104 Conley Dr Chestertown, MD 21620
Chestertown AreaEstimated payment $1,539/month
Highlights
- Traditional Architecture
- Central Air
- Heat Pump System
- No HOA
About This Home
Price Improvement! Now offered at $239,900
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, you’ll 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!
Listing Agent
(410) 823-0033 realtor@cummingsrealtors.com Cummings & Co. Realtors Brokerage Phone: 4108230033 License #5009962 Listed on: 06/17/2026
Townhouse Details
Home Type
- Townhome
Est. Annual Taxes
- $2,583
Year Built
- Built in 1979
Lot Details
- 3,000 Sq Ft Lot
Parking
- Driveway
Home Design
- Traditional Architecture
- Slab Foundation
- Vinyl Siding
Interior Spaces
- 1,280 Sq Ft Home
- Property has 2 Levels
Bedrooms and Bathrooms
- 3 Bedrooms
Utilities
- Central Air
- Heat Pump System
- Electric Water Heater
Listing and Financial Details
- Tax Lot 33
- Assessor Parcel Number 1504019881
Community Details
Overview
- No Home Owners Association
- Chester Arms Subdivision
Pet Policy
- Pets Allowed
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $2,888 | $184,300 | $0 | $0 |
| 2025 | $2,583 | $164,800 | $45,200 | $119,600 |
| 2024 | $2,315 | $147,733 | $0 | $0 |
| 2023 | $1,769 | $130,667 | $0 | $0 |
| 2022 | $1,769 | $113,600 | $45,200 | $68,400 |
| 2020 | $1,780 | $113,600 | $45,200 | $68,400 |
| 2019 | $3,650 | $116,700 | $45,200 | $71,500 |
| 2018 | $1,814 | $116,700 | $45,200 | $71,500 |
| 2017 | $1,776 | $116,700 | $0 | $0 |
| 2016 | -- | $118,100 | $0 | $0 |
| 2015 | $1,808 | $118,100 | $0 | $0 |
| 2014 | $1,808 | $118,100 | $0 | $0 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 07/01/2026 07/01/26 | Price Changed | $239,900 | -2.9% | $187 / Sq Ft | |
| 06/17/2026 06/17/26 | For Sale | $247,000 | +6.5% | $193 / Sq Ft | |
| 05/31/2024 05/31/24 | Sold | $232,000 | -1.2% | $181 / Sq Ft | View Prior Sale |
| 04/17/2024 04/17/24 | Price Changed | $234,900 | -2.1% | $184 / Sq Ft | |
| 04/09/2024 04/09/24 | For Sale | $240,000 | +39.9% | $188 / Sq Ft | |
| 06/18/2021 06/18/21 | Sold | $171,500 | -2.0% | $134 / Sq Ft | View Prior Sale |
| 04/22/2021 04/22/21 | Pending | -- | -- | -- | |
| 04/20/2021 04/20/21 | Price Changed | $175,000 | -2.8% | $137 / Sq Ft | |
| 04/15/2021 04/15/21 | For Sale | $180,000 | -- | $141 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $232,000 | Atlantic Title | |
| Deed | $171,500 | None Available | |
| Deed | $134,000 | Attorney | |
| Deed | $115,000 | -- | |
| Deed | $75,000 | -- |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $234,343 | New Conventional | |
| Previous Owner | $172,727 | New Conventional | |
| Previous Owner | $136,734 | New Conventional | |
| Previous Owner | $104,000 | USDA | |
| Previous Owner | $12,000 | Credit Line Revolving |
Source: Bright MLS
MLS Number: MDKE2006686
APN: 04-019881
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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, and is provided by BRIGHT through a licensing agreement.
Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site.
The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale.
Property information displayed is deemed reliable but is not guaranteed.
Copyright 2026 Bright MLS, Inc.
- 104 Acorn Dr
- 121 Metcalf Rd
- 115 Metcalf Rd
- 115 Chester Arms Dr
- 214 Silver Heel Rd
- 3 Haacke Dr
- 249 Island Lark Way
- 2 Scheeler Rd
- 896 Washington Ave
- 200 Manor Ave
- 956 Washington Ave
- 1003 Twin Ct
- 213 Byford Dr
- 1010 Twin Ct
- 212 Washington Ave
- 234 N College Ave
- 201 N Lynchburg St
- 201 N Lynchburg St
- 216 Birch Run Rd
- 305 Roosevelt Dr
- 206 N Mill St
- 128 N Queen St Unit 3
- 104 Maple Ave Unit 4
- 200 Cannon St Unit 1A
- 7501 Church Hill Rd Unit 5
- 119 Watson Rd
- 446 Railroad Ave
- 2957-294H 4-H Park Rd
- 212 Frederick Dr
- 125 Encore Ct
- 310 Del Rhodes Ave
- 6808 Main St
- 9135 Cuckold Point Rd
- 2513 Barrison Point Rd
- 102 Reider Ct
- 2033 Armstrong St
- 8900 Millers Island Blvd
- 4 Poplar Grove Ave
- 4048 Edgewood Rd
- 6204 Baker Cir Unit D
Ask me questions while you tour the home.