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105 N Water St #2, 
Chestertown, MD 21620

$475,000


2

Beds


2

Baths


1,011

Sq Ft


Condo


Virtual Tour

Pending

Listed by

Missy A Aldave

Megan Miller Minderlein

Northrop Realty, 4104651770

Last updated:

September 11, 2026, 07:43 AM

MLS#

MDKE2006680

Source:

BRIGHTMLS

About This Home

105 N Water St #2

Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence combines historic charm, modern comfort, and an enviable waterfront location. Filled with character and warmth, the home features beautiful hardwood floors, soaring ceilings, tall windows, built-ins, and a wonderful period gas fireplace that creates a welcoming focal point in the spacious living room. Two generously sized bedrooms and two beautifully appointed tiled bathrooms provide comfort and style, while an in-unit washer and dryer add everyday convenience. Generous room sizes and abundant natural light enhance the home's inviting atmosphere throughout. The heart of the home is the expansive kitchen and great room at the rear of the residence, overlooking the river. Designed for gathering, entertaining, and everyday living, this impressive space features gorgeous cabinetry, stainless steel appliances, gas cooking, abundant counter space, a farmhouse sink, sunny windows, and plenty of room for dining as well as additional living space. Whether hosting friends, enjoying a quiet morning coffee, or unwinding at the end of the day, it's a room you'll find yourself gravitating toward again and again. Just off the great room, the private balcony overlooks the Chester River and offers sweeping water views in a peaceful waterfront setting. Direct water access and a dedicated boat slip make it easy to enjoy the area's iconic Chester River and everything that life on the water has to offer. Chestertown is steeped in maritime tradition and widely admired for its extraordinary collection of Federal, Georgian, and Victorian architecture. One of the Eastern Shore's most desirable destinations, residents enjoy boutique shopping, fine dining, waterfront attractions, cultural events, and a thriving arts scene. Perfectly positioned along the Chester River, this residence is a historic treasure, a waterfront retreat, and an opportunity to experience the very best of life in one of the Eastern Shore's most cherished communities.

Home Facts

Condo

2 Baths

2 Bedrooms

Built in 1900

Subdivision & Development:

WATER STREET

Price Summary

475,000

$469 per Sq. Ft.

MLS #:

MDKE2006680

Last Updated:

September 11, 2026, 07:43 AM

Added:

2 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

2

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

1,011 Sq. Ft.


Structure

Structure

Architectural Style:

Federal

Building Area:

1,011 Sq. Ft.

Year Built:

1900


Finances & Disclosures

Finances

Price:

$475,000

Price per Sq. Ft:

$469 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.