Change Real Estate Presents:

231 Richard Drive
Chestertown MD 21620

For Sale: $1,150,000.00 Active

List Date: 2026-03-06

Chestertown
5 bedrooms
3 bathrooms
2,956 build ft2
34,507 land ft2

About This Property

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.

Listing Agent: Liddy Campbell. TTR Sotheby's International Realty 410-708-5433 lcampbell@ttrsir.com

Virtual Tours / Videos

https://bit.ly/231RichardDrive

Property Features

Location Information
County:
Subdivision: BYFORD DEVELOPMENT
click to open map in a new window
Interior Features
Appliances:
Interior: Combination Dining/Living, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Galley, Primary Bath(s), Upgraded Countertops
Laundry:
Furnished: None
Flooring: Wood, Carpet
Water: Public
Cooling: Central A/C
Heating: Forced Air
Fireplaces: 1
Windows:
Utilities:
Sewer: Public Sewer
Rooms
Room Type: Bedroom 1
Level: Main
Room Type: Bedroom 2
Level: Main
Room Type: Bedroom 3
Level: Main
Room Type: Bathroom 1
Level: Main
Room Type: Bathroom 2
Level: Main
Room Type: Bedroom 1
Level: Lower 1
Room Type: Bedroom 2
Level: Lower 1
Room Type: Bathroom 1
Level: Lower 1
Exterior Features
Year Built: 1981
Legal Subdivision: Byford Development
Subdivision Name: Byford Development
Parking: Asphalt Driveway
Garage Spaces: 2.0
Schools
Elementary School: None
Junior High School: None
High School: None

IDXListing Courtesy of Liddy Campbell. TTR Sotheby's International Realty 410-708-5433 lcampbell@ttrsir.com

Property Photos [Click to enlarge]

Bright © 2026 Bright, All Rights Reserved.

The data related to real estate for sale on this website comes in part from the INTERNET DATA EXCHANGE (IDX) program of the Bright MLS. Real estate listings held by brokerage firms other than this site owner are marked with the IDX logo.

IDX information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation or other purposes. All listing information is deemed reliable but not guaranteed.

This content was last refreshed on 2026-04-17 04:25 AM. Some properties which appear for sale on this website may subsequently have sold or may no longer be available.

DMCA Notice