Oak Hollow Homes with Pool Community Features

Oak Hollow Homes with Pool Community Features

Welcome to Oak Hollow, a serene and inviting subdivision nestled in the heart of Port Charlotte, Florida. This charming community offers a perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and everyone in between. With its lush landscaping and friendly atmosphere, Oak Hollow is a neighborhood where neighbors become friends and memories are made.

One of the standout features of Oak Hollow is its impressive selection of homes, many of which boast beautiful private pools. Imagine stepping out into your own backyard oasis on a warm Florida day, where you can relax, entertain, and enjoy the sunshine. The poolside lifestyle is at your fingertips, offering a perfect setting for weekend barbecues, family gatherings, or simply unwinding after a long day.

In addition to the stunning homes, Oak Hollow is conveniently located near a variety of amenities. Residents have easy access to shopping centers, dining options, and recreational activities, ensuring that everything you need is just a short drive away. The nearby parks and nature preserves provide ample opportunities for outdoor adventures, whether you enjoy hiking, biking, or simply soaking in the natural beauty of the area.

With its welcoming community spirit, beautiful homes with pools, and prime location in Port Charlotte, Oak Hollow is not just a place to live—it's a place to thrive. Discover the charm of Oak Hollow and find your dream home in this delightful Florida neighborhood today!

Newest Oak Hollow Homes with Pool Community Features

2 Beds ⋅ 2 Baths ⋅ Oak Hollow SubDv. ⋅ 33954 Zip Code

SITUATED ON A RARE DOUBLE LOT, this beautifully maintained 2BR 2BA plus flex room home in Oak Hollow delivers exceptional space, privacy, and value in one of the area’s most desirable deed-restricted communities. From the moment you arrive, the glass impact front door and screened front porch set the tone for a welcoming and well-cared-for residence. Inside, high ceilings and a freshly painted interior create a bright, open feel. The kitchen is both functional and inviting, featuring Corian countertops, stainless steel appliances (approx. 2 years old), a vented microwave to the exterior, abundant cabinetry, and a charming eat-in dining area. Thoughtful upgrades continue throughout, including an LG washer/dryer combo (approx. 2 years old), linen closet, and pull-down attic stairs for added storage. The living space flows seamlessly to the lanai, complete with a motorized sunshade and impact-rated door for comfort and peace of mind. Designed for easy Florida living, the exterior offers accordion hurricane shutters, a new garage screen, and a shed for additional storage. Major updates include a 2023 roof, 2019 AC with ultraviolet light, upgraded electrical system (2019), whole-house water filtration system, and a 22KW whole-house generator serviced annually, along with a new garage door opener. Residents of Oak Hollow enjoy access to a heated pool, fitness center, clubhouse, and tennis courts, all within a beautifully maintained community. A rare combination of space, upgrades, and location—this move-in-ready home is ideal for enjoying the Florida lifestyle year-round.

548 Rose Apple Circle, Port Charlotte

2 Beds ⋅ 2 Baths ⋅ Oak Hollow SubDv. ⋅ 33952 Zip Code

Short Sale. HUGE OPPORTUNITY TO GET THIS IMPECCABLE HOME AT AN UNBELIEVABLE DEAL! Welcome to this charming TURNKEY FURNISHED 2 bed, 2 bath home in the highly desirable community of Oak Hollow! Nestled in a cul-de-sac with MATURE, UPGRADED LANDSCAPING, this unbeatable location offers the perfect blend of beauty and privacy. Check out the numerous upgrades and features of this home including COASTAL-THEMED SOLID SURFACE COUNTERTOPS AND BACKSPLASH IN THE KITCHEN, STAINLESS STEEL APPLIANCES, A NEWLY-ADDED DISHWASHER AND PANTRY IN 2024, NEW ROOF IN 2023, UPDATED BATHROOMS, RECENT INTERIOR AND EXTERIOR PAINTING, AND TILE THROUGHOUT! Enjoy easy access to the screened-in lanai from the living room and primary bedroom! This home is also located in flood zone X500, meaning NO FLOOD INSURANCE REQUIRED IF YOU ARE FINANCING! Underground power lines help preserve the natural beauty and open feel of the neighborhood while PUBLIC WATER AND SEWER provide added convenience and low-maintenance living for everyday ease. Oak Hollow residents get exclusive access to the amenity-rich Oak Hollow Recreation Center, featuring a clubhouse, fitness center, heated pool, tennis/pickleball court, basketball court, playground, horseshoes, bocce ball, and shuffleboard - all included with the low HOA fee! Whether you are looking for a full-time residence or the perfect part-time retreat, this move-in-ready gem is one you do not want to miss out on. Schedule your private showing today, this one is not going to last at this price!

19595 Kapok Court, Port Charlotte

2 Beds ⋅ 2 Baths ⋅ Oak Hollow SubDv. ⋅ 33948 Zip Code

BRAND NEW AIR CONDITIONING AND WATER HEATER JUNE 2026! Other upgrades include IMPACT WINDOWS, Accordion Hurricane Shutter for lanai and UPDATED KITCHEN. This VERY AFFORDABLE and charming, furnished, 2 bedroom, 2 bath condo is the Heart of Port Charlotte and calling your name. This 2nd floor unit comes furnished with just about everything you need to move right in. The two bedrooms are slit on opposite sides of the unit for privacy. The open concept living/dining area is spacious and features ceramic tile floors for easy maintenance. The kitchen has been updated with solid wood cabinets with lazy susan cabinets in the corners for maximum storage, granite counters and stainless steel appliances. The primary bedroom has an en suite bathroom with 2 closets and stacked front loading FULL SIZE washer & dryer. The primary bathroom has a tiled walk in shower stall and water closet separated from the vanity for more privacy. The guest bedroom has built in shelves/storage and a Murphy Bed (the Murphy Bed system is removable if you prefer a regular bed) so you can use it as an office/den until your guests arrive! The home features Verosol blinds on the windows and sliders which provide thermal protection and block out light. Enjoy morning coffee or evening cocktails on your screened in balcony/lanai. The impact windows and an accordion hurricane shutter for the lanai as well as the newly replaced a/c and water heater will help lower your insurance costs making even more affordable to call this place HOME!! Recreational facilities include bocce ball, shuffleboard, screened in pools, clubhouse, horseshoes and you won't be a stranger for long since the neighbors are friendly and just a happy to be in Florida as you are. The reasonable HOA FEE INCLUDES WATER, SEWER, OUTDOOR LIGHTING, GROUND MAINTENANCE, STREET LIGHTS, PEST CONTROL & TRASH COLLECTION. Oaks IV is located near US41 and close to shopping, restaurants, BJ's, Walmart, Home Depot and health care facilities. Allegiant airlines is in Punta Gorda and only about 25 minutes away with new flights being added all the time. The Gulf beaches and Bocca Grande are a short ride away. The Tampa Bay Rays and Atlanta Braves spring training facilities are just minutes away so you'll be able to watch the Pro ball players practice which is Very exciting! Did we mention there are several golf courses within a few minutes drive as well? Port Charlotte is one of the Best Kept Secrets on the Gulf Coast with new housing developments and commerce being built here. Come and grab your little slice of Paradise before it's too late.

19505 Quesada Avenue Unit EE202, Port Charlotte

1 Beds ⋅ 1 Baths ⋅ Oak Hollow SubDv. ⋅ 33948 Zip Code

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 ⋅ Oak Hollow SubDv. ⋅ 33952 Zip Code

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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Kristi Grady- Broker/ Owner

Meet Kristi Grady When it comes to buying or selling a home, having the right real estate professional by your side can make all the difference. At HomeTrust Real Estate & Property Management, we believe every client deserves honest advice, expert guidance, and exceptional service throughout the entire process. Kristi Grady, Broker and Co-Owner of HomeTrust, brings more than 12 years of experience helping buyers, sellers, investors, and families successfully navigate the real estate market throughout Lakeland, Polk County, and Central Florida. Whether you're purchasing your first home, upgrading to your dream home, selling a property, or building an investment portfolio, Kristi is committed to making the process as smooth and stress-free as possible. For buyers, Kristi provides personalized guidance, local market expertise, and skilled negotiation to help clients find the right property at the best possible price. For sellers, she utilizes professional marketing strategies, high-quality photography and video, social media advertising, and proven pricing techniques designed to maximize exposure and achieve top dollar. As a local market expert, Kristi understands the neighborhoods, schools, market trends, and property values that impact buying and selling decisions. Her knowledge and experience help clients make informed decisions with confidence. Kristi also has extensive experience working with real estate investors, assisting with the acquisition, management, and sale of income-producing properties and investment portfolios. She understands the unique goals of investors and provides strategic guidance to help maximize returns and long-term success. In addition, Kristi has a special passion for helping seniors and their families navigate major life transitions. Whether downsizing, relocating closer to family, or moving into assisted or supportive living environments, she provides compassionate guidance and personalized support during what can often be an emotional and challenging process. Known for her communication, professionalism, and dedication to her clients, Kristi takes pride in building lasting relationships and delivering results. Her goal is simple: to help every client achieve their real estate goals while providing a level of service that exceeds expectations. When you're ready to buy, sell, invest, or plan your next move, Kristi is ready to put her experience and expertise to work for you.

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Ryan Grady- REALTOR®/Owner

Meet Ryan Grady Real estate is more than buying and selling homes—it's helping people make some of the biggest financial decisions of their lives with confidence. Ryan Grady, Co-Owner of HomeTrust Real Estate & Property Management, has spent more than 12 years helping buyers, sellers, investors, and landowners navigate the real estate market throughout Lakeland, Polk County, and Central Florida. His passion for helping people, combined with extensive market knowledge and strong negotiation skills, has earned him a reputation for delivering exceptional results while providing a level of service that keeps clients coming back and referring their friends and family. Whether you're a first-time homebuyer, relocating to Florida, searching for investment opportunities, selling a family home, or purchasing commercial land, Ryan understands that every client and every transaction is unique. He takes the time to listen, understand your goals, and develop a strategy designed to help you succeed. One of the qualities clients appreciate most about Ryan is his commitment to communication. Real estate transactions can be stressful, but Ryan believes clients should never be left wondering what comes next. From the initial consultation through closing day, he keeps clients informed, answers questions promptly, and guides them through every step of the process. As a lifelong resident of Polk County, Ryan brings invaluable local knowledge to every transaction. He understands neighborhood trends, school districts, growth patterns, investment opportunities, and the factors that impact property values. This local expertise allows him to help clients make informed decisions whether they are buying, selling, or investing. Ryan and his wife, Kristi, founded HomeTrust Real Estate & Property Management with a simple mission: provide honest advice, exceptional service, and a client-first approach that puts relationships above transactions. Together, they have helped hundreds of families and individuals successfully navigate the real estate process while building a business rooted in trust, integrity, and results. Today, HomeTrust proudly serves buyers, sellers, investors, landlords, and tenants throughout Central Florida. Through professional marketing, expert negotiation, cutting-edge technology, and a commitment to personalized service, Ryan works tirelessly to help clients achieve their real estate goals. When you're ready to make your next move, Ryan is ready to put his experience, knowledge, and dedication to work for you. Your goals become our mission, and your success becomes our success.

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