house
1/28
$1,972/mo
$299,9003bd·1ba·1,248sf
517 Round Top Road, Chestertown, MD 21620
Listing Courtesy of Keller Williams Flagship
Homes for Sale in Chester Harbor, Chestertown, MD
2 active listings · 114 sold since 2020
2
For Sale
$268K
Median Sale Price
14
Median Days on Market
98.3%
Sold-to-List
$205
Price / Sq Ft
Newest homes for sale in Chester Harbor, Chestertown, MD
See all 2 on the mapChester Harbor, Chestertown, MD home price trend
| Year | Median Sale Price | Homes Sold |
|---|---|---|
| 2026 | $309K | 8 |
| 2025 | $319K | 17 |
| 2024 | $337K | 17 |
| 2023 | $302K | 12 |
| 2022 | $240K | 11 |
| 2021 | $240K | 28 |
| 2020 | $215K | 21 |
At the current trend, the median is modeled to reach about $357K in 2027 (estimate).
Cost to buy in Chester Harbor, Chestertown, MD
At today's ~6.63% 30-year rate, the median $268K home in Chester Harbor, Chestertown, MD runs about $1,727/mo with 20% down (principal & interest plus estimated taxes and insurance).
Estimate only — not a loan offer. Actual rate and payment depend on your profile.
Top agents in Chester Harbor, Chestertown, MD
Most active agents by closed sales here over the past 18 months.
- Norma L CourseyBenson & Mangold, LLC2 sales
- Michele A PalmerDoug Ashley Realtors, LLC2 sales
- Lisa P RaffettoColdwell Banker Chesapeake Real Estate Company1 sale
- Mary A JulieLong & Foster Real Estate, Inc.1 sale
- Retha J ArrabalDoug Ashley Realtors, LLC1 sale
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Chester Harbor, Chestertown, MD real estate FAQ
How many homes are for sale in Chester Harbor, Chestertown, MD?
There are 2 homes currently for sale in Chester Harbor, Chestertown, MD.
How much do homes sell for in Chester Harbor, Chestertown, MD?
The median sale price in Chester Harbor, Chestertown, MD is $268K, based on 114 sales since 2020 (ranging from $199K to $400K).
How fast do homes sell in Chester Harbor, Chestertown, MD?
Homes in Chester Harbor, Chestertown, MD typically go under contract in about 14 days on market (median).
Do homes in Chester Harbor, Chestertown, MD sell above asking?
Over the past 12 months, homes in Chester Harbor, Chestertown, MD sold for an average of 98.3% of list price — below asking.
What is the price per square foot in Chester Harbor, Chestertown, MD?
Homes in Chester Harbor, Chestertown, MD have sold for a median of $205 per square foot since 2020.
Is the Chester Harbor, Chestertown, MD housing market heating up or cooling down?
The median sale price in Chester Harbor, Chestertown, MD has risen from $215K in 2020 to $309K in 2026. At the current trend, the median is on track for roughly $357K in 2027 (modeled estimate).
Who are the top real estate agents in Chester Harbor, Chestertown, MD?
The most active agents in Chester Harbor, Chestertown, MD over the past 18 months are: Norma L Coursey (Benson & Mangold, LLC) — 2 sales; Michele A Palmer (Doug Ashley Realtors, LLC) — 2 sales; Lisa P Raffetto (Coldwell Banker Chesapeake Real Estate Company) — 1 sale.
