The Orlando Health / Town of Windermere Run Among the Lakes turned twenty-five this year, and the town marked the occasion the way Windermere marks most things that matter: together, on its own home ground, with neighbors showing up for one another and cheering at every turn.
Windermere’s new Ward Trail bridge opened days before school started. Town Consultant Engineer John Fitzgibbon and the team who made the ten-week deadline.
Keegan and Natalie Berry followed the people they love to Windermere, settling one house away from Natalie’s parents to raise three daughters surrounded by family.
Matt and Kerry McKissock built a life on faith, hard work and gratitude, from Army service to Windermere Dentistry and a family rooted in Central Florida.
Stephen and Amanda Lewis found their way to Windermere on a pandemic-era car date and have been pouring their energy into the community ever since.
After more than 15 years of service, outgoing Windermere Mayor Jim O’Brien and his wife, Kristin, reflect on rebuilding the town’s foundation, the Ward Trail, and a family legacy of showing up.
From the Pocono Mountains to Lake Down, Joe and Amanda Ferst built a family rooted in gratitude, and left one line on their Centennial bench open on purpose.
From an Ocoee baseball legacy to custom homes along the Butler Chain, Bob and Jody Sorenson have built Sorenson Construction, and a family, on faith and trust.
From Toronto to a healthcare technology company and a vineyard wedding in Italy, Arjun and Sara Kumar found home in Windermere, and with it, Solvino.
Keene’s Pointe-raised guitarist Caitlin Caggiano found her way from Nashville heartbreak to a global guitar academy, Disney stages and a home on Main Street.
Meet Mike Kleinfelt of Windermere Photography, the decorated law enforcement officer whose camera brings our feature families to life every month.
Symphony storytimes, Halloween crafts, a fall plant clinic and book clubs: the Orange County Library System has a season full of treats for every age.
A new 100,000-square-foot event venue makes the Walt Disney World Swan and Dolphin the largest convention hotel on the US Eastern Seaboard.
Serge, owner of Windermere’s Olive Luxury Ride, built his chauffeur service on three words: luxury, comfort, reliability.
Windermere’s own Lee Howell and Wonderly Lights of Orlando design custom holiday, permanent roofline and landscape lighting for homes across Isleworth, Bay Hill, Keene’s Pointe and Golden Oak.
Motor Volta brings Orange County its first luxury car condominium, and it started with a Windermere neighbor who ran out of room.
September is Library Card Sign-up Month. OCLS Director Steve Powell on everything a free library card unlocks, from streaming to Local Wanderer passes.
It began in 1966 with two boys and a prayer. Sixty years later, Edgewood Children’s Ranch is still a home and a school where children find hope.
The Orlando Health Town of Windermere Run Among the Lakes turned twenty-five, with an anniversary medal honoring a hometown hero and a place for everyone.
For the first time, celebrity chefs Michael Mina and Todd English will lead a joint tasting at the Walt Disney World Swan and Dolphin Food & Wine Classic.
Trenton Postell of V Pizza Lake Buena Vista on why imported ingredients and a wood-fired oven still matter, from the August 2026 Butler Chain Living.
Steve Powell of the Orange County Library System on the value of your library and the West Oaks Branch 25th anniversary celebration.
The Nurture Place has brought trauma-informed counseling and family support to Central Florida since 2019, and Nurture Night celebrates that mission.
For a quarter century, the Run Among the Lakes has been one of Windermere’s traditions, and Neighbors of Windermere is proud to sponsor it.
The Simon Simaan Group is the Official Medal Awards Sponsor of the 2026 Windermere Run Among the Lakes, and runners helped pick the medal.
The 17th annual Walt Disney World Swan and Dolphin Food & Wine Classic returns Nov. 20 and 21, and the 2026 menu line-up is here.
Steve Powell of the Orange County Library System on July programs for America’s 250th and summer reading.
Windermere’s Tyler Price is one of 18 students worldwide accepted into Juilliard’s drama program.
Greg Wilhoyte of Action Water Sports on the freedom of a day on the water with family and friends.
A Community Spotlight on Windermere’s most refreshing new venture, a lemonade stand with a very serious leadership team.
Jocklyn Mundy on 25 years of the Town of Windermere Run Among the Lakes, coming Saturday, Oct. 10.
A Community History piece by Izzy Ramos on America’s 250th and Windermere’s place in that story.
Tickets are on sale for the fan-favorite outdoor festival at the Walt Disney World Swan and Dolphin, Nov. 20 and 21.
A Charity Spotlight letter from Jeff Fitzgerald, Executive Director of Edgewood Children’s Ranch.
Summer at Your Library is back at the Southwest Branch, with reading challenges, free books and programs for the whole family.
Celebrity chefs, award-winning wine lists and complimentary childcare make the Walt Disney World Swan and Dolphin a dining destination close to home.
Little Solia calls her family’s magazine feature “a princess story” and asks for it at bedtime. Moments like this are why we love telling your stories.
Nearly 200 guests filled The Pines at Windermere on Valentine’s night for the sold-out inaugural Boots & Salutes, supporting Healing Warriors Week.
