231 Richard Dr, Chestertown, MD 21620
Local realty services provided by:CENTURY 21 Home Team Realty
Upcoming open houses
- Sat, Mar 0711:00 am - 01:00 pm
- Tue, Mar 2411:00 am - 01:00 pm
Listed by: liddy campbell
Office: ttr sotheby's international realty
MLS#:MDKE2005900
Source:BRIGHTMLS
Price summary
- Price:$1,279,000
About this home
Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town convenience.
*
With five (plus) bedrooms accommodating up to fourteen guests and three full baths, the home is designed for comfort, flexibility, and enjoyment. Multiple indoor and outdoor gathering spaces make it ideal for those seeking a full-time residence, a weekend retreat, a multi-generational destination, or a strong investment property with outstanding rental potential.
*
On the main level, a cozy den with a wood-burning fireplace captures Chester River views, creating a warm and welcoming spot to relax after a day on the water. Additional living spaces provide room for groups to spread out—whether entertaining, working remotely, or simply taking a quiet moment to unwind. The primary suite offers its own private vantage point with a picture window overlooking the pool and riverfront—perfect for greeting the sunrise or watching wildlife glide across the water.
*
Outdoor living is where this property truly shines. Enjoy a covered patio for shaded summer crab feasts, a large deck with a stone fireplace for crisp evenings, and an in-ground pool that looks out toward the shore. With immediate water access, you’ll launch kayaks, paddle boards, and jet skis right from your backyard—ideal for embracing the river lifestyle. A two-car attached garage provides convenient storage for gear, bikes, and all the water toys. It could also be the perfect space to keep your street legal golf cart which the Town Of Chestertown now allows!
*
Your new home is also just a short walk from the full-service Chestertown Marina with the potential for a transferable slip—already paid through the 2026 boating season—ensuring you can enjoy hassle-free access to Chester River fun. Additionally, it's a quick ride to the Chester River Yacht & Country Club, where you can indulge in 18 holes of golf, relax by the pool, enjoy happy hour or meals at the full restaurant and bar, and partake in a host of other fantastic member benefits.
*
Whether you’re making it your full-time home, your getaway from the city, or your next strategic investment, this property delivers the best of Chestertown living—waterfront, walkable, and wonderfully welcoming. Embrace a lifestyle of leisure and convenience in this exceptional location.
Contact an agent
Home facts
- Year built:1981
- Listing ID #:MDKE2005900
- Added:1 day(s) ago
- Updated:March 03, 2026 at 02:32 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:3
- Full bathrooms:3
- Flooring:Carpet, Wood
- Dining Description:Combination Dining/Living
- Bathrooms Description:Primary Bath(s)
- Kitchen Description:Kitchen - Galley, Upgraded Countertops
- Bedroom Description:Entry Level Bedroom
- Basement:Yes
- Basement Description:Connecting Stairway, Fully Finished, Heated, Interior Access, Outside Entrance, Walkout Level
Heating and cooling
- Cooling:Central A/C
- Heating:Forced Air, Oil
Structure and exterior
- Year built:1981
- Lot Features:Cul-de-sac, Level, Rear Yard, River, Tidal Wetland
- Architectural Style:Raised Ranch/Rambler
- Construction Materials:Block, Brick, Vinyl Siding
- Exterior Features:Deck(s), Patio(s), Porch(es)
- Foundation Description:Block, Slab
- Levels:2 Stories
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$1,279,000
- Tax amount:$8,665 (2025)
Features and amenities
- Laundry features:Has Laundry
- Pool features:In Ground
New listings near 231 Richard Dr
- Coming Soon
$309,900Coming Soon3 beds 2 baths301 Lincoln Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006170Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC - New
$375,000Active2 beds 1 baths787 sq. ft.117 Water St N #2a, CHESTERTOWN, MD 21620
MLS# MDKE2006166Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$350,000Active7 beds 6 baths850 sq. ft.117 Water St N #2b, CHESTERTOWN, MD 21620
MLS# MDKE2006168Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$1,600,000Active7 beds 6 baths5,400 sq. ft.117 Water St N #1a, 1b, 2a, & 2b, CHESTERTOWN, MD 21620
MLS# MDKE2006158Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$685,000Active3 beds 3 baths3,000 sq. ft.117 Water St N #1a, CHESTERTOWN, MD 21620
MLS# MDKE2006162Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$200,000Active1 beds 1 baths700 sq. ft.117 Water St N #1b, CHESTERTOWN, MD 21620
MLS# MDKE2006164Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$795,000Active0.1 Acres201 N Lynchburg St, CHESTERTOWN, MD 21620
MLS# MDKE2006144Listed by: RE/MAX ASSOCIATES-HOCKESSIN - Coming Soon
$440,000Coming Soon3 beds 2 baths104 Garland Ave, CHESTERTOWN, MD 21620
MLS# MDQA2016264Listed by: CROSS STREET REALTORS LLC - New
$795,000Active-- beds 2 baths2,045 sq. ft.201 N Lynchburg St, CHESTERTOWN, MD 21620
MLS# MDKE2006142Listed by: RE/MAX ASSOCIATES-HOCKESSIN
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.