Windermere
A lakeside town tucked among ancient oaks and the Butler Chain of Lakes, Windermere pairs small-town charm with quick access to Orlando’s job hubs and theme parks. Buyers come for the water, golf, and schools; visitors come for the quiet, upscale, Old Florida vibe.
Quick Snapshot
| Category | At-a-Glance |
|---|---|
| Region | Central Florida / Greater Orlando; west of Downtown Orlando, near Walt Disney World |
| Vibe | Lakeside, upscale suburban, family-friendly, golf and boating culture |
| Housing Mix | Primarily single-family homes and gated estates; select townhomes/condos in nearby districts; blend of established neighborhoods and newer builds |
| Commute | SR‑429, Florida Turnpike, SR‑408, CR‑535; roughly 25–35 minutes to Downtown Orlando and MCO; 10–20 minutes to Disney |
Why Move to Windermere
- Lakes-and-oaks lifestyle with a walkable town center, local markets, and access to private and public boat ramps.
- Proximity to major employers in tourism, healthcare, tech, and higher education across Orlando, plus specialty medical and research corridors.
- Outstanding outdoor recreation: the Butler Chain of Lakes, nature preserves, and multiple private golf clubs within a short drive.
- A close-knit community feel with civic events, neighborhood amenities, and a reputation for well-kept streets and active HOAs.
Neighborhoods & Entertainment Districts
Windermere is best known for the Town of Windermere—an oak-canopied grid of lanes between Lake Butler and Lake Down—along with prestigious gated communities in the surrounding 34786 area. Isleworth and Lake Butler Sound are synonymous with custom estates and golf; Keene’s Pointe surrounds a Jack Nicklaus–designed course; and Summerport/Lake Burden brings a newer, more walkable option near shopping and dining. For evenings out, residents gravitate to Restaurant Row on Sand Lake Road, Hamlin Town Center in Horizon West, historic Plant Street in Winter Garden, and Disney Springs.
- Town of Windermere (Downtown & Lakes Streets) — Historic, small-scale streets (many intentionally unpaved), shady parks, public docks, and a true village feel. Price point trends high given lake access and limited inventory; suits buyers craving charm and community over new-build uniformity.
- Keene’s Pointe — A gated, master-planned favorite for golfers and active families, wrapped around The Golden Bear Club course. Home sizes vary from executive homes to lakefront estates, offering a broad range within a well-amenitized setting.
- Summerport & Lake Burden (Lakeside Village area) — Newer single-family homes and townhomes with neighborhood pools, trails, and pocket parks. Walkable to everyday retail and dining; a relatively attainable entry into the Windermere lifestyle.
Schools & Education
Windermere is served by Orange County Public Schools (OCPS), one of Florida’s largest districts. Zoning varies by neighborhood; many families cite strong community involvement and a breadth of advanced coursework at the secondary level. Local private options include Windermere Preparatory School (IB continuum) and several faith-based schools nearby. Across OCPS, students can apply to magnet programs (arts, STEM, IB, world languages) and career/technical pathways. Colleges and training hubs—Valencia College West Campus, Rollins College, UCF, and Full Sail—are generally within a 20–45 minute drive, depending on traffic.
| Level | Examples | Notes |
|---|---|---|
| Elementary | Windermere Elementary; Sunset Park Elementary; Keene’s Crossing Elementary | Neighborhood schools with arts/STEM enrichment and robust parent groups; zones vary by address. |
| Middle | Bridgewater Middle; Gotha Middle; Southwest Middle (nearby) | Honors, electives in technology/arts; after-school activities and athletics. |
| High | Windermere High; Olympia High (zoned in some areas) | AP courses and career/technical tracks; competitive athletics; district-wide magnets and IB programs available by application at select campuses. |
Note: School options and performance can vary by attendance zone; buyers should verify current zoning and ratings.
Cost of Living & Housing
Windermere commands a premium compared with the broader Orlando market, largely due to lakefront property, gated communities, and proximity to major amenities. That said, prices vary widely by waterfront status, lot size, age of home, and HOA/club requirements. Townhomes and smaller-lot homes in adjacent districts can offer a more approachable entry point, while estate homes along the Butler Chain can reach eight figures. Day-to-day costs (utilities, groceries) are similar to the metro average; homeowners insurance and HOA/club dues can be the bigger swing factors.
| Item | Typical Range | Context |
|---|---|---|
| Single-Family Home | $700,000 – $2,000,000+ | Established non-lakefront to newer, amenitized communities; lakefront and golf estates can exceed $3M–$10M+. |
| Townhome/Condo | $350,000 – $700,000 | Primarily in newer districts near Lakeside Village/Hamlin; HOA/condo fees vary by community and amenities. |
| Rent (2–3 BR) | $2,400 – $4,500/mo | Newer construction and waterfront/gated locations trend higher; single-family leases add a premium. |
| Overall Costs | Above nearby metros | Higher home values and potential club/HOA dues; utilities on par with Orlando; toll roads common for commuting. |
Insurance & HOA note: In Florida, homeowners insurance and HOA/condo fees can materially affect monthly costs; obtain current quotes.
Outdoors, Activities & Lifestyle
Life in Windermere revolves around the lakes, parks, and year-round sunshine. Many residents own boats or paddleboards, and even non-boat owners enjoy sunsets from town piers and park benches under the oaks. Golf is a social staple, whether you play within Windermere’s gated clubs or nearby courses in Dr. Phillips and Bay Hill. Family attractions—from neighborhood movie nights to theme-park weekends—are close enough to be casual.
- Butler Chain of Lakes — Boating, waterskiing, fishing, and sunset cruises across interlinked spring-fed lakes; public ramps and private club marinas serve access.
- Tibet-Butler Nature Preserve — Miles of shaded trails through pine flatwoods and cypress swamps; birding and family-friendly loops off CR‑535.
- R.D. Keene Park & Town Facilities — Sports fields, boat ramp access, playgrounds, and community courts; active youth leagues.
- Private Golf & Nearby Venues — Keene’s Pointe’s Golden Bear Club and, just beyond the town line, Isleworth; Bay Hill hosts the PGA Tour’s Arnold Palmer Invitational each spring.
- Markets & Community Events — A weekly farmers market in the town center and periodic food-truck gatherings foster a small-town feel.
- Seasonal highlight — Early spring art shows and holiday parades draw neighbors to Main Street without overwhelming the quiet residential pace.
Getting Around & Commute
Windermere is primarily a driving community. CR‑535, Conroy‑Windermere Road, Apopka‑Vineland Road, SR‑429, the Florida Turnpike, and SR‑408 connect residents to job centers and airports. Typical drive times are 25–35 minutes to Downtown Orlando and Orlando International Airport, and 10–20 minutes to Walt Disney World and the attractions area, depending on traffic and toll-road usage. LYNX bus service is limited here; SunRail stations are reachable by car but not within the town core. Inside the Town of Windermere, local streets are calm and golf cart/bike-friendly, with unpaved lanes deliberately maintained to discourage cut-through traffic.
Who It’s Ideal For
- Growing families seeking strong school access, neighborhood amenities, and a close-to-everything suburban base.
- Professionals and entrepreneurs who value a lakeside lifestyle with quick reach to Orlando’s employment corridors and airports.
- Retirees prioritizing low-maintenance living near golf, water, and year-round recreation.
Tips for Homebuyers
- Expect tight inventory for historic town-core homes and true lakefront; new listings often draw quick interest, especially in winter/spring. Get pre-approved and be ready to tour on short notice.
- Weigh new-construction in adjacent districts versus established neighborhoods with mature trees and larger lots; finishes and HOA rules differ widely.
- Review HOA, condo, and—where applicable—CDD fees; confirm what amenities and maintenance are covered and whether club memberships are optional or required.
- In a lake-rich area, verify flood zones, elevation, and storm protections. Request wind-mitigation and four-point inspections to inform insurance quotes.
- Lake access rights, docks, and seawall conditions matter; understand permitting and riparian rules before budgeting for improvements.
FAQ
Is Windermere a good place to raise a family?
Many families choose Windermere for its school access, community events, and outdoor lifestyle—think bikes to the park, afternoons on the lake, and weekend sports. The tradeoff is cost: homes, insurance, and activity fees can run higher than the Orlando average. If you value a quieter, neighborhood-centered environment with strong amenities, it’s a compelling fit.
How does the cost of living compare to nearby areas?
Housing is the main premium. Non-lakefront homes in gated communities often cost more than comparable homes in neighboring Winter Garden, Ocoee, or Dr. Phillips, and true lakefront carries a substantial additional premium. Utilities and groceries are broadly in line with the region, while tolls, HOA dues, club memberships, and insurance can increase monthly costs.
What’s the housing stock like?
You’ll find a spectrum: historic cottages and custom homes in the town core; master-planned, amenity-rich communities from the late 1990s onward; and luxury lakefront estates in gated enclaves. Townhomes and condos are available mainly in newer nearby districts for buyers seeking lower maintenance and a more attainable price point.
Bottom Line
Windermere blends lake-country serenity with metropolitan convenience—an uncommon mix in Central Florida. If your wish list includes boating, golf, and leafy streets near high-performing schools and major employers, it belongs on your short list. Expect to pay a premium for the address and for lake access, but you’ll gain a lifestyle that feels both resort-like and neighborly. For discerning buyers and travelers, Windermere delivers an easygoing, upscale version of the Orlando experience.
