Living in Windermere, FL: Scenic Lakes, Luxury Homes & Lifestyle Near Orlando

Set along the shimmering Butler Chain of Lakes, Windermere, FL offers a lifestyle defined by comfort, privacy, and natural beauty.

Just a short drive from downtown Orlando, this lakeside town feels worlds away from the city’s fast pace. With a population of just over 3,500, Windermere, FL is known for its close-knit community, well-kept neighborhoods, and peaceful, tree-lined streets.

Many residents are drawn to this small lakeside enclave for its top-rated public and private schools, and its access to outdoor recreation. Locals enjoy everything from paddleboarding on the lake to family picnics at the city’s many parks or hikes through its nearby nature preserves. Community events—like holiday parades and movie nights under the stars—add to the small-town feel, making it an easy place to connect with neighbors.

At present, homes for sale in Windermere, FL range from modern lakefront estates with private docks to elegant homes tucked into quiet cul-de-sacs. For buyers looking for a blend of luxury living and everyday ease—without sacrificing access to Orlando’s entertainment, dining, and airport, Windermere, FL offers a smart, balanced lifestyle that’s hard to find anywhere else in the region.

Healthcare Options

Find medical and healthcare facilities in and around Windermere, FL

Windermere, FL enjoys easy access to some of the best hospitals in FloridaInvesting in homes for sale in Windermere, FL means getting easy access to high-quality healthcare, ensuring residents have peace of mind when it comes to their medical needs. Several major hospitals are located just a short drive away, offering advanced treatment options, emergency care, and a wide range of specialties. Within the community, residents also benefit from family-focused medical practices that provide services such as primary care, pediatrics, internal medicine, and chiropractic care. Many facilities accept walk-ins, making it easy to receive timely care without extensive wait times.

Orlando Health – Health Central
AdventHealth Winter Garden
Orlando Health – Horizon West Hospital
Orlando Health Arnold Palmer Hospital for Children Specialty Practice
Orlando Health Physician Associates
Windermere Medical Center

Recreation and Activities

Where to have fun, be entertained, and learn

Windermere, FL offers a wealth of attractions and adventuresSurrounded by sparkling lakes and lush preserves, Windermere, FL is a haven for outdoor enthusiasts. The area’s scenic parks and nature trails invite leisurely strolls, birdwatching, and moments of quiet reflection beneath the canopy of towering oaks. The nearby chain of lakes offers ample opportunities for paddleboarding, kayaking, and fishing in serene waters. Wildlife sightings, from playful squirrels to graceful wading birds, add to the sense of natural immersion. Cyclists and walkers can explore nearby paved trails that wind through Central Florida’s gently rolling terrain, offering a healthy, scenic way to connect with the landscape. Whether on the water or under the trees, Windermere, FL’s outdoor activities create a lifestyle rooted in nature and year-round recreation.

Tibet-Butler Nature Preserve
West Orange Trail
Lake Bessie Park
Lake Butler Scenic Trail
Windermere Town Hall Park

Shopping Options

Choose from different shopping experiences in Windermere, FL, from boutiques to local markets

Windermere, FL has a plethora of shopping optionsWindermere, FL offers a refreshingly curated shopping experience, blending the charm of local boutiques with the convenience of nearby retail destinations. At its downtown core, charming storefronts and specialty shops reflect Windermere, FL’s lakeside elegance, showcasing everything from artisan gifts to wellness goods. Just beyond the town’s quiet streets lie open-air centers and village-style plazas that provide a wider array of shopping and dining options. Farmers markets bring the community together with local produce and handcrafted finds, while nearby lifestyle centers cater to broader retail needs without sacrificing the small-town atmosphere.

Windermere Village Center
Shoppes of Windermere
Lake Buena Vista Factory Stores
Westside Shoppes
The Grove Orlando
The Marketplace at Dr. Phillips
Lakeside Village Center
Winter Garden Village at Fowler Groves
Windermere Farmers Market

Dining Out

Discover the different flavors of Windermere, FL

Windermere, FL offers top-tier restaurants and dining spaces.While Windermere, FL is best known for its serene lakes and upscale homes, it’s also worth mentioning that this lakeside enclave is also a destination for elevated yet approachable dining. The town’s culinary scene blends global flair with local charm, inviting residents to savor everything from inventive Asian street food to hearty Southern comfort fare. Friendly cafes, intimate bistros, and chef-driven kitchens are tucked along tree-lined streets, creating a relaxed yet refined atmosphere. Whether you’re indulging in a slow weekend brunch or looking for bold international flavors, you’ll find something for you in Windermere, FL.

Fine Dining & Special Occasion Restaurants

Ocean Prime (Dr. Phillips)
Chatham’s Place (Dr. Phillips)
The Chef’s Table at the Edgewater (Downtown Winter Garden)

Casual Dining & Local Favorites

Market To Table (Downtown Winter Garden)
The Hangry Bison (Winter Garden)
Mangoni (Downtown Winter Garden)
Seito Sushi (Dr. Phillips)
Rocco’s (Dr. Phillips)
Sixty Vines (Dr. Phillips)
Bar Taco (Dr. Phillips)
Dragonfly Robata Grill & Sushi (Dr. Phillips)
Bosphorous Turkish Cuisine (Dr. Phillips)
The Whole Enchilada (Winter Garden)
Urban on Plant Kitchen & Bar (Downtown Winter Garden)

Desserts & Cafés

Scoops Old-Fashioned Ice Cream Store (Downtown Winter Garden)
Dixie Cream Cafe (Windermere)
Foxtail (Dr. Phillips)
CFS (Dr. Phillips
La Carraia Florida Gelateria
Axum Coffee (Downtown Winter Garden)
Paloma Coffee Co. (Windermere)

Find Homes For Sale in Windermere, FL

Buyers are drawn to Windermere, FL for its scenic charm, top-tier schools, the curated lifestyle, and upscale homes for sale. For those seeking a refined yet grounded community in the heart of Central Florida, Windermere, FL is a place where life feels beautifully balanced.

Ready to start looking at homes for sale in Windermere, FL? Call 407.900.0771 or send an email to schedule your personalized consultation.