231 Richard Drive, Chestertown, MD 21620 - Photo 1

1/1

$1,050,000

Sold
Closed
Single Family
5 Beds
3 Full Baths
2,956 Sq. Ft.
2 Car Garage
Updated 6 days ago

1/1

Property Description

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.

Full Property Details

Full Property Details for 231 Richard Dr

General

Sold For: $1,050,000
Taxes: $8,665 (2025)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDKE2005900
Added to Site: 127 day(s) ago

Interior

Number of Rooms: 8
Rooms/Areas: Bedroom 2, Bedroom 3, Bedroom 1, Bathroom 1, Bathroom 2
Interior Features: Combination Dining/Living, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Galley, Primary Bath(s), Upgraded Countertops
Fireplace: Yes
Number of Fireplaces: 1
Fireplace(s): Heatilator
Flooring: Wood, Carpet

Rooms

Bathrooms

Total Bathrooms: 3
Full Bathrooms: 3
Main Floor Baths: 2
Main - Full Baths: 2
Lower Floor Baths: 1
Lower - Full Baths: 1

Bedrooms

Total Bedrooms: 5
Bedrooms Lower: 2
Bedrooms Main & Up: 3

Other Rooms

Laundry: Has Laundry, Main Floor

Additional Information

Pool: Yes
Private Pool: Yes
Pool Description: In Ground

Exterior

Porch/Patio/Deck: Deck(s), Patio(s), Porch(es)

Parking

Garage: Yes
Garage Spaces: 2
Total Spaces: 5
Parking Features: Asphalt Driveway
Parking Type: Attached Garage, Driveway
Garage Description: Additional Storage Area, Garage - Side Entry, Garage Door Opener, Inside Access

Location

Municipality: Chestertown
County: KENT
Subdivision: BYFORD DEVELOPMENT
Driving Directions: GPS, sign posted
Location Details: River
City Limits: Yes

School Information

School District: Kent County Public Schools

Heating & Cooling

Central air: Yes
Cooling Type: Central A/C
Cooling Fuel: Electric
Heating Type: Forced Air
Heating Fuel: Oil
Water Heater: Electric

Utilities

Sewer: Public Sewer
Water: Public
Dist. to Water: 0 Blocks

Structural Information

Architectural Style: Raised Ranch/Rambler
Structure Type: Detached
Builder: Sommers
Construction: Block, Brick, Mixed, Vinyl Siding
Basement: Yes
Basement Entrance: Yes
Basement Desc.: Walkout Level, Fully Finished, Interior Access, Outside Entrance, Heated, Connecting Stairway
Foundation: Block, Slab
Stories Description: Lower 1, Main
Square Feet: 2,956
Sq. Ft. Source: Assessor
Living Area: 2,956 Sq. Ft.
Finished Above Grnd: 2,956 Sq. Ft.
Basement Finished: 100%
Year Built: 1981
Year Built Source: Assessor

Unit Information

Unit 1

Bathrooms-Lower: 1
Bedrooms-Lower: 2

Lot Features

Property View: River
Lot Size (Acres): 0.79
Lot Size (Sq. Ft.): 34,507
Lot Size Source: Assessor
Zoning: R-2
Lot Description: Cul-de-sac, Level, Rear Yard, Tidal Wetland
Fencing (Description): Wrought Iron, Partially

Water Features

Water Front: Yes
Water View: Yes
Navigable Water: Yes
Water Access: Yes
Water Access Desc: Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Sail, Swimming Allowed, Waterski/Wakeboard
Water Front Type: River
Water Front Name: CHESTER RIVER
Docks: 1
Non-Power Boats: 1

Financial Considerations

Price Per Sq. Ft.: $389.04
Assessment Year: 2025
City/TownTax: $2,395
City/TownTax Freq: Annually
County Tax: $6,270
County Tax Freq: Annually
Tax w/Assessment: $552,000
Tax Amount: $8,665
Tax Year: 2025
Terms: Standard Sale
Tax Total Finished Sq. Ft.: 2956

Disclosures and Reports

Ownership: Fee Simple

Listed by TTR Sotheby's International Realty, Liddy Campbell
Sold by RE/MAX Chesapeake, Joseph A Zang III

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Listing agent

— 231 Richard Dr —

Liddy Campbell

TTR Sotheby's International Realty

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Schools

Schools serving 231 Richard Dr

School District:Kent County Public Schools

Name	Grades	Distance
H. H. Garnett Elementary School 320 Calvert Street, Chestertown, MD 21620	PK-5	0.7 mi
Kent County Middle School 402 East Campus Avenue, Chestertown, MD 21620	6-8	0.3 mi
Kent County High School 25301 Lambs Meadow Road, Worton, MD 21678	9-12	5.2 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 231 Richard Dr

Date

Details

Price

Change

Source

6/26/2026

Sold

$1,050,000

-8.7%

MLS

4/13/2026

Price Reduced

$1,150,000

-10.09%

MLS

3/06/2026

Listed

$1,279,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Beds
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Total Baths
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Updated 4 days ago

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Active
Updated 5 days ago

0.5
Acres

Listed by DMV Prime Properties, Michael A. Kelczewski

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Price Reduced

-$51,000 (-6%)

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Active
Updated 11 hours ago

4
Beds
2
Total Baths
3,300
Sq. Ft.

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Sold

$1,100,000

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Single Family
Closed

5
Beds
4
Total Baths
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Sq. Ft.

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Beds
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Sq. Ft.

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$1,095,000

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Closed

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Beds
2
Total Baths
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Sq. Ft.

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$1,050,000

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Single Family
Closed

3
Beds
1
Total Bath
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Sq. Ft.

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231 Richard Drive, Chestertown, MD 21620 (MLS# MDKE2005900) is a Single Family property that was sold at $1,050,000 on June 26, 2026. Want to learn more about 231 Richard Drive? Do you have questions about finding other Single Family real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.

231 Richard Dr Chestertown, MD 21620

Full Property Details for 231 Richard Dr

General

Interior

Rooms

Bathrooms

Bedrooms

Other Rooms

Additional Information

Exterior

Parking

Location

School Information

Heating & Cooling

Utilities

Structural Information

Unit Information

Unit 1

Lot Features

Water Features

Financial Considerations

Disclosures and Reports

Listing agent

Get Pre-Approved Today

Be ready to buy your new home!

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Schools serving 231 Richard Dr

Price & Sales History for 231 Richard Dr

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