Best Real Estate Agents in Winter Park, FL• Updated
Looking for the best real estate agent in Winter Park, FL? This page ranks the top realtors in Winter Park by actual transaction data — not reviews or paid ads. Whether you want to find a top listing agent in Winter Park, FL or buy a home in Winter Park, our 2026 rankings use verified sales records, days on market, and price retention to surface the highest-performing agents.
Market Pulse: Opportunity 📈
The Winter Park, FL real estate market is currently a Buyer's Market. Homes are retaining 92% of their value (Sale Price to List Price Ratio). With 11 active listings and 4 closed sales this month, inventory remains at 15 months of supply. Trends over the last half-year show median values moving up by 12%, while Average Days on Market has decreased by 7%. Listings in Winter Park are moving 13 days faster than the Orange average.
Top Listing & Buyer's Agents in Winter Park, FL
Detached Homes
Mid-Market Detached Home Market Trends Median Price Market Trend The average price in the Mid-Market Detached Home segment has softened by 46% over the last 2 months. Days On Market Avg. Market Trend Lower is better Days on market for Mid-Market Detached Home is decreasing, with homes now staying on market for 59 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the Mid-Market Detached Home market is strengthening, with the Sale Price to List Price Ratio now at 101%.
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Townhomes
Entry Level Townhome Market Trends Median Price Market Trend The Entry Level Townhome tier commands a price of $215K. Days On Market Avg. Market Trend Lower is better Townhome homes in the Entry Level range average 52 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Entry Level Townhome assets receive 99% of list price.
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Mid-Market Townhome Market Trends Median Price Market Trend The average price in the Mid-Market Townhome segment has risen by 155% over the last 2 months. Days On Market Avg. Market Trend Lower is better Days on market for Mid-Market Townhome is decreasing, with homes now staying on market for 34 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the Mid-Market Townhome market is strengthening, with the Sale Price to List Price Ratio now at 100%.
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Condo/Co-op
Entry Level Condo/Co-op Market Trends Median Price Market Trend The Entry Level Condo/Co-op tier commands a price of $77K. Days On Market Avg. Market Trend Lower is better Condo/Co-op homes in the Entry Level range average 98 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Entry Level Condo/Co-op assets receive 87% of list price.
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Multi-Family (2-4 Unit)
Ultra-Luxury Multi-Family (2-4 Unit) Market Trends Median Price Market Trend The Ultra-Luxury Multi-Family (2-4 Unit) tier commands a price of $1M. Days On Market Avg. Market Trend Lower is better Multi-Family (2-4 Unit) homes in the Ultra-Luxury range average 114 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Ultra-Luxury Multi-Family (2-4 Unit) assets receive 67% of list price.
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Winter Park Real Estate Market Trends July 2026
Inventory Breakdown by Segment
| Property Type | Entry Level | Mid-Market | Ultra-Luxury | Total |
|---|---|---|---|---|
| Condo/Co-op | 2 | — | — | 2 |
| Detached Home | — | 3 | 6 | 9 |
Market Insights & FAQ
How is the real estate market in Winter Park, FL performing right now?
The data indicates a stable environment in Winter Park, FL. Inventory is at 15 months, meaning a balanced environment with steady turnover. Inventory levels provide a healthy range of options for prospective buyers.
What are the current pricing trends for Winter Park, FL real estate?
Currently, $610,000 represents the median entry point in Winter Park, FL. Over the past half-year, home values in Winter Park have moved upward by approximately 12% based on regional transaction data.
Are sellers in Winter Park, FL getting their full asking price?
Buyers have room for negotiation in Winter Park, FL, with a Sale Price to List Price Ratio of 92%. On average, properties in Winter Park are transitioning from active to sold status in 61 days.
Who is the best agent to sell my home in Winter Park?
Based on closed transaction data, Tika Van Den Hurk ranks at the top of our Winter Park leaderboard earning an algorithm performance score of -268. Agent Algo's rankings are built entirely from real deal outcomes — not reviews or paid placements — so this reflects actual results in the local market.
How does the Winter Park, FL market compare to Orange trends?
Winter Park, FL maintains a distinct profile within the broader Orange region. Median home values are currently 46% higher than the regional average, reflecting the unique demand and inventory dynamics of Winter Park.
Which agent is best for buying a Ultra-Luxury Multi-Family (2-4 Unit) in Winter Park, FL?
Buyers targeting Ultra-Luxury Multi-Family (2-4 Unit) homes in Winter Park, FL may want to work with Ahmed Hamada. Their buyer transactions in the Ultra-Luxury Multi-Family (2-4 Unit) category in Winter Park, FL reflect genuine niche experience — a meaningful advantage over agents working this segment only occasionally.
Which agent is best for buying a Entry Level Condo/Co-op in Winter Park, FL?
Our data flags Mauricio Padilla as a top buyer's advocate for Entry Level Condo/Co-op properties in Winter Park, FL. Our algorithm surfaces Mauricio Padilla based on actual closed buyer deals in the Entry Level Condo/Co-op market. That's the kind of specific, verifiable track record buyers should look for in an agent.
Who is a top listing agent for Mid-Market Detached Home homes in Winter Park, FL?
Among agents with recent closings in the Mid-Market Detached Home space, Tika Van Den Hurk has the strongest performance metrics in Winter Park, FL. For sellers who want to move efficiently without overpricing, their track record in the Mid-Market Detached Home niche shows they deliver timely closes — consistently faster than the segment norm.
Who is a top listing agent for Entry Level Condo/Co-op homes in Winter Park, FL?
Robert Castro has been particularly active in Winter Park's Entry Level Condo/Co-op segment, and the numbers back it up. They've built a consistent track record in the Entry Level Condo/Co-op category specifically — not just broad volume, but demonstrated results in this exact niche in Winter Park, FL.
Who is a top listing agent for Ultra-Luxury Multi-Family (2-4 Unit) homes in Winter Park, FL?
When looking specifically at Ultra-Luxury Multi-Family (2-4 Unit) transactions, Maria Tenner consistently surfaces as a top performer in Winter Park, FL. Our algorithm ranks them based on closed transaction outcomes in the Ultra-Luxury Multi-Family (2-4 Unit) segment, not self-reported volume or marketing activity. The ranking reflects actual local performance.