Trying to choose between Doctor Phillips and Windermere? You are not alone. Both offer strong value in southwest Orlando, yet the day-to-day feel, price points, and lot sizes can be very different. In this guide, you will see how they compare on home prices, lake access, schools, HOAs, and commutes so you can match the right neighborhood to your lifestyle. Let’s dive in.
Quick take: how they differ
Doctor Phillips gives you convenience and variety. You get a wider range of condos, townhomes, and single-family homes near Sand Lake Road’s Restaurant Row and the I‑Drive corridor. Typical median listing prices are lower here than in Windermere.
Windermere offers lake life and estate living. Many neighborhoods sit on or near the Butler Chain of Lakes, with larger lots, private docks in certain pockets, and gated country-club communities. Median listing prices tend to be higher, especially for lakefront and golf-course properties.
Home prices and housing options
- Windermere: The median listing price sat around $1.03 million as of December 2025, according to Realtor.com. Prices vary by neighborhood. Gated enclaves like Isleworth and Keene’s Pointe often trade in the multi-million range, while in-town homes without direct lake access can list lower.
- Doctor Phillips: The median listing price was about $609,000 as of December 2025 on Realtor.com, with a broad mix of condos, townhomes, and single-family homes. Other data sources may show different medians because they use different methods, which is normal.
What this means for you: If you want more choices under seven figures or an attached home, Doctor Phillips usually offers more options. If you want a luxury lakefront estate or a large golf-club lot, Windermere provides a deeper selection at those price points.
Lot sizes and lake life
Windermere’s identity is tied to the Butler Chain of Lakes, a connected system of 13 lakes with thousands of surface acres. Buyers here often prioritize boating, private docks, and long-water views. Explore the system with this Butler Chain overview.
Supply for new true lakefront parcels is limited. Orange County planning policies for the Butler Chain area have historically encouraged larger lots and lower subdivision intensity in sensitive waterfront areas, which helps explain scarcity and premium pricing. You can see context in the county comprehensive plan excerpts here.
Typical Windermere lots in estate communities range from roughly half an acre to multi-acre parcels in select pockets, with significant premiums for direct lake frontage and dock rights. In Doctor Phillips, you will find smaller lakes and golf-course frontage options. Many single-family lots are under half an acre, and there is also a meaningful condo and townhome presence. This setup favors buyers who want a suburban footprint with quick access to dining and retail, rather than a large estate setting.
Schools and zoning basics
Both areas are served by Orange County Public Schools. Attendance zones can cross neighborhood lines, so always confirm the school that matches a specific property using the OCPS tools. Start with the OCPS attendance zone map library.
- Windermere: Common public options for many addresses include Windermere Elementary, Chain of Lakes or Bridgewater for middle school depending on the neighborhood, and Windermere High. Public rating sites list Windermere Elementary as highly rated; you can review neutral, third-party data on its GreatSchools profile. Always verify the exact feeder pattern for your target address.
- Doctor Phillips: Many addresses feed to Dr. Phillips Elementary, Southwest Middle, and Dr. Phillips High. You can learn more about the elementary campus at the Dr. Phillips Elementary School site. As with Windermere, confirm zoning by property address.
Tip: School boundaries and programs can change. Before you make an offer, use OCPS’s Find My School tool and confirm with the district.
HOAs, clubs, and community style
- Windermere: You will find a high share of guard-gated and master-planned communities, often with formal HOAs. In some enclaves, there are optional or required country-club memberships. Buyers should review HOA covenants, fee schedules, and any separate club initiation costs early in the process.
- Doctor Phillips: You will see a mix of HOA types. There are condo and townhome associations near Restaurant Row, traditional single-family HOAs, and golf-community arrangements. Fee levels and amenities vary by community, which gives you more flexibility if you have a target budget for monthly dues.
Commutes and daily convenience
- Disney: From many Windermere addresses, the drive to Walt Disney World can be in the 15 to 25 minute range depending on the exact location and traffic. Doctor Phillips addresses can be even closer by distance and time. For a quick reference, see the approximate route from Windermere to Disney on Travelmath.
- Universal and I‑Drive: Both areas sit near the tourism corridor, so typical drives to Universal and International Drive are often 20 to 30 minutes, depending on where you start and traffic.
- Hospitals and major employers: You have convenient access to regional employers like Disney and Universal, and to major medical facilities. For example, Orlando Health Dr. P. Phillips Hospital is near Doctor Phillips, and AdventHealth has locations throughout the metro.
Always test-drive your commute at your usual travel time. Traffic patterns shift during events and peak seasons.
Who each area fits best
Choose Windermere if you want
- A true lake lifestyle with private docks and boating on the Butler Chain
- Larger lots and estate-scale homes in gated or country-club settings
- A quieter, small-town center with country-club and waterfront recreation
Choose Doctor Phillips if you want
- Short, simple access to Restaurant Row and dense dining and retail
- A broader range of price points, including condos and townhomes
- Convenient proximity to theme-park employment and major corridors
How to decide: a quick checklist
Use this list to compare any two homes you are considering:
- Schools: Confirm the exact OCPS zone for the property with the attendance zone map library.
- Waterfront: If lake access matters, verify whether the property fronts the Butler Chain and what that means for permitting, docks, and use. Start with this Butler Chain overview, then review county rules.
- HOA and clubs: Request the current HOA covenants, dues, and any separate club initiation or membership costs before you offer.
- Commute: Drive the route to your employer, school, and regular errands at your normal times.
- Price and product fit: Decide whether you want condos and townhomes nearby, or prefer single-family and estate-scale options.
Next steps
If you are early in your search, set two saved searches, one in each area. Compare days on market, price trends, and how quickly homes you like go under contract. When you are ready to tour, focus on three to five homes per area that align with your non-negotiables, like commute time, lake access, or HOA style.
When you want a clear plan, connect with a local expert who works both sides of Sand Lake Road and the Butler Chain. We can help you weigh trade-offs, verify zoning, and negotiate with confidence.
Ready to zero in on your best fit? Connect with Paulette Williams to compare live inventory in Windermere and Doctor Phillips, and get a FREE Market Report tailored to your budget and timeline.
FAQs
How do prices compare between Windermere and Doctor Phillips in 2026?
- Realtor.com reported a December 2025 median listing price near $1.03M for Windermere and about $609K for Doctor Phillips, with wide variation by neighborhood.
What is the Butler Chain of Lakes and why does it matter?
- It is a connected system of 13 lakes prized for boating and waterfront living; true Butler Chain frontage is limited, which supports premium pricing and estate-scale lots. Learn more in the Butler Chain overview.
Which area is closer to Disney and Universal?
- Many Doctor Phillips addresses sit slightly closer by distance, but both areas offer short drives; check a route such as Windermere to Disney and test it at your commute time.
How do school zones work in Windermere and Doctor Phillips?
- Both are served by OCPS, and zones vary by street; always verify a property’s assigned schools using the OCPS attendance zone map library before you offer.
Are HOA or club fees common in these areas?
- Yes. Windermere has many gated and club communities that may include separate membership costs; Doctor Phillips offers a wider mix of fee structures. Request current HOA and club documents for any home you are considering.
