Find the perfect Windermere real estate agent

We analyze millions of home sales to find the best performing real estate agents.

Top Windermere real estate agents

HomeLight analyzes hundreds of thousands transactions to identify the best real estate agents of Windermere. And here's what we know about the top 3% of the 999 active Windermere real estate agents: compared to the average agent, the top 3% work 1.8x more transactions and move homes 40.01 days faster.

"I was delighted with the service that HomeLight provided to assist in my search for a good Realtor to act for me in the sale of my condo.. My condo sold in three days and was the easiest property transaction I have ever had. Thank you."

Jennifer C.

See how 20 of the top REALTORS® and real estate agents in Windermere, FL stack up

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Abby N.
RE/MAX 200 Realty
About Abby

Welcome to your #1 resource for buying and selling real estate in the Central Florida region! Find out for yourself why Abby Nelson has led her team to be one of the TOP REAL ESTATE TEAMS in the country. Abby is both a proud Recipient of Orlando Magazine’s Hot 100 Award and recognized as a Five Star Professional for several years. Abby and her team have also been named one of The Wall Street Journal’s Top 250 Teams by Transaction Sides! As one of the top agents in the Central Florida area, Abby can assist you with ALL of your real estate needs.

Abby's reviews

"Working with Abby is always a pleasure. She is an experienced professional that I trust completely ..."

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Condo Transactions
160
Townhome Transactions
130
Single Family Home Transactions
1.2k
Achievements
  • Top Negotiator 2020
  • Top Producer 2020
  • Sells Homes Fast 2020
  • Move Safe Certified 2020
  • HomeLight Home Loans Specialist 2020
  • Title & Escrow Specialist 2020
NAR Certifications
REALTOR®
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Kathryn S.
Keller Williams At The Parks
About Kathryn

Kathryn Stelljes PA, Residential Real Estate Professional - Kathryn is the owner of the ThinkLiveBe Team at Keller Williams Realty at the Parks in Orlando, Florida. As a graduate of the University of Central Florida and the Art Institute of Pittsburgh Kathryn has both knowledge and expertise in selling and design. She has earned a Bachelor's Degree in Marketing, a degree in Residential Planning, holds designations in home staging and short sales, and earned the extensive Graduate Realtor Institute Designation (GRI). Her background in these design fields and passion for real estate technology has advanced her ability to market listings for sale in the realm of residential real estate. As a long time Orlando resident and market expert, she understands the trends for home-buying in the Downtown Orlando, College Park, and Winter Park markets. Understanding the local market and needs allows her to sell her listings for top dollar and provide expert advice to home buyers who wish to live in the neighborhoods near Downtown Orlando and Winter Park. Over the years, she has sold many homes across Central Florida and believes that customer service is key to listing and selling homes successfully. Her goal is to utilize her specialized knowledge to give the best service in Orlando and retain them as clients for life.

Kathryn's reviews

"Kathryn was extremely helpful in helping me find my first home. She only showed me those homes that ..."

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Single Family Home Transactions
370
Condo Transactions
50
Townhome Transactions
27
Achievements
  • Top Producer 2020
  • Top Producer 2019
  • Move Safe Certified 2020
  • HomeLight Home Loans Specialist 2020
  • Title & Escrow Specialist 2020
NAR Certifications
REALTOR®
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Alex & Amy V.
The Vastardis Team
About Alex & Amy

If you are looking for a Realtor, look no further. The Vastardis Team offers professional services for individuals and companies moving into or out of the Greater Orlando real estate market. Their pursuit for new technology, marketing techniques, and real estate trends guarantees that your real estate transaction and experience will be top notch. The Vastardis Team has helped over 2100 families with their real estate needs and have produced more than $515 million in sales. With such impressive numbers, The Vastardis Team has earned their place as the Number 1 Coldwell Banker Agents in the Greater Orlando area as well as the Top 100 in Florida. Amy and Alex pride themselves on customer service and satisfying all their client's needs. They will make your home buying or selling experience enjoyable thanks to their hard work and expertise.

Alex & Amy's reviews

"Alex did a great job in finding what we were looking for."

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Townhome Transactions
73
Single Family Home Transactions
680
Condo Transactions
70
Achievements
  • Top Producer 2020
  • Top Producer 2019
  • Move Safe Certified 2020
  • HomeLight Home Loans Specialist 2020
  • Title & Escrow Specialist 2020
NAR Certifications
REALTOR®
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Jennifer W.
Wemert Group Realty
About Jennifer

Last year, we sold homes 25 days faster and for 3% more money than the average Realtor in our area. Put our experience and dedication to work for you. We are expert negotiators, skilled at finding hidden inventory, and will work tirelessly to help you with your real estate goals. Our team's 1200+ Client Testimonials across the web demonstrate that we are highly experienced, technical, and we serve with our hearts. Our team has been a Hot 100 Agent in Orlando continuously since 2004, Real Trends named us in 2020 one of the TOP 20 TEAMS in the NATION... What this means for you is that we will use our time, knowledge, and expertise to help you reach your real estate goals and that we are here and ready to serve. We look forward to working with you.

Jennifer's reviews

"Local experts in the Orlando market and lead by team leader Jenny Wemert who is passionate about her..."

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Townhome Transactions
400
Condo Transactions
350
Single Family Home Transactions
4.2k
Achievements
  • Top Producer 2020
  • Top Negotiator 2020
  • Sells Homes Fast 2020
  • Top Producer 2019
  • Top Negotiator 2019
  • Move Safe Certified 2020
NAR Certifications
REALTOR®
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Chris C.
Creegan Group
About Chris

*Most Homes Sold 2016 through 2020, Orlando Regional Realtor Association* *358 Homes sold in the last year* *#1 Boutique Brokerage since 2016* *Orlando Magazine Hot 100 Realtor* *Orlando Regional Realtor Association - Top Producer Club * DIAMOND Club Member* *Orlando Style Magazine Top 10 Realtor* *Voted Orlando's 32 best* *Published by the Winter Park/ Maitland Observer as selling the most number of homes per year* Chris Creegan is the Broker/Owner of Creegan Group. With two convenient locations to serve you Winter Park/Maitland and Downtown Winter Garden, our office services Orange, Seminole, Lake, Volusia, Osceola, and Polk Counties. Originally licensed in 2006, Chris and his team have seen the ups and downs of the real estate market and they know how to help our customers properly navigate the complex market. Whether the market is a buyer's market or a seller's market, let their experience work for you! At Creegan Group, they employ only full-time, full-service agents, dedicated to providing the highest level of customer service in the industry. Creegan Group agents have more training, more experience, and more resources available to the standard agent.

Chris's reviews

"Chris created a seamless selling experience for us. He listened to our goals and completely exceede..."

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Single Family Home Transactions
1.4k
Townhome Transactions
81
Condo Transactions
93
Achievements
  • Top Producer 2019
  • Move Safe Certified 2020
  • HomeLight Home Loans Specialist 2020
  • Title & Escrow Specialist 2020
NAR Certifications
REALTOR®
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Christopher B.
The Pinnacle Homes Group at Keller Williams Classic Realty
About Christopher

Chris Bessette is a founder of The Pinnacle Homes Group at Keller Williams and has been assisting buyers and sellers purchase and sell residential real estate since 2007. The team has been ranked the #1 Sales Team in the Keller Williams Dr. Phillips Market Center since 2010! Our team mission is to help buyers and sellers navigate the complexities of a real estate transaction based on our professional knowledge and experience, treating all parties with respect, honesty, and care in order to build life-long relationships and help establish communities.

Christopher's reviews

"Chris is a highly skilled and easy to work with realtor. He is professional, courteous, knowledgeab..."

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Single Family Home Transactions
630
Condo Transactions
72
Townhome Transactions
39
Achievements
  • Top Producer 2020
  • Move Safe Certified 2020
  • HomeLight Home Loans Specialist 2020
  • Title & Escrow Specialist 2020
NAR Certifications
REALTOR®
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David M.
Keller Williams Heritage Rlty
About David

With David's business background and education he has been able to build one of the top real Estate Sales Teams within Central Florida. Other than leading his team he works mainly with home owners in Central Florida who are trying to get their homes sold for top dollar and within a short period of time! His results in these two areas consistently outperforms the averages in Metro Orlando! For the past five years he has been able to help his sellers get their homes sold for 1 to 4% more (sold to list price) and under contract in half the amount of time than the average in Central Florida. By helping his sellers get their house in top showing condition prior to listing and by providing maximum exposure to 100% of the buyers during the listing period, he is able to create very high demand for their homes which ultimately leads to a higher sales price and being under contract within a shorter period of time. His success can be mainly attributed to the way he does business with his clients; he works more as a consultant than a sales person. By asking his sellers the right questions he is able to find out what's important to them about the selling their house which then enables him to meet and exceed their expectations! About David Grew up in Jacksonville, FL but has lived in Central Florida for over 20 years Double Major in Management and Marketing as well as a Masters in Business Administration from the University of North Florida. Real Estate Industry since 2006 President and Listing Specialist for team The Miller Realty Group has been recognized numerous times for being the Top 100 REALTORs in Metro Orlando by Orlando Magazine Soccer Coach for Orlando City Youth Soccer

Single Family Home Transactions
520
Townhome Transactions
38
Condo Transactions
22
Achievements
  • Top Producer 2020
  • Top Negotiator 2019
  • Move Safe Certified 2020
NAR Certifications
REALTOR®
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Simon S.
The Simon Simaan Group
About Simon

The Simon Simaan Group has more than 50+ years of combined real estate experience with over $170 Million Sold since its inception. Currently ranked Top 1% of Realtors in Central Florida with a 5 Star customer satisfaction rating on every sale. Orlando Style Magazine 5 Star Realtor, Orlando Magazine Hot 100 Realtor, Best of Zillow Agent. The group composes of extraordinary property specialists that are hardworking and determined with outstanding problem-solving techniques and transparent communication skills. Knowledgeable with local, national, & international clientele and exceptional skills in contract negotiation gives Simon and his team an unquestionable edge in today’s real estate environment. “Our savvy approach to residential sales and listings offers in-depth knowledge, a variety of specialties, and strong negotiating. We also utilize exquisite marketing paired with unparalleled service to showcase our homes.” Simon’s background as a General Contractor for an international construction company brings a broad and in-depth knowledge of Buying and Selling a home. Simon has an understanding of different cultures, having done business, traveled, and lived in many parts of the world. “We know that buying or selling real estate is a major event in people’s lives and we have the compassion and knowledge to help with this financial, legal, and emotional experience.” All of this is done with total confidentiality and proven results. The Simon Simaan Group is highly motivated and always willing to go the extra mile to ensure that the deal is done correctly to the clients' satisfaction. Simon believes in the importance of integrity and fairness by utilizing all available resources. In addition, Simon, who is local to the area since 1985, has won numerous real estate awards, featured in notable publications, and earned a great reputation in real estate. “I was not only impressed by Simon's in-depth knowledge of the real estate market in Orlando, but also by the professional and knowledgeable way in which he carried out the whole process of selling my house. My phone calls and questions were responded to promptly, and he always explained very clearly and intelligently what was happening every step of the way.” -June K “I don't know if words can express how amazing of a professional he is. He was somehow able to anticipate all of my needs and met every one of them.” -Tim L “Our experience with Simon Simaan as our realtor was excellent. Simon is caring, capable, professional, an exceptional communicator and always projected honesty and integrity. We highly recommend Simon Simaan as your realtor of choice if you are buying or selling a property in the Orlando.” -Stan & Diana P

Simon's reviews

"Exceptional in every aspect "

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Townhome Transactions
30
Single Family Home Transactions
180
Condo Transactions
18
Achievements
  • Top Producer 2020
  • Top Producer 2019
  • Move Safe Certified 2020
  • HomeLight Home Loans Specialist 2020
  • Title & Escrow Specialist 2020
NAR Certifications
REALTOR®
Ask a question
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Kyle M.
Upwell Realty
About Kyle

Kyle Madorin has gained wide recognition in Orlando and nationally for his exceptional concierge service in real estate. Ranked as one of the Top 100 Agents in the country by RateMyAgent in 2021, he offers his clients a rare level of personalized attention that diverse positions in customer relations have fine-tuned. 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 500 Agent by Orlando Real Producers Magazine. Fortified by numerous agent of the year awards and a HomeLight top producer designation, Kyle is a former chairman of his previous brokerage’s Agent Leadership Council. A Certified Luxury Home Marketing Specialist (CLHMS) and Million Dollar Guild appointee, Kyle has achieved top performance levels in the luxury sector. Still, he provides the same high-touch service to all clients, regardless of price point. After growing up in Chicago’s west suburbs, Kyle studied public relations at Bradley University, where he obtained an advanced internship in guest relations with The Walt Disney Company. Kyle quickly fell in love with Orlando while making his mark at Walt Disney World, earning positions as a Magic Kingdom tour guide and as a VIP guide for celebrities and visiting dignitaries. Through Disney’s extensive training regimen and Kyle’s hands-on experiences in these unique roles, he developed the high standards of personalized service and attention to detail for which he is known. Recruited to Greenwich, Connecticut, as the executive administrator for the former CEO of Lord & Taylor and chairman of the board of Ann Taylor, he further engaged his talent for delivering singular client experiences. After Hurricane Katrina hit New Orleans, Kyle andhis wife, Shalea, relocated to Louisiana to help her parents rebuild their company. Shalea and Kyle used their acumen to assist with the expansion of her family’s wedding business into the No. 1 venue in New Orleans and a destination for weddings throughout the region. After seven successful years of growth, and spurred by his own experiences in the field, Kyle sought a new challenge with a new ceiling: real estate. Real estate professionals, according to Kyle, are not salespeople but service providers. 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 — from first-time homebuyers to luxury property investors and relocators — receives Kyle’s equal care and attention as they find real estate success together. Aided by Kyle’s advanced problem-solving skills and tech-forward approach, success is the only outcome. Kyle met Shalea while working at Disney World, and the couple now enjoys sharing their love of the Disney theme parks with their two sons. A Life Loyal member of the Sigma Chi International Fraternity, he finds time to give back to his community by volunteering with organizations such as the Fisher House Foundation and United Abolitionists.

Townhome Transactions
37
Condo Transactions
43
Single Family Home Transactions
220
Achievements
  • Sells Homes Fast 2020
  • Top Producer 2020
  • Sells Homes Fast 2019
  • Top Negotiator 2019
  • Move Safe Certified 2020
  • Title & Escrow Specialist 2020
NAR Certifications
REALTOR®
Ask a question
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Barrett S.
Keller Williams Advantage Realty
About Barrett

Barrett Spray is a real estate agent with Keller Williams Advantage Rlty in Florida and has been in the real estate business for 27 years. Barrett's coverage area includes all 7 counties in Central Florida. HomeLight ranks Barrett as one of the top 2% of agents in Central Florida for successfully selling homes and as one of the top 1% of agents for condos. Numbers aside, Barrett started a real estate team because the minimum is never enough for this guy. He always wants to do more, learn more, achieve more, help more. The team, through the different personality profiles of its individual members and their unique expertise, is far more effective as a group than he ever was alone. As a team we're all here to learn and grow from each other and give our clients the best, most well-rounded experience we can and none of us would have it any other way.

Barrett's reviews

"Barrett demonstrated knowledge about the market. He clearly explained the steps leading to closing...."

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Townhome Transactions
120
Condo Transactions
100
Single Family Home Transactions
460
Achievements
  • Top Negotiator 2019
  • Move Safe Certified 2020
  • HomeLight Home Loans Specialist 2020
  • Title & Escrow Specialist 2020
NAR Certifications
REALTOR®
Ask a question
View profile

Find your perfect real estate agent in Windermere

Why you need a top real estate agent in Windermere, FL

Hiring a real estate agent is a big decision, and it can be an overwhelming process. HomeLight uses trusted data to simplify your search. For example, would you prefer a highly experienced top agent doing 1015 transactions a year, or the average agent who does 202 transactions a year? It’s probably a no brainer. Let’s see what kind of time and money you could save with a top Windermere agent!

Top Seller's Agents

Windermere top real estate agents make $26,607 more on home sales and sell in under 50 days. That's 5200.2% more money and 1.8x faster than a sale from an average agent's transaction.

Sale Price / List Price (%)

Days on Market
Lower is better

Homes Sold / Yr


Top Buyer's Agents

The top 3% Windermere buyer's agents buy 1.8x more homes in the same area and save $114,354 on their clients' home purchases. That's 53.6% more savings than the average home sale!

Condos Sold / Yr

Homes Purchased / Yr

Sale Price / List Price (%)
Lower is better

Ratings and reviews of top real estate agents in Windermere, FL

Top Agents
4.9 stars
Avg. Agents
4.9 stars

Top real estate agents in Windermere score an average rating of 4.9 out of 5 stars, compared to the typical Windermere agent who scores only 4.9 stars. We collect the latest ratings and reviews of top real estate agents in Windermere and update them here to show you what their past clients have to say.

Recent reviews for Windermere real estate agents and REALTORS

Picture of M.S. Livingston
M.S. Livingston
Coldwell Banker Residential Re
Dec 12, 2020

“I contacted Matt after finding one of his listings online. I made a quick visit and found the house to be exactly as described and we made the deal long distance effortlessly...even the closing! Matt's years of experience in this community make him an invaluable source of contacts and vendors. Mo...“

Picture of Maria Helioti
Maria Helioti
Keller Williams Realty
Nov 02, 2020

“ Simply put, Kostas is amazing. Words can't fully express the gratitude we have for Kostas Karatzas. He was so easy going, genuine, and helped us through the stressful events of selling our home and buying another. He went light-years above and beyond anyone's reasonable expectations, coordinating...“

Picture of Tabbitha Radin
Tabbitha Radin
Lakefront Investment Realty
Oct 28, 2020

“We have bought and sold a lot of properties and the experience we had with David was excellent. The marketing of our property was very professional and we had it under contract and closed faster than we could have hoped. If we want to sell or buy in the future then we will 100% use David and we woul...“

Picture of Cleo Miller
Cleo Miller
TC Orlando Homes
Jan 12, 2021

“Mr. Soto listened to our situation and helped us develop a great plan to sell our property and home. We felt comfortable throughout the process because of being kept up to date as to the next step along the way to success. Anyone who chose to use TC Orlando Homes would surely get the very best pro...“

Picture of Beth Watson
Beth Watson
Keller Williams Realty
Nov 10, 2020

“Shout Out to Shaunda Hall with Keller William Classic Reality. We listed our house early October and closed yesterday! I was able to put my trust in Shaunda from the get go and she didn’t let me down. Quick to respond when I had questions and always on the ball when I had request. What a gr...“

"HomeLight immediately identified 3 top-notch, high producing real estate agents that knew the market where my home was located. After speaking with them, I chose one superbly qualified, experienced agent. The house sold in one day! "

Lindsay K.

HomeLight Client

"We believe we received the highest price for our home through her tireless efforts. We would highly recommend HomeLight in the future for anyone desiring to find a reputable real estate agent in their area."

Laurie F.

HomeLight Client

"HomeLight had the agent credibility during my selection process and also had my confidence that I had a partner standing behind the work my agent did... All in all, my experience with HomeLight was quick, easy and effective. "

Matt S.

HomeLight Client

Check out some of our other resources for Windermere homeowners

When's the best time to sell your home in Windermere?
Use housing market data in Windermere to learn the best and worst months to sell your home.
How much commission do real estate agents make?
Use this calculator and real estate agent commissions data to find out.
Sell your house in Windermere fast
Find out what cash buyers are willing to pay for your home right now.
Advice from America’s Top Agents
Get the latest real estate tips and learn how to sell your home faster and for more money.
Simple real estate calculators
Use our free calculators to help you make informed financial decisions when buying or selling a home.
Find out what your home is worth
Get a free estimated value of your home in less than 2 minutes.

Find your perfect real estate agent in Windermere, FL