Windermere / Dr. Phillips

Tranquil and exclusive, Windermere and Doctor Phillips are some of Florida’s most prestigious communities.

Welcome to Windermere and Doctor Phillips

Luxury homes and historic beauty in the Orlando suburbs. Discover Windermere FL real estate!
Tranquil and exclusive Windermere and Doctor Phillips are some of Florida’s most prestigious communities. Sprawling lawns and quiet, leafy streets create an oasis of suburban bliss and the ideal backdrop for family life. Those lucky enough to call Windermere home wake to the sun shining on expansive estates and picturesque lakefront views while Orlando waits to be explored less than half an hour away. Doctor Phillips offers an even tonier experience, with stunning properties with grand pools set in lush backyards, tropical gardens spilling over stone walls and trellises, and custom homes in the most coveted neighborhoods in Florida.   
Named for England’s Lake Windermere, the Florida namesake began as many exclusive Florida towns did – as a luxurious winter getaway for wealthy northerners. The beauty and balmy weather charmed those who visited, and this lovely enclave soon became a coveted destination in its own right. Doctor Phillips, named for the doctor-philanthropist who developed its former citrus groves, dazzles residents with sprawling gated estates, Mediterranean-style architecture, cathedral ceilings, and gourmet kitchens fit for a Michelin chef.

What to Love About Doctor Phillips & Windermere FL Real Estate 

  • World-class dining on famed Restaurant Row
  • Outstanding public schools and private academies
  • Affluent neighborhoods with opulent estates
  • Proximity to Disney and Orlando International Airport

People & Lifestyle

Posh and highly sought-after, Windermere and Doctor Phillips offer secluded gated communities and high-level privacy, making these enclaves perfect for celebrity and high-profile residents. Those who appreciate Florida’s nature and outdoor recreation will delight in the wild beauty of this unique spot. With picturesque surroundings, like the Butler Chain of Lakes, these beautiful towns set the scene for a life of beauty and wonder. If you are interested in searching the Windermere real estate market, contact our team today!

Dining, Entertainment & Shopping

From impeccable cuisine to luxe private clubs, Windermere and Dr. Phillips were made for those with refined tastes and sophistication. Restaurant Row in Dr. Phillips shines with culinary stars and acclaimed chefs and offers a carefully curated collection of first-class bistros and elegant dining rooms. Chef-owned Christini's is one of the Orlando area’s finest restaurants, with an award-winning menu of authentic Italian cuisine and a sophisticated setting. Stylish and modern, Kabooki dazzles with fresh sushi and creative Pan-Asian fare, while buzzy Rocco's Tacos delights with classic Mexican dishes and over 400 varieties of tequila, and chic Slate elevates New American fare. Yellow Dog Eats offers a decidedly casual vibe, with a menu of sandwiches and barbeque, as well as a dog-friendly patio. Nearby, the posh feel of Feather and Quill is as coveted as the scratch cuisine.

Those interested in the private club experience will relish the exclusive ambiance of London House. Inspired by British refinement and luxury, this elite society offers a white-glove butler experience and limited membership. The esteemed Corona Cigar Co. showcases the finest products and tasting packages, while Orange County Sportsmen's Club is a private boating club dating back to 1931. 

Things to Do

Friday mornings in Windermere are a favorite among residents, who flock to Town Square Park for the weekly Farmers’ Market. The centerpiece of Keene’s Pointe, the prestigious Golden Bear Club invites members to enjoy the impeccable Jack Nicklaus-designed golf course, lined with majestic oaks and towering cypress trees, as well as the luxurious clubhouse. Set on the edge of picturesque Lake Isleworth, RD Keene Park offers lushly landscaped grounds for lounging, picnicking, or soccer games. Over in Doctor Phillips, golf reigns supreme with the legendary Arnold Palmer Invitational, while the stylish Trellis 925 is the acclaimed event venue for all the biggest celebrations. Leisurely days are spent at Dellagio Town Center. From spa visits and lunches to ballroom dancing lessons and fine dining, this is the premier destination for relaxation and refinement in Doctor Phillips. 


Windermere and Doctor Phillips offer an outstanding selection of highly sought-after schools, including:



Search All Homes for Sale in Windermere FL

For Sale

Real Estate & Homes for Sale

Work With Us

Core4 Group is equipped to provide clients with experienced representation and personalized professional service. Contact us today to start your home searching journey!

Follow Us on Instagram