Circle Square Woods Homes for Sale

Circle Square Woods Homes for Sale

Welcome to Circle Square Woods, an enchanting subdivision nestled in the heart of Ocala, Florida, within the picturesque Marion County. This vibrant community is a hidden gem, offering a serene lifestyle surrounded by the natural beauty of Florida's lush landscapes. With its charming tree-lined streets and friendly neighbors, Circle Square Woods is the perfect place for families, retirees, and anyone looking to embrace the tranquility of suburban living.

The homes for sale in Circle Square Woods boast a diverse range of architectural styles, catering to various tastes and preferences. Whether you’re searching for a cozy single-family home or a spacious residence, you’ll find properties that offer modern amenities, open floor plans, and beautifully landscaped yards. Each home is designed with comfort and convenience in mind, making it easy to settle in and create lasting memories.

Residents of Circle Square Woods enjoy access to a wealth of community amenities, including parks, walking trails, and recreational facilities that encourage an active lifestyle. The community’s prime location means you’re just a short drive away from Ocala’s vibrant downtown area, where you can explore charming shops, delightful dining options, and cultural attractions.

With its combination of community spirit, beautiful homes, and convenient access to local amenities, Circle Square Woods is more than just a place to live; it’s a place to thrive. Discover your dream home today in this exceptional Ocala subdivision, where a warm welcome awaits you!

Newest Circle Square Woods Homes for Sale

2 Beds ⋅ 2 Baths ⋅ OM731150 MLS

Don’t miss this charming 2-bedroom, 2-bath villa in the sought-after On Top of the World community! Situated on a wide street with mature landscaping, this home offers comfortable Florida living with plenty of potential. One of the standout features is the spacious Florida room, providing valuable additional living space that can easily be used as a home office, gym, hobby room, reading area, or simply extra space to relax and enjoy the Florida lifestyle. Yes, there are several villas currently available, but this one deserves a closer look. It is priced to sell and offers an excellent opportunity for someone looking to make On Top of the World their home. Enjoy the convenience of being close to shopping, restaurants, medical facilities, golf, and the many amenities and activities On Top of the World has to offer. The community is known for its extensive recreational opportunities and active-adult lifestyle. Come see why this villa stands out from the others. It may be exactly what you’ve been looking for!

8665 Sw 94th Street Unit B, Ocala

2 Beds ⋅ 2 Baths ⋅ OM728681 MLS

Welcome to this fully furnished, move-in-ready villa. This home has been completely remodeled with new flooring and new windows throughout. It features a stunning, brand-new kitchen equipped with new appliances, custom cabinets, elegant countertops, a stylish backsplash, and two convenient lazy susans. Both bathrooms have been updated with high vanities and walk-in tiled showers with built-in seating benches. Additional upgrades include a new Florida room, a private paver patio, a new garage door, and a new air conditioning system. With a 2018 roof and a 2022 water heater, this home offers stress-free living in an amenity-enriched community.

8891 Sw 96th Lane Unit B, Ocala

2 Beds ⋅ 2 Baths ⋅ OM728166 MLS

Welcome to this beautifully maintained Charlotte model villa in the sought-after Friendship Village of On Top of the World, Ocala's premier 55+ community. Offering 1,484 square feet of thoughtfully designed living space, this inviting 2-bedroom, 2-bath home combines comfort, convenience, and low-maintenance living. Step inside to discover luxury vinyl plank flooring in both bedrooms, while the main living areas, kitchen, bathrooms feature attractive ceramic tile for easy upkeep. The open-concept floor plan is bright and welcoming, creating the perfect setting for everyday living and entertaining. A standout feature of this home is the climate-controlled Florida room providing additional living space to enjoy year-round—ideal for relaxing with your morning coffee, entertaining guests, or pursuing your favorite hobbies in comfort.The oversized one-car garage offers plenty of room for your vehicle plus extra space for a golf cart, workshop, or storage. A built-in mezzanine provides even more storage, making it easy to keep everything organized. Enjoy the exceptional lifestyle that On Top of the World is known for, with amenities including golf, resort-style pools, fitness centers, pickleball and tennis courts, walking trails, clubs, restaurants, and endless social activities. Conveniently located near shopping, dining, medical facilities, and all that Ocala has to offer, this move-in-ready villa is ready for you to call home. Schedule your private showing today and experience the best of active adult living!

8711 Sw 96th Lane Unit C, Ocala

2 Beds ⋅ 2 Baths ⋅ OM725643 MLS

Completely Remodeled INSIDE. Roof 2022, A/C 2023, Hot Water Heater is new. This spacious open floor plan 2 Bed 2 Bath with a Bonus Room (office). Inside of home has been completely updated with stainless steel appliances. all floors replaced with beautiful hardwood floors matching throughout the home. Both bathrooms completely remodeled and all ceiling fans replaced. This home is move in ready. If you are looking for a 2/2 this one is worth taking a personal tour of today.

8743 Sw 90th Lane Unit A, Ocala

2 Beds ⋅ 2 Baths ⋅ GC540724 MLS

PRICE IMPROVEMENT!! Seller is motivated. Welcome to the highly desirable On Top of the World 55+ community, where comfort, entertainment, and maintenance-free living come together! Situated on a desirable corner lot and within short distance to all the amazing amenities, this beautifully maintained home offers the perfect blend of convenience and active living. Enjoy resort-style amenities including a clubhouse, pickleball courts, swimming pools, fitness centers, bingo nights, and countless social activities. The monthly HOA covers lawn care, exterior house painting, sprinkler system maintenance, gate access, trash service, dumpsters, mailboxes, and even a golf cart sticker for added convenience. This move-in ready home features fresh interior paint completed in 2025, updated flooring, a new roof in 2025, A/C replaced in 2023, and a water heater installed in 2021. Enjoy peace of mind with Leaf Filter gutter protection throughout the home and annual pest control service. The spacious lanai includes beautiful plantation shutters installed in 2020, adding a versatile and elegant touch to the home while providing excellent natural light control and privacy. The renovated primary bedroom completed in 2021 adds a modern and comfortable touch, while the kitchen offers stainless steel appliances, tile flooring, and plenty of functionality. Bathrooms feature cozy carpeting for added comfort. If you are looking for an active 55 community with endless amenities, low-maintenance living, and a prime location, this home is a must-see!

9820 Sw 89th Terrace Unit E, Ocala

2 Beds ⋅ 2 Baths ⋅ OM724573 MLS

Nestled down a quiet, tree-canopy lined road in On Top Of The World, you will find 9357 C SW 82nd Terrace, Ocala FL. This property sits at the front edge of the OTOW community- making it just 1 mile from Wawa, 1.4 miles from Publix, 0.8 miles from Sprouts, and so much more. It also backs up to a retention pond- so you can enjoy the view of mature, lush landscaping. The floors are new, the paint is fresh, and the price is right to bring your vision to life. There’s even a workbench already in the garage! A sky tube provides abundant natural light, and the plantation shutters are already in place to keep the light out when you don’t want it. An enclosed Florida Room faces the green back yard area. 2 spacious bedrooms and 2 bathrooms with stone tiling and walk in closets provide comfort and function. A breakfast nook off the kitchen provides a cozy place to read the news and sip your coffee, with a separate dining area to sit for dinners with friends. Move in ready, or update it to your hearts desire.

9357 Sw 82nd Terrace Unit C, Ocala

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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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