Homes for Sale in Great Oak Estates, Chestertown, MD
No homes on the market right now — but 13 have sold here since 2020. Homes move fast; get notified first.
0
For Sale
$609K
Median Sale Price
8
Median Days on Market
99.0%
Sold-to-List
$195
Price / Sq Ft
Great Oak Estates, Chestertown, MD home price trend
| Year | Median Sale Price | Homes Sold |
|---|---|---|
| 2026 | $695K | 3 |
| 2025 | $609K | 3 |
| 2024 | $1.4M | 1 |
| 2023 | $938K | 2 |
| 2022 | $519K | 2 |
| 2021 | $400K | 1 |
| 2020 | $270K | 1 |
At the current trend, the median is modeled to reach about $1.1M in 2027 (estimate).
Cost to buy in Great Oak Estates, Chestertown, MD
At today's ~6.63% 30-year rate, the median $609K home in Great Oak Estates, Chestertown, MD runs about $3,932/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 Great Oak Estates, Chestertown, MD
Most active agents by closed sales here over the past 18 months.
- Liddy CampbellTTR Sotheby's International Realty1 sale
- Michele A PalmerDoug Ashley Realtors, LLC1 sale
- Lona Sue ToddTaylor Properties1 sale
- Daniel HercherChesapeake Real Estate Associates, LLC1 sale
- Hayley A NorrisSelect Land & Homes, LLC1 sale
Be first when a home hits the market in Great Oak Estates, Chestertown, MD
Homes here sell fast and rarely come up. Turn on instant alerts and we'll email you the moment a new one is listed.
Great Oak Estates, Chestertown, MD real estate FAQ
How many homes are for sale in Great Oak Estates, Chestertown, MD?
There are no homes for sale in Great Oak Estates, Chestertown, MD right now. 13 have sold here since 2020 — the market moves fast, so set up an alert to hear the moment one is listed.
How much do homes sell for in Great Oak Estates, Chestertown, MD?
The median sale price in Great Oak Estates, Chestertown, MD is $609K, based on 13 sales since 2020 (ranging from $348K to $1.5M).
How fast do homes sell in Great Oak Estates, Chestertown, MD?
Homes in Great Oak Estates, Chestertown, MD typically go under contract in about 8 days on market (median).
Do homes in Great Oak Estates, Chestertown, MD sell above asking?
Over the past 12 months, homes in Great Oak Estates, Chestertown, MD sold for an average of 99.0% of list price — below asking.
What is the price per square foot in Great Oak Estates, Chestertown, MD?
Homes in Great Oak Estates, Chestertown, MD have sold for a median of $195 per square foot since 2020.
Is the Great Oak Estates, Chestertown, MD housing market heating up or cooling down?
The median sale price in Great Oak Estates, Chestertown, MD has risen from $270K in 2020 to $695K in 2026. At the current trend, the median is on track for roughly $1.1M in 2027 (modeled estimate).
Who are the top real estate agents in Great Oak Estates, Chestertown, MD?
The most active agents in Great Oak Estates, Chestertown, MD over the past 18 months are: Liddy Campbell (TTR Sotheby's International Realty) — 1 sale; Michele A Palmer (Doug Ashley Realtors, LLC) — 1 sale; Lona Sue Todd (Taylor Properties) — 1 sale.