Section Image Section Image

Explore Similar Homes Within 10 Miles of Kennedyville, MD

  • 304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    /31

    $209,900

    • 3 Beds
    • 2.5 Baths
    • 1,199 Sq Ft

    304 Hilltop Ln, Chestertown, MD 21620

    The townhouse is the second from the end and has three bedrooms and 2.5 baths. The slider door provides easy access to the patio and there is a stack washer on the main level, kitchen has the needed appliances. Located in Chestertown you can enjoy all of the amenities of this historic town, the Farmer's Market, Washington College is only a couple of minutes away, the many parks, marinas, and

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 824-5679

    304 Hilltop Ln, Chestertown, MD 21620
  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /20

    $212,000

    • Land
    • 1.95 Acres
    • $108,718 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • 866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    /34

    $299,000

    • Studio
    • 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
  • 0 Private Spry ( Lot 50) Ln, Worton, MD 21678
    0 Private Spry ( Lot 50) Ln, Worton, MD 21678
    /2

    $209,000

    • Land
    • 2.64 Acres
    • $79,167 per Acre

    0 Private Spry ( Lot 50) Ln, Worton, MD 21678

    Build your dream home on this 2.64-acre cul-de-sac homesite in the peaceful Montabello Hills II community of Worton, MD. This is an approved buildable lot that is ready for your vision, . Enjoy privacy, natural beauty, and a quiet setting just minutes from Chestertown and the Chesapeake Bay. Approved Site Plan SRA Approved Low HOA Fees Ideal for Custom or Vacation

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    0 Private Spry ( Lot 50) Ln, Worton, MD 21678
  • 146 N Main St, Galena, MD 21635
    146 N Main St, Galena, MD 21635
    146 N Main St, Galena, MD 21635
    /27

    $273,000

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

    146 N Main St, Galena, MD 21635

    SMALL TOWN AMERICA - come turn grandmother's cottage into your new charming home! This affordable two story center hall traditional home features hardwood floors, gorgeous old wood work and staircase, great front porch for watching parades and cozy rear screened porch with shaded deck for summer BBQ's. The home is being sold AS-IS to settle an estate, but it perfectly habitable and the right

    John Carroll Village Real Estate Company LLC

    146 N Main St, Galena, MD 21635
  • 925 Round Top Rd, Chestertown, MD 21620
    925 Round Top Rd, Chestertown, MD 21620
    925 Round Top Rd, Chestertown, MD 21620
    /19

    $300,000

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    925 Round Top Rd, Chestertown, MD 21620

    Welcome to this cute-as-a-button home in the water-access community of Chester Harbor! Whether you're starting out, downsizing, or simply looking to simplify your lifestyle, this move-in ready gem offers the perfect balance of comfort, convenience, and charm. Set on a spacious third of an acre lot, this home offers just the right amount of space—three bedrooms, one full bath, and room to grow

    Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, Chestertown, MD 21620
  • 624 High St, Chestertown, MD 21620
    624 High St, Chestertown, MD 21620
    624 High St, Chestertown, MD 21620
    /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
  • 300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    /20

    $220,000

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

    300 Hilltop Ln, Chestertown, MD 21620

    Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch.Enjoy the convenience of a patio out back—perfect for relaxing or

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
  • 25 Locust St, Earleville, MD 21919
    25 Locust St, Earleville, MD 21919
    25 Locust St, Earleville, MD 21919
    /33

    $235,000

    • 1 Bed
    • 1 Bath
    • 708 Sq Ft

    25 Locust St, Earleville, MD 21919

    Discover your dream getaway in this spacious 1-bedroom bungalow, designed to comfortably host up to six guests. This stunning property is an absolute must-see! Nestled on an expansive double lot, it offers parking for three vehicles—perfect for entertaining your friends and family. Spend your days soaking up the sun at the beach and your evenings celebrating on the spacious deck. Your new getaway

    Amy Walton Patterson-Schwartz - Greenville

    25 Locust St, Earleville, MD 21919
  • 866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    /22

    $299,000

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

    866 Washington Ave, Chestertown, MD 21620

    Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use

    Jeff Guthrie Cross Street Realtors LLC

    866 Washington Ave, Chestertown, MD 21620
  • 14075 Crataegus Ct, Galena, MD 21635
    14075 Crataegus Ct, Galena, MD 21635
    14075 Crataegus Ct, Galena, MD 21635
    /3

    $219,000

    • Land
    • 2.88 Acres
    • $76,042 per Acre

    14075 Crataegus Ct, Galena, MD 21635

    Located in the community of Gentle Winds just minutes from the Eastern Shore and 10 minutes to Middletown, Delaware, this 2.88-acre private lot is shaped like a baseball field (and approximately the same size as a professional baseball field). Enclosed by mature trees for maximum privacy and complimented by 2 large beautiful trees (similar to large bonsai trees), this land is the ideal setting

    Norman Domingo XRealty.NET LLC

    14075 Crataegus Ct, Galena, MD 21635
  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /5

    $225,000

    • Land
    • 0.96 Acre
    • $234,375 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    /7

    $250,000

    • Land
    • 0.93 Acre
    • $268,817 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated at the highly visible corner of Scheeler Road and Haacke Drive, this 0.93+/- acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the County, this is a rare find in a desirable location with great potential for visibility and customer

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • 26670 Maple Ave, Still Pond, MD 21667
    26670 Maple Ave, Still Pond, MD 21667
    26670 Maple Ave, Still Pond, MD 21667
    /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
  • 2101 Dudley Corners Rd, Crumpton, MD 21628
    2101 Dudley Corners Rd, Crumpton, MD 21628
    2101 Dudley Corners Rd, Crumpton, MD 21628
    /4

    $259,900 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    2101 Dudley Corners Rd, Crumpton, MD 21628

    2-bedroom, 1-bath home situated on a spacious one acre lot. A bonus room off the kitchen offers the flexibility to easily convert into a third bedroom, home office, or hobby space.The property features a detached garage with electricity, ideal for storage or a workshop,. Enjoy the peace and privacy of country living while still being conveniently located near local amenities.

    Tina Brown Benson & Mangold, LLC

    2101 Dudley Corners Rd, Crumpton, MD 21628
  • 112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    /6

    $280,000 Coming Soon

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

    112 Metcalf Rd, Chestertown, MD 21620

    Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedrooms with 1 1/2 baths . It has an open concept on the main floor, kitchen has beautiful white shaker cabinetry, large island, granite countertops, stainless steel appliances, and luxury vinyl flooring. Large covered patio off the kitchen leading out to the back yard. A new shed was just installed for extra

    Steven Knopf Engel & Völkers Annapolis

    112 Metcalf Rd, Chestertown, MD 21620
Maryland Kent County Kennedyville

Real Estate & Homes in Kennedyville, MD under $300,000

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

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group