Tennis and Pickleball in Windermere: Town Courts, Private Clubs, and Community Programs
Where residents actually play — from Main Street to Isleworth to the HOA leagues
The Town of Windermere, FL owns six lighted tennis courts and one dedicated pickleball court, all resident-only. Three tennis courts are located at Park Among the Lakes on Main Street, and three more are at the Windermere Recreation Center on Park Avenue. A Town tennis pass costs $25 per year, is valid October 1 through September 30, and is available only to residents of the incorporated Town of Windermere. The Park Among the Lakes courts reopened March 9, 2026, following a resurfacing project. Private racquet options include Isleworth Golf & Country Club, The Golden Bear Club at Keene's Pointe, and the Windermere Tennis & Pickleball Club for HOA-connected communities.
Here's something most newcomers to Windermere don't realize until they're already unpacked: the Town's tennis courts are gated, key-access, and resident-only — and that's by design. If you're moving here for the racquet sports lifestyle, the question isn't really "are there courts?" It's "which courts can I actually use, and what does that mean for where I should buy?"
That distinction matters more in Windermere than almost anywhere else in metro Orlando. The incorporated Town of Windermere is roughly two square miles with about 3,400 residents, while the broader 34786 ZIP code stretches across dozens of subdivisions in unincorporated Orange County. Town courts only serve the first group. Everyone else plays at private clubs, HOA amenity centers, or public courts in adjacent communities. Let's break down where tennis and pickleball actually happen across this area.
Town of Windermere Courts: Resident-Only, Pass Required
The Town owns and operates two separate tennis facilities, and both are gated. You need a key to get in, and you can only get a key if you live inside the incorporated Town limits.
Park Among the Lakes (Main Street)
Located on Main Street between East 2nd and East 3rd Avenues, Park Among the Lakes is the racquet hub for downtown Windermere. It has three lighted, secured tennis courts and one lighted, secured pickleball court — the only dedicated public pickleball court in the Town's park system. Other amenities include parking, a bike rack, picnic tables, and shaded benches.
Worth noting: these courts reopened on March 9, 2026, following a resurfacing project, so the playing surface is fresh as of this writing. Locals call them the "Main Street Courts."
Windermere Recreation Center (Park Avenue)
Often called Butler Bay by long-time residents, the Recreation Center sits on Park Avenue and offers three more lighted tennis courts, plus a sand volleyball court, picnic pavilions, a kayak launch onto Lake Crescent, and lakefront frontage. It's a multi-use park, but the courts get heavy use — show up early on weekends if you want a guaranteed spot.
How to Get a Tennis Pass
Tennis passes are $25 per year, valid October 1 through September 30, and are not pro-rated. Get yours early in the cycle to maximize value. To purchase:
- Where: Town Administration, 614 Main Street, Building 100
- Hours: Monday–Friday, 8:30 AM to 4:30 PM
- Phone: 407-876-2563, ext. 5327
- Payment: Check, money order, Visa, MasterCard, or Discover (no American Express, no cash)
If you're considering a home inside Town limits and racquet access matters to you, neighborhoods like Windermere Town, Windermere Downs, and Magnolia Park are walkable to the Main Street courts. Balmoral is an easy bike ride.
Private Club Courts: Isleworth, Keene's Pointe, and Beyond
For most of the 34786 ZIP code outside Town limits, racquet sports happen behind the gate at one of the area's private clubs. The big two:
Isleworth Golf & Country Club
The most exclusive racquet sports operation in Windermere sits inside Isleworth, the Arnold Palmer–designed guard-gated community on the Butler Chain of Lakes. The club's tennis facility includes hard courts and clay courts, full pro shop services, junior programs, and adult clinics. Membership is by invitation and tied to property ownership inside the gates. If you're considering this lifestyle, our Isleworth Golf & Country Club guide covers the full membership picture.
The Golden Bear Club at Keene's Pointe
Inside Keene's Pointe, the Jack Nicklaus–designed golf community on Lake Tibet-Butler, The Golden Bear Club operates a full racquet sports program with multiple tennis courts and pickleball lines now overlaid on select courts. Like Isleworth, it's a guard-gated community where club access is generally tied to homeownership. For a deeper look, see our Golden Bear Club at Keene's Pointe overview.
Windermere Tennis & Pickleball Club
Here's one a lot of buyers don't know about: the Windermere Tennis & Pickleball Club is a privately-owned, HOA-managed facility serving residents of several connected Windermere-area communities. It runs a full programming calendar — adult lessons, drills, league teams, and a junior academy for intermediate and advanced players — under a director of tennis. Court reservations are required, and guests must be accompanied by a homeowner in good standing. If you're touring homes in HOA neighborhoods that include club access, ask your agent specifically whether membership is bundled or separate.
Community and HOA Programs Across the 34786 Area
Beyond the Town courts and the marquee private clubs, racquet sports in Windermere are scattered across master-planned community amenity centers. Most have at least overlay pickleball lines on existing tennis courts, and several run organized league play through their HOAs:
- Summerport: The largest master-planned community in the 34786 area includes resident tennis and increasingly active pickleball groups.
- Windermere Trails: Family-focused master plan with pool, parks, and resident court access.
- Lakes of Windermere: Older master plan with mature trees and neighborhood amenities including courts.
- Providence and Waterstone: Newer gated master plans with resort-style amenity packages.
If court access ranks high on your list, the relevant question for any Windermere-area HOA is the same: how many courts, are they lighted, are pickleball lines painted, and is there organized league play? Answers vary widely by community, so verify before signing.
Where to Play If You Don't Live Inside the Town
If you're house-hunting and want to play before you buy, here are realistic options. Many Dr. Phillips and Horizon West public parks and YMCA facilities run open pickleball play sessions and tennis drop-ins. The LA Fitness Signature Club and Orangetheory locations covered in our Windermere 34786 gyms and fitness studios guide are useful for off-court conditioning. Winter Garden and Gotha also offer accessible park courts within a short drive.
What the Locals Know
The single most useful thing to understand about racquet sports in Windermere is the residency line. The Town's six tennis courts and one pickleball court are an excellent perk, but they only matter if your address is inside the incorporated Town limits — roughly two square miles centered on Main Street and the historic core. Buyers in Isleworth, Keene's Pointe, Summerport, Bay Hill, or any of the dozens of subdivisions in unincorporated Orange County will not have access, no matter how close they live.
Pickleball is also catching up faster on the private side than on the public side. The Town has one dedicated court, but most of the actual league pickleball happening across the 34786 ZIP is on overlay lines at HOA and private club courts. If pickleball is the priority over tennis, factor that into your neighborhood search.
For a full picture of outdoor recreation in the area — parks, lakes, trails, and Butler Chain access — explore our comprehensive Windermere parks and recreation guide and our Windermere sports and athletics guide.
For Town pass forms, current court hours, and program announcements, visit the official Town of Windermere website.
Thinking about a Windermere home with court access? Browse Windermere gated homes for sale or contact David Myers directly for a neighborhood-by-neighborhood breakdown of amenity packages.
