Oak Hollow Real Estate

Oak Hollow Real Estate

Welcome to Oak Hollow, a serene subdivision nestled in the heart of Florida, where charm meets modern living. This picturesque community is designed for those who appreciate the beauty of nature while enjoying the conveniences of contemporary life. Oak Hollow is characterized by its lush landscapes, mature oak trees, and well-maintained sidewalks, making it a perfect haven for families, retirees, and anyone seeking a tranquil lifestyle.

Residents of Oak Hollow enjoy a tight-knit community atmosphere, where neighbors become friends and gatherings are a regular delight. The subdivision features a variety of beautifully designed homes that cater to diverse tastes and budgets, ensuring that everyone can find their perfect abode. From charming single-family homes to spacious townhouses, each property reflects the warm and inviting spirit of Florida living.

One of the standout features of Oak Hollow is its prime location. Just a short drive away, you’ll find a plethora of shopping, dining, and entertainment options, along with access to some of Florida's stunning beaches. The nearby parks and recreational facilities offer ample opportunities for outdoor activities, from hiking and biking to picnicking and playground fun.

Families will appreciate the proximity to highly-rated schools, ensuring that children receive a quality education within a supportive community. With its blend of natural beauty, friendly neighbors, and convenient amenities, Oak Hollow is not just a place to live; it’s a place to thrive. Come discover the charm of Oak Hollow and make this delightful subdivision your new home in sunny Florida!

Newest Listings in Oak Hollow

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

Oak Hollow SubDv. ⋅ 33954 Zip Code

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 ⋅ Oak Hollow SubDv. ⋅ 33954 Zip Code

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

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

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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Kenneth Weir

With over 20 years of experience in New York, Kenny brings deep market knowledge, sharp negotiation skills, and a client first approach to every transaction. In February 2025, I relocated to Ocala, Florida where I quickly earned my Florida Real Estate license in March 2025 and began helping buyers and sellers confidently navigate the market in the Horse Capital of the World. For several years while working with clients in the Real Estate market in NYC and Long Island I worked for a title company as a settlement closer.This background gave me a unique advantage. I understand contracts,title issues, and the closing process from the inside out. My clients will experience the benefit of smoother transactions, fewer surprises, and strong protection from start to finish.I'm known for my clear communication, honest guidance, and dependable service. I focus on making the buying or selling experience as stress-free as possible. Whether working with first-time buyers, relocating families, or seasoned investors I am committed to helping clients make smart real estate decisions and feel confident every step of the way.

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