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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
Melissa Vance profile picture
Mainframe Real Estate

Melissa Vance

Completed Profile
7 reviews
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17years of experience
22sales in the last 12 months
275transactions all-time
The Hard Working Nice Guy's Team  profile picture
Re/max 200 Realty

The Hard Working Nice Guy's Team

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40years of experience
0sales in the last 12 months
1,325transactions all-time
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PRIME AGENT
Meagan McCutcheon profile picture
Century 21 Alton Clark

Meagan McCutcheon

Completed Profile
View Profile
7years of experience
9sales in the last 12 months
68transactions all-time

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

Re/max Town And Country

Kelly Sue Stonebreaker

Open 8:00 AM - 9:00 PM
Usually responds in 30 minutes
21 years of experience
62 sales in last 12 months
600 transactions all-time
Serves Winter Park

About

I have been a Florida resident for 32 years, I moved here from Battle Creek MI in 1982. I am a member of BNI, am the President of the Professional Connections Group, Secretary of the Oviedo Police Foundation and prior Board Member of Hope Helps, Inc. I am a former marathon runner, I have 4 beautiful grandchildren and love Junior Mints! I have also been a licensed realtor since 2003. I am now the team leader of Stonebreaker Home Team with RE/MAX Town & Country. Alongside my daughter, Tori Myers, fellow amazing agent, Christine Bowen plus our team administrator & dedicated transaction coordinator, we work hard to help you achieve your real estate dreams. Whether you are looking to sell your property, buy a new one or both, we will work alongside you to create a seamless real estate transaction so you don't have to stress it! When you're with family, you're home! We can't wait to have you be a part of our real estate family!

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Achievements

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Top Volume Producer 2025

RE/MAX Chairman's Club, Top Producer, ORRA Gold award, REAL Producer's Top 500

Graduate Degree

GRI, Licensed real estate agent

Business Highlights

Buyer Representative, Condominiums, Distressed Properties, Farm/Ranch
Satisfaction guaranteed

Goyal & Decoster

Renata Dove

Open 9:00 AM - 9:00 PM
Usually responds in 1 hr
Prime Agent Badge
PRIME AGENT
1 year of experience
Serves Winter Park

About

I have over 20 years of experience in negotiations from small business owners to C-Level 1-10 Billion dollar Enterprises. My background experience enables me to sell your home and/or find your perfect home maximizing your profit in the shortest amount of time. Your goal is my goal. I love what I do serving my clients. I am passionate to help you achieve your goals and start the next chapter of your life. I provide an exclusive VIP Client experience and your satisfaction guaranteed.

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Achievements

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Top Negotiator 2025
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Top Listing Agent 2025
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Top Producer 2025

Top Producer May 2023

Graduate Degree, Rollins College
Organizational Communication/Business

Licensed real estate agent

Business Highlights

First Time Buyers, Luxury Properties, New Homes, Relocation
Award for Top Producer 14 listings in the month of May 2023
Award for Top Producer 8 Live Listings

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

The Rampersad Team

Christina Rampersad

Open 24 hours
Usually responds in 5 minutes
9 years of experience
58 sales in last 12 months
352 transactions all-time
Serves Winter Park

About

Christina Rampersad is an experienced Real Estate Agent currently serving the competitive Central Florida and beyond housing market. She is in the top 1% of her brokerage and is also one of the top 250 realtors in Central Florida. Christina has a demonstrated history of working in the real estate industry and is recognized by clients for her superior customer service and attention to detail. Skilled in Analytics, Banking, Sales, New Home Sales, and Investment Properties, she can assist you with all of your real estate needs.

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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 Listing Agent 2025

Top 1% brokerage performance

Associate's Degree

Licensed real estate agent, SRS, SFR, A-REO, Pricing Strategy Advisor, Real Estate Negotiation Expert

Business Highlights

Military (relocation), Distressed Properties, New Homes, Luxury Properties
Top Negotiator award Meets deadlines
Top in communication
Meets deadlines

Compass Florida Llc

Dallas Ackley

5 reviews
Open 10:00 AM - 5:00 PM
Usually responds in 10 minutes
11 years of experience
69 sales in last 12 months
300 transactions all-time
Serves Winter Park

About

As a second-generation REALTOR, Dallas Ackley was born with a passion and natural talent for real estate and with a background of interior design, can help buyers turn a house into a dream home or help sellers stage their home to get top dollar. She's been recognized as a Top Producing Agent and is in the top 1% of Central FL Realtors. Customer service is a top priority. Dallas will help guide and educate you through every step of the process from contract to close. She is trustworthy and works from her heart..she is knowledgeable from short sales to investment property to new constructions homes. Always looking for continued growth to better serve her clients, Dallas has earned her Graduate Realtor Institute designation providing her with a solid foundation of knowledge and skills to navigate the current real estate climate. In addition, she has earned the premier seller representation credential of SRS and the accredited buyer representation designation, ABR.

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Achievements

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Top Listing Agent 2025
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Top Buyer's Broker 2025
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Top Sales Producer 2025

Rookie of the year 2014,President's Award 2016, Top Producer 2016/17, Entrepreneur of the Year-WCR, 2018, Top Sales Agent 2018,2019, 2020, 2021

Bachelor's Degree, SIUE
Bachelors of Science

GRI, ABR, GREEN, RSPS, SRS

Business Highlights

1031 Tax Exchange, Concierge Services, Condominiums, First Time Buyers
Top 1% of Central Florida Agents

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
  • J L

    "Great realtors. My home sold in five days!"
    Joe L. from Illinois / Sold a home using RealEstateAgents.com
  • B W

    "My selected agent was very thorough, professional, and attentive to my needs. He was absolutely the BEST!"
    Bonnie W. from Indiana / Sold a home using RealEstateAgents.com
  • J S

    "Had issues with the title company, which agents handled."
    John S. from Arizona / Sold a home using RealEstateAgents.com
  • 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:

The median prices are rising year over year
More homes are being listed than sold
55
balanced market
Buyer's Market
0102030405060708090100
Seller's Market
Real Time Market Profile

Median List Price

$688K

Per Square Foot

$388

Days on Market

111

Total Listings

223

Market Action Index

55

Median List Price

Sun, Jun 21, 2026

Median List Price
1 Year

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