townhouse
1/50
$4,997/mo
$759,9003bd·5ba·2,583sf
8048 Windward Key Drive, Chesapeake Beach, MD 20732
Listing Courtesy of Compass
Homes for Sale in Windward Key, Chesapeake Beach, MD
3 active listings · 16 sold since 2020
3
For Sale
$688K
Median Sale Price
8
Median Days on Market
98.2%
Sold-to-List
$262
Price / Sq Ft
Newest homes for sale in Windward Key, Chesapeake Beach, MD
See all 3 on the mapWindward Key, Chesapeake Beach, MD home price trend
| Year | Median Sale Price | Homes Sold |
|---|---|---|
| 2026 | $835K | 1 |
| 2024 | $775K | 3 |
| 2023 | $650K | 2 |
| 2022 | $665K | 2 |
| 2021 | $690K | 3 |
| 2020 | $645K | 5 |
At the current trend, the median is modeled to reach about $844K in 2027 (estimate).
Cost to buy in Windward Key, Chesapeake Beach, MD
At today's ~6.63% 30-year rate, the median $688K home in Windward Key, Chesapeake Beach, MD runs about $4,438/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 Windward Key, Chesapeake Beach, MD
Most active agents by closed sales here over the past 18 months.
- Scott P McinerneyRE/MAX One1 sale
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Windward Key, Chesapeake Beach, MD real estate FAQ
How many homes are for sale in Windward Key, Chesapeake Beach, MD?
There are 3 homes currently for sale in Windward Key, Chesapeake Beach, MD.
How much do homes sell for in Windward Key, Chesapeake Beach, MD?
The median sale price in Windward Key, Chesapeake Beach, MD is $688K, based on 16 sales since 2020 (ranging from $540K to $816K).
How fast do homes sell in Windward Key, Chesapeake Beach, MD?
Homes in Windward Key, Chesapeake Beach, MD typically go under contract in about 8 days on market (median).
Do homes in Windward Key, Chesapeake Beach, MD sell above asking?
Over the past 12 months, homes in Windward Key, Chesapeake Beach, MD sold for an average of 98.2% of list price — below asking.
What is the price per square foot in Windward Key, Chesapeake Beach, MD?
Homes in Windward Key, Chesapeake Beach, MD have sold for a median of $262 per square foot since 2020.
Is the Windward Key, Chesapeake Beach, MD housing market heating up or cooling down?
The median sale price in Windward Key, Chesapeake Beach, MD has risen from $645K in 2020 to $835K in 2026. At the current trend, the median is on track for roughly $844K in 2027 (modeled estimate).
Who are the top real estate agents in Windward Key, Chesapeake Beach, MD?
The most active agents in Windward Key, Chesapeake Beach, MD over the past 18 months are: Scott P Mcinerney (RE/MAX One) — 1 sale.
