104 Conley Drive Chestertown, MD ^$ 247,000

104 Conley Drive

^$ 247,000

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Open House 6/19 11am - 1pm

104 Conley Drive

Chestertown, MD, 21620

^$ 247,000

Bedrooms3 Baths1.1 Sq 1,280

Monthly Estimate*

^$ 1,521

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Townhouse for sale in Chestertown, MD

for $247,000 with 3 bedrooms and 1 full bath, 1 half bath. This 1,280 square foot townhouse was built in 1979 on a lot size of 0.07.

Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, youll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!

Open House

6/19/2026 11:00 AM - 1:00 PM

104 Conley Drive Chestertown, MD

* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Townhouse Active

Price

^$ 247,000

Bedrooms

Full Bath

Half Bath

Property Type

Townhouse

Taxes

^$ 2,583

Style

Traditional

Lot Size

0.07

Year Built

1979

Town/City

Chestertown

County/Region

Kent

MLS | Web ID

MDKE2006686

Features

General

Living Area 1280

Sewer Public Sewer

Heating Heat Pump(s)

Cooling Central A/C

Possession Settlement

Zoning R-4

Architectural Style Traditional

Construction Materials Vinyl Siding

School District KENT COUNTY PUBLIC SCHOOLS

Year Built 1979

Levels 2

Tax Year 2025

Ownership Fee Simple

Cool Fuel Electric

Municipality Chestertown

Section 0

Accessibility None

County KENT

New Construction N

Property Type Residential

HOA N

Subdivision Name CHESTER ARMS

Garage Y/N N

Water Access Y/N N

Other Structures Above Grade Below Grade

Full Baths 1

Status ACTIVE

Directions GPS

City CHESTERTOWN

Senior Community Y/N N

Lot Size Units Square Feet

Lot Size Square Feet 3000.00

Tax Annual Amount 2583.0

Home Warranty Y/N N

Structure Type End of Row/Townhouse

Condo/Coop Association fee Y/N N

Bathrooms Count Main Level 1.00

Price Per Sq Ft Total AG 192.97

Vacation Rental Y/N N

Standard Status Active

Year Built Source Assessor

Legal Subdivision CHESTER ARMS

Tax Lot 33

Interior

Heating Fuel Electric

Hot Water Electric

Basement (Y/N) N

Heating Y/N Y

Fireplace Y/N N

Above Grade Finished Area 1280

Half Baths 1

Central Air Y/N Y

Total Bedrooms 3

Below Grade Finished Area 0

Main Level Bedrooms 0

Below Grade Finished Area Unit Type Square Feet

Below Grade Finished Area Source Assessor

Above Grade Finished Area Source Assessor

Above Grade Finished Area Unit Type Square Feet

Total Baths 2

Exterior

Pool No Pool

Water Source Public

Inclusions Couch and Rug in Living Room

Type of Parking Driveway

Foundation Details Slab

Water View Y/N N

Lot Size Acres 0.07

Lot Size Source Assessor

Waterfront Y/N N

Land Assessed Value 45200.00

Navigable Water Y/N N

Water Oriented Y/N N

Internal Only

Street Number 1 104

* Excluded Features

List By

Cummings & Co. Realtors

Broker

heathernkooser@gmail.com

Affordability Calculator

$1,736

Per Month

Monthly Principal & Interest: $1,521
Monthly Property Taxes: $215
Monthly Home Insurance: --

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Yearly Home Insurance

Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends
Schools

Townhouse listings in Chestertown, MD

Average List Price ^$370,686

Percent of Sale Price 50%

About Chestertown, MD

5,312 Population

10% Since 2002

^$47,055 Median Income

32.86 Median Age

18% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

3535796 Elementary School

3533824 Middle School

Unknown High School High School

See complete school information

Pricing History

Date	Price	Price Change	Description
6/17/2026	$247,000		Listed Price

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104 Conley Drive, Chestertown, MD, 21620 is a Townhouse for sale at $247,000 with 1,280 sqft and a lot size of 0.07. 104 Conley Drive has 3 bedrooms, 1.1 baths, and was built in 1979. The property's zip code is 21620 which is in Chestertown, MD

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker Reciprocity^SM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

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104 Conley Drive

Townhouse for sale in Chestertown, MD

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