CHARIS REALTY GROUP

Georgian

109 WATER STREET N

CHESTERTOWN , MD 21620

MLS#: MDKE2002442

$865,000

Status: Closed
Listing number: MDKE2002442
Listing provided by: Select Land & Homes, LLC
Listing agent phone: None
Last update: 2 years ago
On site: 2 years ago
Browse Properties
CHESTERTOWN - Residential

Property

Beds

5

Full Baths

3

1/2 Baths

1

Year Built

1739

Sq.Footage

3,030

Welcome to the Esau Watkins House (circa 1739), believed to be the earliest remaining dwelling on the Chester River in Historic Chestertown, the capitol of Kent County, Maryland. Rarely does a home of this significance become available in the heart of Chestertown’s famed Water Street district. This five-bedroom, three-and-one-half-bath historic gem offers captivating, unobstructed views of the unspoiled Chester River. Notable features of this home include extensive random width wood plank flooring, proportionally balanced trim work, gorgeous scalloped built-in corner cupboards, a sun-filled riverside enclosed porch, a living room with wood burning fireplace, spacious second-floor primary suite, adequate “step-in” closets, and storage, walk out full basement, lush waterside garden, and sea-walled frontage with pier deck for water access. This highly sought-after location is within a short, pet-friendly, walking distance to several well-reviewed restaurants, two delicious bakeries, intriguing boutique shops/galleries, and the highly acclaimed Downtown Chestertown Farmer’s Market. The Chester River offers endless watersports, world-class crabbing, fishing, kayaking, and undisturbed shoreline exploration. Chestertown is home to Washington College, the Chestertown Tea Party, and the sailing ship “Sultana.” Come Enjoy! Please note that the property history and previous listing information is incorrect!

Features & Amenities

Interior

  • Other Interior Features

    Ceiling Fan(s)

  • Total Bedrooms

    5

  • Bathrooms

    3

  • 1/2 Bathrooms

    1

  • Above Grade Finished Area

    3030.0

  • Basement YN

    YES

  • Cooling YN

    YES

  • Cooling

    Ceiling Fan(s), Window Unit(s)

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Oil

  • Pet friendly

    N/A

Exterior

  • Garage

    No

  • Construction Materials

    Brick

  • Other Exterior Features

    Awning(s), Other

  • Parking

    On Street

  • Pool

    No

  • Waterfront YN

    YES

  • View

    Water, River, Panoramic

Area & Lot

  • Lot Features

    Waterfront

  • Lot Size(acres)

    0.09

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Georgian

Price

  • Sales Price

    $865,000

  • Tax Amount

    12205.0

  • Sq. Footage

    3, 030

  • Price/SqFt

    $285

HOA

  • Association

    No

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • Foundation Details

    Brick/Mortar

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

What is 3 + 4 ?


Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

KENT

Elementary School

Middle School

High School

Listing Courtesy of William H Norris III , Select Land & Homes, LLC

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent Marsha DeGirolamo

AGENT

Marsha DeGirolamo

Call Marsha today to schedule a private showing.

(240) 731-6911

marsha@charisrealty.com


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
Welcome to the Esau Watkins House (circa 1739), believed to be the earliest remaining dwelling on the Chester River in Historic Chestertown, the capitol of Kent County, Maryland. Rarely does a home of this significance become available in the heart of Chestertown’s famed Water Street district. This five-bedroom, three-and-one-half-bath historic gem offers captivating, unobstructed views of the unspoiled Chester River. Notable features of this home include extensive random width wood plank flooring, proportionally balanced trim work, gorgeous scalloped built-in corner cupboards, a sun-filled riverside enclosed porch, a living room with wood burning fireplace, spacious second-floor primary suite, adequate “step-in” closets, and storage, walk out full basement, lush waterside garden, and sea-walled frontage with pier deck for water access. This highly sought-after location is within a short, pet-friendly, walking distance to several well-reviewed restaurants, two delicious bakeries, intriguing boutique shops/galleries, and the highly acclaimed Downtown Chestertown Farmer’s Market. The Chester River offers endless watersports, world-class crabbing, fishing, kayaking, and undisturbed shoreline exploration. Chestertown is home to Washington College, the Chestertown Tea Party, and the sailing ship “Sultana.” Come Enjoy! Please note that the property history and previous listing information is incorrect!

109 WATER STREET N

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

Related Properties

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. 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.
#MDKE2005892

CHESTERTOWN

106 LANDING LANE

3 Beds

3 Baths

2,092 Sq.Ft.

$799,900

MLS#: MDKE2005892

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. 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.
#MDKE2005956

CHESTERTOWN

#35 LANDING LANE

3 Beds

2 Baths

1,964 Sq.Ft.

$786,900

MLS#: MDKE2005956

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private second floor balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. 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.
#MDKE2005958

CHESTERTOWN

#36 LANDING LANE

3 Beds

2 Baths

1,964 Sq.Ft.

$753,500

MLS#: MDKE2005958

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and large walk-in closet. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. 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.
#MDKE2005960

CHESTERTOWN

#37 LANDING LANE

3 Beds

2 Baths

1,964 Sq.Ft.

$765,900

MLS#: MDKE2005960

**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.
#MDKE2005894

CHESTERTOWN

104 LITTLE HARBOR WAY

3 Beds

2 Baths

1,980 Sq.Ft.

$849,900

MLS#: MDKE2005894

**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.
#MDKE2005950

CHESTERTOWN

102 LITTLE HARBOR WAY

3 Beds

2 Baths

1,964 Sq.Ft.

$839,500

MLS#: MDKE2005950

Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the home. On the second level you'll find two bedrooms and two bathrooms. There's extra room for an office nook. The third bedroom encompasses the entire third floor and has a great view of the Chester River. You'll enjoy the large back balcony with views of historic Chestertown. The third level could be used as the primary bedroom; there is a large full bathroom and closet. The townhomes have a private driveway, so you'll never worry about finding a parking space. Take advantage of the easy access to Wilmer Park and Chestertown Marina, located just across the street. This townhouse is located in the heart of all Chestertown has to offer! Just a short distance to shops, restaurants, renowned bakeries, and the year-round farmers market by Fountain Park. You will have a front-row seat to the Downrigging Festival! Not to mention the many festivals held in downtown Chestertown throughout the year.
#MDKE2005812

CHESTERTOWN

228 S WATER ST

3 Beds

3 Baths

2,310 Sq.Ft.

$878,000

MLS#: MDKE2005812

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. 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.
#MDKE2005952

CHESTERTOWN

104 LANDING LANE

3 Beds

3 Baths

2,192 Sq.Ft.

$813,900

MLS#: MDKE2005952

Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season and a true haven for butterflies and hummingbirds. You will delight in an outdoor sitting area under a lovely shade tree. The main level features gleaming hardwood floor, a semi-open floor plan with a cozy fireplace perfect for cool evenings, and abundant natural light that creates a calming atmosphere throughout. The large primary suite offers comfort and convenience, and there is the option for a second bedroom on the main level. Current owners have opted to make that room a large office, and it features two closets. The kitchen is a dream — spacious enough for a large island and a generous breakfast area that easily fits a full-sized table. There is a mural border that shows scenes of historic Chestertown. Pantry and plenty of storage. Upstairs, you’ll find two large bedrooms and a full hall bath, ideal for guests or loved ones. Each bedroom offers walk-in storage — no attic ladders needed! Solar operated fans keep the attic spaces cool. Additional highlights include leased solar panels which have been paid out, a large garage with ample storage, additional storage shed with electric and water. , and a fantastic location just minutes from the Chester River and the Chester River Yacht and Country Club. Two zone for heating and cooling. Come see this charming home for yourself — it’s the perfect blend of beauty, comfort, and thoughtful design!
#MDKE2005796

CHESTERTOWN

7844 CHESTER COURT

4 Beds

2 Baths

3,248 Sq.Ft.

$745,000

MLS#: MDKE2005796

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service