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Chestertown, MD Homes for Sale with Pool

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  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /41

    $569,000

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

    103 Landing Ln, Chestertown, MD 21620

    Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 981-2534

    103 Landing Ln, Chestertown, MD 21620
  • 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
    /22

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,315 Sq Ft

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

    Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and second floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $759,000 New Construction

    • 3 Beds
    • 3.5 Baths

    212 Landing Ln, Chestertown, MD 21620

    Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm.This elegant 3-bedroom, 2.5-bath residence is designed to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 883-7032

    212 Landing Ln, Chestertown, MD 21620
  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    /90

    $2,750,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper,

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • 23620 Land's End Rd, Chestertown, MD 21620
    23620 Land's End Rd, Chestertown, MD 21620
    23620 Land's End Rd, Chestertown, MD 21620
    /30

    $4,850,000

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft

    23620 Land's End Rd, Chestertown, MD 21620

    80 private acres beautifully situated on the highly prized Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. One of only 4 properties on Orchard Point and sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to

    Stacy Kendall

    23620 Land's End Rd, 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

    $695,000

    • 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

    • 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
  • 23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    /77

    $4,850,000

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft

    23620 Lands End Rd, Chestertown, MD 21620

    Hartwell Estate features 80 private acres with pristine, panoramic views on the mouth of the Langford and Chester River. This light filled custom built home and property captures the essence of serene living on Maryland's Eastern Shore. One of only 4 premiere properties at the end of Quaker Neck, often called "Kent County's Gold Coast" is sited to take advantage of the natural landscape with

    Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
Maryland Kent County Chestertown

Homes for Sale with Pool in Chestertown, MD

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 54 days on the market compared to the national average of 52 days. The median sale price for homes in Chestertown, MD over the last 12 months is $355,000, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$355,000
Median Single Family Sale Price
$380,000
Median Townhouse Sale Price
$283,000
Median 2 Bedroom Sale Price
$482,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$218
Number of Homes for Sale
34
Last 12 months Home Sales
89
Months of Supply
4.60
Median List Price
$369,900
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 8 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Chestertown, MD and discover your ideal residence.

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