Kelly Bainbridge
RE/MAX Chesapeake
(667) 202-0074
15 Total Sales
1 in Chestertown
$210,000 Price
Estimated Value: $688,935
Beautiful and spacious 3- bedroom home in historic Chestertown. Just a short distance from vibrant shops, restaurants, and the scenic Chester River waterfront.
The gourmet kitchen has a beautiful wood-top island and stainless steel appliances. The kitchen leads to the large formal dining room, featuring the original stone fireplace, updated with a gas insert. The living space is designed for both comfortable living and effortless entertaining. During the winter, enjoy the wood burning fireplace in the living room, or warm up in the beautiful sunroom, just off of the living space. Downstairs there’s a full bathroom and bedroom, as well as a half bath. Upstairs you’ll find two full bathrooms and two bedrooms. additionally, there's a studio or office nook, which could be used as extra sleeping space. This property also features a unique opportunity for extra income. Part of the second-floor can become it's own apartment, complete with a kitchen, full bathroom, and a private entrance from the driveway. The one bedroom apartment is perfect for guests, an in-law suite, or as a rental unit. Outside, a fenced-in yard with a covered patio offers a private oasis for relaxing evenings. The private driveway leads to a spacious barn garage with three barn doors. The barn offers ample storage, space for a small vehicle, or could be used as a workshop. This home truly has it all, in the heart of Chestertown!
Last Agent to Sell the Property
(410) 275-2118 realestate@gunthermcclary.com Gunther-McClary Real Estate Listed on: 08/22/2025
Co-Listed By
(410) 275-2118 realestate@gunthermcclary.com Gunther-McClary Real Estate License #6078249
Last Buyer's Agent
(410) 778-3779 rdkeaveney@gmail.com Cross Street Realtors LLC License #662142
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Kelly Bainbridge
RE/MAX Chesapeake
(667) 202-0074
15 Total Sales
1 in Chestertown
$210,000 Price
John Burke
Gunther-McClary Real Estate
(443) 252-2392
84 Total Sales
10 in Chestertown
$178K - $865K Price Range
Kimberly Taylor
American Premier Realty, LLC
(667) 771-6705
123 Total Sales
1 in Chestertown
$499,900 Price
Frederick Golding
RE/MAX Advantage Realty
(667) 239-8179
107 Total Sales
1 in Chestertown
$275,000 Price
Martha Suss
Coldwell Banker Realty
(844) 547-5539
24 Total Sales
1 in Chestertown
$660,000 Price
Gretchen Wichlinski
Compass
(667) 230-5069
96 Total Sales
1 in Chestertown
$795,000 Price
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 | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $695,000 | None Listed On Document | ||
| Gillespie Patrick | $365,000 | None Available | |
| Baldwin A Stuart & Frances R | $98,000 | -- | |
| Galbreath Galbreath E | $53,000 | -- |
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 | Borrower | Loan Amount |
|---|---|---|---|
| Open | $445,000 | ||
| Previous Owner | Gillespie Patrick | $292,000 | |
| Previous Owner | Baldwin A Stuart | $35,000 | |
| Previous Owner | Baldwin A Stuart | $25,000 |
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 |
|---|---|---|---|---|---|
| 11/05/2025 11/05/25 | Sold | $695,000 | -6.7% | $279 / Sq Ft | |
| 08/29/2025 08/29/25 | Pending | -- | -- | -- | |
| 08/22/2025 08/22/25 | For Sale | $745,000 | +104.1% | $299 / Sq Ft | |
| 01/11/2018 01/11/18 | Sold | $365,000 | -2.7% | $145 / Sq Ft | View Prior Sale |
| 11/17/2017 11/17/17 | Pending | -- | -- | -- | |
| 11/10/2017 11/10/17 | For Sale | $375,000 | -- | $149 / Sq Ft |
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 | $6,738 | $429,933 | $0 | $0 |
| 2025 | $6,346 | $404,900 | $206,700 | $198,200 |
| 2024 | $6,041 | $385,433 | $0 | $0 |
| 2023 | $5,735 | $365,967 | $0 | $0 |
| 2022 | $5,396 | $346,500 | $206,700 | $139,800 |
| 2021 | $5,219 | $339,767 | $0 | $0 |
| 2020 | $5,219 | $333,033 | $0 | $0 |
| 2019 | $5,103 | $326,300 | $206,700 | $119,600 |
| 2018 | $5,071 | $326,300 | $206,700 | $119,600 |
| 2017 | $4,908 | $326,300 | $0 | $0 |
| 2016 | -- | $326,300 | $0 | $0 |
| 2015 | $4,757 | $326,300 | $0 | $0 |
| 2014 | $4,757 | $326,300 | $0 | $0 |
Seller's Agent in 2025
John Burke
Gunther-McClary Real Estate
(443) 206-3727
84 Total Sales
Seller Co-Listing Agent in 2025
Julia Hilfiker
Gunther-McClary Real Estate
(443) 480-6770
51 Total Sales
Buyer's Agent in 2025
Richard Keaveney
Cross Street Realtors LLC
(410) 708-6470
40 Total Sales
Seller's Agent in 2018
Mary Fielding
Coldwell Banker Chesapeake Real Estate Company
(410) 708-4852
26 Total Sales
Source: Bright MLS
MLS Number: MDKE2005558
APN: 04-022335
Ask me questions while you tour the home.