Newhouse
1/48
$5,753/mo
$875,0004bd·3ba·2,280sf
37 Skippers Point Road, Oakland, MD 21550
Listing Courtesy of Taylor-Made Deep Creek Sales
Homes for Sale in Skippers Point, Oakland, MD
2 active listings · 8 sold since 2020
2
For Sale
$707K
Median Sale Price
11
Median Days on Market
100.2%
Sold-to-List
$410
Price / Sq Ft
Newest homes for sale in Skippers Point, Oakland, MD
See all 2 on the mapSkippers Point, Oakland, MD home price trend
| Year | Median Sale Price | Homes Sold |
|---|---|---|
| 2025 | $530K | 1 |
| 2024 | $1.5M | 3 |
| 2021 | $378K | 2 |
| 2020 | $647K | 2 |
At the current trend, the median is modeled to reach about $1.0M in 2026 (estimate).
Cost to buy in Skippers Point, Oakland, MD
At today's ~6.63% 30-year rate, the median $707K home in Skippers Point, Oakland, MD runs about $4,564/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 Skippers Point, Oakland, MD
Most active agents by closed sales here over the past 18 months.
- Steven C RitchieRailey Realty, Inc.1 sale
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Skippers Point, Oakland, MD real estate FAQ
How many homes are for sale in Skippers Point, Oakland, MD?
There are 2 homes currently for sale in Skippers Point, Oakland, MD.
How much do homes sell for in Skippers Point, Oakland, MD?
The median sale price in Skippers Point, Oakland, MD is $707K, based on 8 sales since 2020 (ranging from $326K to $1.8M).
How fast do homes sell in Skippers Point, Oakland, MD?
Homes in Skippers Point, Oakland, MD typically go under contract in about 11 days on market (median).
Do homes in Skippers Point, Oakland, MD sell above asking?
Over the past 12 months, homes in Skippers Point, Oakland, MD sold for an average of 100.2% of list price — at or above asking.
What is the price per square foot in Skippers Point, Oakland, MD?
Homes in Skippers Point, Oakland, MD have sold for a median of $410 per square foot since 2020.
Is the Skippers Point, Oakland, MD housing market heating up or cooling down?
The median sale price in Skippers Point, Oakland, MD has fallen from $647K in 2020 to $530K in 2025. At the current trend, the median is on track for roughly $1.0M in 2026 (modeled estimate).
Who are the top real estate agents in Skippers Point, Oakland, MD?
The most active agents in Skippers Point, Oakland, MD over the past 18 months are: Steven C Ritchie (Railey Realty, Inc.) — 1 sale.
