown, MD 21620

    Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
  • /65

    $849,900

    • 4 Beds
    • 2 Baths
    • 2,880 Sq Ft

    21 6th Ave, Betterton, MD 21610

    This incredibly private retreat property is situated on 9+ acres in Northern Kent County Maryland overlooking it's own private lake loaded with record size fish and includes a nearly new 2800+/- sq. foot home built in 2020, two detached 3-bay metal shop buildings, and a vast variety of native wildlife including bald eagles, herons, turkeys, deer, and multiple waterfowl species. The home itself

    William Norris Select Land & Homes, LLC

    21 6th Ave, Betterton, MD 21610
  • /25

    $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 "parade route," and just two blocks from the Rock Hall Harbor/ Chesapeake Bay. Welcoming home with a first floor primary bedroom, and large living room with a woodstove. There is a formal dining room, or you could enjoy meals outside in the fenced in back yard! Upstairs offers two more bedrooms, a full bath and an additional room, perfect

    Lynn Hilfiker Gunther-McClary Real Estate

    5686 S Main St, Rock Hall, MD 21661
  • /53

    $539,000

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

    11960 Flour Mill St, Kennedyville, MD 21645

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

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    11960 Flour Mill St, Kennedyville, MD 21645
  • /46

    $230,000

    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft

    26670 Maple Ave, Still Pond, MD 21667

    The listing includes 26670 Maple Avenue with a 1920 dwelling of 2024 SF on .54 acre of land as well as 26680 Maple Avenue dwelling of 1680 SF on .624 acre of land and a parcel of land 100 X 160. Both homes are in need of major repair; however, one will find potential. Final perc information for sewage system will be provided by Kent County Health Department when water table is acceptable which

    Debbie Meikle Doug Ashley Realtors, LLC

    26670 Maple Ave, Still Pond, MD 21667
  • /41

    $400,000 New Construction

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

    21739 Centennial Ln, Rock Hall, MD 21661

    100% FINANCING AVAILABLE!! The seller is offering a special incentive by providing a credit to cover the buyer's first three months of mortgage payments with-in house financing, making this an even more attractive opportunity!Welcome to your brand-new home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle, and vibrant coastal charm. This

    James Schaecher Keller Williams Flagship

    21739 Centennial Ln, Rock Hall, MD 21661
  • /41

    $410,000 New Construction

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

    21733 Centennial Ln, Rock Hall, MD 21661

    100% FINANCING AVAILABLE!! The seller is offering a special incentive by providing a credit to cover the buyer's first three months of mortgage payments with in-house financing, making this an even more attractive opportunity!Welcome to your brand-new home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle, and vibrant coastal charm. This

    James Schaecher Keller Williams Flagship

    21733 Centennial Ln, Rock Hall, MD 21661
  • /23

    $314,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    4921 Piney Neck Rd, Rock Hall, MD 21661

    Welcome to your new home in the historic harbor town of Rock Hall! Quality new construction built with meticulous attention to detail. This 3 bedroom/2 bath home is clean and sleek with modern, tasteful upgrades and color palette. Every appliance and ammenity is brand new, from the HVAC to the bathroom vanities and recessed lighting. Any chef would be thrilled with this substantial kitchen

    Andy Batch Keller Williams Select Realtors of Annapolis

    4921 Piney Neck Rd, Rock Hall, MD 21661
  • /25

    $259,900 Open Sun 1PM - 2:30PM

    • 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 this spring. 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

    103 Metcalf Rd, Chestertown, MD 21620
  • /35

    $364,000 Open Sat 2PM - 3:30PM

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

    13840 Duck Hollow Dr, Galena, MD 21635

    Welcome to Shorewood Estates, a water privileged community on Swantown Creek just off the Sassafras River. This well maintained home offers an updated kitchen with granite counter tops, a master bedroom and bath with two other bedrooms and bath on the main level and a large family room on the lower level along with a sewing room or home office. There is a detached screened porch perfect for a

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    13840 Duck Hollow Dr, Galena, MD 21635
  • /2

    $180,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 2,048 Sq Ft

    12765 Still Pond Rd, Still Pond, MD 21667

    Welcome to 12765 Still Pond Road on Maryland’s Eastern Shore. This 2,000+ sq ft Colonial sits on a landscaped lot with pastoral views and offers incredible rehab potential. Just 3 miles from Betterton Beach, 10 minutes to historic downtown Chestertown, and 15 miles to the harbor town of Rock Hall, the location provides easy access to waterfront recreation, dining, and shopping.The home

    Carlyn Lowery EXP Realty, LLC

    12765 Still Pond Rd, Still Pond, MD 21667
  • /3

    $164,000

    • 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

    Anastasia Zivkovic Cummings & Co. Realtors

    234 N College Ave, Chestertown, MD 21620
  • /16

    $110,000

    • 3 Beds
    • 2 Baths
    • 1,376 Sq Ft

    11054 Austin Ln, Worton, MD 21678

    ONLINE AUCTION: Bidding begins 10/7/2025 @ 10:00 AM. Bidding ends 10/9/2025 @ 12:00 PM. List Price is Suggested Opening Bid. Deposit: $20,000. Single Family Home located in the Knights Landing area of Kent County, MD. JUST MINUTES to the many attractions of the Chestertown area. Est. Value $250k+. Easy access to major traffic artery Lambs Meadow Rd. Property is occupied. Buy this property for a

    Adam Shpritz Ashland Auction Group LLC

    11054 Austin Ln, Worton, MD 21678

Showing Results 41 - 76, Page 2 of 2

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