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Chestertown, MD 1-Story Homes for Sale

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  • 247 Blakefield Dr, Chestertown, MD 21620
    247 Blakefield Dr, Chestertown, MD 21620
    247 Blakefield Dr, Chestertown, MD 21620
    /17

    $425,000

    • 3 Beds
    • 3 Baths
    • 2,572 Sq Ft

    247 Blakefield Dr, Chestertown, MD 21620

    Unlock the door to your future with an exclusive offer: Qualify for an exceptional 5.05% financing rate and $2,300 per month payment for one year. $7,000 lender-specific grant available on this property OR $21,250 in down payment assistance meaning no down payment is required. ARM financing also available at 5.25% rate for 5 years. Taxes and insurance not included. Buy direct and receive a FREE,

    Agent Photo

    Vinny Steo

    Your Home Sold Guaranteed Realty

    (443) 706-8420

    247 Blakefield Dr, Chestertown, MD 21620
  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /24

    $320,000

    • 3 Beds
    • 1.5 Baths
    • 1,096 Sq Ft

    222 Dutchess Rd, Chestertown, MD 21620

    Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 927-1169

    222 Dutchess Rd, Chestertown, MD 21620
  • 107 Malone Ave, Chestertown, MD 21620
    107 Malone Ave, Chestertown, MD 21620
    107 Malone Ave, Chestertown, MD 21620
    /27

    $290,000

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

    107 Malone Ave, Chestertown, MD 21620

    Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bedroom, 1 Bath home is ready for you to make new memories, grow your family or downsize while enjoying single level living. Hardwood Floors throughout the living room and bedrooms have recently all been refinished. Through the front door is the well-lit family room with a large bay

    Agent Photo

    Barbara McPhail

    Douglas Realty LLC

    (410) 705-2953

    107 Malone Ave, Chestertown, MD 21620
  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    /42

    $279,000

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Charm: Your Gateway toEastern Shore LivingCompletely Renovated Cottage with River Views & Endless PossibilitiesDiscover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifullytransformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristineChester River. Whether you're seeking a weekend escape, investment

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 282-1137

    134 Char Nor Manor Blvd, Chestertown, MD 21620
  • 21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    /16

    $370,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    21111 Texas Ave, Chestertown, MD 21620

    COMING SOON in Tolchester Estates!Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up

    Glory Bee Costa Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /44

    $399,000

    • 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
  • 213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    /23

    $319,900

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

    213 Central Dr, Chestertown, MD 21620

    Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached "pole barn" style garage. Fenced back yard. This

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    213 Central Dr, Chestertown, MD 21620
  • 100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    /16

    $245,000

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft

    100 Metcalf Rd, Chestertown, MD 21620

    Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! Your Dream Home Checklist: * NO HOA! Freedom & Savings! * One-Level Living: Easy breezy! * Open Concept: Perfect for entertaining! The heart of the home is the spectacular eat-in

    Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
  • 23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    /29

    $349,900

    • 3 Beds
    • 1 Bath
    • 1,805 Sq Ft

    23110 Old Fairlee Rd, Chestertown, MD 21620

    Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impressed by this stunning ranch home that has undergone a complete, top-to-bottom renovation! Offering 1800 sq. ft. of newly renovated finished interior space, this property is much bigger than it looks and provides true move-in ready convenience with zero deferred maintenance. Upgrades Inside & Out! Enjoy peace

    Thomas Huston Real Broker LLC

    23110 Old Fairlee Rd, Chestertown, MD 21620
  • 8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    /30

    $339,000

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    8750 Georgetown Rd, Chestertown, MD 21620

    Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bed, 2-bathroom home situated on 1 acre with public water/sewer, no HOA, and a detached garage with electric. Whether you're dreaming of a workshop, a hobby space, extra storage, or room for your equipment, this property delivers flexibility that’s hard to find at this price point. Inside, you’ll love the

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    8750 Georgetown Rd, Chestertown, MD 21620
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    /16

    $167,000

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft

    141 Prospect St, Chestertown, MD 21620

    INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find!Located just minutes from Chestertown and Washington College. Plenty of space and character, it’s a rare opportunity to create something

    Jeff Guthrie Cross Street Realtors LLC

    141 Prospect St, Chestertown, MD 21620
  • 118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    /19

    $695,000 Coming Soon

    • 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 place that instantly feels like a breath of fresh air. Set inside the sought-after Chester River Landing community, this completely reimagined 3-bedroom, 2-bath waterfront condo offers the rare mix of modern comfort and true Eastern Shore charm. From the moment you walk in, the views of the Chester River pull you in. The entire condo was taken down to the

    Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
  • 611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    /18

    $299,000

    • 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
  • 318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    /21

    $269,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    318 Lincoln Dr, Chestertown, MD 21620

    Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    318 Lincoln Dr, Chestertown, MD 21620
  • 127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    /26

    $215,000

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft

    127 Wood Duck Ln, Chestertown, MD 21620

    Tom Riccio RE/MAX Point Realty

    127 Wood Duck Ln, Chestertown, MD 21620
  • 7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    /24

    $250,000

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    7521 Pine Ave, Chestertown, MD 21620

    Priced to sell! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. Bring your vision for this home to life and add instant equity with cosmetic updates! It has been lovingly maintained with a newer roof and

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    7521 Pine Ave, Chestertown, MD 21620
  • 109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    /31

    $344,900

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    109 Wilton Rd, Chestertown, MD 21620

    Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike. The home boasts a large

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
Maryland Kent County Chestertown

1-Story Homes for Sale in Chestertown, MD

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 49 days on the market compared to the national average of 53 days. The median sale price for homes in Chestertown, MD over the last 12 months is $377,500, up 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$377,500
Median Single Family Sale Price
$392,500
Median Townhouse Sale Price
$283,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$216
Number of Homes for Sale
27
Last 12 months Home Sales
94
Months of Supply
3.40
Median List Price
$375,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
10%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 17 one-story homes for sale, catering to individuals and families who value the simplicity and accessibility of single-level living. Whether you're entering the real estate market for the first time, transitioning to a downsized lifestyle, or simply prioritizing the convenience of a single-story layout, these homes offer a variety of options to explore. From cozy bungalows to spacious ranch-style houses, the one-story homes for sale in Chestertown, MD come in various architectural styles and sizes, ensuring there's something to accommodate every preference and lifestyle.

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