townhouse
1/26
$1,808/mo
$275,0003bd·3ba·1,900sf
104 Acorn Drive, Chestertown, MD 21620
Listing Courtesy of Cross Street Realtors LLC
Homes for Sale in Oak Hollow, Chestertown, MD
1 active listing · 11 sold since 2020
1
For Sale
$280K
Median Sale Price
14
Median Days on Market
99.0%
Sold-to-List
$145
Price / Sq Ft
Newest homes for sale in Oak Hollow, Chestertown, MD
See all 1 on the mapOak Hollow, Chestertown, MD home price trend
| Year | Median Sale Price | Homes Sold |
|---|---|---|
| 2026 | $295K | 3 |
| 2025 | $283K | 3 |
| 2022 | $248K | 2 |
| 2021 | $238K | 2 |
| 2020 | $179K | 1 |
At the current trend, the median is modeled to reach about $317K in 2027 (estimate).
Cost to buy in Oak Hollow, Chestertown, MD
At today's ~6.63% 30-year rate, the median $280K home in Oak Hollow, Chestertown, MD runs about $1,808/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 Oak Hollow, Chestertown, MD
Most active agents by closed sales here over the past 18 months.
- Grace M CrockettDoug Ashley Realtors, LLC2 sales
- Lisa P RaffettoColdwell Banker Chesapeake Real Estate Company1 sale
- Amy L LarrauriChesapeake Real Estate Associates, LLC1 sale
- Kristina L HylandColdwell Banker Chesapeake Real Estate Company1 sale
- Krystal ZellnerCrown Homes Real Estate1 sale
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Oak Hollow, Chestertown, MD real estate FAQ
How many homes are for sale in Oak Hollow, Chestertown, MD?
There is 1 home currently for sale in Oak Hollow, Chestertown, MD.
How much do homes sell for in Oak Hollow, Chestertown, MD?
The median sale price in Oak Hollow, Chestertown, MD is $280K, based on 11 sales since 2020 (ranging from $207K to $296K).
How fast do homes sell in Oak Hollow, Chestertown, MD?
Homes in Oak Hollow, Chestertown, MD typically go under contract in about 14 days on market (median).
Do homes in Oak Hollow, Chestertown, MD sell above asking?
Over the past 12 months, homes in Oak Hollow, Chestertown, MD sold for an average of 99.0% of list price — below asking.
What is the price per square foot in Oak Hollow, Chestertown, MD?
Homes in Oak Hollow, Chestertown, MD have sold for a median of $145 per square foot since 2020.
Is the Oak Hollow, Chestertown, MD housing market heating up or cooling down?
The median sale price in Oak Hollow, Chestertown, MD has risen from $179K in 2020 to $295K in 2026. At the current trend, the median is on track for roughly $317K in 2027 (modeled estimate).
Who are the top real estate agents in Oak Hollow, Chestertown, MD?
The most active agents in Oak Hollow, Chestertown, MD over the past 18 months are: Grace M Crockett (Doug Ashley Realtors, LLC) — 2 sales; Lisa P Raffetto (Coldwell Banker Chesapeake Real Estate Company) — 1 sale; Amy L Larrauri (Chesapeake Real Estate Associates, LLC) — 1 sale.