Under Contract

MLS: #MDKE2005900, Listed By: Liddy Campbell, TTR Sotheby's International Realty, Source:Bright MLS

231 Richard Drive

CHESTERTOWN, MD 21620
Mark as Favorite
Bed 5

Bed

Bath 3

Bath

SqFt2,956

Sqft

Acres0.79

Acre(Lot)

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 wi th 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.

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Detail Ic Property Details

Property Type : Residential

Price : $1,150,000

AD Id : 75974517

MLS Id : MDKE2005900

Beds : 5

Lot Size : 0.79 Acre

Living Area Size : 2,956

Year Built : 1981

Garage : 2

County : KENT

Subdivision: Byford Development

  • Map Map

Map

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Feature Features

  • Bedroom Information

    Total beds: 5

    Bathroom Information

    Total Baths: 3 Full Baths: 3

    Room Information

    Rooms Total: 8 Has Basement: Yes Basement: Finished, Exterior Entry, Walk-Out Access, Interior Entry
  • Flooring Information

    Wood, Carpet
  • Interior Features

    Appliances: Electric Water Heater Laundry Features: Main Level
  • Heating & Cooling

    Has Heating: Yes Heating: Oil, Forced Air Has Cooling: Yes Cooling: Central Air, Electric Water front: 1

  • Building Information

    Year Built: 1981 Building Area Total: 2956 Construction Materials: Block, Brick, Vinyl Siding Stories: 2 Frontage Length: 190 Patio And Porch Features: Deck, Patio, Porch Pool Features: In Ground, Private Private Pool: Yes Water front Features: River Front View: Water, River

  • Lot Information

    Lot Size Acres: 0.79 Lot Size Source: Assessor Lot Size Square Feet: 34507 Lot Description: Wetlands, Cul-De-Sac, Level, Back Yard, Waterfront

    Property Information

    Subdivision: BYFORD DEVELOPMENT Source Property Type: Residential Postal Code Plus 4: 1647 Property SubType: Single Family Residence Levels: Two Property Age: 45

  • Listing Price Information

    Listing Price: $1150000

  • Tax Information

    Parcel Number: 1504010264 Tax Year: 2025 Annual Tax: $8665

  • Parking Information

    Parking Total: 5 Garage Door Opener, Asphalt, Garage, Driveway, Inside Entrance, Attached

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 2

  • Location Information

    Direction: GPS, sign posted WaterSource: Public
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
1904 Pondtown Road, Chestertown, MD, 21620 $265,000 3 1 1,967 1,967 SqFt
204 Double Creek Road, Chestertown, MD, 21620 $565,000 3 3 2,927 2,927 SqFt
240 Merganser Drive, Chestertown, MD, 21620 $399,000 3 2 1,120 1,120 SqFt
118 Grant Court, Chestertown, MD, 21620 $457,500 3 2 1,664 1,664 SqFt
109 Wilton Road, Chestertown, MD, 21620 $344,900 3 2 1,392 1,392 SqFt
215 Fairview Drive, Chestertown, MD, 21620 $425,000 3 3 1,784 1,784 SqFt
208 Central Drive, Chestertown, MD, 21620 $299,000 3 1 1,120 1,120 SqFt
704 Truslow Road, Chestertown, MD, 21620 $440,000 3 3 2,060 2,060 SqFt
101 Coleman Drive, Chestertown, MD, 21620 $524,900 3 3 2,268 2,268 SqFt
205 River Road, Chestertown, MD, 21620 $869,900 4 3 2,877 2,877 SqFt

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which ByOwner participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

ByOwner last updated this listing 06/10/2026 @ 05:32

MLS: MDKE2005900 LISTED BY: Liddy Campbell, TTR Sotheby's International Realty 410-673-3344 SOURCE: Bright MLS

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