Top Realtors and Real Estate Agents in Oakland, MD

    Rankings based on verified MLS transaction data. Last updated September 2026. No pay-to-play.

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    Sheila Howell profile picture
    BadgeTop Agent

    (27)

    Sheila Howell

    Lake Homes Realty

    8 Years of experience

    30+ Sales in the last 12 months

    Top 1.2%

    in Oakland, MD

    $92.1M

    All-Time Sales

    $280K - $2.8M

    Price Range

    12%

    Negotiated Off List

    Sean Brink profile picture
    BadgeTop Agent

    (73)

    Sean Brink

    Precise Real Estate & Dev

    28 Years of experience

    20+ Sales in the last 12 months

    Top 12.4%

    in Oakland, MD

    $178.4M

    All-Time Sales

    $270K - $2.8M

    Price Range

    13%

    Negotiated Off List

    Adam Murphy profile picture
    BadgeTop Agent

    (37)

    Adam Murphy

    ReMax Realty Centre - The Fox Team

    10 Years of experience

    48+ Sales in the last 12 months

    Top 13.2%

    in Oakland, MD

    $87.3M

    All-Time Sales

    $380K - $2.1M

    Price Range

    4%

    Negotiated Off List

    Stephen MacGray profile picture
    BadgeTop Agent

    (7)

    Stephen MacGray

    Charis Realty Group

    9 Years of experience

    77+ Sales in the last 12 months

    $157.8M

    All-Time Sales

    $110K - $830K

    Price Range

    10%

    Negotiated Off List

    Ana Dubin profile picture
    BadgeTop Agent

    (89)

    Ana Dubin

    Long and Foster

    11 Years of experience

    43+ Sales in the last 12 months

    $212.4M

    All-Time Sales

    $500K - $3M

    Price Range

    4

    Sold in Oakland, MD

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    Jake VanMeter profile picture
    BadgeTop Agent

    (7)

    Jake VanMeter

    RE/MAX Real Estate Group

    16 Years of experience

    10+ Sales in the last 12 months

    $33.7M

    All-Time Sales

    $110K - $760K

    Price Range

    9%

    Negotiated Off List

    Rich Phillips profile picture
    BadgeTop Agent

    (65)

    Rich Phillips

    Northrop Realty

    19 Years of experience

    36+ Sales in the last 12 months

    Top 14.8%

    in Oakland, MD

    $154.7M

    All-Time Sales

    $310K - $1.5M

    Price Range

    4%

    Negotiated Off List

    Sheri Ball profile picture
    BadgeTop Agent

    Reviews not yet available

    Sheri Ball

    Alpine Lake Vacations & Sales

    32 Years of experience

    40+ Sales in the last 12 months

    $26.9M

    All-Time Sales

    $90K - $650K

    Price Range

    3

    Sold in Oakland, MD

    Levi Loveless profile picture
    BadgeTop Agent

    (360)

    Levi Loveless

    RE/MAX Realty Group

    4 Years of experience

    131+ Sales in the last 12 months

    Top 16%

    in Oakland, MD

    $841.6M

    All-Time Sales

    $410K - $3.4M

    Price Range

    Mike Myslinski profile picture
    BadgeTop Agent

    (44)

    Mike Myslinski

    Kelly and Co Realty

    5 Years of experience

    74+ Sales in the last 12 months

    $80.2M

    All-Time Sales

    $360K - $1.3M

    Price Range

    177

    Total Number Of Homes Sold

    The numbers speak
    for Oakland.

    Every agent above earned their place with closed sales, not advertising. Tell us about your home and our algorithm picks the Oakland agents whose results fit it.

    Oakland agents analyzed for these rankings

    days faster: top-ranked agents sell in 22 days, the Oakland market in 138

    median sale price in Oakland

    Find the right agent for your Oakland sale.

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    Do Top Oakland Agents Sell Faster?

    The 10 top-ranked agents on EffectiveAgents in Oakland sell in a median of 22 days, compared with the Oakland market median of 138 days on market.

    Top-ranked agents22 days
    Oakland market138 days

    About 116 days faster (84% quicker than the Oakland market)

    Median days to sale reported by the top-ranked Oakland agents on EffectiveAgents, compared with the Oakland market median days on market. Agent figures reflect each agent's reported sales history.

    When Is the Best Time to Sell a House in Oakland?

    Based on the last 24 months of verified MLS market data, homes in Oakland sell fastest and closest to asking when they go under contract in May. To hit that window, plan to list around March.

    Median days on market by month (shorter is faster)

    77Jan59Feb199Mar44Apr56May36Jun94Jul90Aug82Sep89Oct93Nov69Dec

    May

    Best month to sell

    56 days

    Typical time on market

    96.5%

    Of asking price

    Seasonal averages from the last 24 months of Oakland, MD sales. Individual results vary with price, condition, and how the broader market moves. A local agent can pinpoint the right timing for your home.

    What These Numbers Mean for Oakland Buyers and Sellers

    The Housing Market Trends module above shows a market in Oakland where the signals point in different directions, which makes reading negotiating leverage more nuanced than a single headline number suggests. The median sale price sits at $329,843 and has moved +51.6% year over year, while homes are measured at a median of 138 days on market. With 7.1 months of supply and 44.1% of listings recording a price cut, sellers are not automatically in control, and buyers have real room to negotiate on properties that have lingered.

    The counterweight is that 20.0% of homes still closed above asking and 42.5% went under contract within two weeks. That split tells buyers to separate the market into two segments: correctly priced, move-in-ready homes that draw fast competition, and everything else that sits and eventually cuts price. On the sharp listings, expect to compete near or above list; on aged inventory, an offer below the 94.58% average sale-to-list ratio is defensible.

    For sellers, the 138 day median and the high price-drop share argue for disciplined pricing at launch rather than testing a high number and correcting later. Homes priced accurately capture the early two-week window; those that miss it join the slower-moving pool. With 12 active listings and 2 homes sold in the latest month, positioning matters more than volume. Across 250 licensed agents in the area, the difference between an agent who prices to the data and one who chases a number is measurable in both final price and time on market.

    What Oakland Home Prices Mean for You

    Understanding the true cost of homeownership in Oakland goes beyond the listing price. These calculators break down what today's market conditions mean for your budget, your timeline, and your negotiating position.

    Income Required to Buy in Oakland
    $102,400
    Median home price$329,843
    Down payment (20%)$65,969
    Loan amount$263,874
    Monthly payment (PITI)$2,389

    Based on 28% debt-to-income ratio, 7.24% mortgage rate (as of October 29, 2026), 30-year fixed loan, 1.15% property tax rate, $275/mo insurance. Actual requirements vary by lender.

    Oakland Market Temperature
    Buyer's Market Balanced Seller's Market
    Buyer's Market
    Days on Market 138 days
    Sale-to-List Price 94.58%
    Price Trend (YoY) +51.6%
    Estimated Monthly Payment
    Total Monthly Payment
    $2,389
    Principal & Interest
    $1,798
    Property Taxes
    $316
    Insurance
    $275
    PMI
    $0

    Based on $329,843 median home price with 20% down at 7.24% (as of October 29, 2026) for 30 years. Property tax estimated at 1.15% of home value.

    Oakland Market: Then vs Now
    Median Sale Price
    One Year Ago $217,503
    Today $329,843
    +51.6%
    Days on Market
    One Year Ago 47 days
    Today 138 days
    +91 days days
    Sale-to-List Price
    One Year Ago 94.7%
    Today 94.58%
    -0.08%
    What this shift means: Compared with a year ago, prices moved +51.6%, the sale-to-list ratio shifted -0.08%, and market time reflects a +91 days change. Read together, that combination means buyers have gained more time to evaluate homes while sellers of well-priced properties are still capturing close-to-asking outcomes. The takeaway for both sides is that pricing precision now carries more weight than it did last year.

    Year-over-year data reflects the most recent rolling period from Oakland MLS records. Prior year values calculated from current figures and published YoY changes.

    What to Look for in a Oakland Realtor

    Choosing an agent on name recognition alone overlooks what actually moves a transaction: pricing accuracy, negotiation, and a track record verified across real closings rather than advertising spend. In a market with 138 day median times and 44.1% of listings taking price cuts, that difference shows up directly in your net proceeds or purchase price. Our top-ranked agent in Oakland is Sheila Howell at Lake Homes Realty, with 259 career transactions, an all-time sales volume of $91.6M, and 27 client reviews. That transaction depth matters when negotiating in the 21550 area, where correctly priced homes can draw competition while aged listings require a different strategy entirely. An agent who has managed both scenarios reads offers, appraisal gaps, and contingencies with more precision. When reviewing candidates among the 22 EffectiveAgents-ranked professionals here, look at review patterns over time rather than a single rating: consistency across many closings signals repeatable process, while a handful of scattered reviews tells you far less about how an agent performs under pressure.

    How We Rank Oakland Real Estate Agents

    Our rankings are built from verified MLS transaction data, not advertising spend. For every agent we analyze more than fifteen performance signals, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results (how far above or below list price an agent's clients actually close), price-point fit, and verified reviews. The agents shown first are those whose verified results put them at the top of the Oakland market today.

    Agents cannot pay for placement in these rankings. The underlying data refreshes as new closed transactions are reported, so rankings shift with real market performance. Learn how we rank agents.

    250

    agents analyzed

    15+

    performance signals

    $0

    paid for placement

    Rankings reviewed by Kevin Stuteville, Licensed Florida Real Estate Broker (License BK3068131), Founder of EffectiveAgents.

    Data last updated: September 2026

    Oakland Real Estate Agent FAQs

    Who is the best real estate agent in Oakland, MD?

    The top-ranked agent in Oakland, MD on EffectiveAgents is Sheila Howell at Lake Homes Realty, with 259 transactions, 27 client reviews, and $91.6M in all-time sales volume. EffectiveAgents ranks agents using a data-driven methodology that analyzes verified transaction history, closing outcomes, and client review patterns rather than advertising. Of roughly 250 licensed agents in the area, 22 met the criteria to be ranked. The best fit still depends on your property type and goals, so compare several ranked agents before deciding.

    How were these Oakland real estate agents ranked?

    Rankings are built from verified MLS transaction data. We analyze more than fifteen performance signals for every agent, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results, price-point fit, and verified reviews. Agents cannot pay for placement.

    How many real estate agents are in Oakland?

    Our data covers 250 real estate agents serving the Oakland area. The count represents agents with transaction activity recorded in our Oakland market data, not simply everyone holding a license.

    What does the median sale price in Oakland mean for sellers?

    Oakland's median sale price is $329,843 as of September 2026. Half of recent sales closed above that figure and half below. It is a useful baseline for understanding the market, but an experienced local agent will price your home against comparable recent sales in your neighborhood, not the citywide median.

    How long does it take to sell a house in Oakland?

    In Oakland, homes are selling in a median of 138 days, and the year-over-year figure reflects a +91 days change in market time. Your actual timeline depends heavily on pricing and condition: 42.5% of homes went under contract within two weeks, while others sat long enough that 44.1% of listings recorded a price cut. Accurate initial pricing, professional preparation, and correct positioning against the 12 active listings are the factors most likely to move a sale toward the faster end of that range.

    Does it cost anything to use EffectiveAgents?

    No. EffectiveAgents is free for home buyers and sellers, with no obligation to work with any agent we match you with.

    Do agents pay to be ranked or featured?

    No. Agents cannot pay for placement anywhere in these rankings. Positions are earned from verified transaction performance only.

    What commission do Oakland realtors charge?

    Commissions are negotiable and vary by agent, service level, and transaction. There is no set rate, and recent industry changes have made commission structures more flexible than ever. Discuss the structure directly with your agent before signing a listing or buyer agreement.

    Should I use a local Oakland agent or a national brand?

    The individual agent matters more than the brand on the sign. Offices within the same national franchise vary widely in performance, and the agent you hire, not the logo, prices your home, negotiates your contract, and manages your closing. A strong local agent brings firsthand knowledge of Oakland neighborhoods, pricing patterns, and buyer activity. Compare agents on verified local results such as recent sales, days on market, and negotiation outcomes rather than name recognition.

    What questions should I ask a Oakland realtor before hiring them?

    Ask how many homes they have closed in Oakland in the past year, what their average sale-to-list ratio is, and how much of their business is in your neighborhood and price range. Ask how they will market your home or find you listings, and how often they will communicate. Strong agents answer with specifics. Verified transaction data is the fastest way to confirm what you hear.

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