Search homes for sale in Windermere, FL including single-family homes, luxury real estate and new listings with Core4 Group.
Windermere, Florida's real estate market embodies the epitome of luxury living, offering discerning buyers an exclusive glimpse into upscale suburban elegance. As of April 2024, the luxury real estate market in Windermere remains vibrant, showcasing an impressive array of homes and estates nestled within this prestigious community. From sprawling lakefront properties boasting panoramic views of the pristine Butler Chain of Lakes to meticulously designed custom-built homes in gated communities, Windermere presents an array of options for those seeking a blend of sophistication and tranquility. Beyond its stunning residences, Windermere is renowned for its top-rated schools, championship golf courses, and proximity to world-class entertainment and dining options, making it an ideal destination for those seeking an unparalleled lifestyle in Central Florida. For those ready to explore the homes for sale in Windermere, Florida, the realtors from Core4 Group stand ready to provide expert guidance and personalized service. With their deep understanding of the local market dynamics and commitment to exceeding client expectations, the Core4 Group offers comprehensive support to navigate the homebuying process seamlessly.To embark on your journey to homeownership in Windermere, Florida, contact the realtors from Core4 Group today for unparalleled service and exceptional results.
Windermere, Florida (ZIP 34786) offers 215 active real estate listings with a median price of $1,049,000 and an average price per square foot of $438. Featuring luxury lakefront estates along the Butler Chain of Lakes and gated communities like Isleworth and Keene's Pointe, properties spend an average of 63 days on the market.
Median List Price | Active Inventory | Avg Days on Market | Median Price / Sq Ft | Market Condition |
|---|---|---|---|---|
$1,049,000 | 215+ Active Listings | 63 Days | $438 / Sq Ft | Balanced Luxury Market |
Looking to Buy or Sell in Windermere, FL?
Whether searching for a private lakefront dock on Lake Butler or evaluating high-net-worth estate values, the local advisors at Core4 Group deliver expert representation.
Windermere, Florida's real estate market embodies the epitome of luxury living, offering discerning buyers an exclusive glimpse into upscale suburban elegance. As of 2026, the luxury real estate market in Windermere remains vibrant, showcasing an impressive array of homes and estates nestled within this prestigious Orange County community. From sprawling lakefront properties boasting panoramic views of the pristine Butler Chain of Lakes to meticulously designed custom-built homes in gated communities, Windermere presents an array of options for those seeking a blend of sophistication and tranquility.
Beyond its stunning residences, Windermere is renowned for top-rated public and private schools, championship golf courses, and proximity to world-class entertainment and dining options in neighboring Dr. Phillips and Orlando. Explore local culinary highlights in our Windermere dining guide or compare surrounding markets like Celebration and Reunion Resort.
Single-Family Homes
$650,000 to $2,500,000: Established neighborhood homes, spacious yards, and gated golf communities like Keene's Pointe.
Lakefront Estates
$2,000,000 to $15,000,000+: Exclusive waterfront compounds on the Butler Chain of Lakes with private boathouses and docks.
Townhomes & Condos
$380,000 to $750,000: Low-maintenance residences near Summerport Village and the Conroy Windermere corridor.
Gated Golf Communities
$1,200,000 to $10,000,000+: Luxury estates in Isleworth, Keene's Pointe, and Lake Butler Sound.
Windermere is served by top-performing Orange County Public Schools along with prestigious private academies:
Note: School zoning boundaries are subject to annual district review. Prospective home buyers should verify specific property address assignments with Orange County Public Schools.
1. Butler Chain of Lakes Access
Windermere surrounds 11 interconnected freshwater lakes, offering private boating, water skiing, and pristine shoreline recreation.
2. World-Class Security & Privacy
Features renowned 24-hour manned gated enclaves such as Isleworth, Reserve at Lake Butler Sound, and Keene's Pointe.
3. Prime Orlando Proximity
Located just 15 minutes from Restaurant Row in Dr. Phillips, 20 minutes from Downtown Orlando, and minutes from Walt Disney World.
Source Notes: Windermere active inventory, price trends, and school rankings verified via Stellar MLS data, Orange County Property Appraiser records, and Florida Department of Education reports as of July 2026.
Browse current MLS listings for single-family homes, townhomes, and luxury lakefront estates in Windermere, FL.
The Core4 Group is equipped to provide clients with experienced representation and personalized professional service across Windermere, Dr. Phillips, and Greater Orlando. Led by licensed real estate specialists Marissa Crawford and Michael Crawford, our team brings unmatched local insight to high-net-worth real estate transactions. Contact Core4 Group today to start your Windermere home search.
The median list price for homes in Windermere, FL is approximately $1,049,000, with prices ranging from $380,000 for low-maintenance townhomes to over $15,000,000 for expansive waterfront compounds on the Butler Chain of Lakes.
The Butler Chain of Lakes is a prestigious chain of 11 interconnected clear-water lakes surrounding Windermere, Florida, world-famous for luxury lakefront estates, private boathouses, and bass fishing.
Top gated communities in Windermere include Isleworth Golf & Country Club, Keene's Pointe, Reserve at Lake Butler Sound, and Windermere Downs.
Windermere is located approximately 12 miles southwest of Downtown Orlando, with typical commute times of 20 to 25 minutes via State Road 408 or Interstate 4.
