11

Chestertown, MD Homes for Sale under $800,000

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  • 108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    /5

    $635,000

    • Land
    • 3,920 Sq Ft
    • $7,055,556 per Acre

    108 Little Harbor Way, Chestertown, MD 21620

    Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    108 Little Harbor Way, Chestertown, MD 21620
  • 36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    /26

    $753,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    36 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    36 Landing Ln, Chestertown, MD 21620
  • 204 Double Creek Rd, Chestertown, MD 21620
    204 Double Creek Rd, Chestertown, MD 21620
    204 Double Creek Rd, Chestertown, MD 21620
    /46

    $565,000

    $47K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,927 Sq Ft

    204 Double Creek Rd, Chestertown, MD 21620

    Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The

    Grace Crockett Doug Ashley Realtors, LLC

    204 Double Creek Rd, Chestertown, MD 21620
  • 106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    /24

    $799,900

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,092 Sq Ft

    106 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Julia Hilfiker Gunther-McClary Real Estate

    106 Landing Ln, Chestertown, MD 21620
  • 37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    /24

    $765,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    37 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath

    Julia Hilfiker Gunther-McClary Real Estate

    37 Landing Ln, Chestertown, MD 21620
  • 7828 Country Club Ln, Chestertown, MD 21620
    7828 Country Club Ln, Chestertown, MD 21620
    7828 Country Club Ln, Chestertown, MD 21620
    /68

    $799,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,857 Sq Ft

    7828 Country Club Ln, Chestertown, MD 21620

    Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room

    Sarah King Cross Street Realtors LLC

    7828 Country Club Ln, Chestertown, MD 21620
  • 103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    /53

    $550,000

    • 5 Beds
    • 3.5 Baths
    • 3,816 Sq Ft

    103 Sutton Way, Chestertown, MD 21620

    103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and

    Liddy Campbell TTR Sotheby's International Realty

    103 Sutton Way, Chestertown, MD 21620
  • 35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    /26

    $786,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    35 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Julia Hilfiker Gunther-McClary Real Estate

    35 Landing Ln, Chestertown, MD 21620
  • 101 Coleman Dr, Chestertown, MD 21620
    101 Coleman Dr, Chestertown, MD 21620
    101 Coleman Dr, Chestertown, MD 21620
    /56

    $519,900

    $5K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,268 Sq Ft

    101 Coleman Dr, Chestertown, MD 21620

    Tucked away just south of the scenic Chester River and moments from the timeless charm of Chestertown, this inviting home offers a warm and welcoming retreat in the heart of Queen Anne’s County. Surrounded by the natural beauty of Maryland’s Eastern Shore, the setting feels peaceful and relaxed—where quiet mornings and golden sunsets become part of everyday life.Inside, the home is designed

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    101 Coleman Dr, Chestertown, MD 21620
  • 201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    /3

    $750,000

    $45K PRICE DROP
    • Land
    • 4,356 Sq Ft
    • $7,500,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    Located in an area that has the potential for dense project of affordable homes. There are 6 lots total. 4 are vacant and a church sits on the other two. Lots of different uses of the property and/or the lots for this project.

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /46

    $685,000

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

    117 N Water St Unit 1A, 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 1A, Chestertown, MD 21620
Maryland Kent County

Real Estate & Homes in Chestertown, MD under $800,000

Home Prices in Chestertown, MD

The median home sale price in Chestertown, MD is $359,900, down 5% year-over-year. Homes in Chestertown sell in 41 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$359,900
Median Single Family Sale Price
$375,000
Median Townhouse Sale Price
$264,900
Median 2 Bedroom Sale Price
$323,250
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$214
Number of Homes for Sale
30
Last 12 months Home Sales
97
Months of Supply
3.70
Median List Price
$359,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-5%
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