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575 MADISON AVENUE, NEW YORK, NY 10022. 212.891.7000 © 2025 DOUGLAS ELLIMAN REAL ESTATE. EQUAL EMPLOYMENT OPPORTUNITY PROVIDER. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES, OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS, AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT, OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY.LISTING DATA REFRESHED ON OCT 20 2025 AT 10:26 AM.

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LITTLE HARBOR WAY 1

chestertown, MD 21620

$1,800,000

  • 4 BR
    3 BA, 1 HALF BA
    APPROX. 3,540 SF

INTERESTED? LET'S CONNECT

**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 suite.
Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry.
Designed with future needs in mind, this home also offers the option of a residential elevator for effortless access across all levels.
Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community.
Deep water boat slips are available for lease or purchase. The community amenities include two docks, pool, grilling and outdoor dining area right on the water, large firepit, area to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more!
Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Details

3,540 Sq Ft

Condo

$636 Monthly Maintenance/CC

$2,569 Annual Tax

MLS/Listing ID MDKE2004992

Amenities & Features

Cooling - Central Air

Construction - Hardi Plank Type

Rip Rap

Walk-in Closets

Upgraded Countertops

Recessed Lighting

Ceiling Fans

Elevator

Heating - Natural Gas

Heating - Electric

Refrigerator

Microwave

Disposal

Dishwasher

Crawlspace

Style - Coastal

Hardwood

Ceramic Tile

Carpet

BRIGHT

Source of Data: BRIGHT MLS

estimate my mortgage

TOTAL MONTHLY COST

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  • PRINCIPAL & INTEREST

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  • PROPERTY TAXES

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HOME PRICE
DOWN PAYMENT
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INTEREST

Interested in LITTLE HARBOR WAY 1?

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the BrightMLS. Real estate listings held by brokerage firms other than Douglas Elliman of VA are marked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website.

All information deemed reliable but not guaranteed. Last date updated: 10/20/2025.
Source: Bright Multiple Listing Service, Inc.

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