Oak Hollow Real Estate

Oak Hollow Real Estate

Welcome to Oak Hollow, a hidden gem nestled in the heart of Florida! This picturesque subdivision offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and anyone seeking a peaceful retreat.

Oak Hollow is renowned for its lush, tree-lined streets and beautifully landscaped yards, creating an inviting atmosphere that feels like home from the moment you arrive. The community is designed with a focus on outdoor living, featuring ample green spaces, walking trails, and playgrounds that encourage residents to embrace the Florida sunshine.

One of the standout features of Oak Hollow is its diverse range of homes, accommodating various lifestyles and budgets. From charming single-family residences to spacious two-story designs, each property boasts unique architectural details and modern amenities. Many homes come equipped with energy-efficient appliances and smart home technology, ensuring that residents enjoy both comfort and convenience.

Living in Oak Hollow means enjoying a vibrant community spirit. Neighbors often gather for seasonal events, fostering friendships that last a lifetime. The subdivision is conveniently located near top-rated schools, shopping centers, and recreational facilities, making it easy for residents to access everything they need.

For those who love the outdoors, Oak Hollow is just a short drive from stunning Florida beaches and beautiful parks, perfect for weekend getaways or leisurely strolls. With its serene environment, friendly community, and prime location, Oak Hollow is more than just a place to live; it’s a lifestyle waiting to be embraced. Come discover your new home in Oak Hollow today!

Newest Listings in Oak Hollow

3 Beds ⋅ 2 Baths ⋅ N6145326 MLS

WELCOME TO OAK HOLLOW, A DEED-RESTRICTED COMMUNITY featuring this beautifully maintained home offering a wonderful combination of thoughtful updates and valuable storm protection features. Major improvements to the home include 2022 Roof, 2021 AC, 2022 Hot Water Heater, 2025 Impact Windows providing peace of mind for years to come. Step inside to an inviting interior with high ceilings and vinyl flooring throughout and tile in the primary with the most inviting soaking tub. The kitchen features warm-toned granite countertops and light cabinets and a newer range with a convenient built-in air fryer feature. Ceiling fans in the living and bedrooms while plantation shutters provide an attractive finishing touch in the front bedroom. The primary suite is a beautiful sanctuary with direct access to the lanai through a sliding glass door. Additional highlights include an epoxy-coded garage floor. With significant improvements already completed, desirable community amenities, and a comfortable blend of indoor and outdoor living, this Oak Hollow home is ready to welcome its new owner. Schedule your showing today!

449 Rose Apple Circle, Port Charlotte

Virtually Staged. Cleared Canal Lot in Port Charlotte – PLANS AND SURVEY INCLUDED Build your dream home in the desirable Woodlands section of Oak Hollow. This cleared freshwater canal lot has CITY WATER AND SEWER AVAILABLE, and over 95% of the property outside the flood zone according to the available survey. Enjoy the community amenities, including an Olympic-size heated pool, private clubhouse, fitness center, billiard room, and shuffleboard, all in a beautiful park-like setting. Sale includes a full set of completed house plans and survey, potentially saving valuable time and upfront development costs. The property is also reported to be outside the Scrub-Jay area. Blueshine Builder LLC is available as an optional builder and can provide construction options and pricing. Buyer is not required to use Blueshine Builder and may select any properly licensed contractor. Plans are done. Survey is done. LOT IS CLEARED. Bring your vision and start building! Buyer to verify flood zone, utilities, environmental, permitting, and building requirements.

493 Ricold Terrace, Port Charlotte

3 Beds ⋅ 2 Baths ⋅ C7528805 MLS

Seller is offering 2% toward the buyer’s closing costs PLUS a home warranty! Welcome to this well-maintained 3-bedroom, 2-bath, 2-car garage home in Oak Hollow in central Port Charlotte. This home features an owned solar system, an open floor plan with cathedral ceilings, abundant natural light, tile flooring throughout, and triple sliding glass doors leading to the covered, screened lanai. The kitchen features granite countertops, ample cabinet space, and a dining area. The split-bedroom floor plan offers a spacious primary suite with a walk-in closet and an en-suite bath with a walk-in shower. Two guest bedrooms with vaulted ceilings share a full guest bathroom. Additional features include an inside laundry room, hurricane protection, a 2019 roof, and mature landscaping. Located in the Shadowmoss section of Oak Hollow, residents enjoy access to a clubhouse, heated community pool, fitness center, park, playground, and tennis courts. Conveniently located near the Murdock shopping and dining district, golf courses, schools, medical facilities, historic downtown Punta Gorda, boating, fishing, entertainment, and Gulf beaches. Schedule your private showing today!

483 Winwood Court, Port Charlotte

OWNER FINANCING AVAILABLE - LARGE LOT RE ZONING MINUTES TO THE VILLAGES! Discover the perfect setting for your dream home on this beautiful 1.88-acre parcel with RE (Residential Estate) zoning. Ideally located just off Hwy. 441 and Hwy. 42, this property offers the perfect blend of privacy and convenience. Enjoy a peaceful setting with no neighbors directly behind you, providing added privacy and a serene backdrop for your future home. The paved road frontage provides easy access, while the generous acreage gives you plenty of space for a custom estate, workshop, garden, or outdoor living area. Situated near Lake Weir and just minutes from The Villages, you’ll have quick access to shopping, dining, entertainment, and recreation while still enjoying the quiet feel of country living. Whether you’re ready to build now or invest for the future, this property offers location, space, and privacy all in one exceptional opportunity.

Se 99th Avenue, Summerfield

1 Beds ⋅ 1 Baths ⋅ C7520563 MLS ⋅ S-208 BLDG.

Welcome to The Oaks 3!!! Any local who has been in town for years will tell you The Oaks has been a premiere condo community since its inception in 1985. POURED CONCRETE buildings set among 23 acres with--you guessed it--lots of oak trees. The location of the community is in the heart of Port Charlotte with grocery shopping (Publix and a Walmart Marketplace), restaurants, YMCA, and a host of other services. In fact, if you feel like getting your steps in while you take care of your errands, you can take the sidewalks! This unit boasts a fantastic private water view that will delight you with the antics ducks and other waterfowl. The Oaks 3 has a pool for the residents, outdoor grills, shuffleboard, and bocci ball. This is the perfect nesting spot for anyone needing only one nice-sized bedroom. The living room/dining room are spacious. A low, reasonable HOA fee of $274 for ALL the amenities is a win! The lanai deck will be your favorite coffee/ beverage area to enjoy the tranquil setting. Make your appointment today!

19505 Quesada Avenue Unit S208, Port Charlotte

2 Beds ⋅ 2 Baths ⋅ C7519494 MLS

PRICE REDUCED! **OWNER OFFERING FINANCING!!!** Situated on a cul-de-sac, in the Oak Hollow Community, this 2 bedroom, 2 bath home has been completely updated! With vaulted ceilings throughout the main living area and kitchen, this home feels much larger than it is. There is new luxury vinyl throughout. The roof was replaced in 2025, York HVAC system in 2025 including all new ductwork, new hot water heater, kitchen and baths completely remodeled in 2025. There are all new light fixtures and fans throughout. The kitchen has beautiful solid wood cabinetry and stainless appliances. The ensuite primary bedroom, with sliders for light and outdoor access, features a completely remodeled bathroom with tiled shower with custom glass enclosure. The remodeled guest bath has a tub/shower combination which has a custom glass enclosure, also. Enjoy relaxing on your newly screened lanai accessible through sliders from the living room. This home has been freshly painted, both inside and out and has new landscaping including new sod. Oak Hollow is a deed restricted community with access to the Oak Hollow recreational Center including a clubhouse, heated pool, exercise, room, playground and more! The HOA fee is extremely affordable ($208 per quarter). All this in a wonderful location within close proximity to restaurants, shopping, library, parks, golf courses, fishing and more. Call today to schedule your showing!

20005 Goldcup Court, Port Charlotte

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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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