Oak Hollow Real Estate

Oak Hollow Real Estate

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 suburban tranquility and vibrant Florida living, making it an ideal place for families, retirees, and everyone in between.

Oak Hollow is characterized by its lush, tree-lined streets and beautifully landscaped properties, providing a picturesque backdrop for your dream home. The subdivision features a variety of home styles, from cozy single-family residences to spacious modern designs, each offering unique architectural touches that reflect the warm Florida aesthetic.

One of the standout features of Oak Hollow is its proximity to a wealth of amenities. Residents can enjoy easy access to nearby parks, recreational facilities, and the stunning Gulf Coast beaches that are just a short drive away. Whether you’re looking to spend a day boating, fishing, or simply soaking up the sun, the natural beauty of the area is sure to captivate you.

Families will appreciate the quality education options available in the vicinity, with several highly-rated schools located just minutes from the community. Additionally, Oak Hollow is conveniently situated near shopping centers, dining options, and healthcare facilities, ensuring that all your daily needs are met with ease.

With its friendly atmosphere and strong sense of community, Oak Hollow invites you to experience the best of Florida living. Discover your new home in this delightful subdivision, where comfort, convenience, and charm await you at every turn!

Newest Listings in Oak Hollow

$242,500
3 Beds ⋅ 2 Baths ⋅ Oak Hollow SubDv. ⋅ 33954 Zip Code
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
$175,000
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
$109,999
Oak Hollow SubDv. ⋅ 34491 Zip Code
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
$136,900
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
$117,900
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
$224,900
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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