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Nestled among the pristine Butler Chain of Lakes, just 15 minutes from downtown Orlando, Windermere is Central Florida's epitome of refined lakeside luxury.
With a population of approximately 3,200 residents, this exclusive enclave blends serene natural beauty with sophisticated amenities, offering a coveted escape for affluent families, executives, and retirees. Known for its guard-gated communities, world-class golf courses, and A-rated schools, Windermere delivers an unparalleled lifestyle where waterfront estates meet effortless elegance—only 20 minutes from Disney's magic and Orlando's vibrant energy.
Savor farm-to-table flavors at local gems like Feather and Quill, where craft cocktails pair with bone marrow croquettes and filet mignon, or unwind at Hooked Seafood for fresh catches with lake views. For family fun, Dixie Cream Café serves all-American comfort food amid colorful, nostalgic vibes. Nearby, The Grove offers eclectic eateries from Italian at Manzzo to sizzling hibachi at Mikado Japanese Steak House—perfect for date nights or group gatherings. Annual events like the Windermere Farmers Market bring live music, artisanal bites, and community spirit every Saturday.
Indulge in boutique bliss at Windermere's historic Main Street, featuring Tim’s Wine Market for rare vintages and Five Star Florida Finds for unique local crafts. The Grove at Windermere provides one-stop luxury with high-end retailers, Trader Joe’s, and specialty shops. For bigger hauls, Winter Garden Village (10 minutes away) boasts upscale chains like Nordstrom Rack and Williams Sonoma, all while maintaining Windermere's intimate, low-key vibe.
Embrace the great outdoors on the Butler Chain of Lakes with boating, kayaking, or scenic tours via Florida Lake Tours—spot wildlife amid 14 interconnected waterways. Championship golf at Isleworth or Keene’s Pointe challenges pros and novices alike, while parks like Lake Street Park and Deputy Scott Pine Community Park offer trails, playgrounds, and yoga sessions. Wellness seekers thrive at local spas or fitness centers in gated enclaves, with equestrian trails and tennis courts enhancing the resort-like daily routine.
Windermere prioritizes excellence in education, boasting some of Central Florida's top-rated public and private institutions—ideal for families seeking academic rigor and extracurricular depth.
Windermere's market remains a beacon for luxury investment, with steady appreciation driven by limited inventory and high demand. As of November 2025, the median home price sits at $1.02M.
Windermere's gated enclaves like Isleworth and Keene’s Pointe epitomize exclusivity, with 24/7 security and HOA fees covering lush landscaping, tennis, and events. Community spirit thrives through holiday parades, volunteer initiatives, and multigenerational parks—fostering neighborly bonds in a tranquil, family-focused enclave.
At Own Luxury Homes®, we specialize in Windermere's elite properties, leveraging CEO/Broker Ryan Brown's decades of Central Florida expertise to match discerning clients with their ideal lakeside legacy. Our concierge service handles everything from virtual tours to custom lot sourcing, ensuring seamless transitions into this prestigious haven. With over $500M in luxury sales, we deliver insider access to off-market gems and market-savvy negotiations.
Contact Ryan Brown, CEO & Broker at Own Luxury Homes®
407-900-7030
What our clients are saying
- Buyer, Greenwich, CT The team at Own Luxury Homes made relocating from London effortless. They handled every detail, from property tours to closing coordination. Their knowledge of the Greenwich market helped us find our dream home in the perfect neighborhood.
~ Michael O'Brien
After months of searching, Own Luxury Homes found us the perfect Southampton estate with ocean views and privacy. Their negotiation skills saved us considerably, and their local expertise was invaluable for understanding property regulations.
~ Thomas Ashford
- Seller, Scottsdale, AZ I was impressed by Own Luxury Homes' digital marketing and international reach. Our desert contemporary sold to a buyer from overseas within 45 days. Their communication throughout the process was outstanding.
~ Sophia Patel
Bought our Winter Park home through Ryan Brown and couldn't be happier. They were responsive, knowledgeable, and really advocated for us throughout negotiations. Best luxury realtors in Central Florida!
~ Christopher T.
Relocated for work and Own Luxury Homes made finding our Keene's Pointe home easy. They understood our timeline and budget, showing us only the best properties. Excellent service for Orlando luxury real estate!
~ David L.
Sold our modern Laureate Park home with Own Luxury Homes and couldn't be happier. They understand the Lake Nona luxury market and brought serious buyers from day one. Highly recommend for Central Florida luxury real estate!
~ William H.
Our Bay Hill home sold in record time thanks to Ryan Brown. He positioned our property perfectly in the Dr. Phillips luxury market and brought multiple offers. True professionals in high-end Orlando real estate.
~ Mark A
- Buyer, Aspen, CO I searched for the perfect ski-in/ski-out property for two years before finding Own Luxury Homes. They understood exactly what I wanted and connected me with an off-market listing that exceeded my expectations. Their discretion and attention to detail were exceptional.
~ David Chen
Selling our Malibu beachfront home required discretion and expertise—Own Luxury Homes delivered both. Their high-net-worth buyer network and understanding of coastal luxury properties resulted in a quick sale at our target price. Highly recommend!
~ Phan Lo
Own Luxury Homes made our dream of owning a Mediterranean-style villa a reality. They were patient during our year-long search in Coral Gables and never pressured us. When we found the right property, they negotiated expertly on our behalf.
~ Patrick Sullivan
- Buyer, Nantucket, MA Finding a waterfront compound on Nantucket seemed impossible until Own Luxury Homes presented several exclusive opportunities. Their relationships with local sellers gave us access to properties not publicly listed. Worth every penny.
~ James Wellington
Own Luxury Homes understood the unique appeal of our modern Hill Country estate. Their staging recommendations and professional photography made our listing stand out. We closed in record time with zero stress.
~ Amanda Rodriguez
As a first-time luxury home buyer, I appreciated Own Luxury Homes' patient guidance through the process. They negotiated favorable terms and connected me with excellent local resources for property management.
~ Christopher Blake
Found our perfect Baldwin Park townhome through Ryan with Own Luxury Homes. They know every street in this Winter Park area and showed us properties before they hit the market. Their Orlando luxury real estate expertise is outstanding.
~ Patricia M.
Best real estate experience we've ever had. Selling our Winter Park home was stress-free thanks to Own Luxury Homes. They handled everything professionally and got us top dollar. If you're selling luxury real estate in Orlando, call them first.
~ Robert P.
- Seller, Beverly Hills, CA Own Luxury Homes sold our estate for well above asking price. Their network of high-net-worth buyers and strategic pricing approach delivered results quickly. I'd recommend them to anyone selling luxury real estate in LA.
~ Rebecca Thompson
I interviewed several luxury brokers before choosing Own Luxury Homes, and I'm glad I did. They positioned our modern desert home beautifully and attracted qualified buyers immediately. Their marketing was sophisticated and effective.
~ Elena Morrison
Own Luxury Homes exceeded every expectation when selling our lakefront retreat. Their understanding of the Lake Tahoe luxury market and connections with serious buyers resulted in a smooth transaction. The entire process felt effortless.
~ Catherine Delaney
Just purchased our renovated College Park historic home through Own Luxury Homes. They know the Orlando luxury neighborhoods like no one else and helped us find a gem in this sought-after area. Outstanding service!
~ Nicole R
The Own Luxury Homes team marketed our Gulf-front property to their exclusive network and secured a cash offer within two weeks. Their expertise in the luxury market is unmatched in Southwest Florida.
~ Victoria Nguyen
Bought our waterfront Keene's Point estate with Own Luxury Homes and the experience was flawless. They negotiated expertly and knew everything about Windermere luxury communities. Couldn't ask for better representation!
~ Susan C
Own Luxury Homes exceeded all expectations selling our Windermere estate. Their luxury market expertise and professional network brought qualified buyers quickly. Worth every penny for high-end Orlando real estate.
~ Lisa H.
Selling our Golden Oak Disney luxury home was seamless with Own Luxury Homes. They understand the unique market for properties near Disney and attracted the right buyers immediately. Closed in 30 days at our target price!
~ Thomas G
We relocated from California and needed help finding a luxury home in Lake Nona. Ryan with Own Luxury Homes was patient, professional, and found us an amazing modern estate. They know every luxury neighborhood in Orlando inside and out!
~ Michelle K.
Own Luxury Homes helped us find a historic downtown mansion that perfectly blended Southern charm with modern amenities. Their knowledge of Charleston's luxury market and architectural nuances was invaluable throughout our search.
~ Robert Fitzgerald
- Seller, Miami Beach, FL Working with Own Luxury Homes to sell our oceanfront property was seamless. Their marketing strategy showcased our home beautifully, and we had multiple qualified offers within three weeks. The team's professionalism and market knowledge made all the difference.
~ Jennifer Martinez
Working with Own Luxury Homes was fantastic. They helped us navigate the competitive Dr. Phillips luxury market in the height of the pandemic frenzy and negotiate a great deal on our new home. True experts in Orlando high-end real estate.
~ Jeremy S.
Own Luxury Homes exceeded expectations selling our Lake Tibet Butler waterfront property. Their Winter Park luxury market expertise and professional network made all the difference. Best real estate team in Orlando!"
~ Daniel F.
Finally found our forever home in Windermere! Ryan with Own Luxury Homes understood exactly what we wanted and showed us only properties that fit our criteria. Their knowledge of luxury communities around Orlando is exceptional.
~ Amanda T.
Own Luxury Homes marketed our Celebration luxury property beautifully. Their photography and staging recommendations made our home shine. Sold for well above asking in the competitive Orlando market!
~ Richard T.
Ryan found us an incredible estate in Lake Butler Sound. His knowledge of Windermere's waterfront communities is unmatched. They made buying our luxury Orlando home completely stress-free!
~ Elizabeth N.
Just closed on our dream home in Windermere! The Own Luxury Homes team made the entire process seamless. They really know the luxury market in Central Florida and found us the perfect waterfront property. Highly recommend for anyone looking at high-end homes in the Orlando area.
~ Sarah M.
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