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Cell: (410) 259-3680
Office: (410) 876-3500
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25440 Learman Road, Chestertown, MD 21620

$3,000,000
  • 25440 Learman Road, Chestertown, MD 21620 Main Photo

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New to the Market Coming Soon
BEDS3 BATHS2 full 2 partial SQUARE FEET3,142 MLS#MDKE2006468
STATUSCOMING SOON PROPERTY TYPEResidential - Single Family SUBDIVISIONQUAKER NECK SCHOOLKENT COUNTY PUBLIC SCHOOLS

Property Description

Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, featuring 560 feet of prime water frontage on the Chester River and a private 140-foot dock with 7 feet of mean low water, perfect for all your adventures. ** The heart of this property is the beautifully renovated 3-bedroom, 2 full bath, 2 half bath main home, meticulously remodeled in 2018 with the highest quality materials and fixtures. The residence boasts sweeping water views from nearly every room, allowing you to enjoy picturesque sunrises Chester River. ** As you enter, you are greeted by a grand living room featuring a striking five-foot fireplace set within a soaring vaulted ceiling, creating a warm and inviting atmosphere. Expansive windows frame the breathtaking views and fill the space with natural light, enhancing the open-concept design that is perfect for both relaxing and entertaining. ** The gourmet kitchen is a chef's dream, equipped with top-of-the-line stainless steel appliances, custom cabinetry, an oversized island with seating, and elegant custom stone and wood countertops. This thoughtfully designed space allows for effortless meal preparation and entertaining. ** Retreat to the luxurious primary suite, a true sanctuary featuring its own private walled garden, offering a serene escape for relaxation and outdoor enjoyment. The suite also includes a cozy fireplace, perfect for creating a romantic ambiance. The spa-like bathroom is designed for ultimate relaxation, a spacious glass-enclosed double head shower, and dual vanities with exquisite finishes. A generous walk-in closet provides ample storage, ensuring organization and convenience. ** The outdoor living features of this luxurious estate are truly exceptional, designed to create an idyllic sanctuary for relaxation and entertainment. At the heart of the outdoor space is a stunning waterfront concrete pool, refurbished in 2018, offering a refreshing retreat on warm summer days while providing breathtaking views of the Chester River. Surrounding the home, the professionally designed landscaping enhances the natural beauty of the property, featuring lush gardens, vibrant plantings, and mature ornamental trees. The side patio, complete with a charming brick fire pit, invites gatherings with friends and family, perfect for cozy evenings under the stars. The poolside patio off the main living room makes alfresco dining a breeze. Additionally, the private walled garden serves as a tranquil oasis, offering a serene space to unwind amidst nature, making this outdoor area the perfect complement to the luxurious lifestyle this estate offers. ** Accommodate guests or staff in the charming 3-bedroom, 2-bath guest/caretaker's cottage, built in 2013. A spacious 2.5-bay workshop provides ample storage for your outdoor equipment and hobbies. ** This exceptional property seamlessly blends luxury and tranquility, offering a unique opportunity to own a piece of paradise on the Eastern Shore. Don’t miss your chance to experience the charm and elegance of this extraordinary waterfront estate!

25440 Learman Road | MLS# MDKE2006468

This single family home located at 25440 Learman Road, Chestertown, MD 21620 is currently listed for sale with an asking price of $3,000,000. This property was built in 1955 and has 3 bedrooms and 2 full and 2 partial baths with 3142 sq. ft. Learman Road is located in the QUAKER NECK subdivision within the KENT COUNTY PUBLIC SCHOOLS school district. Search QUAKER NECK real estate on www.homesalesbyjay.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Outside Entrance, Unfinished, Sump Pump
Cooling: Central A/C, Programmable Thermostat, Zoned
Fireplaces: 2
Fuel Type: Electric, Propane - Owned
Garage: 4
Heating: Central, Programmable Thermostat, Zoned, Heat Pump -
Home Style: Traditional, Coastal
Lot Size: 11.00 Acres
Stories: 2.0
Taxes: $18,103
Year Built: 1955

Feature Descriptions

Accessibility: Doors - Swing In, Level Entry - Main
Additional Structures: Above Grade, Below Grade
Exterior: Brick
Fireplace: Gas/Propane, Mantel(s), Metal, Screen, Wood, Brick
Lake Name: Chester River
Lot: Backs to Trees, Front Yard, Landscaping, Partly Wooded, Private, Rear Yard, Secluded, Tidal Wetland
Lot Dimensions: 11.00 Acre(S)
Parking Features: Circular Driveway, Gravel Driveway, Asphalt Driveway, Private
Parking Notes: 9 Total Parking Spaces
Sewer: Private Septic Tank, Septic Exists
Special View Info: River, Scenic Vista, Water
SQFT Above Finished: 3142
SQFT Total Finished: 3142
Structure Type: Detached
Total Garage/Parking Spaces: 9
Water: Private, Well
Water Access: Private Access
Waterfront: Private Dock Site, Rip-Rap
Wooded: Yes

Local Schools

School District: KENT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: TTR Sotheby's International Realty
Agency Phone: 4106733344

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Estimated Payment

$ 9,060.28 per month $6,676.70 Principal & Interest $1,508.58 Property Tax $875.00 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 05/27/2026. The listing information on this page last changed on 05/27/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 05/27/2026 12:20:37 AM EST) or Bright MLS (last updated Wed 05/27/2026 12:13:28 AM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Agent License Information: 
Licensed in Maryland
Jay Cinquegrani 

1030 Baltimore Blvd, Suite 150, Westminster, MD 21157
410-876-3500

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