10

Chestertown, MD Homes for Sale under $400,000

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  • 21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    /26

    $339,900

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft

    21125 Iowa Ave, Chestertown, MD 21620

    Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to call home. Inside, you’ll find a bright and inviting layout featuring a Florida Room, a spacious dining room with a cozy fireplace, and two comfortable bedrooms. The large living room is filled with natural light and showcases

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 405-2192

    21125 Iowa Ave, Chestertown, MD 21620
  • 202 Waldo Dr, Chestertown, MD 21620
    202 Waldo Dr, Chestertown, MD 21620
    202 Waldo Dr, Chestertown, MD 21620
    /3

    $389,000

    • 3 Beds
    • 1.5 Baths
    • 2,055 Sq Ft

    202 Waldo Dr, Chestertown, MD 21620

    A Place Full of Possibility in Byford Development Tucked in the heart of the Byford community, just minutes from everything Chestertown has to offer, this welcoming rancher is ready for its next chapter. Step inside and feel the charm of traditional hardwood floors, the glow of a wood-burning fireplace in the spacious family room, and the comfort of a home that’s been well-loved. The layout flows

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 971-7157

    202 Waldo 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
  • 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

    Charming 3-bedroom, 2-bath rancher in the desirable Chester Harbor community. Situated on a spacious 0.76-acre lot, this home offers comfortable one-level living with a bright layout, private primary suite, and plenty of outdoor space to enjoy. Detached two-car garage provides ample storage and parking. Conveniently located just minutes from historic downtown Chestertown, marinas, shops, and

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • 301 Lincoln Dr, Chestertown, MD 21620
    301 Lincoln Dr, Chestertown, MD 21620
    301 Lincoln Dr, Chestertown, MD 21620
    /40

    $309,900

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    301 Lincoln Dr, Chestertown, MD 21620

    Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of thoughtfully updated living space. The open floor plan creates a seamless flow between the living, dining, and kitchen areas — ideal for both everyday living and entertaining.The spacious kitchen features a central island, stainless steel appliances, and ample cabinetry, making it as functional as it is

    Heather Dolan Chesapeake Real Estate Associates, LLC

    301 Lincoln Dr, Chestertown, MD 21620
  • 2032 Pondtown Rd, Chestertown, MD 21620
    2032 Pondtown Rd, Chestertown, MD 21620
    /2

    $325,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    2032 Pondtown Rd, Chestertown, MD 21620

    Coming Soon!

    Joie White Northrop Realty

    2032 Pondtown Rd, Chestertown, MD 21620
  • 117 N Water St Unit 2B, Chestertown, MD 21620
    117 N Water St Unit 2B, Chestertown, MD 21620
    117 N Water St Unit 2B, Chestertown, MD 21620
    /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
  • 104 Flying Cloud Dr, Chestertown, MD 21620
    104 Flying Cloud Dr, Chestertown, MD 21620
    /2

    $399,900 Coming Soon

    • 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 2,300 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
  • 154 Longfellow Dr, Chestertown, MD 21620
    154 Longfellow Dr, Chestertown, MD 21620
    154 Longfellow Dr, Chestertown, MD 21620
    /26

    $315,000

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft

    154 Longfellow Dr, Chestertown, MD 21620

    Located in the water-oriented community of Chester Harbor just outside of historic Chestertown, 154 Longfellow Drive offers the ideal blend of convenience and Eastern Shore living. This single-level home is situated on a cleared and fenced 0.34 acre-parcel and a voluntary HOA fee provides access to the community boat ramp and waterfront park. Less than a mile and a half from Route 213, enjoy

    Katie Stecklair Cross Street Realtors LLC

    154 Longfellow Dr, Chestertown, MD 21620
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, 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
Maryland Kent County Chestertown

Real Estate & Homes in Chestertown, MD under $400,000

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 50 days on the market compared to the national average of 55 days. The median sale price for homes in Chestertown, MD over the last 12 months is $375,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$375,000
Median Single Family Sale Price
$387,000
Median Townhouse Sale Price
$272,450
Median 2 Bedroom Sale Price
$375,000
Median 1 Bedroom Sale Price
$242,500
Average Price Per Sq Ft
$218
Number of Homes for Sale
34
Last 12 months Home Sales
96
Months of Supply
4.30
Median List Price
$377,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home

Explore the array of homes and houses for sale under $400,000 in Chestertown, where you'll find 10 options tailored for those seeking affordable real estate opportunities. Whether you're interested in spacious family homes, modern townhouses, or cozy bungalows, Chestertown offers a diverse range of choices to match your needs and financial considerations. Take advantage of these affordably-priced properties to make your move into the real estate market in Chestertown, MD.

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