Top Realtors and Real Estate Agents in Winter Park, FL
Rankings based on verified MLS transaction data. Last updated May 2026. No pay-to-play.

Top 0.13%
in Winter Park, FL
$306.3M
All-Time Sales
$400K - $3.2M
Price Range
15%
Negotiated Off List

Top 0.59%
in Winter Park, FL
$218.6M
All-Time Sales
$390K - $3.6M
Price Range
5%
Negotiated Off List

Top 0.63%
in Winter Park, FL
$166.9M
All-Time Sales
$180K - $2.2M
Price Range
7%
Negotiated Off List

Top 0.88%
in Winter Park, FL
$402.3M
All-Time Sales
$210K - $3M
Price Range
5%
Negotiated Off List

Top 1.09%
in Winter Park, FL
$246.3M
All-Time Sales
$530K - $8.8M
Price Range

(74)
Barrett Spray
Keller Williams Advantage Realty
34 Years of experience
85+ Sales in the last 12 months
Top 1.18%
in Winter Park, FL
$354.3M
All-Time Sales
$200K - $3.1M
Price Range
4%
Negotiated Off List

Top 1.31%
in Winter Park, FL
$219.5M
All-Time Sales
$220K - $2.7M
Price Range
7%
Negotiated Off List

(7)
Brandon Geers
Compass - Fusilier Realty Group | The Pixley Berkowitz Team
6 Years of experience
32+ Sales in the last 12 months
Top 1.35%
in Winter Park, FL
$90.1M
All-Time Sales
$660K - $6M
Price Range
5%
Negotiated Off List

Top 1.43%
in Winter Park, FL
$216.8M
All-Time Sales
$250K - $3.1M
Price Range
6%
Negotiated Off List

Top 1.81%
in Winter Park, FL
$230.6M
All-Time Sales
$220K - $2.2M
Price Range
6%
Negotiated Off List

Top 1.85%
in Winter Park, FL
$217.4M
All-Time Sales
$270K - $1.8M
Price Range
5%
Negotiated Off List

(332)
Christopher Bessette
Keller Williams Classic
19 Years of experience
75+ Sales in the last 12 months
Top 1.89%
in Winter Park, FL
$413.1M
All-Time Sales
$280K - $3.8M
Price Range
5%
Negotiated Off List

Top 1.98%
in Winter Park, FL
$140M
All-Time Sales
$210K - $1.3M
Price Range
4%
Negotiated Off List

Top 2.15%
in Winter Park, FL
$134.6M
All-Time Sales
$210K - $1.2M
Price Range
4%
Negotiated Off List

Top 2.19%
in Winter Park, FL
$403.5M
All-Time Sales
$230K - $2.2M
Price Range
4%
Negotiated Off List

(4)
Wendy Maher
Sotheby's International Real Estate
9 Years of experience
1+ Sales in the last 12 months
Top 2.32%
in Winter Park, FL
$42.6M
All-Time Sales
$900K - $5.5M
Price Range

Top 2.36%
in Winter Park, FL
$592.8M
All-Time Sales
$190K - $2.3M
Price Range
6%
Negotiated Off List

(50)
Yuly Rodriguez
Douglas Edmund Real Estate LLC
17 Years of experience
12+ Sales in the last 12 months
Top 2.4%
in Winter Park, FL
$51.2M
All-Time Sales
$160K - $850K
Price Range
3%
Negotiated Off List

Top 2.44%
in Winter Park, FL
$252.8M
All-Time Sales
$310K - $1.9M
Price Range
3%
Negotiated Off List

Top 2.48%
in Winter Park, FL
$114.3M
All-Time Sales
$150K - $2.3M
Price Range

(49)
Dione Collier-Larkin
Berkshire Hathaway Home Services
22 Years of experience
32+ Sales in the last 12 months
Top 2.48%
in Winter Park, FL
$131.1M
All-Time Sales
$320K - $22M
Price Range
4%
Negotiated Off List

Top 2.74%
in Winter Park, FL
$197.7M
All-Time Sales
$280K - $1.6M
Price Range
4%
Negotiated Off List

Top 2.74%
in Winter Park, FL
$223.2M
All-Time Sales
$220K - $4.8M
Price Range
3%
Negotiated Off List

Top 2.74%
in Winter Park, FL
$123M
All-Time Sales
$200K - $1.7M
Price Range
5%
Negotiated Off List

Top 2.74%
in Winter Park, FL
$69.1M
All-Time Sales
$250K - $2.1M
Price Range
4%
Negotiated Off List
Winter park Housing Market Trends
Median Sale Price
$835,750
+21.56% year-over-yearMedian Days on Market
21
-8 days year-over-yearSale-to-List Price
94.61%
-2.13% year-over-yearHomes Sold Above List Price
13.6%
+4.0% year-over-yearOff the Market in 2 Weeks
43.6%
+9.6% year-over-yearListings With Price Drops
36.6%
+2.3% year-over-yearMonths of Supply
3.9
Realtors in Winter park
2,375
Verified MLS market data through May 2026.
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 May.
Median days on market by month (shorter is faster)
June
Best month to sell
32 days
Typical time on market
96.9%
Of asking price
Seasonal averages from the last 24 months of Winter Park, FL 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 Winter Park Buyers and Sellers
Winter Park's housing market currently carries a median sale price of $835,750, and the Housing Market Trends module above shows prices moved +21.6% year over year. To understand where leverage actually sits, look past the headline price and read the competitive indicators together. With homes selling at an average sale-to-list ratio of 94.61% and only 13.6% of homes closing above their asking price, most transactions are settling below list. That points to room for negotiation rather than bidding wars. At the same time, 43.6% of homes leave the market within two weeks, so well-priced, move-in-ready properties still move quickly while overpriced listings sit.
Inventory tells a similar story. With 172 active listings and 3.9 months of supply, conditions favor neither side decisively, though a notable 36.6% of listings have recorded price reductions. That share of price drops, paired with a median 21 days on market, signals that sellers who anchor to aspirational pricing are being forced to correct. For buyers, this means patience and a data-backed offer below list is often reasonable. For sellers, accurate pricing from day one captures the fast-moving segment of demand.
Across the four Winter Park zip codes (32789, 32790, 32792, and 32793), pricing dynamics vary meaningfully block to block, which is where local expertise matters. Of the 2,375 licensed agents operating in the area, only a fraction consistently deliver measured results. Working with an agent who understands these micro-level patterns is the difference between guessing at a number and pricing or offering with evidence.
What Winter Park Home Prices Mean for You
Understanding the true cost of homeownership in Winter Park goes beyond the listing price. These calculators break down what today's market conditions mean for your budget, your timeline, and your negotiating position.
| Median home price | $835,750 |
| Down payment (20%) | $167,150 |
| Loan amount | $668,600 |
| Monthly payment (PITI) | $5,373 |
Based on 28% debt-to-income ratio, 6.66% mortgage rate (as of July 30, 2026), 30-year fixed loan, 1.15% property tax rate, $275/mo insurance. Actual requirements vary by lender.
Based on $835,750 median home price with 20% down at 6.66% (as of July 30, 2026) for 30 years. Property tax estimated at 1.15% of home value.
Year-over-year data reflects the most recent rolling period from Winter Park MLS records. Prior year values calculated from current figures and published YoY changes.
What to Look for in a Winter Park Realtor
Choosing an agent on name recognition or a familiar sign in the yard rarely correlates with the outcome you get at the closing table. What matters is measured transaction history and negotiation results across market conditions like today's. EffectiveAgents analyzed 522 transactions to rank the 103 agents who consistently perform in Winter Park. Among them, stands out, having closed a verified volume of transactions with substantial all-time sales. Negotiation skill is measurable here: with the market's average sale-to-list ratio at 94.61% and 36.6% of listings taking reductions, an agent who protects your price or secures a favorable discount adds real dollars. Experience across the 32789, 32792, and 32793 zip codes helps an agent price and position accurately in neighborhoods that behave differently. When reviewing candidates, look at review patterns over time, not just a single rating. Consistency across many closings signals reliability far better than one glowing testimonial.
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: May 2026
Winter Park Real Estate Agent FAQs
Who is the best real estate agent in Winter Park, FL?
Jennifer King of Corcoran Premier Realty ranks among the top agents in Winter Park, FL, with a verified 609 lifetime transactions and $304.0M in all-time sales volume. EffectiveAgents identifies top agents through an objective methodology that analyzes closed transaction history, sales volume, and client outcomes rather than advertising or self-reported claims. Of the 2,375 licensed agents in the area, only 103 meet our ranking criteria. The best agent for you depends on your property type, price range, and neighborhood, so compare several verified matches before deciding.
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 2,375 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 $835,750 as of May 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 Winter Park?
In Winter Park, the median home sells in about 21 days, and market time reflects a -8 days change compared with last year. Your actual timeline depends on pricing, condition, and location. With 43.6% of homes leaving the market within two weeks, accurately priced and well-presented properties move fastest, while 36.6% of listings that required price reductions typically sit longer. Factoring in the escrow period after an accepted offer, most sellers should plan for the full process to run several weeks beyond the initial days on market.
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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