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Homes for Sale in Windermere, FL

Map of Windermere Homes for Sale

For Sale

Looking for Luxury Homes in Windermere?

Windermere Real Estate Market Trends

What is the housing market like in Windermere today? In November 2024, Windermere home prices were down 11.7% compared to last year, selling for a median price of $1.5M. On average, homes in Windermere sell after 19 days on the market compared to 62 days last year. There were 2 homes sold in November this year, down from 3 last year.

$1,478,500

Median Sale Price

2

# of Homes Sold

19

Median Daus on Market

Living In Windermere

Your Guide To

Living In Windermere

Toni Marie Cafferty

Windermere, FL, located in the heart of Central Florida, is renowned for its picturesque lakes, charming small-town atmosphere, and luxurious properties. This exclusive community, situated just southwest of Orlando, offers a serene and sophisticated living environment with easy access to world-class amenities and attractions. The real estate market in Windermere features a diverse array of properties, including sprawling lakefront estates, modern single-family homes, and elegant townhouses. Home buyers are drawn to Windermere for its exceptional quality of life, scenic beauty, and proximity to both natural and urban attractions, making it a coveted destination for families, professionals, and retirees alike.

Living in Windermere means enjoying a unique blend of tranquility and luxury. The town is known for its well-maintained neighborhoods, top-rated schools, and abundant recreational opportunities. Residents appreciate the area's strong sense of community, rich history, and convenient access to the vibrant cultural and economic centers of Orlando. Whether you're relaxing by one of Windermere's pristine lakes, exploring the local shops and restaurants, or enjoying a peaceful evening in your exquisite home, Windermere offers an unparalleled living experience. With its combination of natural beauty and modern conveniences, Windermere continues to attract discerning home buyers seeking an idyllic and upscale lifestyle.

Windermere Housing Market FAQs

Windermere, FL, offers a wide range of homes for sale, including luxury estates, single-family homes, waterfront properties, and townhouses. The area is known for its upscale neighborhoods, beautiful landscapes, and access to numerous lakes.

 

The price range for homes in Windermere varies significantly. Single-family homes typically start around $400,000, while luxury estates and waterfront properties can range from $1 million to over $10 million, depending on the size, location, and features.

Homes in Windermere often feature open floor plans, modern kitchens with high-end appliances, spacious master suites, and extensive outdoor living areas. Many properties include private pools, landscaped yards, and access to private docks or lakefront views.

 

Windermere is highly desirable for its serene environment, top-rated schools, and proximity to Orlando’s attractions. The town offers a blend of luxury living and natural beauty, with numerous parks, golf courses, and lakes providing ample recreational opportunities.

 

Potential buyers can find homes for sale in Windermere by searching online real estate listings, attending open houses, and working with experienced local real estate agents. To get personalized assistance and access to exclusive listings, contact Toni Marie Cafferty, a trusted real estate agent specializing in Windermere properties.

 

Buyers should consider the home’s location within Windermere, proximity to schools and amenities, property size and layout, and overall condition. It’s also important to evaluate potential property value appreciation, community amenities, and any homeowners association (HOA) regulations.

 

Popular neighborhoods in Windermere include Keene’s Pointe, known for its luxury homes and golf course; Isleworth, a prestigious gated community with waterfront properties; and Windermere Trails, which offers family-friendly amenities and new construction homes. Each neighborhood provides unique features and lifestyle benefits.

 

Residents of Windermere enjoy access to a variety of amenities, including top-rated schools, upscale shopping and dining, parks, golf courses, and numerous lakes for boating and fishing. The area is also conveniently located near Orlando’s theme parks and cultural attractions.

 

Windermere Area Overview

Why Invest in Windermere Real Estate

Windermere is more than just a beautiful place to live—it’s a smart investment opportunity. Its thriving local economy, prestigious communities, and consistent property appreciation make it one of Central Florida’s most desirable real estate markets. Whether you’re looking for a primary residence, vacation home, or long-term investment, Windermere offers unmatched value and lifestyle benefits.

Prime Location and Accessibility

Windermere’s unbeatable location near downtown Orlando provides easy access to major employers, shopping districts, and entertainment hubs. Residents enjoy a short commute to Walt Disney World and the Orlando International Airport, while still living in a quiet, upscale community away from the city’s congestion. This balance of convenience and exclusivity makes Windermere one of the most desirable areas for both homeowners and investors.

Luxury Living and Scenic Lakes

Set along the renowned Butler Chain of Lakes, Windermere offers stunning waterfront homes, private docks, and lush natural surroundings. Its gated neighborhoods, such as Isleworth and Keene’s Pointe, feature world-class golf courses, tennis clubs, and resort-style amenities. The combination of luxury properties and breathtaking scenery creates a lasting appeal that keeps Windermere real estate in high demand.

Strong Property Appreciation

Windermere’s limited land availability, high construction standards, and consistent demand have driven steady home value growth over the years. The area’s reputation for luxury living means properties here tend to maintain and appreciate in value, even during broader market fluctuations—making Windermere real estate a secure and rewarding investment.

Top-Rated Schools and Family Appeal

Windermere is home to some of the best schools in Orange County, including Windermere Preparatory School and Olympia High School. Families are drawn to the area for its exceptional education options, low crime rates, and well-maintained neighborhoods. These family-friendly qualities add to the town’s long-term stability and help maintain strong buyer and rental demand.

Thriving Local Economy and Lifestyle

Beyond its stunning homes, Windermere offers a dynamic lifestyle supported by nearby shopping, dining, and cultural attractions. The local economy benefits from its proximity to Orlando’s thriving industries in tech, healthcare, and tourism. Residents enjoy a strong sense of community with weekly farmers’ markets, boutique shops, and outdoor activities—all of which contribute to the area’s charm and sustained investment appeal.

Windermere Real Estate Updates

Windermere

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!

Windermere

Important Things to Know When Renovating Your Windermere Home

Toni Marie Cafferty  |  August 3, 2023

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

Windermere

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.

Windermere

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.

Windermere

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.

Windermere

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

Toni Marie Cafferty  |  February 24, 2024

Unlocking the Door to Your Dream Home.

Windermere

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.

Windermere

How to Increase Your Home Value in Windermere

May 24, 2023

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

Windermere

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.

Windermere

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.

Work With Toni Marie