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Chestertown, MD Homes for Sale with Community Pool

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  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    /27

    $1,800,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    **Price increase due to the home’s expanded footprint—over 1,200 additional square feet!**Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 118 Little Harbor Way Unit 201, Chestertown, MD 21620
    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    /35

    $675,000

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft

    118 Little Harbor Way Unit 201, Chestertown, MD 21620

    An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and Chester River. It is nearly impossible for the body, mind and spirit of its residents and guests not to be "in a good place" on the cloudiest or most challenging of days. River House, with only five private residences, occupies the best real estate within

    Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /69

    $559,000 Open Sun 11AM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, 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 stunning waterfront retreat in the coveted Chester River Landing community. This beautifully reimagined 3-bedroom, 2-bath condo has been thoughtfully taken down to the studs and rebuilt with high-quality finishes and timeless style. Nearly everything inside is brand new, offering the comfort and peace of mind of a modern build within an established

    Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
Maryland Kent County Chestertown

Homes for Sale with Community Pool in Chestertown, MD

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 51 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 $359,000, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$359,000
Median Single Family Sale Price
$380,000
Median Townhouse Sale Price
$286,250
Median 2 Bedroom Sale Price
$399,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$219
Number of Homes for Sale
37
Last 12 months Home Sales
93
Months of Supply
4.80
Median List Price
$372,573
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 4 homes for sale with a community pool, allowing residents to relax and socialize in a shared pool area. These homes provide residents with access to resort-style amenities, offering the convenience of enjoying communal pool facilities without the upkeep required for a private pool. Whether it's a townhouse, condominium, or single-family home, each residence features community pool access, adding value to the property. Take a look at the homes for sale with community pools in Chestertown, MD.

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