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Modern Homes for Sale in Chestertown, MD

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  • /31

    $898,000

    • 3 Beds
    • 3.5 Baths
    • 2,172 Sq Ft

    226 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-3661

    226 S Water St, Chestertown, MD 21620
  • /51

    $385,000

    $10K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,534 Sq Ft

    107 Flying Cloud Dr, Chestertown, MD 21620

    NEW PRICE – Exceptional value for over 2,500 square feet of newer construction in the Village of Chestertown! A stunning 2023-built home with well-designed architectural elevations; two tone complimentary shades which beautifully compliment these unique features. The curb appeal captures your attention and the welcoming front porch invites you to slow down and relax.. your home! Step through the

    Cynthia Gardner CENTURY 21 New Millennium

    107 Flying Cloud Dr, Chestertown, MD 21620
  • /49

    $1,450,000

    • 4 Beds
    • 5 Baths
    • 4,257 Sq Ft

    22470 Fairgale Farm Ln, Chestertown, MD 21620

    Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away.The home features 4 bedrooms and 5 full

    Ashton Kelley Gunther-McClary Real Estate

    22470 Fairgale Farm Ln, Chestertown, MD 21620
  • /30

    $394,900

    $5K PRICE DROP
    • 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 2,500 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
  • /26

    $340,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,972 Sq Ft

    214 Silver Heel Rd, Chestertown, MD 21620

    Price Reduction! VERY motivated seller—open to all reasonable offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer construction—major

    Chris Kendall Cross Street Realtors LLC

    214 Silver Heel Rd, Chestertown, MD 21620

Home Prices in Chestertown, MD

Home Price Trends

Median Sale Price
$361,950
Median Single Family Sale Price
$392,500
Median Townhouse Sale Price
$264,900
Median 2 Bedroom Sale Price
$350,000
Median 1 Bedroom Sale Price
$242,500
Average Price Per Sq Ft
$212
Number of Homes for Sale
37
Last 12 months Home Sales
98
Months of Supply
4.50
Median List Price
$375,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-2%
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