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, in the vibrant Charlotte County. This charming community offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and anyone seeking the quintessential Florida lifestyle.

Oak Hollow is renowned for its stunning homes, many of which feature private pools, providing residents with their own personal oasis to enjoy year-round. Imagine stepping out into your backyard to soak up the sun or hosting a weekend barbecue with friends and family by your sparkling pool. The community’s design encourages outdoor living, with ample space for relaxation and recreation.

In addition to the inviting homes, Oak Hollow boasts a variety of community features that enhance the overall living experience. Residents can enjoy beautifully landscaped common areas, walking trails, and parks, perfect for morning strolls or evening jogs. The friendly atmosphere fosters a sense of belonging, where neighbors become friends and community events bring everyone together.

Located just a stone's throw away from shopping, dining, and entertainment options, Oak Hollow offers the perfect balance of suburban serenity and urban convenience. With easy access to major highways, you can explore the stunning Gulf Coast beaches, vibrant cultural attractions, and the natural beauty that Florida is known for.

Discover the charm of Oak Hollow, where your dream home with a pool awaits. Experience the ultimate Florida lifestyle in a community that truly feels like home. Come and see for yourself why Oak Hollow is the perfect place to create lasting memories!

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

Start Your Search

Mikel Chaffee

Mike understands that buying and selling your home is one of, if not the biggest, financial decisions you will make. He knows first-hand the unparalleled value of hard work, dedication and exemplary service. With 13 homes sold in 2025 alone, putting him in the top percentile across the nation. Mike often works with his mom, Debi Chaffee Rose, as a mother-son team. Clients love their collaborative work and combined focus. Mike has a degree in management and operations, and for a number of years held his PGA Golf Certification. This experience gives him an intimate knowledge of many diverse golf and country club communities that make up the Florida lifestyle. 13 Years licensed as a Realtor, he is ready to put his experience to work, for you in any facet. Mike spends his free time with his beautiful wife Meghan, and their 4 Kids here in the town he was raised in, Bradenton Florida. They enjoy going and exploring the sunshine state together as a family.

Learn More