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FloridaWinter Park

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Winter Park, FL, is a picturesque city known for its stunning landscapes and cultural richness, making it an ideal location for families and homebuyers alike. With attractions like the enchanting Mead Botanical Garden and the renowned Charles Hosmer Morse Museum of American Art, residents can experience both natural beauty and artistic inspiration on a daily basis.

The real estate market in Winter Park is competitive, underscoring the importance of partnering with a skilled licensed real estate agent. A top real estate agent brings invaluable expertise, helping buyers navigate the complexities of the market with ease and ensuring the best possible investment. RealEstateAgents.com exclusively collaborates with the leading agents in the area, making the process of finding a trusted professional simple and efficient, ultimately enhancing your home buying experience.

Featured Agents in Winter Park, FL

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PRIME AGENT
Martha J Grasty profile picture
Exp Realty Llc

Martha J Grasty

Completed Profile
3 reviews
View Profile
22years of experience
55sales in the last 12 months
The Hard Working Nice Guy's Team  profile picture
Re/max 200 Realty

The Hard Working Nice Guy's Team

View Profile
40years of experience
0sales in the last 12 months
1,325transactions all-time
Prime Agent Badge
PRIME AGENT
Didem Hanley profile picture
Lpt Realty Llc

Didem Hanley

2 reviews
View Profile
19years of experience

Compare 15 top-performing real estate agents in Winter Park, FL

Century 21 Alton Clark

Meagan Mc Cutcheon

Completed Profile
Usually responds in 1 hr
Prime Agent Badge
PRIME AGENT
7 years of experience
9 sales in last 12 months
68 transactions all-time
Serves Winter Park

About

With over 20 years of experience in sales and marketing, Meagan McCutcheon is a distinguished Florida REALTOR® known for her exceptional track record within the industry. Born in Washington D.C. and having lived in various cities across the U.S. and abroad, Meagan brings a global perspective to her work. Recognized among the top 15% of agents worldwide in her first year, she continues to receive accolades for her outstanding achievements. Leveraging her expertise in sales, negotiations, and strategic planning, Meagan is dedicated to helping clients maximize their investments in Florida real estate. Her passion for challenges drives her to craft tailored solutions that meet each client's unique needs, ensuring a seamless and rewarding real estate experience. Let Meagan guide you towards finding your ideal home or investment property, backed by a proven record of success and unwavering commitment to client satisfaction.

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Achievements

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Sells Homes Fast 2025
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Top Negotiator 2025
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Top Luxury Buyer's Agent 2025

Top 500 Orlando Real Producers, Top 50 in the state of Florida for Century 21 in 2023, Pace Setter Gold 2023, Masters Diamond Award 2023, Gold Production Award 2023, Silver Production Award 2022, Masters Emerald Award 2021, Gold Production Award 2021, Gold Production Award 2020

Bachelor's Degree, University of Florida

Licensed real estate agent

Business Highlights

Military (relocation), VA loans, Distressed Properties, New Homes
Strategic Visionary: Meagan McCutcheon stands out for her unmatched ability to craft tailored solutions that meet each client's unique needs, ensuring a seamless and rewarding real estate experience.
Outstanding Achievements: Recognized among the top 15% of agents worldwide in her first year, Meagan continues to receive accolades for her exceptional track record within the industry.
Proven Record of Success: With over 20 years of experience in sales and marketing, Meagan leverages her expertise in negotiations and strategic planning to help clients maximize their investments in Florida real estate.

Upwell Realty

Kyle Madorin

5 reviews
Open 24 hours
Usually responds in 15 minutes
12 years of experience
62 sales in last 12 months
281 transactions all-time
Serves Winter Park

About

Kyle has been an Orlando real estate agent since 2013. In addition to being Gold Key Certified for Excellence in Professionalism by the Orlando Regional Realtor® Association, he has consistently performed in the top 1% of real estate agents in the Orlando area and has been recognized as a Top 100 Agent by Orlando Real Producers Magazine. Fortified by numerous agent of the year awards and a HomeLight top producer designation, Kyle is a Certified Luxury Home Marketing Specialist (CLHMS) and Million Dollar Guild appointee, but provides the same high-touch service to all clients, regardless of price point. Kyle believes real estate agents are service providers--not salespeople. Motivated by a genuine commitment to his clients’ goals and happiness, he channels his broad experience to exceed expectations throughout every transaction. Kyle’s business mindset centers on collaboration: Every client receives Kyle’s equal care and attention as they find real estate success together.

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Achievements

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Top Producer 2025
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Top Orlando Agent 2025
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Top Negotiator 2025

2021 Orlando Top 100 Agent, 2021 & 2022 Top 100 Agent in the United States - RateMyAgent.com

Bachelor's Degree, Bradley University
Public Relations

CLHMS

Business Highlights

Buyer Representative, Concierge Services, First Time Buyers, Luxury Properties

Keller Williams Legacy Realty

Johnny Aybar

Completed Profile
Open 8:00 AM - 7:00 PM
Usually responds in 15 minutes
Prime Agent Badge
PRIME AGENT
10 years of experience
14 sales in last 12 months
110 transactions all-time
Serves Winter Park

About

Hi, I'm Johnny Aybar, Realtor and Team Lead at the Aybar Homes Team. I pride myself on always doing the right thing and what's in the best interest of my clients. With over 8 years’ experience in Real Estate, I have helped 100's of families Buy, Sell or Invest in Real Estate. I am also a 10 year Army Veteran; and given my Military background, I still have the heart of servant. I'm a husband, and a father of two adult daughters. Some of my interests involve days at the beach with family, riding my Harley and playing pool with friends. Whether you need some guidance in Real Estate or just need some advice on the best beaches, give me a call!

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Achievements

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Sells Homes Fast 2025
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Top Negotiator 2025
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Top Company Agent 2025

Top Producer 2018-2023, 5 Star Service, Top achieving Coach for 2021

Bachelor's Degree, Strayer University
Business Managment, 2010 - 2013

Licensed real estate agent, CDPE

Business Highlights

Military (relocation), VA loans, Distressed Properties, New Homes
Veteran Owned

Brown Home Group

Brown Home Group KWR

Usually responds in 1 hr
Prime Agent Badge
PRIME AGENT
10 years of experience
126 sales in last 12 months
1,122 transactions all-time
Serves Winter Park

About

The Brown Home Group @ Keller Williams Realty have been working hard. Each of our full-time, licensed Realtors are committed to reaching your goals of selling your home for top dollar or purchasing your dream home. Our full team of Realtors and assistants ensure that every details of your home sale or home purchase is handled with diligence and efficiency. Our team functions seamlessly to support every aspect of the process, from meeting with you for the first consultation to closing the sale. Buying or selling your home can be a complicated process to let us make it easy for you. With our in-depth knowledge of the current market and our experience, we have what it takes to fulfill your goals. Our sales volume consistently ranks us in the top 1% of all real estate teams in the nation. Call or e-mail us today. We'd love to meet you and show you the difference of working with an experienced Real Estate Specialist.

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Achievements

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Top Sales Producer 2025
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Sells Homes Fast 2025
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Top Luxury Listing Agent 2025

Top 1% Orlando, Hott Elite 2018-2024

Bachelor's Degree, Florida Metropolitan University
Business Marketing / Management, 1988 - 1990

Licensed real estate agent, CCIM, GRI, CDPE

Brown Home Group KWR's Video

Watson Realty Corporation

Russie Weidl Pa

Completed Profile
67 reviews
Open 8:00 AM - 10:00 PM
Usually responds in 5 minutes
Prime Agent Badge
PRIME AGENT
27 years of experience
33 sales in last 12 months
1,500 transactions all-time
Serves Winter Park

About

As your Realtor, it is my job to make your real estate buying and selling process as smooth as possible for you. You will get a full time real estate professional who goes the extra mile to help you achieve your goals. That means providing quality information and service that can benefit you immediately. I will be happy to provide all the information you need to buy or sell real estate in Lake Mary, Sanford, Heathrow, Orlando, Oviedo, Winter Springs, Debary, Deltona, Deland, Winter Park, College Park, Casselberry, Longwood, Apopka, Maitland, Winter Garden and surrounding areas. As the premier real estate agent, I look forward to serving you and will be happy to help at any time. I will put my 23 years of real estate expertise to work for you!

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Achievements

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Top Sales Producer 2025
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Top Negotiator 2025
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Top Listing Agent 2025

Gold Pinnacle 2006-2022, Rising Star 1999, Silver Pinnacle 2003, Best in Client Satisfaction 2006-2023, Presidents Club 2001,

Bachelor's Degree, Northwestern Business

GRI

Russie Weidl Pa's Video

We've introduced over 4,940,482 buyers and sellers to top local real estate agents in the past 15 years

  • R V

    "The service was great and the recommendation of the realtor was fantastic. The realtor was fair and honest he gave me a very reasonable selling price and follow the listing all the way through. The house sold within the first week."
    Rita V. from Tennessee / Sold a home using RealEstateAgents.com
  • A C

    "I used the website to identify potential agents in the new city I was moving too. I ultimately went with one of the recommended agents and had a very smooth home buying process."
    Alexis C. from Iowa / Bought a home using RealEstateAgents.com
  • R J

    "My realtor was very professional in every aspect of the sale. My house sold within a week. She called or texted me through out the whole process."
    Ruth J. from Ohio / Sold a home using RealEstateAgents.com
  • S M

    "We found an excellent Realtor, who guided us through the sale and did an excellent job along the way."
    Steve M. from Florida / Sold a home using RealEstateAgents.com
  • J B

    "Very professional, we had a great experience."
    Jon B. from Wisconsin / Bought a home using RealEstateAgents.com
  • S K

    "The agent you recommended was fantastic. He stayed in touch throughout the process. He kept us informed every step of the way. The sale was quick and couldn't have gone smoother. Would definitely recommend to anyone else and will definitely use in the future if needed."
    Stanley K. from Indiana / Sold a home using RealEstateAgents.com
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  • J S

    "Had issues with the title company, which agents handled."
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  • J H

    "We had a very unique situation... My sister and I live in different states and the house belonged to our deceased Mother... Service was great could not have been any better..."
    Joe H. from Texas / Sold a home using RealEstateAgents.com

Sell your Winter Park home with confidence

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Winter Park Housing Market Report

Market Action Index

We are extensively tracking the housing market in Winter Park, FL. Here are the strongest factors contributing to this score:

More homes are being listed than sold
The average home has been on the market a short time
49
balanced market
Buyer's Market
0102030405060708090100
Seller's Market
Real Time Market Profile

Median List Price

$602K

Per Square Foot

$347

Days on Market

105

Total Listings

297

Market Action Index

49

Median List Price

Sun, Sep 20, 2026

Median List Price
1 Year

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