Homes for Sale in Oakland, MD

93 active listings · 1,497 sold since 2020

For Sale

$350K

Median Sale Price

Median Days on Market

94.8%

Sold-to-List

$189

Price / Sq Ft

Newest homes for sale in Oakland, MD

See all 93 on the map

321 N 3rd Street, Oakland, MD 21550

Listing Courtesy of CENTURY 21 New Millennium

256 Jeffrey Lane #28, Oakland, MD 21550

Listing Courtesy of Railey Realty, Inc.

1499 Foster Road, Oakland, MD 21550

Listing Courtesy of Railey Realty, Inc.

961 Cedar Lane, Oakland, MD 21550

Listing Courtesy of Taylor-Made Deep Creek Sales

112 E Pennington Street, Oakland, MD 21550

Listing Courtesy of Lake Homes Realty, LLC

255 Thornberry Road, Oakland, MD 21550

Listing Courtesy of Railey Realty, Inc.

995 Betts Lane, Oakland, MD 21550

Listing Courtesy of Taylor-Made Deep Creek Sales

187 Lower Penn Point Drive, Oakland, MD 21550

Listing Courtesy of Railey Realty, Inc.

104 Roman Ridge Road #21, Oakland, MD 21550

Listing Courtesy of Railey Realty, Inc.

Oakland, MD home price trend

Year	Median Sale Price	Homes Sold
2026	$399K	91
2025	$425K	205
2024	$385K	195
2023	$316K	201
2022	$333K	198
2021	$371K	317
2020	$295K	290

At the current trend, the median is modeled to reach about $428K in 2027 (estimate).

Cost to buy in Oakland, MD

At today's ~6.63% 30-year rate, the median $350K home in Oakland, MD runs about $2,260/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 Oakland, MD

Most active agents by closed sales here over the past 18 months.

Jonathan D BellRailey Realty, Inc.21 sales
Elizabeth S Spiker HolcombTaylor Made Deep Creek Vacations & Sales20 sales
Nick Fratz-OrrRailey Realty, Inc.17 sales
Nina A BeitzelRailey Realty, Inc.17 sales
Justin D LillerRailey Realty, Inc.14 sales

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Oakland, MD real estate FAQ

How many homes are for sale in Oakland, MD?

There are 93 homes currently for sale in Oakland, MD.

How much do homes sell for in Oakland, MD?

The median sale price in Oakland, MD is $350K, based on 1,497 sales since 2020 (ranging from $90K to $1.6M).

How fast do homes sell in Oakland, MD?

Homes in Oakland, MD typically go under contract in about 24 days on market (median).

Do homes in Oakland, MD sell above asking?

Over the past 12 months, homes in Oakland, MD sold for an average of 94.8% of list price — below asking.

What is the price per square foot in Oakland, MD?

Homes in Oakland, MD have sold for a median of $189 per square foot since 2020.

Is the Oakland, MD housing market heating up or cooling down?

The median sale price in Oakland, MD has risen from $295K in 2020 to $399K in 2026. At the current trend, the median is on track for roughly $428K in 2027 (modeled estimate).

Who are the top real estate agents in Oakland, MD?

The most active agents in Oakland, MD over the past 18 months are: Jonathan D Bell (Railey Realty, Inc.) — 21 sales; Elizabeth S Spiker Holcomb (Taylor Made Deep Creek Vacations & Sales) — 20 sales; Nick Fratz-Orr (Railey Realty, Inc.) — 17 sales.

Homes for Sale in Oakland, MD

Newest homes for sale in Oakland, MD

Oakland, MD home price trend

Cost to buy in Oakland, MD

Top agents in Oakland, MD

Get new-listing alerts for Oakland, MD

Oakland, MD real estate FAQ

How many homes are for sale in Oakland, MD?

How much do homes sell for in Oakland, MD?

How fast do homes sell in Oakland, MD?

Do homes in Oakland, MD sell above asking?

What is the price per square foot in Oakland, MD?

Is the Oakland, MD housing market heating up or cooling down?

Who are the top real estate agents in Oakland, MD?

Neighborhoods & Subdivisions in Oakland, MD