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Holiday Heights Fort Myers Beach Florida Homes for Sale

Naples Florida Real Estate

Holiday Heights Fort Myers Beach Real EstateHoliday Heights Fort Myers Beach

Homes For Sale4$1.3M - $5M
Land For Sale4$900K - $1.8M
Last updated at 2:26pm 03/23/2026

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$4,950,000
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Holiday Heights NEW

5640 Williams Dr, Fort Myers Beach, FL 33931

Homes - 3,417 ft² / 4,473 ft² - 3 Car Garage

5 Bed / 4 Baths / 1 Half / Pool / Spa

Built 2004
Holiday Heights Fort Myers Beach Homes for Sale: Luxury Bayfront Estate | Expansive Bay Views & Resort-Style Living! Imagine waking up each morning to panoramic 180° Bay Views, where the sun rises gracefully over the bay and sets in a blaze of color on the horizon. 30,000 lb Synergy Boatlift, 5 ensuites, elevator, 3+ car garage. Nearly every room in this home captures breathtaking views, immersing you in the beauty of coastal living. After sunset, retreat to the dock, the lanai, or your private master deck to watch the stars emerge—on a clear night, hundreds sparkle above, and you may even glimpse rockets launching from Cape Canaveral. The soothing sound of the distant ocean waves completes the picture of tranquility. The newly remodeled heated saltwater pool and spa create your own private resort. Relax with music or a favorite show on the lanai’s large-screen TV, or gather for a cozy movie night under the stars. With five spacious en-suite bedrooms, the home provides ultimate privacy and comfort for family and guests alike. The open-concept kitchen and dining areas accommodate up to 14, making it perfect for entertaining on any scale. Every detail of this residence is designed for both luxury and function. A 3+ car garage with a newly finished multi-coat polyurea floor offers abundant storage, while numerous large closets ensure everything has its place. Beyond the home, the lush landscape is adorned with fragrant flowering plants and stately palms, creating a true tropical retreat. For the boating enthusiast, the private dock system is unparalleled. Outfitted with a 30,000 lb. Synergy boat lift and new boathouse roof, a double IMM Quality PWC lift, fish cleaning station, and 50-amp shore power, it has been fully re-decked with premium AZEK materials for durability and style. Launch your kayak or paddleboard from the floating EZ Dock and explore mangrove islands teeming with dolphins, manatees, stingrays, & native birds—even the occasional bald eagle. Quick Gulf access means you can reach Big Carlos Pass in about 12 minutes, enjoy a trip to Naples or Marco Island in just over an hour, or head north for a scenic ride to Cabbage Key. At home, cast a line off the dock for snapper or sheepshead while enjoying the evening migration of ibis or the sight of dolphins gliding by. This smartly equipped residence ensures modern comfort with high-speed mesh Wi-Fi extending throughout the home, pool deck, and dock. Even while aboard your boat, you can stream video seamlessly. Smart Leviton lighting controls, newer appliances—including GE Profile washer/dryer, KitchenAid dishwasher, and microwave/convection combo—and thoughtfully included furnishings (7 TVs and more) make this property move-in ready. With deeded neighborhood beach access just a 15-minute stroll away, you’ll also enjoy daily sunset gatherings with neighbors on the white sands of the Gulf. This home is more than a residence—it’s an experience of refined coastal living, where every sunrise, sunset, and starry night is yours to savor.



$2,299,000
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Holiday Heights

5596 Avenida Pescadora, Fort Myers Beach, FL 33931

Homes - 2,193 ft² / 5,176 ft² - 2 Car Garage

3 Bed / 3 Baths / Pool / Spa

Built 1961
Holiday Heights Fort Myers Beach Homes for Sale: Coastal Waterfront Retreat with Panoramic Estero Bay Views & Gulf Access! Delightfully decorated in a breezy coastal theme, this exceptional 3-bedroom, 3-bath waterfront home offers the ultimate blend of luxury, comfort, and coastal charm. Perfectly situated at the end of a quiet cul-de-sac, this rare property spans nearly ½ acre (.49 acres) and showcases approximately 300 feet of wraparound waterfront along Estero Bay and a scenic intersecting side canal — creating a truly breathtaking backdrop from sunrise to sunset. Beautifully remodeled in 2023, this residence shines inside and out with thoughtful upgrades and high-end finishes. A new metal roof and impact-resistant doors and windows provide lasting peace of mind, energy efficiency, and storm protection. The light-filled interior features an open-concept design that captures sweeping bay views from nearly every room, inviting you to relax and embrace the laid-back Florida lifestyle. Step outside to your private tropical oasis — complete with a heated pool and spa, surrounded by lush landscaping and unobstructed water views. For boating enthusiasts, 2 covered boat lifts (16,000 and 18,000 lb.) and jet ski lifts make it effortless to explore the open water, while a short 10-minute ride to the Gulf of America opens endless opportunities for deep-sea fishing, island hopping, or sunset cruising. Enjoy your morning coffee on the observation pier, cast a line in your backyard, or simply unwind poolside as dolphins and seabirds drift by. The home’s 2-car deep garage offers ample storage and parking for vehicles, golf carts, or beach gear. Inside, you’ll find stylish finishes, and modern lighting that seamlessly blend functionality with coastal elegance. Every detail has been considered — from the smart layout to the thoughtful updates that make this home truly move-in ready. Location is everything, and this one checks every box. You’re just a short stroll to the white sugar-sand beaches, and close to some of the area’s most exciting destinations — including Jimmy Buffett’s Margaritaville Resort, Santini Plaza, Publix, and the newly developed downtown entertainment and dining district. Whether you’re in the mood for live music, fine dining, or boutique shopping, it’s all just minutes away. This home offers something for everyone — boating, fishing, entertaining, or simply soaking in the stunning views. It’s a rare opportunity to own nearly half an acre of prime waterfront in one of Southwest Florida’s most desirable areas. Experience the magic of Estero Bay and the Gulf of America lifestyle — schedule your private showing today!



$1,500,000
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Holiday Heights

5650 Williams Dr, Fort Myers Beach, FL 33931

Homes - 2,326 ft² / 2,746 ft² - 2 Car Garage - 2 Carport

3 Bed / 3 Baths / Pool

Built 1971
Holiday Heights Fort Myers Beach Homes for Sale: This BAY Front island paradise offers an opportunity to restore one of the most premier locations on Fort Myers Beach or rebuild. The home is 2,326 square feet and is certified structurally sound. Originally designed as a bay front three-bedroom, three-bathroom, two-car garage home, The home also has a large, screened lanai and swimming pool that have been meticulously maintained. The home also includes a paver driveway, extra paver parking, and paver sidewalks around both sides of the home extending to a newer composite boat dock and newer seawall and cap. The screened pool cage has undergone refurbishment with fresh paint and screening. The garage door is an insulated impact to code door. The front of the Williams home has an enjoyable screened lanai. The owner has installed a new air conditioning system and an updated electrical box in the garage, new pool pump, new well pump, irrigation system and a 500-gallon underground propane tank and so much more. The property is fenced and situated on the private Williams Drive, emphasizing its appeal as a distinctive asset. 5650 Williams is a beautiful piece of paradise on quiet circular drive across from St. Raphael Church. It’s a real Gem waiting for renovation.



$1,340,000
Decrease*
$55K
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Holiday Heights

5660 Williams Dr, Fort Myers Beach, FL 33931

Homes - 2,264 ft² / 2,759 ft² - 2 Car Garage

3 Bed / 3 Baths / Pool

Built 1969
Holiday Heights Fort Myers Beach Homes for Sale: Oversized premium lot with stunning Estero Bay views and direct Gulf access. Nestled in a top neighborhood, perfect for boaters and nature lovers. Minutes from beaches, dining, and shopping. Sold as-is for lot value—build your dream home in paradise!




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Need professional assistance selling your property at Holiday Heights Fort Myers Beach? Find out how an Area Specialist can help to generate more property exposure in order to get the most money for your investment in the least amount of time.Contact Us.
*Just Listed: new properties that came on the market within the last 30 days.
*Decrease/Increase: listing values that are being recorded within the last 30 days.
*Foreclosures/Short Sale: Please note, all properties are subject to bank approval. Buyers must be pre-approved or show proof of funds before submitting an offer.

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