Windermere vs. Dr. Phillips: A Comprehensive Comparison of Lifestyle, Home Prices, and Amenities

Location & Lifestyle

Windermere and Dr. Phillips are two of the most sought-after communities in Orlando, Florida, offering luxurious living with distinct lifestyles.

Windermere is a charming town known for its lakefront luxury homes on the Butler Chain of Lakes. Located about 14 miles southwest of downtown Orlando, it provides a serene, small-town atmosphere with lush landscapes and exclusive gated communities like Isleworth, Keene’s Pointe, and Lake Butler Sound.

Ideal for those who love boating, fishing, and golf course living, Windermere is a paradise for those seeking tranquility and prestige.

Dr. Phillips, just 13 miles from downtown Orlando, offers a vibrant urban-suburban mix with easy access to world-class entertainment and dining. Home to the famous “Restaurant Row,” it’s a haven for food lovers and professionals who enjoy city amenities while living in an upscale neighborhood.

With proximity to Universal Orlando, Walt Disney World, and International Drive, it’s perfect for those wanting an active lifestyle with convenience at their doorstep.

Windermere vs. Dr. Phillips Housing Market & Home Prices

Both areas boast luxury real estate, but they differ in price range and housing styles.

Windermere Housing Market:

•Median home price: $699,526 – $947,500

•Housing costs: 43.5% higher than Dr. Phillips

•Offers new construction homes, luxury waterfront estates, and golf course properties

•Price range: From $400,000 condos to multi-million-dollar estates

Dr. Phillips Housing Market:

•Median home price: Approximately $650,000 (as of January 2025)

•Housing costs: 23.3% lower than Windermere

•Diverse housing options, including condos, townhomes, and single-family residences

•Established neighborhoods with mature landscaping and some new construction homes

If you’re looking for exclusive, high-end gated communities with private golf courses and lakefront properties, Windermere may be your best fit. If you prefer a central location with easier access to dining, shopping, and theme parks, Dr. Phillips could be ideal.

Amenities & Community Features

Both areas offer luxury amenities, but each caters to different lifestyles.

Windermere Amenities:

•Exclusive gated communities like Isleworth and Keene’s Pointe

•Private golf courses and upscale clubhouses

•Waterfront homes on the Butler Chain of Lakes with private docks

•Strong community events (weekly farmers markets, monthly food truck nights, annual art festivals)

•Top-rated public and private schools, including Windermere High School

Dr. Phillips Amenities:

•Famous “Restaurant Row” with world-class dining

•Proximity to Universal Orlando, Disney, and SeaWorld

•High-end shopping and entertainment options

•Urban-suburban mix with family-friendly parks and recreation

•Top-rated schools like Dr. Phillips High School and Windermere Preparatory School

Windermere is perfect for those who value exclusivity, golf course living, and lakeside retreats, while Dr. Phillips is ideal for those who want urban conveniences with suburban charm.

Cost of Living: Windermere vs. Dr. Phillips

Both communities offer upscale living, but the cost of living varies:

Windermere:

•Overall cost of living is 11.6% higher than Dr. Phillips

•Higher home prices and luxury community fees

•Utilities and healthcare costs slightly lower than the national average

Dr. Phillips:

•More affordable housing compared to Windermere

•Lower cost of living, making it more accessible to a wider range of buyers

•Offers a balance between affordability and upscale living

If budget is a primary factor, Dr. Phillips provides a lower-cost alternative to Windermere while still offering luxury real estate and amenities.

Community & Safety

Both communities are known for their safety and strong sense of community.

Windermere:

•Close-knit community feel with local events

•Has its own police department, ensuring enhanced security

Dr. Phillips:

•Family-friendly neighborhoods with a mix of professionals and retirees

•Well-maintained, safe communities with access to city conveniences

Both are highly desirable places to live, with low crime rates and excellent schools.

Windermere vs. Dr. Phillips: Which One is Right for You?

Both communities provide a high standard of living, but your choice will depend on your lifestyle, budget, and preferences.

•If you want exclusive lakefront estates, private golf course communities, and a quiet, small-town feel, Windermere is ideal.

•If you prefer a vibrant lifestyle with access to dining, shopping, and theme parks while still living in an upscale neighborhood, Dr. Phillips is a great option.

Whether you’re upsizing, downsizing, investing, or buying your first home, both Windermere and Dr. Phillips offer luxury real estate options tailored to your needs.

As a luxury Realtor specializing in Windermere and Dr. Phillips real estate, I can help you find the perfect home that matches your lifestyle. Contact Andy Neal today to explore your options and navigate the Orlando luxury housing market.