Oak Hollow Homes for Sale

Oak Hollow Homes for Sale

Welcome to Oak Hollow, a hidden gem nestled in the heart of Port Charlotte, Florida! This charming subdivision offers a unique blend of tranquility and convenience, making it the perfect place to call home. With its lush landscapes and serene atmosphere, Oak Hollow is designed for those who appreciate the beauty of nature while enjoying the comforts of modern living.

The homes for sale in Oak Hollow are a delightful mix of architectural styles, catering to a variety of tastes and preferences. From cozy single-family residences to more spacious properties, each home is thoughtfully designed with quality craftsmanship and attention to detail. Many of these homes feature open floor plans, expansive backyards, and modern amenities, ensuring that you have everything you need for comfortable living.

Living in Oak Hollow means you’re just a stone's throw away from Port Charlotte’s vibrant community. Residents enjoy easy access to a plethora of shopping, dining, and entertainment options, as well as beautiful parks and recreational facilities. Whether you’re looking to spend a day at the beach, explore local hiking trails, or indulge in the culinary delights of nearby restaurants, Oak Hollow places you at the center of it all.

For families, the area boasts excellent schools and a welcoming community atmosphere, making it an ideal choice for those looking to settle down. With homes for sale in Oak Hollow, you have the opportunity to invest in a lifestyle that balances relaxation with adventure. Discover your dream home in Oak Hollow today, and embrace the Florida lifestyle you’ve always desired!

Newest Oak Hollow Homes for Sale

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

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. ⋅ 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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