Four Baths! LOTS of storage in this nearly new construction! See tall ships sailing the Chester River from your front porch and live in the heart of Chestertown's thriving Historic District! This historic home located at Chestertown Marina has seen extensive remodel as recently as 2021. The first floor bedroom suite addition has a full bath, a sitting room, a walk-in closet, and a separate entrance. It's also perfectly positioned to be used as an extension of the first floor space when you are not housing guests. Live in the heart of it all & enjoy being just steps from the waterfront and all Chestertown has to offer including the quiet & calm of day to day life with a splash of occasional spice from Festivals like Tea Party in May, and Downrigging in November! This desirable Water Street address provides premium access to coffee shops, bakeries, farmer's market, festival events, music, art district, rail-trail, restaurants, shops, live theater, and more. Walk everywhere! And when you come home with your Saturday Farmer's Market goodies, enjoy cooking on gorgeous Heartland appliances that compliment the hand crafted free-standing cabinetry in the kitchen. A first floor guest suite added by local builder Jay Yerkes includes a sitting room connected to the house via a mudroom/porch. Above the mudroom is a second story deck that was built to hold a hot tub* (with double 2x8 joists according to the owner!) This private water-view deck leads to a walk-in attic which was also built to support future finished space.* Anderson composite dual pane windows custom fitted with planation shutters were installed throughout the home- all are easy to open & energy efficient. The mudroom is fully insulated to allow open doors between the house and the rooms of the guest suite or lock the doors for complete separation & versatility. This home is adaptable to many ways of living! With bedrooms on every floor to be used as you like, the 3rd floor waterview suite with a full bath & a walk-in closet could just as easily be a den or a bunk room. The lawn next-door is under separate ownership & is not part of this sale. *Buyer to verify feasibility of any expansion plans. Centrally located for travel, your choice of BWI or Philadelphia International airports are just 90 minutes away. Explore the possibilities at 206 S Water St and imagine yourself here. It's a special place to live!
For sale
Price cut: $50.3K (7/27)
$648,750
206 S Water St, Chestertown, MD 21620
4beds
2,008sqft
Est.:
Single Family Residence
Built in 1900
1,888 Square Feet Lot
$-- Zestimate®
$323/sqft
$-- HOA
What's special
Separate entranceSteps from the waterfrontPrivate water-view deckHand crafted free-standing cabinetrySecond story deckGorgeous heartland appliances
- 32 days
- on Zillow |
- 1,296 |
- 31 |
Zillow last checked: 7 hours ago
Listing updated: July 29, 2025 at 03:54am
Listed by:
Beth Ostrander 610-256-3704,
Doug Ashley Realtors, LLC 410-810-0010
Source: Bright MLS,MLS#: MDKE2005362

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 1
Rooms
- Room types: Living Room, Kitchen, Bedroom 1, In-Law/auPair/Suite
Bedroom 1
- Features: Walk-In Closet(s)
- Level: Upper
Other
- Level: Main
Kitchen
- Features: Pantry, Kitchen - Electric Cooking
- Level: Main
Living room
- Features: Fireplace - Gas
- Level: Main
Mud room
- Level: Main
Heating
- Heat Pump, Electric, Propane
Cooling
- Ductless, Zoned, Electric
Appliances
- Included: Dishwasher, Washer, Dryer, Oven/Range - Electric, Refrigerator, Electric Water Heater
- Laundry: Mud Room
Features
- Attic, Bathroom - Stall Shower, Soaking Tub, Entry Level Bedroom
- Windows: Double Pane Windows, Energy Efficient, Screens, Casement
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 2,008
- Total interior livable area: 2,008 sqft
- Finished area above ground: 2,008
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Parking features: Free, On Street
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Pool features: None
- Has spa: Yes
- Spa features: Bath
- Has view: Yes
- View description: Marina, River
- Has water view: Yes
- Water view: Marina,River
- Waterfront features: River
- Body of water: Chester River
Lot
- Size: 1,888 Square Feet
- Features: Downtown
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1504004965
- Zoning: R-5
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Coastal,Cottage
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Block
- Roof: Architectural Shingle
Condition
- Excellent
- New construction: No
- Year built: 1900
- Major remodel year: 2021
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Fiber Optic, Broadband, Cable
Community & HOA
Community
- Subdivision: Chestertown Historic District
HOA
- Has HOA: No
Location
- Region: Chestertown
- Municipality: Chestertown
Financial & listing details
- Price per square foot: $323/sqft
- Tax assessed value: $518,600
- Annual tax amount: $7,755
- Date on market: 7/10/2025
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional,USDA Loan,VA Loan,FHA
- Inclusions: Plantation Shutters Throughout, Propane Cast Iron Heater / Gas Fp
- Ownership: Fee Simple
- Loading
- Loading