About 206 S Water St
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 of 206 S Water St
| MLS® # | MDKE2005840 |
|---|---|
| Price | $619,000 |
| Bedrooms | 4 |
| Bathrooms | 3.50 |
| Full Baths | 3 |
| Half Baths | 1 |
| Square Footage | 2,008 |
| Acres | 0.04 |
| Year Built | 1900 |
| Type | Residential |
| Sub-Type | Detached |
| Style | Colonial, Coastal |
| Status | Active |
Community Information
| Address | 206 S Water St |
|---|---|
| Subdivision | CHESTERTOWN HISTORIC DISTRICT |
| City | CHESTERTOWN |
| County | KENT-MD |
| State | MD |
| Municipality | Chestertown |
| Zip Code | 21620 |
Amenities
| Amenities | Crown Molding, Entry Lvl BR, Master Bath(s), Wood Floors |
|---|---|
| Is Waterfront | No |
Interior
| Interior Features | Floor Plan-Traditional |
|---|---|
| Appliances | Dishwasher, Disposal, Dryer, Oven/Range-Electric, Washer/Dryer Stacked, Washer |
| Heating | Heat Pump(s) |
| Cooling | Ductless/Mini-Split, Zoned |
| Has Basement | No |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| Fireplaces | Gas/Propane |
| # of Stories | 3 |
| Stories | 3 |
Exterior
| Exterior | Frame |
|---|---|
| Exterior Features | Porch(es) |
| Foundation | Crawl Space |
School Information
| District | KENT COUNTY PUBLIC SCHOOLS |
|---|
Additional Information
| Date Listed | October 22nd, 2025 |
|---|---|
| Days on Market | 2 |
| Zoning | R-5 |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | TTR Sotheby's International Realty |
|---|