Colonial, Coastal

206 S WATER STREET

CHESTERTOWN , MD 21620

MLS#: MDKE2005840

$619,000

Status: Active
Listing number: MDKE2005840
Listing provided by: TTR Sotheby's International Realty
Listing agent phone: None
Last update: 14 hours ago
On site: 13 days ago
Browse Properties
CHESTERTOWN HISTORIC DISTRICT - Residential

Property

Beds

4

Full Baths

3

1/2 Baths

1

Year Built

1900

Sq.Footage

2,008

Live in the heart of Chestertown’s Historic District—see your boat from your front porch! Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story waterview deck—built strong enough to support a hot tub or additional living area (double 2x8 joists per owner). Andersen composite dual-pane windows with plantation shutters offer energy efficiency and easy operation. Ample storage includes two walk-in closets plus a walk-in attic. Located on desirable Water Street, you’re just steps from the waterfront, Wilmer Park, shops, restaurants, bakeries, pubs, Farmer’s Market, arts district, and more. Cook and entertain in style with Heartland appliances and handcrafted cabinetry in the kitchen. 206 S. Water Street—a “feels-like-new” historic home in Chestertown’s most walkable location. Note The vacant lot next door is not part of this property. Separate owner.

Features & Amenities

Interior

  • Other Interior Features

    Kitchen Island, Crown Molding

  • Total Bedrooms

    4

  • Bathrooms

    3

  • 1/2 Bathrooms

    1

  • Above Grade Finished Area

    2008.0

  • Basement YN

    NO

  • Cooling YN

    YES

  • Cooling

    Zoned, Ductless, Electric

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Electric, Propane, Heat Pump

  • Main Level Bedrooms

    1

  • Pet friendly

    N/A

Exterior

  • Garage

    No

  • Construction Materials

    Frame

  • Parking

    On Street

  • Patio and Porch Features

    Porch

  • Pool

    Yes

  • Pool Features

    None

  • Waterfront YN

    NO

Area & Lot

  • Lot Size(acres)

    0.04

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Colonial, Coastal

Price

  • Sales Price

    $619,000

  • Tax Amount

    7755.0

  • Sq. Footage

    2, 008

  • Price/SqFt

    $308

HOA

  • Association

    No

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Water Source

    Public

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 Thomas C Williams Jr. , TTR Sotheby's International Realty

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 ChristyIssler

Broker | Owner

ChristyIssler

Call Christy today to schedule a private showing.

(235) 551-212

christy@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.
Live in the heart of Chestertown’s Historic District—see your boat from your front porch! Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story waterview deck—built strong enough to support a hot tub or additional living area (double 2x8 joists per owner). Andersen composite dual-pane windows with plantation shutters offer energy efficiency and easy operation. Ample storage includes two walk-in closets plus a walk-in attic. Located on desirable Water Street, you’re just steps from the waterfront, Wilmer Park, shops, restaurants, bakeries, pubs, Farmer’s Market, arts district, and more. Cook and entertain in style with Heartland appliances and handcrafted cabinetry in the kitchen. 206 S. Water Street—a “feels-like-new” historic home in Chestertown’s most walkable location. Note The vacant lot next door is not part of this property. Separate owner.

206 S WATER STREET

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

Related Properties

$$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$ Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office setup Curb appeal abounds with an inviting brick front and an attached two-car garage. Step inside to find a bright and open main level featuring a cozy fireplace in the great room, a large formal dining area filled with natural light, and a chef's kitchen with abundant cabinetry and high-quality appliances including a wall oven, cooktop, refrigerator, dishwasher, and built-in microwave. Upstairs, retreat to your luxurious primary suite, complete with a tray ceiling, spacious layout, double vanities, soaking tub, and separate shower — a true personal oasis. Three additional bedrooms offer plenty of space for family, guests, or a home office. Enjoy year-round comfort with a two-zone HVAC system, and take advantage of the generous quarter-acre lot for outdoor activities, gardening, or future expansion. Located in the sought-after community of Coventry Farms, this move-in-ready home combines modern convenience with small-town charm. Don’t miss your opportunity to own this beautiful home — schedule your private tour today and start living the Coventry Farms lifestyle!Please use booties provided at the front door. PET FRIENDLY COMMUNITY
#MDKE2005610

CHESTERTOWN

116 HARLAN LOOP

5 Beds

3 Baths

4,585 Sq.Ft.

$519,000

MLS#: MDKE2005610

Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn. Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury countertops and a sunroom bump-out with ample natural light—ideal for morning coffee, reading, or cozy dinners. Upstairs, the spacious primary suite offers a true retreat with a walk-in closet, en suite bathroom, and the convenience of an upstairs laundry room. The fully finished basement adds exceptional versatility, featuring its own private entrance, kitchenette, full bath with steam sauna, and open-concept living/bedroom area—perfect for guests, or entertaining. A dedicated workroom completes the lower level, ready for projects or hobbies. Outside, enjoy your fenced-in backyard oasis complete with a deck. This home has been meticulously cared for and thoughtfully updated, including: New roof, gutters, and gutter covers (2025) New HVAC system – furnace and A/C (2024) New 80-gallon water heater (2022) Fully renewed basement (2022) with new flooring, carpet, paint, and dual sump pumps Finished garage (2022) Ornamental Fence (2020)
#MDKE2005636

CHESTERTOWN

100 ADELA WAY

4 Beds

3 Baths

4,499 Sq.Ft.

$515,000

MLS#: MDKE2005636

Welcome to 515 N Kent Street in the heart of Chestertown! This charming two story home features a half-circle driveway, 1-car attached garage, and inviting brick patio leading to the front door. Step inside and you’ll love the gorgeous hardwood floors throughout the main level (2022). The formal living room showcases a wood-burning fireplace with a brick mantel, creating a warm and welcoming space. The kitchen and dining room were completely updated in 2022 with custom Amish cabinetry, quartz countertops, a farm sink, and a large island—perfect for cooking and gathering. Just off the kitchen, the laundry room offers washer/dryer, ample storage, and eye-catching brick tile flooring. From here, step into the cozy family room with wood stove, built-ins, and access to the screened porch and brick patio overlooking the private backyard. A full bath with shower and matching brick tile floors is conveniently located off the family room and garage entry. Upstairs, you’ll find four spacious bedrooms with carpet and a full bath with tub/shower. The partial basement with French drain provides flexible space for storage or playroom use, with indoor/outdoor access. This home has been well maintained with numerous updates: sewer line replaced (2017), new heat pump with central AC (2018), 50-year architectural shingle roof (2019), breaker panel and hot water heater (2024). A truly move-in ready home with character, comfort, and thoughtful upgrades—don’t miss this one!
#MDKE2005592

CHESTERTOWN

515 N KENT STREET

4 Beds

2 Baths

3,165 Sq.Ft.

$499,900

MLS#: MDKE2005592

Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and one bedroom in the walk out basement, there’s plenty of space for family and guests. The open-concept living area is perfect for gatherings, featuring ample natural light and gorgeous views of the surrounding landscape & lake! Enjoy convenience and comfort with two full bathrooms on the second, one full bath on the lower level and an additional half bath on the first, designed with modern fixtures and finishes. The finished walk-out basement provides excellent additional living space, bath/bedroom & perfect for a game room, entertainment area, or a private office. It also offers direct access to the beautiful outdoors. The property spans 2.62 acres, providing ample room for outdoor activities, gardening, or simply unwinding in nature. The partially wooded area enhances your privacy while allowing for serene nature walks right in your backyard & along the Lakes edge! Located on Urieville Lake, enjoy fishing, boating, kayaking and other recreational activities just moments from your doorstep. This private setting is perfect for those looking to escape the hustle and bustle of city life. Urieville Lake is about 35 acres in size and is shaped like the letter Y. The average depth is about 3 feet and supports a standard bass/bluegill fishery and is managed accordingly. Anglers may also occasionally catch other species including pumpkinseed sunfish, brown bullhead catfish, golden shiners and common carp. Welcome home!
#MDKE2004586

CHESTERTOWN

11040 KYLIE LANE

4 Beds

3 Baths

3,884 Sq.Ft.

$649,000

MLS#: MDKE2004586

Welcome to 101 Birch Run Rd., Chestertown, MD! 3 Bedrooms | 2 Full Baths | Oversized 2-Car Garage | .42 Acres Discover this stunning full-brick rancher located in the heart of historic Chestertown! Every inch of this 3-bedroom, 2-bath home has been completely updated with a sophisticated modern flair while maintaining an inviting, boutique-style warmth throughout. Step inside to find a bright, open-concept layout where the brand-new kitchen flows seamlessly into the family room—perfect for entertaining or relaxing by the cozy fireplace. The kitchen features sleek finishes, contemporary cabinetry, stylish lighting, and premium appliances. Both full baths have been fully renovated with today’s top design trends, creating a spa-like experience at home. The home’s thoughtful floor plan and attention to detail shine through every room—from fresh flooring and fixtures to elegant accents that elevate the overall aesthetic. Enjoy peace of mind with a new roof featuring 50-year architectural shingles (transferable warranty included). The oversized two-car garage provides ample space for parking and storage, while the landscaped .42-acre lot offers just the right amount of yard to enjoy without a lot of upkeep. Ideally situated within walking distance to the Chester River, Washington College, and Chestertown’s charming downtown —boutiques, shops, restaurants, and regular community events await. Bring your boat, kayak, paddle-board, or jet ski and experience the best of Eastern Shore living!
#MDKE2005810

CHESTERTOWN

101 BIRCH RUN ROAD

3 Beds

2 Baths

1,961 Sq.Ft.

$499,999

MLS#: MDKE2005810

Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of a traditional "Four Square". This prominent STAND-OUT RESIDENCE, crafted by acclaimed master builder Walter Pippin, extends a warm welcome to anyone driving (only 25mph please!) or strolling from the college campus to town, along the historically scenic Washington Avenue. The gracious flow of its' first floor, with discreet powder room and comfortable kitchen with radiant floor heating, the abundance of windows throughout, and more make this corner brick home, with wrap-around porch, tended landscape and white picket fence an exceptional offering. Four bedrooms, three baths, and a separate laundry room are approached by the original 3-level oak staircase. Off-street parking and charming two-car garage with curve-track doors is the envy of many downtown residents. Tucked behind the residence and garage is a super-comfortable and cozy slate patio for entertaining, grilling, reading or just chilling. An authentic Widow's Walk tops the house, for the adventurers yearning to view the fireworks or hide-away for a brief escape.
#MDKE2005538

CHESTERTOWN

200 WASHINGTON AVENUE

4 Beds

3 Baths

2,917 Sq.Ft.

$695,000

MLS#: MDKE2005538

New on site 4 days ago
Nestled in the serene Chester Harbor community of Chestertown, MD, 302 Rosin Drive offers an idyllic waterfront lifestyle along the tranquil shores of Rosin Creek. Perched on an elevated lot with stunning vistas of Rosin Creek, this charming home blends classic Eastern Shore character with modern comforts. Imagine mornings with coffee overlooking the water, afternoons kayaking from your backyard and evenings just minutes from historic Chestertown's shops, dining, and Washington College. Seamless indoor-outdoor flow make this the ultimate retreat—perfect for entertaining with indoor and outdoor spaces. This home has a complete in-law-suite perfect for hosting guests, accommodating extended family, or creating a private home office with serene water views. This deceivingly large 5-bedroom, 4-bath home features; extensive landscaping, lovely gazebo and brand-new roof.
#MDQA2015470

CHESTERTOWN

302 ROSIN DRIVE

5 Beds

4 Baths

4,157 Sq.Ft.

$574,000

MLS#: MDQA2015470

Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that features a peninsula island with a breakfast bar and cabinetry that offers ample storage and workspace including a separate pantry. Off from the kitchen is a room overlooking the back yard that offers access to the back yard. The primary suite is privately located in rear of home being complete with shower stall, tub, large vanity as well as a linen closet. The two additional bedrooms are located on the opposite wing of home offering separation. The finished basement is quite a highlight with a six-foot glass walk-out door onto the large rear private patio that overlooks an open wooded area that features mature trees, flowering shrubs and perennials. The pleasure of seeing deer and wild turkey stroll through and the morning sound of birds offers a peaceful retreat. Now to come back inside the basement, you will find it amazing. The main room coming in is very large being open to a kitchenette. The large room having a gas fireplace is presently used as a game room. The game room opens to a sitting room with half-bath access. There are additional rooms in the basement that includes a large workshop and another sizable room that could be used as a theatre room, work-out room or for whatever the need may be. The stairs from the basement up into the main level includes a chair lift. The home has a generator and solar panels for energy efficiency, as well as a yard sprinkler system and soaker hoses to keep the landscaping looking its best. This home being located in the historic town of Chestertown offers convenience to the Chester River, cultural festivities, waterfront parks, rail-trail, The Farmers Market, YMCA, hospital, shops and Washington College. The public record reflects the main level being 2135 SF with the lower level being 1800 S.F.
#MDKE2005536

CHESTERTOWN

251 DEVON DRIVE

3 Beds

2 Baths

4,264 Sq.Ft.

$595,000

MLS#: MDKE2005536

Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing, keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board, great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.
#MDKE2005670

CHESTERTOWN

103 LANDING LANE

2 Beds

2 Baths

2,500 Sq.Ft.

$559,000

MLS#: MDKE2005670

- 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