Windermere Trails Real Estate Guide: Luxury Homes, Lifestyle, and Market Trends in Windermere, FL

Windermere Trails is a sought-after community located in the heart of Windermere, Florida, offering a perfect blend of modern elegance, scenic lake views, and family-focused amenities. As one of Central Florida’s top luxury Realtors, I’m excited to introduce you to this exceptional neighborhood. Whether you’re buying your first luxury home or relocating to take advantage of Windermere’s top-rated schools and prime location, this guide covers everything you need to know about Windermere Trails, including real estate trends, pricing, community highlights, and how it compares to other high-end neighborhoods in the area.

About Windermere Trails and Its Builders

Windermere Trails is a master-planned community developed between 2012 and 2018 by highly respected builders such as Meritage Homes, Beazer Homes, and Mattamy Homes. Located off Reams Road in Southwest Windermere, this community offers approximately 743 properties, including spacious single-family homes and low-maintenance townhomes. With its clean architectural lines, premium interior finishes, and close proximity to the Butler Chain of Lakes, Windermere Trails has become one of the most desirable places to live in 34786.

Home Prices in Windermere Trails

Single-family homes in Windermere Trails start around $450,000 for a three-bedroom, 1,600-square-foot property and can reach up to $1.2 million for expansive six-bedroom estates offering up to 4,936 square feet of living space. Many homes include high-end upgrades such as granite countertops, stainless steel appliances, private pools, and lakefront views of Lake Reams, Lake Sharp, or Lake Spar. Townhomes in the community start near $329,000 for two-bedroom units with 1,476 square feet and can go up to $598,000 for four-bedroom, three-bath residences with open-concept layouts and modern finishes. The median home price in Windermere Trails sits at approximately $540,000, reflecting its balance of luxury and value in a competitive market.

Real Estate Market Trends

Windermere Trails continues to see strong demand, with the average days on market currently around 71. In February 2021, the average sale price reached $762,452, a figure that highlights the consistent appreciation of homes in this community. As of May 27, 2025, there are only 99 homes actively listed in the entire 34786 zip code, which contributes to a competitive buying environment marked by multiple-offer scenarios.

Windermere Trails Compared to Other Windermere Neighborhoods

Understanding how Windermere Trails stacks up against other neighborhoods helps buyers make informed decisions. Here’s a quick look at average home prices:

Windermere Trails: $540,000

Keenes Pointe: $950,000

Signature Lakes: $600,000

Belmere: $650,000

Windermere Trails stands out for offering luxury-style homes and resort-like amenities at a more accessible price point than communities like Keenes Pointe or Lake Butler, making it ideal for buyers seeking high value without compromising on lifestyle.

Why Windermere Trails Is a Smart Investment

Windermere Trails is not just a great place to live, it’s also a sound real estate investment. With a historical appreciation rate of roughly 7 percent annually, the community continues to attract long-term homeowners and investors alike. Its location, just minutes from Walt Disney World, Universal Studios, and SeaWorld, coupled with access to top-rated schools and premium amenities, ensures sustained demand and future growth potential.

Windermere Trails Amenities and Lifestyle

Living in Windermere Trails means enjoying a variety of high-end amenities in a tranquil, walkable setting. The community includes a resort-style swimming pool with cabanas, a splash pad for children, a dog park with a wash station, a fitness trail with outdoor workout stations, and multiple playgrounds and picnic pavilions. Residents also benefit from scenic walking and biking paths that meander through lush landscapes and around serene lakes like Lake Reams and Lake Sharp. Waterfront homes in the neighborhood offer direct access to some of Central Florida’s most beautiful views and recreational opportunities on the Butler Chain of Lakes.

Shopping, Dining, and Everyday Convenience

Windermere Trails offers excellent access to shopping and dining options. Just 0.3 miles away, Lakeside Village features a Publix Super Market, restaurants, a medical clinic, and a fitness center. Windermere Village, only 3.5 miles from the neighborhood, offers additional grocery stores, dining venues, and a popular weekly farmer’s market. Residents can also explore Winter Garden Village and Hamlin Town Center, both within a 10-minute drive, for boutique shopping, fine dining, and entertainment options.

Location and Connectivity

Windermere Trails is ideally positioned for commuting and travel. With quick access to the 429 Expressway, I-4, and Florida’s Turnpike, residents can easily reach downtown Orlando, area airports, and business hubs. The community is just south of Disney’s backstage entrance, making it an ideal location for professionals working at the resorts or for families who love being close to world-famous attractions. Nearby, top-rated golf courses like Isleworth and Bay Hill add further appeal for active homeowners.

Top-Rated Schools Serving Windermere Trails

Windermere Trails is zoned for the highly respected West Orange School District, a key driver of local property values and buyer interest. Bay Lake Elementary School is located within the neighborhood and serves grades Pre-K through 5. Bridgewater Middle School provides strong academic and extracurricular programs for grades 6 through 8. Windermere High School offers advanced placement courses, competitive athletics, and an excellent reputation among public high schools in Orange County. For families interested in private education, Windermere Preparatory School, a globally recognized K-12 institution, is located just three miles away.

What Makes Windermere Trails a Unique Place to Live

With a median household income of $131,392, Windermere is known for its affluence, low crime rates, and exceptional quality of life. Windermere Trails embodies the best of this town’s lifestyle, offering a peaceful environment, upscale homes, and a strong sense of community. Whether you’re a growing family, a relocating professional, or a retiree looking for modern comforts in a serene setting, Windermere Trails delivers on all fronts.

Additional Lifestyle Perks

The neighborhood includes features such as manned security gates and surveillance systems, adding peace of mind for homeowners. Healthcare is also easily accessible, with Dr. P. Phillips Hospital located just 11 miles away and Windermere Medical Center available at Lakeside Village. Nearby parks like R.D. Keene Park and Dr. P. Phillips Community Park offer sports fields, boat ramps, and family-friendly recreation options just a short drive from your doorstep.

Work with Andy Neal, Windermere’s Trusted Luxury Realtor

As one of Central Florida’s top-ranked Realtors and a local luxury specialist, I understand the unique appeal of Windermere Trails and how to help buyers and sellers succeed in this competitive market. Whether you’re searching for a move-in-ready home, a waterfront retreat, or a premium investment property, my team and I are here to provide unmatched service, expert negotiation, and exclusive access to listings. Let me guide you through every step of your Windermere Trails real estate journey with confidence and care.

Ready to Tour Windermere Trails?

Let’s find your perfect home in one of Windermere’s most desirable communities. Contact me, Andy Neal, at [Your Phone Number] or visit [Your Website] to start your personalized home search today. With insider knowledge, proven experience, and a passion for helping clients succeed, I’m here to make your move seamless and rewarding.

Disclaimer: All real estate data is deemed reliable but not guaranteed. School zoning and boundaries may change. Please confirm details with the Orange County School District and consult a professional for property inspections and legal advice.