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Winter Park Real Estate

Learn how to live, work, play, and stay in Winter Park, FL — best known for its charming downtown area, beautiful parks, and rich cultural offerings.

Home ⮞ Winter Park Home Search

Homes for Sale in Winter Park, FL

Map of Winter Park Homes for Sale

For Sale

Looking for Luxury Homes in Winter Park?

Winter Park Real Estate Market Trends

In June 2023, Winter Park home prices were up 3.5% compared to last year, selling for a median price of $523K. On average, homes in Winter Park sell after 18 days on the market compared to 6 days last year. There were 80 homes sold in June this year, down from 86 last year.

$522,000

Median Sale Price

80

# of Homes Sold

18

Median Days on Market

Everything You Need

A Guide To

Everything You Need

In Winter Park

Winter Park, FL is best known for its charming downtown area, beautiful parks, and rich cultural offerings. The city is also known for its historic architecture, including the famous Casa Feliz Historic Home Museum, and for being home to Rollins College, one of the top liberal arts colleges in the country. Additionally, Winter Park is known for its chain of lakes, which offer residents and visitors opportunities for boating, fishing, and water sports.

Search for top amenities in each area and learn more about the history, schools, neighborhoods, attractions, and Winter Park houses for sale in the map-based guide by Toni Marie Cafferty .

Winter Park Real Estate Updates

Everything You Need to Know about Getting Your Home Inspected Before Selling

Toni Marie Cafferty  |  November 14, 2024

Preparing for a Smooth Sale in Windermere, FL.

How to Buy a Luxury Home

Toni Marie Cafferty  |  November 14, 2024

Navigating the Luxury Market in Windermere, FL.

7 Tips for Moving with Pets

Toni Marie Cafferty  |  November 14, 2024

Ensure a Smooth and Stress-Free Relocation for Your Furry Companions.

8 Most Googled Questions About Real Estate in 2024

Toni Marie Cafferty  |  November 14, 2024

Get Answers to the Top Real Estate Questions Trending This Year.

Best Golf Courses in Windermere

Toni Marie Cafferty  |  September 14, 2024

Discover the Premier Greens of Windermere, FL.

A Guide to Windermere, FL Parks

Toni Marie Cafferty  |  September 14, 2024

Discover Nature's Oasis in the Heart of Florida's Lake Country.

Things to do in Windermere

Toni Marie Cafferty  |  September 14, 2024

Things to Do in Windermere: Exploring the Charm of Central Florida.

The Ultimate Guide to the Home Inspection Before Buying

Toni Marie Cafferty  |  September 14, 2024

Top tips for the home inspection process.

The Top Attractions in Windermere For Locals or Tourists

Toni Marie Cafferty  |  August 6, 2024

Discover the Hidden Gems of Windermere, Florida.

The Differences Between Buying A Second Home vs Investment Property

Toni Marie Cafferty  |  August 6, 2024

Choosing Between Personal Retreat and Financial Venture.

5 Best Restaurants in Windermere

Toni Marie Cafferty  |  June 26, 2024

Explore Windermere's finest dining destinations and indulge in the culinary delights this charming Florida town has to offer.

The Charm of Living in Windermere, FL

Toni Marie Cafferty  |  June 20, 2024

Experience the Perfect Blend of Luxury and Tranquility.

Discover the Best Places to Hike in and Near Windermere, FL

Toni Marie Cafferty  |  June 20, 2024

Explore the Beauty of Windermere's Natural Trails.

Flipping Houses in Windermere

Toni Marie Cafferty  |  May 29, 2024

Discover the Lucrative Opportunities of Flipping Houses in Windermere with Expert Insights and Strategies for Maximum ROI.

Architectural Landmarks in Windermere

Toni Marie Cafferty  |  May 29, 2024

Discover the Architectural Elegance of Windermere, FL.

10 Best Places to Shop in Windermere

Toni Marie Cafferty  |  May 29, 2024

Explore the Vibrant Shopping Scene in Windermere, FL, Where Charming Boutiques, Unique Specialty Stores, and Convenient Retail Options Await.

5 Home Improvement Tips for Your Luxury Windermere Home

Toni Marie Cafferty  |  September 7, 2022

Changing your space can be a hassle, make sure you’re doing it right.

Your Complete Guide to Golden Oak Luxury Home Architectural Styles

Toni Marie Cafferty  |  September 8, 2022

Get to know the types of homes found in Walt Disney World’s exclusive luxury community.

Maximizing Your Investment: Tips for Buying Property in Winter Park, FL

Toni Marie Cafferty  |  December 15, 2023

Winter Park, Florida: A Hidden Gem for Property Investors.

Luxury Living in Windermere, FL: A Guide to High-End Real Estate

Toni Marie Cafferty  |  February 24, 2024

Elevate Your Lifestyle in the Heart of Florida.

The Benefits of Working with a Windermere, FL Real Estate Agent

Toni Marie Cafferty  |  February 24, 2024

Unlocking the Door to Your Dream Home.

Prepping Your Windermere Home To Sell

Toni Marie Cafferty  |  February 25, 2022

From curb appeal to staging, here’s how to make your home shine.

What to Know Before Moving to a Winter Park Luxury Home

Toni Marie Cafferty  |  June 9, 2022

From market trends to where to buy groceries, everything you need to know about Winter Park.

How to Increase Your Home Value in Windermere

May 24, 2023

Get more out of your home with strategic upgrades and renovations.

Buying a Home in Windermere? Here are Some Frequently Asked Questions

Toni Marie Cafferty  |  July 19, 2023

Get all your questions answered about moving to the quaint waterfront community of Windermere.

Important Things to Know When Renovating Your Windermere Home

Toni Marie Cafferty  |  August 2, 2023

Financial planning and seeking advice are just two things to consider with renovating your home.

Why Winter Garden is the Perfect Place To Buy a Home in 2023

Toni Marie Cafferty  |  September 30, 2023

Raise your family or retire in a family-oriented city with easy access to all the benefits of Orlando.

The Future of Orlando Real Estate: Trends to Watch in 2023 and Beyond

Toni Marie Cafferty  |  September 20, 2023

Insights into the Orland real estate market and what you can expect in the future.

Why Professionally Photographed Homes Sell Faster

Toni Marie Cafferty  |  November 20, 2022

If you’re looking to sell quickly, a professional photoshoot is a must.

How to Confidently Make the Leap From Renter to Homeowner

Toni Marie Cafferty  |  September 26, 2022

Work with professionals to successfully transition to homeownership without the stress.

The Best Fine Dining Restaurants in Central Florida

Toni Marie Cafferty  |  July 27, 2022

Winter Park, Windermere, and Golden Oak all have restaurants to please every palate!

12 Family-Friendly Activities in Lake Nona

Toni Marie Cafferty  |  May 8, 2022

This new and upcoming Orlando neighborhood has a lot to offer families with kids of all ages.

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