Updated regularlyAnalyzed 2,311 agents

Find the top real estate agents in Windermere, FL

We analyzed 2,311 Windermere agents on closed volume, sale-to-list ratio, and review quality. Tell us what you’re looking for and we’ll match you with the best agent, suited for your exact needs.

100% freeNo obligationBased on historical performance
How this works
2,311agents analyzed
Every licensed Windermere agent — not a paid directory.
45M+transactions analyzed nationwide
Our algorithm scores every agent across dozens of variables — volume, sale-to-list, days on market, and more.
200,000+customer testimonials nationwide
Real feedback from real home sellers and buyers, cross-referenced with closed transactions.
100% Freeto you
No markup on commission. Agents pay us only if you close.
MLS, public records, HomeLight database

Featured in

Why it matters who you pick

Top Windermere agents sell faster and for more — here’s the gap.

Data pulled from Windermere listings closed in the last 12 months. The top 3% of agents consistently outperform the rest of the market on every seller metric.

Metric (last 12 months)
Top 3% of Windermere
Average Windermere agent
Top performers…
Sale-to-list ratio
99.9%
94.6%
+5.3 pts higher
Days on market
52
115
63 days faster
Homes sold per year
705
91
7.7× more deals

Based on Windermere listings analyzed over the last 12 months.

Top Real Estate Agents & Realtors® in Windermere, FL

  1. Melissa Hastings5.0/5 (9 reviews)
  2. Warren Davis5.0/5 (2 reviews)
  3. Jim WilsonReal Broker, LLC5.0/5 (2 reviews)
  4. Emily LewisLakeside Realty Windermere Inc.5.0/5 (1 reviews)
  5. Laura Gilmore5.0/5 (1 reviews)
  6. Jay Kendall5.0/5 (1 reviews)
  7. Simon SimaanThe Simon Simaan Group 5.0/5 (1 reviews)
  8. Judy BlackUpside Real Estate, Inc.5.0/5 (1 reviews)
  9. Tara MooreTara Moore Real Estate5.0/5 (1 reviews)
  10. Darrell Nunnelley1.0/5 (1 reviews)
  11. Phat NguyenKeller Williams Advantage II
  12. Sherry Duvall
  13. Valerie Kennedy
  14. Deanna ArmelARMEL REAL ESTATE
  15. Christine Clark-weber
  16. Irhelma Pieterse
  17. Adam Judd
  18. Adam EisenPlatinum Realty Group of Central Florida
  19. Nancy Bhavsar
  20. Kari FleckThe Real Estate Collection LLC
  21. Barbara Burks
  22. Renee Funk
  23. Andrea Endlein
  24. Jamie Leizan
  25. Corey Mathias
  26. Bill Martini
  27. Bistra Iordanova
  28. Sue Webb
  29. Billinda Boldt
  30. Lorena Martinez
  31. Brian Mitnik
  32. Tommy Mydlo
  33. Patrick Hancock
  34. James MartinKeene's Pointe Realty
  35. Mildred Hershiser
  36. Matt TomaszewskiPremier Realty Partners Inc
  37. Ken PozekReal Broker LLC
  38. Christopher ChristensenRegal R.e. Professionals Llc

How Agent Match works

Meet three top Windermere listing agents in under 48 hours

We’ve done the vetting. You pick the fit. The entire service is free — we’re paid by agents only if you close a transaction.

1
Illustration of a home valuation form

Tell us about your home

Two minutes, five questions. Address, timeline, price tier. We auto-fill what we can from public records.

2
Illustration of agent matching results

We match you to 2–3 agents

We shortlist the top agents in your specific neighborhood and price tier — not the whole city list.

3
Illustration of a homeowner interviewing a real estate agent

You interview. Zero obligation.

Meet your matches, compare strategies, and pick the one who fits — or none at all. You're in control the whole way.

“HomeLight is a way to narrow the field and find the right agent for your house sale… Within 36 hours of listing, we had a contract.”

Frank L.

Sold with a HomeLight Agent

“I'd already met two agents on my own. HomeLight's match was better than both. Smooth from handoff through closing.”

James T.

Sold in 9 days

Windermere FAQ

Questions Windermere sellers actually ask.

Answered with live Windermere data. Updated monthly when the MLS refreshes.

The Windermere market is competitive, with well-priced homes typically selling within days of listing at or above asking price. Inventory remains below historical averages, which continues to favor sellers. Median prices have appreciated year-over-year, driven by strong demand and limited supply.
The national average real estate commission is typically between 5% and 6% of the home's final sale price, while the average in Windermere hovers around 3.0%. The exact rate is always negotiable. Post-2024 NAR settlement, buyer-side compensation is now separately negotiated between seller and buyer directly.
Based on HomeLight's data from sold homes in Windermere since 2014, June historically produces the highest sale prices, while July sees homes sell fastest. That said, low inventory year-round means motivated buyers exist in every season, so listing when your home is ready often beats waiting for the "perfect" month.
Prioritize agents with recent Windermere transaction history (25+ closings in the last 12 months), a strong sale-to-list ratio (102%+ is excellent), verifiable client reviews, and proven specialization in your neighborhood and price tier. Always interview 2–3 candidates before deciding.
Well-priced homes in desirable Windermere neighborhoods often accept offers within a week. From list date to close-of-escrow, plan on 30–45 days total, including buyer financing contingencies and inspections.
If timing for peak price, Windermere data points to June as the historically strongest month for sale prices; for the fastest sale, July sees the fewest days on market. That said, holding several months carries real risk — rate shifts or softening demand can reduce your net proceeds. In most cases, listing when your home is ready outperforms trying to time the market.
HomeLight's Agent Match is 100% free for home sellers and buyers, with no obligation to work with the agents we recommend. We collect a referral fee from the agent only if you close a transaction with them — the service costs you nothing extra.
We analyze 45M+ transactions nationwide and score every licensed Windermere agent on recent transaction volume, sale-to-list ratio, days on market, client review quality, and neighborhood specialization. Only the top few percent of Windermere agents make our featured list, and we re-score monthly as new data arrives.
Absolutely — and we encourage it. HomeLight matches you with 2–3 top-performing Windermere agents tailored to your home's location, price tier, and timeline. There's no obligation to work with any of them, and our concierge team can help you prepare questions specific to your neighborhood.
We analyze your home's location, estimated price tier, and your stated timeline, then match you with 2–3 top agents. A HomeLight concierge follows up within minutes to review your matches and answer any questions. The whole process — from submit to first agent conversation — typically takes under an hour.

How we match agents

Out of 2,311 agents in Windermere, we find the 2–3 best to sell your home.

Most agent directories are paid listings. HomeLight is different — our algorithm ranks every licensed Windermere agent on objective transaction data.

45M+ transactions
We score every agent on every sale — recency, price band, and neighborhood — so your match reflects current performance, not old reputation.
Performance weighted
Sale-to-list ratio, days on market, and transaction volume — not star ratings or paid directory placement.
Client satisfaction
200,000+ verified reviews, cross-referenced against actual closed transactions to remove unverified feedback.
Hyperlocal fit
We match you with agents who have a proven track record in your specific neighborhood and price range — not just city-wide.

Agent rankings are updated regularly. Data sourced from MLS, public records, and HomeLight’s transaction database.

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