Top Realtors and Real Estate Agents in Winter Haven, FL
Rankings based on verified MLS transaction data. Last updated August 2026. No pay-to-play.
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Top Agent
$219.1M
All-Time Sales
$30K - $3.7M
Price Range
9%
Negotiated Off List
Top Agent$1.21B
All-Time Sales
$240K - $3M
Price Range
6%
Negotiated Off List
Top Agent$1.9B
All-Time Sales
$440K - $18.9M
Price Range
8%
Negotiated Off List
Top Agent
(87)
Raymond Chadderton
Keller Williams Suburban Tampa
26 Years of experience
35+ Sales in the last 12 months
$504.1M
All-Time Sales
$220K - $1.5M
Price Range
5%
Negotiated Off List
Top Agent$581.8M
All-Time Sales
$290K - $4.4M
Price Range
6%
Negotiated Off List
Top Agent(102)
Jennifer Pichette-Fieo
RE/MAX Realty Unlimited
29 Years of experience
130+ Sales in the last 12 months
$470.2M
All-Time Sales
$200K - $4.4M
Price Range
4%
Negotiated Off List
Top Agent(74)
Barrett Spray
Keller Williams Advantage Realty
34 Years of experience
94+ Sales in the last 12 months
$363M
All-Time Sales
$210K - $3.1M
Price Range
4%
Negotiated Off List
Top Agent$284.4M
All-Time Sales
$220K - $2M
Price Range
5%
Negotiated Off List
Top Agent(74)
Stephanie Barron
United Country Smith & Associates
9 Years of experience
96+ Sales in the last 12 months
$137.7M
All-Time Sales
$180K - $2M
Price Range
9%
Negotiated Off List
Top Agent$412.3M
All-Time Sales
$230K - $2.2M
Price Range
4%
Negotiated Off List
Top Agent$140M
All-Time Sales
$210K - $1.3M
Price Range
4%
Negotiated Off List
Top Agent$87.1M
All-Time Sales
$180K - $920K
Price Range
2
Sold in Winter Haven, FL
Top Agent$128.5M
All-Time Sales
$210K - $1M
Price Range
4%
Negotiated Off List
Top Agent$140.4M
All-Time Sales
$290K - $3M
Price Range
6%
Negotiated Off List
Top Agent$69.8M
All-Time Sales
$250K - $2.1M
Price Range
4%
Negotiated Off List
Top Agent$102.9M
All-Time Sales
$230K - $1.1M
Price Range
3%
Negotiated Off List
Top Agent$61.2M
All-Time Sales
$180K - $1.3M
Price Range
6%
Negotiated Off List
Top Agent$63.3M
All-Time Sales
$260K - $1.4M
Price Range
1
Sold in Winter Haven, FL
Top Agent$84.2M
All-Time Sales
$290K - $2.9M
Price Range
230
Total Number Of Homes Sold
Top Agent$92.1M
All-Time Sales
$230K - $940K
Price Range
4%
Negotiated Off List
Top Agent$37.4M
All-Time Sales
$470K - $3.6M
Price Range
1
Sold in Winter Haven, FL
Top Agent$62.4M
All-Time Sales
$270K - $980K
Price Range
5%
Negotiated Off List
Top Agent$541M
All-Time Sales
$420K - $9.4M
Price Range
10%
Negotiated Off List
Top Agent$20.8M
All-Time Sales
$130K - $850K
Price Range
5%
Negotiated Off List
Top Agent$49.9M
All-Time Sales
$270K - $3.1M
Price Range
3
Sold in Winter Haven, FL
Winter haven Housing Market Trends
Homes in Winter haven take a median 85 days to sell, go for 98.67% of asking, prices are down 1.3% from a year ago. Verified MLS market data through August 2026.
Market temperature
Balanced market
4.8 months of supply. Under 3 favors sellers, over 6 favors buyers.
What homes sell for
$291,232
median sale price
How fast they sell
85 days
median time on market
Supply and competition
4.8 months
of supply on the market
In Winter Haven