Date
Details
Price
Change
Source
12/04/2025
Listed
$839,500
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/23
$839,500
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1/23
Property Description
**To be built! 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 area-perfect 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.
Full Property Details
Full Property Details for 102 Little Harbor Way
General
- Price: $839,500
- HOA FEE: $636/month
- Taxes: $2,351 (2025)
- Status: Active
- Type: Condo
- Source: BrightMLSMidAtlantic
- MLS ID: MDKE2005950
- Updated: 12/17/2025
- Added to Site: 45 day(s) ago
Interior
- Rooms/Areas: Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Laundry
- Interior Features: Walk-in Closet(s), Upgraded Countertops, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Combination Dining/Living, Combination Kitchen/Dining, Combination Kitchen/Living, Dining Area, Family Room Off Kitchen, Floor Plan - Open, Kitchen - Gourmet, Kitchen - Island, Primary Bath(s), Recessed Lighting, Sprinkler System
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Gas/Propane
- Appliances: Dishwasher, Disposal, Water Heater, Oven/Range - Gas, Refrigerator, Microwave, Washer, Dryer
- Flooring: Luxury Vinyl Plank, Carpet
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
- Upper Floor Baths: 2
- Upper - Full Baths: 2
- Main Floor Baths: 1
- Main - 1/2 Baths: 1
Bedrooms
- Total Bedrooms: 3
- Bedrooms Upper: 3
Other Rooms
- Laundry: Has Laundry, Upper Floor
Additional Information
- Shared Amenities: Beach, Boat Dock/Slip, Common Grounds, Jog/Walk Path, Swimming Pool, Pier/Dock, Party Room, Picnic Area, Pool - Outdoor
- Shared Pool: Yes
- Pool: Yes
Exterior
- Exterior Features: Extensive Hardscape, Exterior Lighting, Gutter System, Secure Storage, Sidewalks
- Porch/Patio/Deck: Deck(s), Porch(es)
Parking
- Total Spaces: 2
- Parking Features: Brick Driveway, Private
- Parking Type: Driveway
Location
- Municipality: Chestertown
- County: KENT
- Subdivision: CHESTER RIVER LANDING
- Driving 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.
- Location Details: River
- City Limits: Yes
School Information
- School District: Kent County Public Schools
Community
- Assoc. Fees Include: Common Area Maintenance, Lawn Maintenance, Pier/Dock Maintenance, Pool(s), Road Maintenance, Snow Removal
- Pets Allowed: Yes
- Pets: No Pet Restrictions
Heating & Cooling
- Central air: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Forced Air, Heat Pump - Gas BackUp
- Heating Fuel: Electric, Propane - Metered
- Water Heater: 60+ Gallon Tank, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Dist. to Water: 0 Blocks
Structural Information
- Architectural Style: Coastal, Colonial
- Structure Type: Twin/Semi-Detached
- Builder: Paquin Design Build
- Construction: Combination, HardiPlank Type, Stick Built, Brick
- Foundation: Crawl Space, Block
- Roof: Architectural Shingle
- Walls/Ceilings: Dry Wall
- Stories Description: Main, Upper 1
- Square Feet: 1,964
- Sq. Ft. Source: Estimated
- Living Area: 1,964 Sq. Ft.
- Finished Above Grnd: 1,964 Sq. Ft.
- Year Built Source: Assessor
- Property Condition: Excellent
Additional Structures
- Other Structures: Garage(s)
Lot Features
- Property View: Courtyard, Scenic Vista, River, Trees/Woods, Water
- Zoning: IM
- Lot Description: Premium
Water Features
- Water View: Yes
- Navigable Water: Yes
- Water Access: Yes
- Water Access Desc: Fishing Allowed, Canoe/Kayak, Boat - Powered, Public Beach, Sail, Swimming Allowed, Waterski/Wakeboard, Personal Watercraft (PWC)
- Water Front Type: River
- Water Front Name: Chester River
- Docks: 5
Financial Considerations
- Price Per Sq. Ft.: $427.44
- Condo Fee: $636
- Condo Fee Freq: Monthly
- Assessment Year: 2025
- City/TownTax: $649
- City/TownTax Freq: Annually
- County Tax: $1,701
- County Tax Freq: Annually
- Tax w/Assessment: $150,000
- Tax Amount: $2,351
- Tax Year: 2025
Disclosures and Reports
- Ownership: Condominium
- Condo: Yes
- Lot Number: 20
Listed by Gunther-McClary Real Estate, John J Burke and Gunther-McClary Real Estate, Julia Hilfiker
We Value Your Privacy
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Listing agents
— 102 Little Harbor Way —
John J Burke
Gunther-McClary Real Estate
Julia Hilfiker
Gunther-McClary Real Estate
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 102 Little Harbor Way
School District:Kent County Public Schools
| Name | Grades | Distance |
|---|---|---|
Kent County Middle School 402 East Campus Avenue, Chestertown, MD 21620 | 6-8 | 1.3 mi |
Kent County High School 25301 Lambs Meadow Road, Worton, MD 21678 | 9-12 | 6.1 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 102 Little Harbor Way
Tax History
Tax History for 102 Little Harbor Way
Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,351
—
$150,000
—
2024
$2,351
1%
$150,000
—
2023
$2,336
—
$150,000
—
2022
$2,336
-1%
$150,000
—
2020
$2,351
—
$150,000
—
2021
$2,351
—
$150,000
—
2020
$2,346
1%
$150,000
—
2019
$2,331
3%
$150,000
—
2018
$2,256
—
$150,000
—
2017
$2,256
107%
$150,000
-49%
2016
$1,092
—
$295,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 102 Little Harbor Way
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102 Little Harbor Way, Chestertown, MD 21620 (MLS# MDKE2005950) is a Condo property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 102 Little Harbor Way is currently listed for $839,500 and was received on December 04, 2025. Want to learn more about 102 Little Harbor Way? Do you have questions about finding other Condo real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.