Oak Hollow Homes with Pool Community Features

Oak Hollow Homes with Pool Community Features

Welcome to Oak Hollow, a picturesque subdivision nestled in the heart of Port Charlotte, Florida. This charming community is a hidden gem in Charlotte County, offering a perfect blend of tranquility and modern living. With its lush landscapes and friendly atmosphere, Oak Hollow is an ideal place for families, retirees, and anyone seeking a serene lifestyle in the Sunshine State.

One of the standout features of Oak Hollow is its inviting homes, many of which boast private pools. Imagine stepping into your own backyard oasis, where you can unwind after a long day or host lively gatherings with friends and family. The homes in this community are designed with comfort and style in mind, featuring spacious layouts, modern amenities, and beautiful finishes that cater to a variety of tastes.

Beyond the charming residences, Oak Hollow offers a range of community features that enhance the living experience. The neighborhood is well-maintained and designed for easy navigation, making it a pleasure to stroll or bike around. Residents enjoy a sense of camaraderie, with opportunities to connect through community events and gatherings.

Located conveniently near shopping, dining, and recreational options, Oak Hollow ensures that everything you need is just a stone's throw away. Whether you’re seeking adventure on the nearby waterways or a peaceful day at one of the local parks, this community has it all.

Experience the warmth and charm of Oak Hollow, where your dream home awaits amidst the beauty of Port Charlotte, Florida. Dive into a lifestyle filled with sunshine, community spirit, and the joys of poolside living!

Newest Oak Hollow Homes with Pool Community Features

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

ENJOY THE BEAUTIFUL FLORIDA WEATHER. HOME LOCATED NEAR SHOPPING, RESTAURANTS AND FLORIDA BEACHES. HOME FEATURES SPACIOUS MASTER BEDROOM, UPDATED BATHROOMS, NEWER ROOF, UPDATED KITCHEN , NEW DISHWASHER, FLAT TOP RANGED, BUILT IN MICROWAVE, REFRIGERATOR. WASHER AD DRYER AND AN EXTRA REFRIGERATOR LOCATED IN THE GARAGE. LARGE BACK YARD AND SCREENED PORCH, PLUS EXTRA PATIO FOR GRILLING. HOME IS LOCATED IN A CUL DE SAC WITH LOW TRAFFIC. COMMUNITY HEATED POOL WITH EXERCISE ROOM, TENNIS AND PICKELBALL COURTS, PLAYGROUND AND PLANNED ACTIVITIES. VERY LOW HOA FEES.

471 Insull Court, 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

Start Your Search

Jennifer Garcia

Experience. Strategy. Results. The Legacy Collective Realty is a premier boutique brokerage based in Punta Gorda, Florida, proudly serving buyers and sellers across Southwest Florida and beyond. Founded on integrity, innovation, and results, The Legacy Collective Realty blends personalized service with powerful marketing and global reach, offering every client a truly elevated real estate experience. With over 20 years of real estate expertise and thousands of homes successfully sold, our team has built a strong reputation for excellence in residential, luxury, investment, and new construction properties. Our approach is strategic and modern — combining expert negotiation skills, market knowledge, and cutting-edge digital marketing to achieve exceptional results. At The Legacy Collective Realty, we believe that every property deserves world-class representation, no matter the price point. From initial consultation to closing day, we guide our clients with transparency, communication, and professionalism, ensuring confidence at every step of the journey. Boutique Brokerage • Global Reach Proudly serving Florida’s Gulf Coast communities — from Sarasota to Fort Myers, State-Wide and beyond.

Learn More