Map location of 104 LITTLE HARBOR WAY, CHESTERTOWN, MD 21620
$849,900
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104 Little Harbor Way, Chestertown, MD 21620

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3 Beds
3 Baths
1,980 Sq Ft

Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining areaperfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community.Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! 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.

Listing By: Julia Hilfiker - Gunther-McClary Real Estate mdbmls-r Realty.com
  • MLS# MDKE2005894
  • Date Listed11/10/2025
  • Days on Realty 12 Days
  • Bedrooms 3
  • Bathrooms 2 Full baths, 1 Half baths
  • Lot Size -
  • Sewer Public Sewer
  • Subdivision CHESTER RIVER LANDING
  • Property Type Condominium
  • County KENT
  • Water Public
  • Square Feet 1,980 sq. ft
  • Price Per Sq. Ft $429.24

Interior Features

  • Appliances Gas Range, Gas Oven, Electric Water Heater, Dishwasher, Disposal, Exhaust Fan, Microwave, Refrigerator, Washer, Dryer, Water Heater
  • Flooring Carpet, Vinyl
  • Cooling Central Air, Electric
  • Heating Exhaust Fan, Electric, Propane, Forced Air, Heat Pump

Exterior / Lot Features

  • Exterior Other, Balcony, Lighting, Rain Gutters, Storage
  • Roof Shingle
  • Lot Size Acres -
  • Lot Size SQFT -
  • Lot Features -

Directions

Exit Chestertown Historic District on S Cross St. Continue on S Cross Street past Hodson Boathouse and over small bridge. Once past the bridge make a left turn at Chester River Landing entrance.

Financial Considerations

  • Tax Amount $2,351
  • Terms Cash, Conventional, FHA, VA Loan

Sales & Tax History

Source: Public Records

Population & Environment

Source: Sperling's Best Places

Walkability in MD / 21620

Source: Walkscore

23/100

Car-Dependent

Walk Score ®

48/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 7/100, Transit Score: 0/100, Bike Score: 34/100.

Points of Interest near 104 LITTLE HARBOR WAY, CHESTERTOWN, MD 21620

Frequently Asked Questions for 104 LITTLE HARBOR WAY

Source: Realty.com

104 LITTLE HARBOR WAY, CHESTERTOWN, MD 21620 is a 1,980 sq. ft. condo listed for sale with 3 bedrooms and 3 bathrooms. Realty.com has 22 photos of this condominium, listed at $849,900. View sales and tax history of condos, use our mortgage calculator and more on Realty.com

Realty.com has 22 photos of 104 LITTLE HARBOR WAY.

The full address for this home is 104 LITTLE HARBOR WAY, CHESTERTOWN, MD 21620.

104 LITTLE HARBOR WAY has been listed on Realty.com since Mon November 10, 2025

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 7/100, Transit Score: 0/100, Bike Score: 34/100.

Listing provided courtesy of: Gunther-mcclary Real Estate (tel: 410-275-2118)
Listing agent: Julia Hilfiker (tel: 443-480-6770) (#3353147)

This content last refreshed on 2025-11-22 20:39:35. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Export listing data of 104 LITTLE HARBOR WAY, CHESTERTOWN, MD 21620 : MLS# MDKE2005894

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