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Dear Members:
This year marks our 40th anniversary year at Isleworth, and we celebrate a club community defined by the families and staff who have made Isleworth what it is today. Clubs are interesting enterprises—they are mirror reflections of their membership and staff, and at the same time, they are enduring assets home to shared memories, a physical sense of place, and an ever-present challenge to remain relevant to the families they serve.
Over four decades, Isleworth has risen to this challenge and thrived in large measure because of our ownership. The Lewis family has provided the vision, stability, and resources that have allowed Isleworth to flourish for 40 years. Isleworth has always stood for casual elegance, quality of service, an array of top tier amenities, and a welcoming ambiance where families and friends feel at home. These hallmarks of the Lewises’ stewardship remain at the core of our identity.
With this issue of Legends, we also mark an important transition. We say goodbye to Wayne Sheffield after 10 years of leadership and contributions. Wayne arrived in 2015 and helped regenerate the Club, adding new vitality, relevance, and quality across both our Club and Realty operations. His commitment to our staff and Membership, his hands-on leadership, his passionate participation in Club activities, and his innate ability to continually raise the bar will always be part of his legacy. We thank Wayne for all he has done and wish him, his wife, Carey, and their family the very best as they relocate to Southern California, where Wayne will take the helm of Rolling Hills Country Club.
We are pleased to welcome our new General Manager Cary Massey and his family to Isleworth. Joining us
from Spanish Peaks in Montana, Cary brings decades of experience in culinary excellence, club operations, golf and sporting expertise. He is a consummate professional with a warm personality and a hands-on leadership style that will resonate with our accomplished Isleworth staff and our discerning Membership. Vivienne Lewis and I have encouraged Cary to spend his first several weeks listening and learning—absorbing what makes Isleworth so special—and working collaboratively with us to lead the Club into a new decade of excellence.
Together, we will look after our staff and strive to serve and delight our Membership ensuring Isleworth remains one of the finest club communities in the world. Please join us and our experienced executive team in welcoming Cary and his family to Isleworth.
We have a full season ahead, with a vibrant calendar of activities and programming in the coming months— many of which are highlighted in this issue of Legends.
On behalf of the Lewis family, the Board, and our Executive Team, we want to express our sincere gratitude for your loyalty and your membership at Isleworth. The people truly make the place—we say it often because it’s true. The combination of our remarkable staff and our exceptional Membership is what makes Isleworth unique.

Douglas McMahon Senior Managing Director, Tavistock Group







On behalf of the entire Isleworth team, thank you for your generous contributions to the Employee Holiday Fund. Your support means a great deal to us, and we look forward to serving you in 2026.

Warm congratulations to Alejandro and Hayley Donaldson on the birth of their daughter, Lila Rose, on November 16. Proud grandparents Mr. Louis and Mrs. Maria Donaldson join in celebrating this joyful occasion.
We’re delighted to share the happy news of the birth of Lucy Lewis John on December 3, to parents Dr. Ally John and Dr. Jeremy John.


FRIDAY, JANUARY 9
FRIDAY, FEBRUARY 13
11:30 A.M.
Mahjong continues to bring Members together through strategy, connection, and tradition. Whether you’re a seasoned player or eager to learn, all are welcome to join the table.
Beginners are invited to take part in a three-week introductory series offered on three consecutive Thursdays—January 15, 22, and 29 in the Garden Room, with sessions beginning at 10 A.M. and 6 P.M. Please indicate your preferred session time when signing up.
An optional lunch will follow in Champions Grill.
If you would like to be part of the group, whether to play or to learn, please contact Member Joanne Cross directly at 315.391.9761.
SATURDAY, JANUARY 10
SATURDAY, FEBRUARY 7
9:30 - 10:30 A.M.
Spend the morning with fellow Member Dr. Deukmedjian as he shares his passion for orchids and bromeliads through live repotting demonstrations and engaging discussion. The group meets at the Club on the second Saturday of each month.
To join, please contact Jennifer Self-Kirk at 407.909.2004 or jennifer.self-kirk@isleworth.com.
Gather with fellow Members for engaging conversation as the group explores a thoughtful selection of reads. In January, the group will discuss Happy Wife by Meredith Lavender and Kendall Shores, followed in February by The Diamond Eye by Kate Quinn.
An optional lunch will follow each gathering in Champions Grill.
To join the group, please contact Member Suzie O'Hara directly at 407.256.5970.



Get to know the General Manager guiding Isleworth into its next decade of growth and world-class hospitality.
The Club is proud to welcome Cary Massey as Isleworth’s new General Manager, bringing more than three decades of private club leadership experience and a people-first approach to hospitality. As Isleworth celebrates its 40th anniversary, Cary shares what drew him to the Club, his respect for its legacy, and the values guiding his vision for the future.
Q What first drew you to Isleworth, and what made this opportunity feel like the right next step for you?
A "I had been at my previous club in Montana for four years and was genuinely happy there. I turned down many calls about other opportunities because I wasn’t looking to leave.
When the recruiter first called, it was actually about a position in Los Angeles, which I declined. The next day he said, “Forget that job, I’ve got a better one,” and introduced Isleworth. For the first time in a long time, I was intrigued.
My wife is from Florida, and while I never pictured myself here, visiting Isleworth changed that. We left three degrees and snow and arrived to 75 degrees and sunshine, an exceptional club, and incredibly warm people. Professionally, Isleworth is the kind of Club I’ve spent 35 years working toward. Personally, it felt like the right place for our family and the kind of Club where I could happily spend the rest of my career."
Q As you settle in, what are you most excited to learn about our Members, team, and culture?
A "I’m most excited to understand what truly makes Isleworth, Isleworth. I know the rankings and reputation, but I want to learn the “why” behind them, what Members value most, what we do well, and where we can grow.
I’m also looking forward to better understanding the rhythm of life in Florida and how Isleworth fits into that— seasonality, expectations, and the unique lifestyle our Members enjoy here."
Q In your view, what makes a private club feel truly exceptional, and how do you hope to elevate that experience here?
A "An exceptional private club delivers hospitality, consistency, and value that make Members proud to belong, and eager to recommend it to friends. Members are making a significant investment of both money and time, and the experience needs to reflect that every day.
For me, that means personalized service, genuine warmth, and a high level of execution across the board—from golf and dining to events and daily interactions. At Isleworth, my goal is to protect what’s already excellent while looking for thoughtful ways to refine and enhance the Member experience in ways that feel authentic to the Club."
Q Isleworth has a rich history, what elements of our story or community have stood out to you the most so far?
A "From the outside, I knew Isleworth by its reputation. What stands out to me now is how that history has translated into sustained excellence. Being recognized as a Platinum Club of the World takes years of consistent performance and Member satisfaction.
As Isleworth celebrates its 40th anniversary, I’m impressed by how the original vision has evolved into a modern, world-class Club—one that continues to grow and innovate."
Q How would you describe your leadership style, and how do you hope it will show up in daily life at the Club?
A "I would describe my leadership style as approachable, trusting, and very anti–micromanagement. If you’ve been hired into a role, my assumption is you’ve earned it, and my job is to support you, not hover over you. I care deeply about standards, outcomes, and the Member experience, but I don’t believe in managing by the clock.
At Isleworth, I want to be visible and accessible, more on the first tee or in the dining room than behind a desk."
Q Are there aspects of Club life—golf, dining, fitness, or social events— you’re especially excited to experience firsthand?
A "Golf is a big one for me. I love the game not because I’m chasing a scorecard, but because it gets me outside, around Members, and in tune with the pulse of the Club.
Beyond golf, I’m excited to experience the full lifestyle of Isleworth—dining, social events, and the day-to-day ways Members enjoy the property. But my preference is always to be out on the grounds, connecting with people where they naturally spend their time."
Q What’s a hobby or pastime that helps you unwind and recharge outside of work?
A "Golf is my main outlet and the easiest way for me to mentally reset. I’m also a big sports fan in general.
A lot of my downtime is simply spent with my wife and kids, watching a game, relaxing at home, and enjoying time together. In this industry, those quieter moments with family are often the most recharging."
Q Tell us a bit about your family— the people who support you behind the scenes.
A "We have a big, blended family, and they’re the center of my world. I have two daughters in California, ages 14 and 15, and my wife has three children, so together we have five, four girls and one boy. We turned into an instant “basketball team,” and I wouldn’t have it any other way.
Between visits to see my daughters, FaceTime calls, and supporting our kids through school transitions, our life is very full—but also very rewarding. They’re a huge part of why I’m so committed to making this chapter at Isleworth a success."
Q What do you hope Members understand most about who you are and the values you bring to Isleworth?
A "I hope Members see that I lead with integrity, humility, and a deep respect for both the Membership and the team. I’ve worked with people from every background and believe everyone deserves the same level of courtesy and care.
I firmly believe that if our staff is happy, supported, and proud of what they do, Members will feel that in every interaction. I want Isleworth to be a place where team members stay because they love it here, and where Members feel that stability and positivity every day."


At Isleworth, pasta has moved beyond its traditional supporting role on the menu. It has become a point of focus, shaped by intention, technique, and a growing commitment to in-house production. Through a thoughtfully developed pasta program, the culinary team is refining flavor, texture, and consistency, elevating the dining experience through careful execution.
The approach begins with function. Pasta shapes are selected for how they perform on the plate, not how they appear. Ridged varieties are favored for their ability to hold slow-simmered sauces, while softer forms naturally complement cream-based preparations. Seasonality guides each menu. Winter selections lean into comforting, layered flavors, while warmer months shift toward lighter, herb-driven profiles.
That philosophy comes to life in the Winter Truffle Gnocchi Sardi. Wild winter black truffles, sourced through a local purveyor, are paired with organic trumpet and oyster mushrooms in a restrained alfredo sauce. The gnocchi sardi, chosen for its ridged, shell-like shape, allows the sauce to cling to each bite, creating a balanced interplay of texture and depth.
Technique anchors the program. A growing range of pasta shapes is now produced in-house, blending modern capability with time-honored methods. Dough is evaluated by touch as much as sight, with an emphasis on smoothness, resilience, and balance.

Semolina and high-quality flours provide a heartier structure and a more authentic taste. Hand-rolled pastas such as ravioli and tortellini continue to honor classical technique.
Much of the work happens quietly. Each batch demands patience and attention to detail, from ingredient sourcing to final execution. Ideas are tested and refined without ego, ensuring that every dish feels deliberate and complete.
This focus has also led to a stronger presence of vegetable-forward pasta dishes on the menu. Built with the same care and depth as any other preparation, these offerings have resonated with Members and reinforce a simple belief: when technique is strong, flavor leads.
In the end, the experience at the table matters most. Time, craft, and quality come together to elevate something familiar into something memorable, meant to be appreciated and enjoyed.

With nearly 600 Members already using it, the new Isleworth App is redefining how Members connect with the Club. This guide covers everything you need to get started.
How do I download the new Isleworth App?
Search “Isleworth” in your device’s app store and select the version featuring the gold pin flag icon.
Do I need to delete the old Isleworth app?
Yes, the previous version is no longer supported.
How do I log in?
Use your Member number as your username and your last name in lowercase as your password. These are not the same as your Isleworth Members-Only Website credentials.
If your Member number is three digits, add a leading zero (e.g., 0123).
Spouse Members should add “B” after their Member number (e.g., 1234B).
What if I receive an error when logging in?
Verify that your Member number and last name are entered exactly as required. If issues persist, the Isleworth Marketing Team can assist with resetting your credentials.
Which family members can access the app?
Spouse Members may access the app using their designated login credentials. Children between the ages of 13 and 25 may also have profiles in the app.
What can I do in the new app?
The app provides easy access to fitness and racquets bookings, Golf Kiosk food ordering, the Club calendar, and real-time notifications.
What notifications will I receive through the app?
Notifications are tailored to your selected Interest Groups, ensuring you receive updates most relevant to you.
You can manage these preferences by tapping your profile icon in the top left corner and selecting “Interest Groups.”
Why should I allow the app to use my location?
Location access supports select in-app features while you’re on Club property, helping the app function more smoothly and efficiently. Your location is not tracked when you are off property.
How can I access my statements?
You may view and pay your statement directly in the app. Tap your profile icon in the top left corner and select “View Statement.” You will be prompted to log in using your Isleworth Members-Only Website credentials; you will only need to complete this login once.
If you choose to make a payment, you will then be prompted to enter your PNC Payer Express credentials.
How do racquet bookings work now?
All racquet court, event, and lesson reservations are now managed exclusively through the Isleworth App. The CourtReserve platform is no longer in use.
Will new features be added over time?
Yes. Additional features and enhancements will continue to roll out as the app evolves.
For questions or assistance with login credentials or app access, please contact the Isleworth Marketing Team at marketing@isleworth.com.
THURSDAY, OCTOBER 23














SATURDAY, OCTOBER 25














WEDNESDAY, OCTOBER 29














FRIDAY, NOVEMBER 7














WEDNESAY, NOVEMBER 12














WEDNESDAY, NOVEMBER 26














THURSDAY, NOVEMBER 27














WEDNESDAY, DECEMBER 3

















SUNDAY, JANUARY 11
11:30 A.M. - 1:30 P.M.
Join us for the 11th annual Fenders & Food Trucks. An impressive lineup of Members’ vehicles will be showcased, ranging from exotic and luxury models to classic, antique, and specialty cars.
Luxury automobile and boat brands from across Central Florida will be onsite with select models available for test drives.
New this year, we’re pleased to introduce a shopping experience in the Ballroom, featuring wine for purchase and specialty items from our participating partners.
Dining options will include selection of Isleworth’s signature burgers and hot dogs, Kelly’s Ice Cream, and the Banditos Taco Truck. Members and their accompanied guests may also enjoy a BBQ buffet lunch in Champions Grill. Reservations are required and limited to event attendees.
To reserve a table in Champions, please call 407.909.2000.


WEDNESDAYS
5:30 - 8:30 P.M.
Join us for our signature Family Nights where each week brings a new themed buffet showcasing diverse flavors and favorites the whole family will love.
▷ Tex-Mex | January 7
▷ Members' Favorites | January 14
▷ Route 66 | January 28
In addition to the buffet, a limited à la carte menu will be offered in Champions, while Lake Butler Lounge will be reserved exclusively for adult dining.
Advanced reservations are required and can be made by calling 407.909.2000.
SELECT FRIDAYS & SATURDAYS
LAKE BUTLER LOUNGE
Dinner | 6:00 - 8:00 P.M.
Live Music | 6:30 - 9:30 P.M.
Enjoy an evening of great food and drinks, elevated by live performances from local musicians on select Friday and Saturday nights throughout the season.
Supervised childcare will also be available in the Bull Pen. Reservations must be made by 2:00 P.M. the day of.
TALENT LINEUP
▷ January 2 | Luis Rexach
▷ January 3 | Jen & Dave
▷ January 9 | Don Soledad
▷ January 10 | Jen Rae
▷ January 16 | Jose Rodriguez
▷ January 17 | Don Soledad
▷ January 23 | Rick Voigt
▷ January 24 | Dave Smith
▷ January 30 | Alex Bodytko
▷ January 31 | Marc Clermont
Limited seating is available. Advanced reservations are highly recommended and can be made by calling 407.909.2000.
We kindly ask that Members and their guests adhere to the Club’s dress code.

THURSDAY, JANUARY 22
Cocktails | 6:00 P.M.
Dinner | 7:00 P.M.
THURSDAY, JANUARY 1
Dining Reservations | 11:00 A.M. - 2:00 P.M.
Begin 2026 on a celebratory note with a delicious brunch buffet, complemented by a Bloody Mary & Mimosa Bar and live entertainment from a strolling magician.
To reserve your spot, please call 407.909.2000. We kindly ask that any reservation cancellations be made at least 72 hours in advance.
The Clubhouse and Fitness Center will close at 4:00 P.M.
Experience an extraordinary evening with Chappellet, the renowned Napa Valley estate celebrated for its pioneering spirit and the mountain-grown character of its Pritchard Hill wines. Hosted by the Chappellet family, the dinner features a curated selection of their most acclaimed vintages paired with a thoughtfully crafted multi-course menu.
Advanced reservations are required and can be made by calling 407.909.2000.


WEDNESDAY, JANUARY 28
5:30 - 8:30 P.M.
Hit the open road at our Route 66 Family Night, where adventure and creativity await around every turn. Take the wheel as remote-control race cars zip around a custom track, sending families head-to-head in the race to capture the checkered flag. Get creative at the mini Matchbox car coloring station and bring your design to life.
Advanced reservations are required and can be made by calling 407.909.2000.



SATURDAY, FEBRUARY 14
7:00 - 10:00 P.M.
Share an elegant evening with your sweetheart as we celebrate a night of romance and roses. Begin with cocktails and hors d’oeuvres before enjoying a prix fixe dinner. The evening concludes with live music and dancing.
Supervised childcare will be available in the Bull Pen.
Advanced reservations are required and can be made by calling 407.909.2000.


SELECT FRIDAYS & SATURDAYS
LAKE BUTLER LOUNGE
Dinner | 6:00 - 8:00 P.M.
Live Music | 6:30 - 9:30 P.M.
Enjoy a relaxed evening of great food and drinks, paired with live performances from talented local musicians on select Friday and Saturday nights.
Supervised childcare will also be available in the Bull Pen. Reservations must be made by 2:00 P.M. the day of.
TALENT LINEUP
▷ February 6 | Luis Rexach
▷ February 7 | Jose Rodriguez
▷ February 13 | Jen & Dave
▷ February 20 | Rick Voigt
▷ February 21 | Jen Rae
▷ February 27 | Juan
▷ February 28 | Dave Smith
Limited seating is available. Advanced reservations are highly recommended and can be made by calling 407.909.2000.
We kindly ask that Members and their guests adhere to the Club’s dress code.
WEDNESDAYS
5:30 - 8:30 P.M.
Join us for our signature Family Nights, where each week features a themed buffet filled with family-friendly favorites.
▷ Taste of Italia | February 4
▷ Mardi Gras | February 11
▷ Land & Sea Extravaganza | February 18
▷ Stuff-A-Plush | February 25
In addition to the buffet, a limited à la carte menu will be offered in Champions, while Lake Butler Lounge will be reserved exclusively for adult dining.
Advanced reservations are required and can be made by calling 407.909.2000.
SUNDAY, FEBRUARY 8
Shades | 11:00 A.M. - 2:00 P.M.
Start off your Super Bowl Sunday at the Club. Before the big game begins, dive into football-themed fun with inflatables and hands-on crafts, challenge friends to classic lawn games, and enjoy music from a live DJ. No tailgate is complete without a spread of game-day favorites.
Advanced reservations are required and can be made by calling 407.909.2000.


THURSDAY, FEBRUARY 12
6:00 - 9:00 P.M.
Celebrate the girlfriends who make life sparkle with an evening dedicated to all things Galentine’s. Sip on martini flights, build your own charcuterie board, and dance the night away. Capture the moment at our Polaroid picture station, enjoy light bites, and add a lasting touch with permanent jewelry by Dora Mae.
Advanced reservations are required and can be made by calling 407.909.2000.

WEDNESDAY, FEBRUARY 18
5:30 - 8:30 P.M.
From coastal classics to hearty land-inspired favorites, enjoy a spread that celebrates both surf and turf. This elevated Family Night features chef-crafted starters, seasonal salads, premium seafood, and signature cuts from the grill, complemented by indulgent desserts and a children’s buffet.
Advanced reservations are required and can be made by calling 407.909.2000.
WEDNESDAY, FEBRUARY 25
5:30 - 8:30 P.M.
Craft a new friend to love at our Stuff-A-Plush Family Night. Our youngest Members can select a cuddly plush, make a special wish, and bring it to life as they hand-stuff it with care. A buffet featuring Members’ favorites will be available to enjoy throughout the evening.
Advanced reservations are required and can be made by calling 407.909.2000.







FRIDAY, MARCH 6
FRIDAY, MARCH 6SUNDAY, MARCH 8
FRIDAY, MARCH 20SATURDAY, MARCH 21
Davis Cup
SATURDAY, MARCH 28



THURSDAY, FEBRUARY 26
Optional Practice Round & Round 1
FRIDAY, FEBRUARY 27 - SATURDAY, FEBRUARY 28
Rounds 2 - 5 & Shootout
This year’s tournament delivers a full schedule of competitive play as teams take on five 9-hole match-play rounds in a best ball format within each flight. Flight winners will advance to a final shootout to determine the overall champion.
Dinners will be served each evening, with Friday’s main dinner open to spouses and significant others. Lunch will be available at the turn, with beverages offered throughout the course.
Please note that registration for this event has closed.

WEDNESDAY, FEBRUARY 18THURSDAY, FEBRUARY 19
Get ready to soak up the island vibes at our Ladies’ Member-Guest, themed Welcome to the Tropics Teams of four will take on a unique format—three best balls on par 5s, two best balls on par 4s, and one best ball on par 3s—making every hole a new adventure.
This event is open to any lady golf Members and their guests. Teams can consist of one Member and three guests or two Members and two guests.
On both days, enjoy breakfast before heading out to play, followed by lunch in Champions Grill.
To register, please contact the Golf Professional Shop at 407.909.2030 or golfshop@isleworth.com.

SUNDAY, JANUARY 25 – TUESDAY, JANUARY 27
Start Time | 9:00 A.M.
The Club’s premier winter tradition returns. This two-person pro-scratch event will be played in a Stableford format with both balls counting toward the team score. Amateur and professional divisions will be awarded, along with optional professional and players’ pools and daily closest-to-the-pin contests.
The Invitational opens with a practice round and welcome reception, followed by round one and an evening event on day two. Day three concludes with round two, breakfast service, and the awards presentation.

TUESDAYS & THURSDAYS
Driving Range | 3:30 - 4:30 P.M.
Learn, play, and have fun on the course. These clinics are a great way for our young golfers to build skills like swinging, putting, and playing with good sportsmanship. Whether they're just starting out or want to get even better, there's something for everyone.
To sign up, please contact Brandon Hartlage at 609.350.9546 or brandon.hartlage@isleworth.com.
LADIES' GOLF CLUB CHAMPIONSHIP
Tuesday, November 4 - Wednesday, November 5

CHAMPION

NET CHAMPION
JUNIOR GOLF CLUB CHAMPIONSHIP
Saturday, November 15 - Sunday, November 16

Thursday, November 20 - Saturday, November 22

Friday, November 28 - Saturday, November 29



Tuesday, December 9 - Wednesday, December 10

CHAMPIONS

LOW GROSS
Friday, December 12 - Saturday, December 13

CHAMPIONS
TUESDAY, NOVEMBER 4 -
WEDNESDAY, NOVEMBER 5














SATURDAY, NOVEMBER 15 -
SUNDAY, NOVEMBER 16














THURSDAY, NOVEMBER 20SATURDAY, NOVEMBER 22














FRIDAY, NOVEMBER 21














FRIDAY, NOVEMBER 28SATURDAY, NOVEMBER 29

















TUESDAY, FEBRUARY 10
Early Rounds | 6:00 - 9:00 P.M.
TUESDAY, FEBRUARY 17
Finals | 6:00 - 9:00 P.M.
Compete for the title in this year’s Pickleball Doubles Club Championship, featuring both men’s and women’s divisions.
The competition concludes with the Finals on Tuesday, February 17, celebrated with a festive Mardi Gras theme, complete with a themed dinner and specialty bar as we crown the champions.
Participation requires a commitment to both dates.
Advanced registration is required and can be made on the Isleworth app or by calling the Racquet Professional Shop at 407.909.2050.


THURSDAY, JANUARY 15
6:00 - 8:00 P.M.
Join us for a fun and relaxed evening on the courts at our Tennis Mixed Doubles Social. Players of all levels are welcome, and no partner is required. Enjoy light refreshments and great company.
Advanced registration is required and can be made on the Isleworth app or by calling the Racquet Professional Shop at 407.909.2050.
SATURDAY, JANUARY 24
9:00 - 11:30 A.M.
Gather your girlfriends for a playful mix of sport and sips. Choose your court—pickleball or tennis—then unwind with rosé and light bites following play.
Advanced registration is required and can be made on the Isleworth app or by calling the Racquet Professional Shop at 407.909.2050.

THURSDAY, JANUARY 29
6:00 – 8:00 P.M.
Join our Tennis Professionals for an engaging evening of instruction, strategy, and match play. Enjoy the opportunity to sharpen your skills, compete alongside fellow Members, and gain on-court insight from the pros.
Advanced registration is required and can be made on the Isleworth app or by calling the Racquet Professional Shop at 407.909.2050.
WEDNESDAY, FEBRUARY 4
8:00 – 9:30 A.M.
Join us for the Final Match of the Ladies’ Doubles Pickleball Flex League. Cheer on your fellow Members while enjoying a courtside breakfast with a juice and mimosa bar, followed by a Pickleball Clinic from 9:30 – 10:30 A.M.
Advanced registration is required and can be made on the Isleworth app or by calling the Racquet Professional Shop at 407.909.2050.


SATURDAY, FEBRUARY 21
8:00 A.M. - 2:00 P.M.
Enjoy a full day of competitive play and camaraderie at our Men’s Tennis Pro Am. The morning begins with breakfast from 8:00 –9:00 A.M., followed by an exciting day on court where participants will have the opportunity to play alongside top pros. Members are welcome to bring their own professional partner to compete.
Following the final matches, join us for lunch and the awards presentation from 12:30 – 2:00 P.M.
Advanced registration is required and can be made on the Isleworth app or by calling the Racquet Professional Shop at 407.909.2050.

WEDNESDAY, FEBRUARY 25
4:30 - 5:30 P.M.
Show your team spirit by wearing your favorite jersey for a fun-filled evening of tennis. Prizes and snacks will be provided. This event is geared toward players ages 6 - 14.
Advanced registration is required and can be made on the Isleworth app or by calling the Racquet Professional Shop at 407.909.2050.
PARENT-CHILD COURT GAMES
Sunday, November 2

CHAMPIONS
AFTER THE FEAST POWER 120
Sunday, November 30

MEN’S CHAMPIONS

LADIES’ CHAMPIONS
MEN'S TENNIS DOUBLES CLUB CHAMPIONSHIP
Saturday, December 6

CHAMPIONS

RUNNERS-UP

SUNDAY
Junior Pickleball Clinic 9:00 – 10:00 A.M. Power 90 Tennis 9:00 – 10:30 A.M.
MONDAY
Ladies’ Tennis A+ & A3 Team Practice 8:00 – 10:00 A.M.
Ladies’ Tennis C++ Team Practice 10:00 A.M. – 12:00 P.M.
Ladies’ Tennis Classic League Practice 10:00 A.M. – 12:00 P.M. USTA Men’s Combo Practice 6:30 – 8:00 P.M.
TUESDAY
Greenhorn & Intermediate Pickleball Clinic 9:30 – 10:30 A.M.
WEDNESDAY
Greenhorn & Intermediate Pickleball Clinic 9:30 – 10:30 A.M.
THURSDAY
Men’s Tennis Practice 7:30 – 9:00 A.M.
FRIDAY
Pickleball Games Court 9:00 – 10:00 A.M.
Power 90 Tennis 9:00 – 10:30 A.M.
SATURDAY
Pickleball Play With the Pro 9:00 – 10:00 A.M.
Advanced registration is required and can be made through the Isleworth App or by calling 407.909.2050.

CLINIC SERIES 6 | JANUARY 5 – JANUARY 21
Drop-In or Make-Up Week: January 26 & January 28
CLINIC SERIES 7 | FEBRUARY 2 – FEBRUARY 18
Drop-In Day: February 23
MONDAY
Ages 4 - 6 Years Old 4:30 – 5:00 P.M.
Ages 6 - 8 Years Old 5:00 – 6:00 P.M.
Ages 8 - 14 Years Old 5:00 – 6:30 P.M.
WEDNESDAY
Ages 4 - 6 Years Old 4:30 – 5:00 P.M.
Ages 6 - 8 Years Old 5:00 – 6:00 P.M.
Ages 8 - 14 Years Old 5:00 – 6:30 P.M.
Advanced registration is required and can be made through the Isleworth App or by contacting Gabriela Garces at 407.909.2050 or gabriela.garces@isleworth.com.
SUNDAY, NOVEMBER 2




























MONDAY
A.M.
A.M.
TUESDAY
A.M.
WEDNESDAY
A.M.
THURSDAY
Restorative Core & Balance 8:00 A.M.
A.M.
FRIDAY
A.M.
A.M.
SATURDAY
Advanced registration is required, and cancellations must be made by noon the day prior to avoid charges.
Sign up by calling the Fitness Center at 407.909.2055, texting the Concierge at 407.269.2596, or emailing spa@isleworth.com.
Kaylee Visser Addy Visser Thea Ruggieri
Jacob Visser Ronan Berry Logan Lieberman
Lindsey Finer Charla Drabant Nicole Ryan
Taha Abdi Isaac Lightman Nick Kikuchi
FABULOUSLY FIT WOMEN
Katie Weaver Lydia Mortensen Francesca Taylor
FABULOUSLY FIT MEN
Hamish Berry Mike Ruggieri Rahul Suchde
FOREVER YOUNG WOMEN
Nan Kearn Paulette Digiannantoni Mary Buchholz
FOREVER YOUNG MEN
John Varley Joseph Kearn David Thomas
THURSDAY, NOVEMBER 27
















SATURDAY, FEBRUARY 7
9:00 A.M. - 12:00 P.M.
Let your little chefs get creative in this hands-on sweets workshop. Kids can learn how to roll, dip, and decorate their own cake pops, choosing from colorful toppings and fun designs to take home and share. This class is designed for ages 5 - 12.
Advanced reservations are required due to limited availability and may be made by contacting Lisa Carew at 407.909.2007 or lisa.carew@isleworth.com.


SELECT FRIDAYS & SATURDAYS
6:00 - 10:00 P.M.
The Bull Pen, our kid-friendly haven for ages 3 - 13, is available exclusively for families dining at the Club. While parents enjoy some well-deserved time to themselves, kids can dive into a space designed entirely for them, filled with exciting games, engaging activities, and plenty of opportunities to play and make new friends.
An à la carte dinner to order will be provided.
Advanced reservations are required by 2:00 P.M. on the day of. To reserve, contact Lisa Carew at 407.909.2007 or lisa.carew@isleworth.com.
SATURDAY, JANUARY 17
6:00 - 10:00 P.M.
Join us for the first in our new series of monthly themed Bull Pen Nights. This month’s Winter Wonderland edition features a festive dinner, seasonal games, creative crafts, and plenty of frosty-themed excitement for all.
Advanced reservations are required by 2:00 P.M. the day of. Please note that participation includes an additional fee beyond the standard Bull Pen Night rate.
SUNDAY, JANUARY 25
5:00 - 7:30 P.M.
Designed to build confidence, poise, and social skills, this interactive class introduces children ages 9 - 12 to the foundations of modern etiquette. Participants will learn fine dining table manners, proper eating techniques, silverware placement, posture, greetings, and more.
A formal, child-friendly coursed dinner—complete with dessert—will be served as part of the instruction. Jackets are required for boys, and formal dress attire is required for girls.
Advanced reservations are required and may be made by contacting Lisa Carew at 407.909.2007 or lisa.carew@isleworth.com.


SATURDAY, FEBRUARY 21
6:00 - 10:00 P.M.
Our monthly themed Bull Pen Nights continue, inviting creativity to take center stage. Our youngest Members will design their own canvas masterpiece in the Bull Pen, then enjoy fresh cookies for dessert and unlimited play throughout the evening.
Advanced reservations are required by 2:00 P.M. the day of.
Please note that participation includes an additional fee beyond the standard Bull Pen Night rate.


As we welcome a new year in our community, we are pleased to share an exciting update from Isleworth Realty. January marks not only a fresh start, but also a moment of growth and momentum for a
firm that continues to play an integral role in our neighborhood.
Isleworth Realty is proud to announce the addition of two outstanding professionals, further strengthening an already exceptional team. Sarah Longwell rejoins Isleworth Realty, bringing with her both professional experience with the firm and a personal connection to the community as a former resident. Her return reflects a true homecoming—one grounded in firsthand knowledge of life within the gates and a genuine understanding of what makes Isleworth so special.
As Sarah puts it, “Coming back feels like coming home. I’m incredibly happy to return to a wonderful neighborhood I know and love, and to reunite with such a talented, supportive team. This firm has always felt special, and I’m grateful to once again be part of a place that truly values relationships, integrity, and community.”
Also joining the team is Carmen Ramirez, who brings a wealth of organizational and management expertise after spending the last two years managing the Tavistock House. Known for her excellence in operations and attention to detail, Carmen adds a new layer of structure and support that enhances the team’s ability to serve clients seamlessly and efficiently.
These strategic additions underscore Isleworth Realty’s ongoing commitment to strengthening its team in thoughtful, meaningful ways. Each new member enhances the firm’s ability to deliver personalized service, discretion, and results—hallmarks of Isleworth Realty’s success within the community.
Looking ahead, Isleworth Realty enters the new year energized and well positioned—reinforced by returning talent, new expertise, and a proven track record of success. Whether welcoming new neighbors or guiding longtime residents through their next chapter, the team remains dedicated to representing our community with professionalism, integrity, and pride.


$71 Million SOLD AND PENDING IN 2025 19 Properties SOLD IN 2025 (YTD)
in
TOTAL TRANSACTIONS SOLD IN 2025
ISLEWORTH HOMES SOLD IN 2025 $5.1M
ISLEWORTH HOMES SOLD IN 2025
For more than 30 years, Isleworth Realty has been the trusted name in luxury real estate within the gates of Isleworth.
As the leading team for buying and selling in this exclusive enclave, Isleworth Realty is consistently recognized both locally and globally for exceptional sales—a testament to the team’s professionalism, market expertise, and unwavering dedication to excellence.
In the past decade alone, Isleworth Realty has closed over $300 million in transactions, including two record-breaking sales, including the highest-priced single-family home sale and the highest-priced vacant lot sale in Central Florida history at $35 million and $15 million, respectively.
Located in Tavistock House just outside Isleworth’s main gate, Isleworth Realty delivers bespoke service and meticulous attention to detail in every transaction, setting the standard for luxury real estate in Central Florida.
That same legacy of excellence now extends beyond the gates with IWR Realty—your dedicated partner for luxury residential real estate throughout Windermere and the larger Central Florida area.
Whether you’re buying or selling outside the gates, our top-producing team of seasoned luxury property specialists is here to guide you every step of the way with the highest level of professionalism and personalized care.

5525 ISLEWORTH COUNTRY CLUB DRIVE
Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living.
The two-story estate is set on a pristine 1.02-acre golf-front home site along Isleworth’s famed championship golf course and from the moment you enter, you’ll be captivated by the artistry in design and modern innovation. The interiors span more than 9,500 square feet living and 13,000 under roof, blending 5 bedrooms, 5.5 baths and an array of indoor and outdoor living areas with uncompromisingly luxurious finishes designed for effortless entertaining and quiet moments alike. At the heart of the home, the showstopping glass-enclosed wine room— temperature-controlled and with more than 2,200-bottle capacity—is a collector’s dream and the ultimate conversation piece.
Outdoor spaces are equally impressive, with an expansive lanai and balcony, a custom swimming pool with fire pits, meticulously landscaped yard adorned with integrated lighting, sound and lush, native greenery and putting green —all overlooking panoramic views of Isleworth’s championship golf course.
Full Bathrooms
Half Bathrooms
Acres






Poised on the shores of Lake Bessie, the 5,548-square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. Custom French entry doors flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas, while a richly appointed library adds warmth and refinement. With its oversized windows capturing endless lake vistas, a large sitting area, exterior balcony, and an en-suite bath featuring dual vanities, a soaking tub, and walk-in shower, the primary suite is a sanctuary of light and serenity.
On the lower level, the estate offers two expansive bonus areas joined by a well-equipped kitchenette. Ideal for gaming, entertaining, or working from home, both spaces connect effortlessly to the sun-drenched pool terrace. A stunning mature oak tree anchors the property’s beautiful lakefront grounds, stretching gracefully toward the water’s edge—a signature of the property’s natural beauty. Beyond the oak tree, Lake Bessie shimmers in full view, offering a breathtaking backdrop to the estate.

5 Bedrooms 4 Full Bathrooms
1 Half Bathroom
5,548 Sq. Ft
0.69 Acre
OFFERED AT $4,900,000


Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout. Beautiful porcelain tile travels throughout the main level from the spacious living room with an oversized modern built-in featuring slate stonework and lit shelves. The spacious primary suite features a large sitting area and an ensuite bathroom with dual vanities, a walk-in closet, modern soaking tub and separate walk-in shower. Completing the main level are the home office, formal dining room, elegant powder bath and center-island kitchen with casual dining area. Two additional bedrooms with balcony access are on the upper level.
Step outside and discover a newly reimagined outdoor living experience. The expansive pool deck has been fully updated with sleek new pavers, while fresh turf and lush landscaping create a vibrant backdrop for relaxation and entertaining. The outdoor kitchen has been thoughtfully upgraded with new granite, a built-in grill, pizza oven, sink, and designer lighting—seamlessly blending function with style. Enjoy evenings around the modern fire pit, take a dip in the resurfaced pool with its brandnew heater, or unwind in the extended backyard.



This beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene primary suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. A richly detailed wood-paneled office and a well-appointed laundry room complete the main level, adding warmth and function.
The home’s thoughtful layout places the secondary bedrooms on the lower level. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless designand beautiful grounds, this remarkable residence is truly a sanctuary to call home.



Crafted by Pellegrini Homes with professionally designed interiors, this exquisite garden villa seamlessly blends architectural sophistication with inviting comfort. Throughout the home, travertine floors and curated details complement a spacious open plan, lending to the home’s exceptional design and craftsmanship. The thoughtfully designed layout includes three bedrooms, one of which is a private cabana suite opening directly to the pool—ideal for guests or quiet retreat. The primary suite features a large bedroom, dual closets and a beautifully finished bath.
The center-island kitchen serves as a culinary showcase with custom cabinetry and premium appliances by Viking, Sub-Zero, and GE Monogram, while the adjoining casual dining area offers views of the pool and lush surroundings. Centered around its picturesque courtyard pool with fireplace, summer kitchen, and hot tub, this remarkable residence offers both privacy and elegance in perfect balance—an exceptional opportunity to live beautifully within one of Isleworth’s most coveted enclaves.



Featuring timeless elegance, this beautifully designed four-bedroom garden villa has been thoughtfully curated to create a refined sanctuary for everyday living and entertaining. Beyond the stately arched main entry door lies a secluded courtyard oasis—a private retreat centered around a sparkling pool, serene waterfall feature, and generous lounging areas.
Inside the main residence, a sense of contemporary sophistication flows through the light-filled kitchen, elegant dining room—highlighted by a statement chandelier—and the spacious grand room. French doors throughout invite the outdoors in, offering lush views from nearly every space and extending the living area to multiple porches and verandas. The living room, centered around a calming fireplace, is the perfect spot to unwind after a long day, while the spa and cascading waterfall nearby add to the sensory appeal. Retreat to the expansive primary suite, where a private porch overlooks vibrant greenery, offering a peaceful start and end to each day.



12540 PARK AVENUE
Located along the shores of Lake Butler in the esteemed gated community of Chaine du Lac, this distinguished estate has been elevated with significant recent improvements, including a brand-new roof, an all-new primary suite, a fully updated outdoor kitchen, and a $100,000 designer lighting package by Lightstyle of Orlando.
Designed for effortless entertaining, the elegant living and dining rooms are highlighted by soaring ceilings and a dramatic double-sided fireplace, while the spacious family room and breakfast nook seamlessly connect to the kitchen and open to serene water views. The all-new primary suite has been fully reimagined with a new spa-like bathroom featuring elevated modern appointments including beautiful vanities, an oversized walk-in shower and a freestanding tub.
The outdoors are equally captivating, with spacious sundeck surrounding a sparkling pool with fire pits. From golden sunsets to every carefully curated detail, the residence is framed by sweeping lakefront vistas and an ambiance of refined living.



A new long elegantly paved driveway leads up to this beautifully updated home in the charming Town of Windermere. With lush views of established landscaping and surrounding trees, this home combines comfort, style, and plenty of space for family and friends. The bright, open kitchen is the heart of the home, featuring granite countertops, stainless steel appliances, and windows that fill the space with natural light. The kitchen flows into the dining area and great room, where vaulted ceilings, a cozy gas fireplace, and warm accent lighting make it the perfect place to gather.
Step through the French doors to an oversized balcony overlooking the pool and privacy landscaping. The primary suite sits on its own level with a large sitting/dressing area and a personal balcony—a true retreat at the end of the day. On the main floor, you’ll find two more bedrooms, a full bath, and a convenient laundry room. The lower level offers a spacious entertainment area, an en-suite bedroom, an additional full bath, and a fifth bedroom which is currently serving as a stylish home gym. All open directly to the pool deck and fenced backyard, creating an easy flow for family fun and entertaining.



New roof installed in September 2025. Discover a rare opportunity to own in the desirable Bay Hill Village, a hidden gem within the prestigious Bay Hill community in Central Florida.
With its sought-after single-story floor plan, this villa is positioned on a beautifully landscaped, oversized lot within the community, ensuring both privacy and tranquility. The stunning residence offers 2, 600 square feet of living space with 3 spacious bedrooms and 2 full and 1 half baths, presenting a perfect blend of comfort and elegance throughout. Step outside to your own private, enclosed courtyard, an idyllic space designed to let you bask in the warmth of the Florida sun, creating the perfect setting for relaxation or entertaining.
Bay Hill Village is a serene enclave featuring only 121 residences surrounded by gorgeous tree-lined and exceptional community amenities which include a clubhouse, fitness center, swimming pool and tennis courts.


MAIN LINE
407.909.2000
CARY MASSEY
General Manager
407.909.2006 cary.massey@isleworth.com
ALAN GHICIAC Assistant General Manager 407.909.2002 alan.ghiciac@isleworth.com
JENNIFER SELF-KIRK Director of Membership 407.909.2004 jennifer.self-kirk@isleworth.com
BRETT CAFFERTY Director of Golf
407.909.2032 bcafferty@isleworth.com
DAN O’CONNELL
Director of Community Association 407.909.2071 dan.oconnell@isleworth.com
MARCO HERRERA
Director of Racquet Sports 407.909.2052 mherrera@isleworth.com
CHRIS STORELLI
Director of Food & Beverage 407.909.2010 chris.storelli@isleworth.com
JASON HALL
Executive Chef 407.909.2025 jhall@isleworth.com
CHRISTINE FREW
Catering & Sales Manager 407.909.2013 cfrew@isleworth.com
LYNN WRIGHT Fitness & Spa Manager 407.909.2055 fitnesscenter@isleworth.com
LISA CAREW Director of Youth Services 407.909.2007 lisa.carew@isleworth.com
ANNIE SNYDER Director of Marketing 407.909.7049 annie.snyder@isleworth.com
DANIELLE FREW
Club Marketing Manager 407.909.2005 dfrew@isleworth.com
MARY GROOM
Member Accounting 407.909.2097 mgroom@isleworth.com
ISLEWORTH SECURITY GATES securityinfo@isleworth.com
SECURITY 407.909.2075
MAIN LINE
407.876.0111
MONICA LOCHMANDY
Broker, Luxury Property Specialist o. 407.909.9934 | c. 407.230.6888 mlochmandy@isleworth.com
MICHELLE CORBIN
Luxury Property Specialist 407.909.9932
michelle.corbin@isleworth.com
SARAH LONGWELL
Luxury Property Specialist 407.876.0111
sarah.longwell@isleworth.com
DAVID PHILPOTT
Isleworth Home Services & Landscaping 407.909.2062 homeservices@isleworth.com
ANNIE SNYDER
Director of Marketing 407.909.7049
annie.snyder@isleworth.com
CARMEN RAMIREZ
Real Estate Assistant 407.876.0111
carmen.ramirez@isleworth.com
Monday, 9:00 A.M. - 4:00 P.М.
Tuesday - Friday, 8:30 A.M. - 5:00 P.M.
Saturday & Sunday, 8:30 A.M. - 4:00 P.M.
All Dining Outlets are Closed on Mondays Advanced Reservations Required
CHAMPIONS GRILL
Breakfast | Tuesday - Sunday, 7:30 - 10:00 A.M.
Lunch | Tuesday - Sunday, 11:00 A.M. - 5:00 P.M.
Dinner | Tuesday, 6:00 - 9:00 P.M.
Wednesday, 5:30 - 8:30 P.M.
Thursday - Saturday, 6:00 - 9:00 P.M.
Sunday, 5:30 - 8:30 P.M.
WINDERMERE ROOM
Thursday - Saturday, 6:00 - 9:00 P.M.
LAKE BUTLER LOUNGE
Tuesday, 6:00 - 9:00 P.M.
Wednesday, 5:30 - 8:30 P.M.
Thursday - Saturday, 6:00 - 9:00 P.M.
Sunday, 5:30 - 8:30 P.M.
MEN’S GRILL
Tuesday - Saturday, 11:00 A.M. - 4:00 P.M.
SWIMMING HOURS
Dawn - Dusk
SHADES DINING HOURS
Tuesday - Sunday, 11:00 A.M. - 4:00 P.M.
GOLF
GOLF COURSE
Tuesday - Sunday, 8:00 A.M. - Dusk
DRIVING RANGE
Tuesday - Sunday, 7:30 A.M. - Half an Hour Before Dusk
GOLF PROFESSIONAL SHOP
Tuesday - Sunday, 7:00 A.M. - 6:00 P.M.
TENNIS & PICKLEBALL COURTS
Monday - Sunday, 7:00 A.M. – 9:00 P.M.
RACQUET PROFESSIONAL SHOP
Monday & Friday, 8:00 A.M. - 2:00 Р.M.
Tuesday - Thursday, 8:00 A.M. - 4:00 P.M.
Saturday & Sunday, 8:00 A.M. - 12:00 P.M.
Monday, 6:00 A.M. - 8:00 P.M.
Including the Locker Rooms
Tuesday - Friday, 6:00 A.M. - 9:00 P.M.
Saturday & Sunday, 7:00 A.M. - 5:00 P.M.
Friday & Saturday, 6:00 - 10:00 P.M.
Advanced Reservations Required by 2:00 P.M. on the Day Of
CLUBHOUSE & RESERVATIONS
407.909.2000
MEMBERSHIP OFFICE
407.909.2004
MEMBER ACCOUNTING
407.909.2097
GOLF PROFESSIONAL SHOP
407.909.2030
RACQUET PROFESSIONAL SHOP
407.909.2050
FITNESS CONCIERGE CELL PHONE
407.269.2596
SECURITY
407.909.2077
