Top Realtors and Real Estate Agents in Winter Haven, FL
Rankings based on verified MLS transaction data. Last updated June 2026. No pay-to-play.
Top Agent
Top 0.14%
in Winter Haven, FL
$260.1M
All-Time Sales
$100K - $1.1M
Price Range
20%
Negotiated Off List
Top Agent
(93)
Brad Martin
Better Homes and Gardens Real Estate- Lifesyles Realty
14 Years of experience
9+ Sales in the last 12 months
Top 0.57%
in Winter Haven, FL
$124.3M
All-Time Sales
$200K - $2.2M
Price Range
7%
Negotiated Off List
Top AgentTop 0.71%
in Winter Haven, FL
$779.6M
All-Time Sales
$170K - $1.9M
Price Range
7%
Negotiated Off List
Top Agent(74)
Casandra Vann
Keller Williams Smart - Home Advisors Team
22 Years of experience
175+ Sales in the last 12 months
Top 0.85%
in Winter Haven, FL
$422.9M
All-Time Sales
$180K - $1.6M
Price Range
5%
Negotiated Off List
Top Agent(60)
Jason Prieto
Keller Williams Realty - The Prieto Group
10 Years of experience
110+ Sales in the last 12 months
Top 1.28%
in Winter Haven, FL
$100.6M
All-Time Sales
$180K - $600K
Price Range
5%
Negotiated Off List
Top AgentTop 2.55%
in Winter Haven, FL
$37.7M
All-Time Sales
$120K - $450K
Price Range
7%
Negotiated Off List
Top AgentTop 4.11%
in Winter Haven, FL
$44.3M
All-Time Sales
$210K - $1.2M
Price Range
7%
Negotiated Off List
Top AgentReviews not yet available
Ken Welch
Century 21 At Your Service Realty
31 Years of experience
13+ Sales in the last 12 months
Top 5.11%
in Winter Haven, FL
$58.4M
All-Time Sales
$150K - $2.1M
Price Range
Top AgentTop 5.25%
in Winter Haven, FL
$204.8M
All-Time Sales
$260K - $1.8M
Price Range
7%
Negotiated Off List
Top AgentTop 5.96%
in Winter Haven, FL
$33.4M
All-Time Sales
$150K - $650K
Price Range
Top AgentTop 6.24%
in Winter Haven, FL
$113.3M
All-Time Sales
$250K - $2.1M
Price Range
5%
Negotiated Off List
Top Agent(11)
Alicia Claircius
Opulent Realty International
6 Years of experience
13+ Sales in the last 12 months
Top 7.09%
in Winter Haven, FL
$28.6M
All-Time Sales
$250K - $2.2M
Price Range
Top AgentTop 8.37%
in Winter Haven, FL
$31.8M
All-Time Sales
$230K - $1.2M
Price Range
Top Agent(43)
Abdias Alexandre
Centric Realty Services, LLC
11 Years of experience
58+ Sales in the last 12 months
Top 8.94%
in Winter Haven, FL
$188.5M
All-Time Sales
$210K - $1.7M
Price Range
4%
Negotiated Off List
Top AgentTop 9.93%
in Winter Haven, FL
$7.4M
All-Time Sales
$140K - $390K
Price Range
Top AgentTop 10.5%
in Winter Haven, FL
$72.3M
All-Time Sales
$270K - $820K
Price Range
6%
Negotiated Off List
Top Agent(28)
Michelle Graham
Keller Williams Realty Smart
12 Years of experience
17+ Sales in the last 12 months
Top 10.64%
in Winter Haven, FL
$46M
All-Time Sales
$200K - $1.1M
Price Range
5%
Negotiated Off List
Top Agent(11)
Katherine Montana-DeJesus
Keller Williams Realty Smart 1
3 Years of experience
19+ Sales in the last 12 months
Top 11.63%
in Winter Haven, FL
$7.5M
All-Time Sales
$240K - $570K
Price Range
Top AgentTop 11.91%
in Winter Haven, FL
$22.4M
All-Time Sales
$180K - $860K
Price Range
Top AgentTop 12.2%
in Winter Haven, FL
$198.1M
All-Time Sales
$280K - $1.6M
Price Range
4%
Negotiated Off List
Top AgentTop 12.34%
in Winter Haven, FL
$39.2M
All-Time Sales
$220K - $1.2M
Price Range
Top AgentTop 13.05%
in Winter Haven, FL
$402.3M
All-Time Sales
$210K - $3M
Price Range
5%
Negotiated Off List
Top AgentTop 13.33%
in Winter Haven, FL
$114.3M
All-Time Sales
$150K - $2.3M
Price Range
Top AgentTop 13.33%
in Winter Haven, FL
$104.5M
All-Time Sales
$180K - $1.2M
Price Range
Top AgentTop 14.33%
in Winter Haven, FL
$126.3M
All-Time Sales
$250K - $1.7M
Price Range
5%
Negotiated Off List
Winter haven Housing Market Trends
Median Sale Price
$294,840
+2.55% year-over-yearMedian Days on Market
79
+17 days year-over-yearSale-to-List Price
98.59%
+0.15% year-over-yearHomes Sold Above List Price
13.2%
+6.3% year-over-yearOff the Market in 2 Weeks
20.3%
+1.8% year-over-yearListings With Price Drops
42.1%
-1.0% year-over-yearMonths of Supply
4.0
Realtors in Winter haven
705
Verified MLS market data through June 2026.
Do Top Winter Haven Agents Sell Faster?
The 24 top-ranked agents on EffectiveAgents in Winter Haven sell in a median of 30 days, compared with the Winter Haven market median of 79 days on market.
About 49 days faster (62% quicker than the Winter Haven market)
Median days to sale reported by the top-ranked Winter Haven agents on EffectiveAgents, compared with the Winter Haven 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 Haven?
Based on the last 24 months of verified MLS market data, homes in Winter Haven 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)
June
Best month to sell
54 days
Typical time on market
98.4%
Of asking price
Seasonal averages from the last 24 months of Winter Haven, 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 Haven Buyers and Sellers
The Housing Market Trends module above establishes the baseline: a median sale price of $294,840, a median of 79 days on market, and an average sale-to-list ratio of 98.59%. Read together, these indicators point to a market where negotiating leverage has shifted toward buyers in Winter Haven. With 4.0 months of supply and 450 active listings against 114 monthly sales, inventory is accumulating faster than it is clearing, which gives buyers more room to negotiate on price and terms.
The clearest signal is that 42.1% of listings have recorded a price reduction, meaning many sellers initially priced above what the market will support. At the same time, only 20.3% of homes go off the market within two weeks, and 13.2% sell above list, so competition is concentrated on correctly priced, move-in ready homes rather than the broader pool. For a buyer, this means an offer near or slightly below list is reasonable on listings that have lingered, while well-priced new inventory still warrants a prompt, competitive bid.
For a seller, the data argues for disciplined pricing from day one. With prices having moved +2.5% year over year and homes taking a +17 days change in market time, overpricing now risks a stale listing and an eventual reduction. Pricing to the 98.59% reality of the market tends to produce faster, cleaner outcomes. Across 705 licensed agents in the area, execution varies widely, which is where working with a measured, verified professional matters most.
What Winter Haven Home Prices Mean for You
Understanding the true cost of homeownership in Winter Haven 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 | $294,840 |
| Down payment (20%) | $58,968 |
| Loan amount | $235,872 |
| Monthly payment (PITI) | $2,078 |
Based on 28% debt-to-income ratio, 6.69% mortgage rate (as of August 6, 2026), 30-year fixed loan, 1.15% property tax rate, $275/mo insurance. Actual requirements vary by lender.
Based on $294,840 median home price with 20% down at 6.69% (as of August 6, 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 Haven MLS records. Prior year values calculated from current figures and published YoY changes.
What to Look for in a Winter Haven Realtor
Choosing an agent on name recognition or ad spend alone overlooks what actually determines outcomes: transaction volume, negotiation results, and consistent client feedback. In a market where 42.1% of listings see a reduction and homes average 79 days to sell, the difference between a data-driven agent and an average one shows up directly in your final price and time on market. Among the 79 EffectiveAgents-ranked professionals serving Winter Haven, top performer Chrissi Jasso at Associate Realty has closed 2,111 transactions with $259.2M in all-time sales volume. That depth matters when negotiating in zip codes like 33880, 33881, and 33884, where correctly pricing against the 98.59% sale-to-list benchmark separates quick closings from stalled listings. Her 109 reviews reflect a pattern of repeat and referral business rather than one-off transactions, a signal worth weighing more heavily than raw agent counts. Reviewing an agent's track record across multiple cycles gives you a clearer read on how they will handle your specific sale or purchase.
How We Rank Winter Haven 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 Haven 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: June 2026
Winter Haven Real Estate Agent FAQs
Who is the best real estate agent in Winter Haven, FL?
The top-ranked agent in Winter Haven, FL is Chrissi Jasso at Associate Realty, with 2,111 transactions, 109 reviews, and $259.2M in all-time sales volume. EffectiveAgents identifies leading agents by analyzing verified transaction history, sales volume, and client review patterns rather than advertising. Of the 705 licensed agents in the area, only 79 meet the ranking criteria. The strongest fit depends on your price range and timeline, so we recommend comparing several ranked agents before deciding.
How were these Winter Haven 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 Haven?
Our data covers 705 real estate agents serving the Winter Haven area. The count represents agents with transaction activity recorded in our Winter Haven market data, not simply everyone holding a license.
What does the median sale price in Winter Haven mean for sellers?
Winter Haven's median sale price is $294,840 as of June 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 Haven?
Homes in Winter Haven currently take a median of 79 days to sell, and market time reflects a +17 days change year over year. Actual timelines vary with pricing accuracy, condition, and location. With 42.1% of listings recording a price cut and 4.0 months of supply, homes priced to the 98.59% sale-to-list reality tend to close faster, while overpriced listings sit longer and often require a reduction before selling.
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 Haven 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 Haven 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 Haven 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 Haven realtor before hiring them?
Ask how many homes they have closed in Winter Haven 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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