Little Harbor Way, Unit 1 • Chestertown, MD 21620

$1,800,000 Beds: 4 • Baths: 3 full 1 partial • Sq. Feet: 3540 • MLS ID: MDKE2004992 • Subdivision: CHESTER RIVER LANDING • School Dist: KENT COUNTY PUBLIC SCHOOLS
**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! 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. View this listing at: http://tomboeshorerealtor.com/mls=MDKE2004992

Property Features

  • Garage: 2
  • Taxes: $2,569
  • Roof Type: Architectural Shingle,Metal
  • Exterior: HardiPlank Type
  • Parking Notes: 2 Total Parking Spaces
  • Special View Info: River,Water,Scenic Vista,Marina,Courtyard
  • Heating: Central,Heat Pump - Gas BackUp
  • Fuel Type: Electric,Propane - Metered
  • Cooling: Central A/C
  • Water: Public
  • Sewer: Public Sewer
  • Stories: 3.0
  • Condo/Coop Fee: $636.00/Monthly
  • Accessibility: Elevator,Other
  • Additional Structures: Above Grade
  • Location Description: River
  • Structure Type: Detached
  • Total Garage/Parking Spaces: 2
  • Pet Restrictions: No Pet Restrictions
  • Appliances: Dishwasher,Disposal,Microwave,Refrigerator,Oven/Range - Gas
  • Rooms: Dining Room,Bedroom 2,Bedroom 3,Bedroom 4,Kitchen,Bedroom 1,Great Room,Laundry,Bathroom 1,Bathroom 2,Bathroom 3
  • Lake Name: Chester River
  • Community Amenities: Boat Dock/Slip,Common Grounds,Pier/Dock,Pool - Outdoor,Beach,Jog/Walk Path,Picnic Area
  • SQFT Total Finished: 3540
  • SQFT Above Finished: 3540
  • Exterior: Extensive Hardscape,BBQ Grill
  • Interior: Elevator,Ceiling Fan(s),Combination Kitchen/Living,Floor Plan - Open,Kitchen - Gourmet,Primary Bath(s),Recessed Lighting,Upgraded Countertops,Walk-in Closet(s)
  • Flooring: Carpet,Ceramic Tile,Hardwood,Luxury Vinyl Plank
  • Waterfront: Rip-Rap
  • Water Access: Canoe/Kayak,Private Access,Boat - Powered,Fishing Allowed,Sail,Waterski/Wakeboard,Swimming Allowed
  • Electric Description: 200+ Amp Service
  • Utilities: Cable TV,Propane - Community,Sewer Available,Under Ground,Water Available

Room Sizes

  • Bedroom 1: 13 x 19 Level: Main
  • Bedroom 2: 15 x 14 Level: Main
  • Bathroom 1: 12 x 7 Level: Main
  • Kitchen: 19 x 19 Level: Upper 1
  • Dining Room: 19 x 20 Level: Upper 1
  • Great Room: 13 x 23 Level: Upper 1
  • Bedroom 3: 16 x 19 Level: Upper 2
  • Bathroom 3: 12 x 9 Level: Upper 2
  • Bedroom 4: 13 x 12 Level: Upper 2
  • Bathroom 3: 6 x 12 Level: Upper 2
  • Laundry: 6 x 9 Level: Upper 2

School Information

  • School District: KENT COUNTY PUBLIC SCHOOLS
Printed March 03, 2026


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Agent License Information: 
Licensed in Maryland
Thomas Boeshore 

100 Piney Narrows Road, Chester, MD 21619
443-589-8080