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Windermere is one of the most desirable places to live in Central Florida because of its luxury real estate, award-winning schools, and prime location near Orlando. The town is surrounded by the Butler Chain of Lakes, offering stunning lakefront estates and gated communities that attract high-end buyers. Limited land availability and strong demand continue to drive up home values in Windermere.
As of 2025, the median listing price for homes in Windermere, FL is around $949,000, with the average home price closer to $1.1 million. Luxury estates on the water or in golf course communities like Isleworth or Keene’s Pointe can easily exceed several million dollars.
The Windermere housing market has experienced some price adjustments since the peak of 2021. While certain homes are seeing price reductions due to overpricing, the long-term trend in Windermere remains strong. Demand for lakefront homes, gated communities, and luxury properties keeps values high compared to neighboring Orlando suburbs.
Yes. For buyers, motivated sellers and builder incentives make now a great time to find value in Windermere real estate. For sellers, properly priced homes are still moving quickly due to low inventory and strong demand. Whether you’re looking to buy a luxury home in Windermere or sell a property, the market offers opportunities in 2025.
Homes in Windermere sell in an average of just 16 days, making it one of the most competitive housing markets in Central Florida. Lakefront properties and homes in gated neighborhoods often receive multiple offers. Buyers need to act quickly and work with an experienced Windermere real estate agent to secure the best deals.
Many sellers are still pricing their homes as if it were 2021, leading to frequent price reductions. However, well-priced Windermere homes especially those on the Butler Chain of Lakes or in luxury golf course communities continue to sell quickly and close near asking price.
Windermere outperforms most Orlando neighborhoods in both value and demand. Home prices in Windermere are typically 20–30% higher due to exclusive lakefront living, gated communities, and the small-town charm combined with luxury amenities. It’s often considered the Beverly Hills of Orlando.
Windermere offers a rare mix of privacy, exclusivity, and convenience. Luxury homebuyers are drawn to gated neighborhoods like Isleworth and Keene’s Pointe, private access to the Butler Chain of Lakes, A-rated schools, and championship golf courses. It’s a unique market where lifestyle and prestige meet.
Top neighborhoods include Isleworth, Keene’s Pointe, Lake Butler Sound, Reserve at Belmere, and Butler Bay. Each offers gated security, luxury amenities, and access to boating, golf, and fine dining. These communities are consistently ranked among the best places to buy luxury homes in Florida.
Windermere residents enjoy private lakes, golf courses, country clubs, A-rated schools, fine dining, and boutique shopping. Its location just minutes from Disney World, Universal Studios, and Downtown Orlando makes it one of the most convenient yet upscale places to live in Central Florida.
Closing costs in Windermere generally range from 3–6% of the loan amount. This includes title fees, taxes, insurance, and other expenses. Working with a knowledgeable Windermere Realtor helps buyers and sellers understand the true costs of closing a real estate transaction.
The cost of living in Windermere is about 42% higher than the national average. Homes average $1.1 million with a price per square foot around $298. Insurance, property taxes, and HOA fees in gated communities can also add to the expense. However, the high quality of life, safety, and amenities make it worthwhile.
On average, homes in Windermere sell within 16 days of listing — much faster than surrounding markets. Luxury homes with lake access or golf views often move even faster when priced competitively
Yes. Builders in Windermere and Horizon West are offering incentives such as closing cost credits, upgrades, and rate buydowns. This makes new construction homes more competitive with resale homes, giving buyers more options in the luxury market.
Common mistakes include underestimating the higher cost of living, overlooking high homeowners’ insurance rates, and not understanding traffic patterns or school zoning. Working with a local Windermere Realtor ensures you avoid costly mistakes and find the best community for your lifestyle.

When it comes time to buy representation matters. Every McKinney agent has went through extensive training to get you what you want. We save our clients big headaches and big dollars too! Our agents lead with passion in their work and are dedicated to making the most seamless experience possible.