231 RICHARD DR, Chestertown, MD 21620
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231 RICHARD DR, Chestertown, MD 21620
231 RICHARD DR, Chestertown, MD 21620
231 RICHARD DR, Chestertown, MD 21620
231 RICHARD DR, Chestertown, MD 21620
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Listed by Liddy Campbell • TTR Sotheby's International Realty
$ 1,150,000
Est. payment /mo
Price Dropped by $129K

231 RICHARD DR Chestertown, MD 21620

5 Beds

3 Baths

2,956 SqFt


UPDATED:

Key Details

Property Type Single Family Home

Sub Type Detached

Listing Status Active

Purchase Type For Sale

Square Footage 2,956 sqft

Price per Sqft $389

Subdivision Byford Development

MLS Listing ID MDKE2005900

Style Raised Ranch/Rambler

Bedrooms 5

Full Baths 3

HOA Y/N N

Abv Grd Liv Area 2,956

Year Built 1981

Available Date 2026-03-06

Annual Tax Amount $8,665

Tax Year 2025

Lot Size 0.792 Acres

Acres 0.79

Property Sub-Type Detached

Source BRIGHT

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.
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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.
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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.
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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!
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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.
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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.

Location

State MD

County Kent

Zoning R-2

Rooms

Other Rooms Bedroom 2, Bedroom 3, Bedroom 1, Bathroom 1, Bathroom 2

Basement Walkout Level, Fully Finished, Interior Access, Outside Entrance, Heated, Connecting Stairway

Main Level Bedrooms 3

Interior

Interior Features Combination Dining/Living, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Galley, Primary Bath(s), Upgraded Countertops

Hot Water Electric

Heating Forced Air

Cooling Central A/C

Flooring Wood, Carpet

Fireplaces Number 1

Fireplaces Type Heatilator

Fireplace Y

Heat Source Oil

Laundry Has Laundry, Main Floor

Exterior

Exterior Feature Deck(s), Patio(s), Porch(es)

Parking Features Additional Storage Area, Garage - Side Entry, Garage Door Opener, Inside Access

Garage Spaces 5.0

Fence Wrought Iron, Partially

Pool In Ground

Waterfront Description Private Dock Site,Sandy Beach

Water Access Y

Water Access Desc Canoe/Kayak,Fishing Allowed,Personal Watercraft (PWC),Private Access,Sail,Swimming Allowed,Waterski/Wakeboard

View River

Accessibility None

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

Attached Garage 2

Total Parking Spaces 5

Garage Y

Building

Lot Description Cul-de-sac, Level, Rear Yard, Tidal Wetland

Story 2

Foundation Block, Slab

Above Ground Finished SqFt 2956

Sewer Public Sewer

Water Public

Architectural Style Raised Ranch/Rambler

Level or Stories 2

Additional Building Above Grade

New Construction N

Schools

School District Kent County Public Schools

Others

Senior Community No

Tax ID 1504010264

Ownership Fee Simple

SqFt Source 2956

Special Listing Condition Standard

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Bright MLS (BMLS)

Nearby Locations

David J. Moore

David J. Moore

Broker Associate | License ID: 609287

+1(410) 777-5848

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231 RICHARD DR