Top Realtors and Real Estate Agents in Winter Park, CO

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

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    Monica Anderson profile picture
    BadgeTop Agent

    (39)

    Monica Anderson

    RE/MAX Peak to Peak

    23 Years of experience

    25+ Sales in the last 12 months

    Top 1.4%

    in Winter Park, CO

    $213M

    All-Time Sales

    $300K - $1.8M

    Price Range

    7%

    Negotiated Off List

    Megan Waymire profile picture
    BadgeTop Agent

    (1)

    Megan Waymire

    Re/Max Peak to Peak

    11 Years of experience

    30+ Sales in the last 12 months

    Top 4.21%

    in Winter Park, CO

    $129.9M

    All-Time Sales

    $380K - $3.2M

    Price Range

    4%

    Negotiated Off List

    Barry Remington profile picture
    BadgeTop Agent

    (111)

    Barry Remington

    W K Real Estate

    14 Years of experience

    43+ Sales in the last 12 months

    Top 9.81%

    in Winter Park, CO

    $328.5M

    All-Time Sales

    $570K - $5.8M

    Price Range

    5%

    Negotiated Off List

    Lori Abbey profile picture
    BadgeTop Agent

    (55)

    Lori Abbey

    Compass

    16 Years of experience

    55+ Sales in the last 12 months

    Top 10.28%

    in Winter Park, CO

    $690.6M

    All-Time Sales

    $560K - $6.7M

    Price Range

    Cameron McClellan profile picture
    BadgeTop Agent

    (105)

    Cameron McClellan

    eXp Realty

    15 Years of experience

    108+ Sales in the last 12 months

    Top 11.21%

    in Winter Park, CO

    $533.9M

    All-Time Sales

    $390K - $2.4M

    Price Range

    4%

    Negotiated Off List

    Ken Boenish profile picture

    (132)

    Ken Boenish

    The Real Estate Company

    Top 0.47%

    in Winter Park, CO

    220

    Sold in Winter Park, CO

    Kristen L Meyer profile picture

    (28)

    Kristen L Meyer

    Re/Max Peak To Peak

    Top 0.93%

    in Winter Park, CO

    171

    Sold in Winter Park, CO

    Gretchen W Brunke profile picture

    Reviews not yet available

    Gretchen W Brunke

    Playground Destination Property

    Top 1.87%

    in Winter Park, CO

    111

    Sold in Winter Park, CO

    Michael S Ayre profile picture

    (72)

    Michael S Ayre

    Ecoluxe Real Estate

    Top 2.34%

    in Winter Park, CO

    59

    Sold in Winter Park, CO

    Lance Gutersohn profile picture

    (43)

    Lance Gutersohn

    Re/Max Peak To Peak

    29 Years of experience

    Top 2.8%

    in Winter Park, CO

    54

    Sold in Winter Park, CO

    1997

    Year Licensed

    Do Top Winter Park Agents Sell Faster?

    The 5 top-ranked agents on EffectiveAgents in Winter Park sell in a median of 43 days, compared with the Winter Park market median of 71 days on market.

    Top-ranked agents43 days
    Winter Park market71 days

    About 28 days faster (39% quicker than the Winter Park market)

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

    When Is the Best Time to Sell a House in Winter Park?

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

    Median days on market by month (shorter is faster)

    86Jan68Feb69Mar63Apr77May49Jun35Jul55Aug72Sep103Oct108Nov126Dec

    June

    Best month to sell

    49 days

    Typical time on market

    98.5%

    Of asking price

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

    How We Rank Winter Park 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 Winter Park 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.

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

    Data last updated: July 2026

    Winter Park Real Estate Agent FAQs

    How were these Winter Park 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 Winter Park?

    Our data covers 165 real estate agents serving the Winter Park area. The count represents agents with transaction activity recorded in our Winter Park market data, not simply everyone holding a license.

    What does the median sale price in Winter Park mean for sellers?

    Winter Park's median sale price is $1,162,418 as of July 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.

    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 Winter Park 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 Winter Park 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 Winter Park 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 Winter Park realtor before hiring them?

    Ask how many homes they have closed in Winter Park 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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