Windermere Real Estate

Windermere Real Estate

Welcome to Windermere, Florida—an enchanting subdivision that perfectly blends luxury living with a charming small-town atmosphere. Nestled in the heart of Orange County, Windermere is renowned for its picturesque landscapes, pristine lakes, and a strong sense of community. This idyllic locale is just a stone's throw away from the vibrant attractions of Orlando, making it an ideal retreat for those seeking tranquility without sacrificing convenience.

Windermere boasts an array of stunning homes, from elegant estates to modern family residences, each designed to cater to diverse lifestyles and tastes. Many properties feature breathtaking views of the surrounding lakes and lush greenery, providing a serene backdrop for everyday life. The subdivision is also home to several exclusive gated communities, ensuring privacy and security for its residents.

Outdoor enthusiasts will appreciate Windermere's abundant recreational opportunities. With numerous parks, walking trails, and access to the beautiful Butler Chain of Lakes, residents can indulge in activities such as boating, fishing, and hiking. The area is also known for its excellent schools, making it a fantastic choice for families.

Windermere's charming downtown area features boutique shops, delightful eateries, and community events that foster a close-knit atmosphere. Whether you're enjoying a leisurely stroll along the lakefront or participating in local festivities, you'll quickly discover why Windermere is more than just a place to live—it's a place to thrive.

Discover the magic of Windermere, where every day feels like a vacation and a warm welcome awaits you at every corner. Come experience the lifestyle you've always dreamed of in this captivating Florida gem!

Newest Listings in Windermere

6 Beds ⋅ 8 Baths ⋅ O6426995 MLS

Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional craftsmanship, and resort-style amenities come together in one of Windermere's most coveted locations. Built in 2024 and spanning approximately 6,900 square feet under air (10,400 total square feet), this custom residence sits on a rare one-acre homesite along the iconic, paved Second Avenue, renowned for its festive holiday displays, spectacular sunsets, and unmatched charm. Designed for both everyday luxury and grand scale entertaining, this 6 bedroom, 7.5 bathroom home offers en-suite bedrooms with walk-in closets, including a private first floor guest suite. The stunning primary retreat features a spa inspired bathroom and a private balcony overlooking the lake, creating the perfect setting to enjoy breathtaking sunsets and nightly Disney fireworks. The heart of the home is a designer chef's kitchen featuring exquisite Cristallo countertops, premium Miele appliances, and seamless flow into the expansive living and entertaining spaces. A dramatic floating wood staircase with a striking stone accent wall serves as an architectural centerpiece, while an elevator provides effortless access to every level. Additional highlights include a custom onyx sink in the powder bath, elegant 8-foot solid wood core doors throughout, motorized blinds, and laundry rooms on both the first and second floors. Step outside to experience a true private resort. The heated infinity edge saltwater pool features a unique acrylic glass viewing wall, allowing swimmers to enjoy underwater lake views unlike anything else. The expansive summer kitchen is equipped with two oversized Big Green Egg grills, a hibachi grill, and generous entertaining areas perfect for hosting unforgettable gatherings. A spacious game room with a full bar, dedicated fitness room, and professionally designed dog run complete the home's exceptional lifestyle offerings. Boating enthusiasts will appreciate the impressive two story private dock with multiple lifts, providing direct access to the famed Butler Chain of Lakes. Car collectors will love the oversized four car garage with an automotive lift, an additional golf cart garage, and an exceptionally long driveway offering abundant guest parking, a rare luxury on Second Avenue. Constructed with impact-rated windows and doors, spray foam insulation, and energy-efficient systems, this home was thoughtfully built to provide superior comfort, security, and efficiency. Combining impeccable design, world-class amenities, spectacular waterfront views, and one of the finest addresses in Central Florida, this remarkable Lake Butler estate represents a rare opportunity to own a nearly new custom home in one of Windermere's most sought after neighborhoods. Be sure to click on the virtual tour links.

724 W 2nd Avenue, Windermere

2 Beds ⋅ 2 Baths ⋅ 852366 MLS

SELLERS WILL INSTALL NEW ROOF AT CLOSING!! Welcome to effortless living in the heart of Windermere! This beautifully updated 2-bedroom 2-bath end unit villa offers modern upgrades and an unbeatable location within an all ages community. Step inside to discover fresh interior paint, stunning floor to ceiling windows in the lanai that provides abundance of natural light and timeless plantation shutters. The renovated kitchen features brand new LG appliances, new solid surface countertops and a stylish tile backsplash, creating a clean and contemporary space for everyday living and entertaining. All new windows throughout for energy efficiency. The open layout flows seamlessly from the dining to the living area, while the spacious primary suite provides ample closet space with 2 walk in closets and an en suite bath.The second bedroom offers flexibility for guests or a home office with direct access to hall bath. Enjoy year-round relaxation in the enclosed lanai, offering tinted glass for privacy and automatic blinds. Both the garage floor and the outdoor patio have been upgraded with "liquid floor" finishes for a durable polished look. The HOA provides exceptional value, covering cable, WiFi, building and grounds maintenance, and access to amenities including a clubhouse, heated pool, shuffleboard courts, community dock with lake access, and RV and boat storage. Perfectly situated near the 47 mile Withlacoochee State Trail, for biking and walking, and just a short stroll to charming downtown Inverness with its local restaurants and shops, this villa truly offers the best of low mantenance living and small-town charm. Move in ready and thoughtfully upgraded, this is Florida living at its finest!

819 Lanark Drive, Inverness

3 Beds ⋅ 3 Baths ⋅ 851231 MLS

Sell the lawnmower, relax, and enjoy the extra space this very stylish well-maintained 3 bedroom, 2½ bath townhouse has to offer along with water and dock access to the lake, a community pool, and clubhouse. An area is also provided for limited parking of boats, RV's. For cycling and walking among nature, take advantage of the Withlacoochee State Trail only steps away. Downtown, restaurants, and shopping are just a short drive away. Rules, useful information, and restrictions are on the web in an easy-to-read format. This townhouse has an enclosed porch with a tiled patio in the rear. (Ring door bell stays with owner.)

826 Lanark Drive, Inverness

6 Beds ⋅ 6 Baths ⋅ O6368185 MLS

Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere with excellent walkability. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a stone-framed cooking alcove, premium JennAir® appliances, custom ceiling-height cabinetry, and a walk-in pantry designed for serious cooks and entertainers. The home offers six bedrooms and six bathrooms, with two main-level owner’s suites providing exceptional functionality and privacy. Multiple living spaces are anchored by a striking floor-to-ceiling stone fireplace and beautiful library with rolling ladder, while upstairs bedrooms and bonus room are thoughtfully designed for comfort and quiet, complemented by quality finishes throughout. Recent updates include a newly installed roof (2024) and windows (2025), enhancing both peace of mind and long-term value. A spacious three-car garage adds both convenience and functionality. Outdoors, the home transitions easily to an entertainer’s retreat with covered porches, fireplace, outdoor kitchen, circular firepit, cabana bath, Tiki hut and lush landscaping. The property also offers the opportunity to add a FRONT GATE for enhanced privacy and security, and allows for a FUTURE POOL ADDITION, giving buyers flexibility to further customize the outdoor living experience. Deeded town resident access to the Butler Chain of Lakes and a prime location within Windermere’s vibrant town center with its new redevelopment complete this rare offering where architectural integrity meets a fun and functional Florida lifestyle.

713 Main Street, Windermere

3 Beds ⋅ 3 Baths ⋅ 850308 MLS

MOVE in READY! The stunning rehab / update on this home is rather impressive! New Appliances, New Flooring, new light fixtures, Fresh paint & much more! Located within view of the community center & community pool, overlooking the pond. This 3/2.5/2 split bedroom plan is extremely spacious with large rooms. Primary bedroom is huge with lots of space in the walk-in closet. The huge Florida room overlooks the water. Huge open kitchen with lots of extra counter & cabinet space. Open kitchen area with breakfast bar, formal dining room. Large 2 car garage with newer washer & dryer. Located minutes to everything Inverness has to offer.

719 Balmoral Court, Inverness

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About Rhonda Cassidy

Meet Rhonda Cassidy Trusted Ocala REALTOR®, Luxury Home Specialist, and Advocate for Buyers & Sellers Throughout Central Florida Real estate isn't just my career—it's my calling. I was born and raised in Ocala, Florida, and for more than five decades I've had the privilege of watching this community grow into one of the most desirable places to call home. It's where I raised my two beautiful daughters, where my grandchildren are creating their own memories, and where my family continues to put down roots. Ocala isn't simply the market I serve—it's home. Before beginning my career in real estate, I spent more than 20 years as a store manager for one of the nation's largest furniture retailers. Those years taught me the importance of leadership, communication, customer service, and earning people's trust. While I enjoyed my career, I always knew there was something else I was meant to do. For years, my mother and I dreamed about getting our real estate licenses together. Life had different plans. After courageously battling breast cancer, she passed away before we ever attended our first class together. I put that dream aside for a while. Then one day, when my employer wanted to relocate me away from Ocala, I realized God was opening a different door. Instead of moving away from the community I loved, I chose to pursue the career that had always been on my heart. I've often said: "My previous career chose me. I chose real estate." Looking back, my only regret is that I didn't pursue it sooner. A Different Kind of Real Estate Experience Buying or selling a home is one of the biggest financial and emotional decisions most people will ever make. It's not something people do every day. That's why I never forget that every transaction represents someone's next chapter. Whether you're purchasing your very first home, relocating to Central Florida, downsizing into a 55+ community, searching for a luxury home, or saying goodbye to a family home filled with memories, I believe you deserve more than someone who simply unlocks doors or places a sign in your yard. You deserve someone who stands beside you every step of the way. My Promise to Every Client When someone hires Rhonda Cassidy, they can expect honesty. I believe the best advice isn't always the easiest advice to hear. My responsibility isn't to tell clients what they want to hear—it's to give them the knowledge, guidance, and perspective they need to make confident decisions. Sometimes that means having difficult conversations. Sometimes it means recommending a different strategy. Sometimes it means protecting a client from making an expensive mistake. No matter the situation, my commitment remains the same: Your best interests will always come before my own. When we work together, I want you to know that I'm in your corner. We're wearing the same team jersey. Solving Problems Is What I Do Every real estate transaction has challenges. Appraisal issues. Inspection concerns. Unexpected repairs. Negotiations. Changing market conditions. My clients often describe me as a problem solver because I focus on finding solutions instead of focusing on obstacles. I believe my job is to carry as much of the stress as possible so my clients don't have to. One seller who originally tried selling his home on his own eventually hired me after realizing how complicated the process had become. He nearly accepted an offer that wasn't in his best interest before we sat down and reviewed his options together. Although we didn't always agree during the process, honesty remained at the center of every conversation. By the time we closed, he sold his home for approximately $26,000 more than he had originally planned. Afterward, he told me several times, "I wish I had hired you sooner." That client has since referred multiple friends and family members to me—not because I told him what he wanted to hear, but because I protected his interests from beginning to end. To me, that's what great representation looks like. Compassion Beyond the Transaction Some of the most meaningful moments in my career have nothing to do with sales prices. I've worked with families who were grieving the loss of a parent while trying to sell a home from another state. During those difficult seasons, I knew they needed more than a Realtor. They needed someone they could trust. I coordinated cleaning out the home. I arranged lawn maintenance. I handled details they couldn't easily manage from hundreds of miles away. My goal was simple: Take as much off their shoulders as possible so they could focus on healing. Real estate isn't always about buying and selling. Sometimes it's about helping people through one of life's biggest transitions with compassion, patience, and understanding. Staying Ahead in a Changing Market Real estate is constantly evolving, and so is my approach. Every Monday is what I call Marketing Monday. It's dedicated time to studying market trends, reviewing competing listings, analyzing pricing strategies, evaluating buyer activity, and looking for opportunities to better position my clients' homes. I also embrace today's technology to provide my clients with a competitive advantage. My marketing strategy includes: Professional digital marketing Artificial intelligence (AI) marketing Search engine optimization (SEO) YouTube video marketing Social media marketing Ongoing market analysis Continuous education and innovation The real estate industry changes quickly, and I believe my clients deserve an agent who never stops learning. Areas of Expertise Throughout my career, I've developed particular expertise in: 55+ communities throughout Ocala and The Villages Golf course communities Luxury homes Pool homes Relocation to Central Florida Residential home sales Buyer representation Seller representation As an eXp Luxury Certified Agent, I understand the unique marketing, negotiation, and presentation strategies required to successfully represent luxury properties while delivering exceptional service to every client, regardless of price point. Leadership, Mentorship, and Giving Back I'm proud to be an eXp Realty ICON Agent, a recognition earned through production, professionalism, and contribution to the company. I'm equally proud to serve as a mentor to new real estate agents. I remember what it felt like when I first entered this business and didn't always know where to turn. Helping other agents build successful careers allows me to give back to an industry that has given so much to me. Watching others succeed is one of the most rewarding parts of my career. Life Outside of Real Estate When I'm not helping clients, you'll usually find me spending time with my family. Being a Nana to my twin granddaughters, Camilla ("Mug") and Charlotte ("Sweet Char"), is one of life's greatest blessings. My husband and I also enjoy playing golf together in an Ocala golf league, spending time on the water fishing, and taking advantage of everything Central Florida has to offer. One of my favorite things about living here is that both Florida's east coast and west coast are just a short drive away. Whether we're enjoying the beach, spending time outdoors, or making memories with family, I'm reminded every day why I love calling this area home. Why Clients Continue to Choose Rhonda Cassidy Clients choose me because they know I'll tell them the truth. They know I'll answer the phone when I'm available—even after traditional business hours—because real estate doesn't always happen between 9 and 5. They know I'll continue learning, adapting, and embracing new technology to better serve them. Most importantly, they know I'll always work as though I'm wearing the same team jersey. When your goals become my goals, we become partners. That's how I believe real estate should be. Ready to Make Your Next Move? Whether you're buying your first home, selling a luxury property, relocating to Ocala, exploring 55+ communities, or simply wondering what your home is worth in today's market, I'd be honored to help. Let's have a conversation about your goals and create a strategy that puts your best interests first.

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