Holiday Heights Real Estate

Holiday Heights Real Estate

Welcome to Holiday Heights, a delightful subdivision nestled in the heart of sunny Florida! This charming community embodies the perfect blend of tranquility and convenience, making it an ideal place to call home. With its picturesque streets lined with lush greenery and vibrant flowers, Holiday Heights offers a serene atmosphere that invites relaxation and enjoyment.

Residents of Holiday Heights benefit from a variety of amenities that cater to an active lifestyle. The community features beautifully maintained parks, walking trails, and playgrounds, providing ample opportunities for outdoor recreation and family bonding. Whether you’re taking a leisurely stroll, enjoying a picnic with loved ones, or watching your children play, the natural beauty of the area enhances every moment.

Location is key, and Holiday Heights does not disappoint. Situated just a short drive from some of Florida’s finest beaches, shopping centers, and dining options, residents can easily access everything they need. The nearby attractions, including theme parks and cultural hotspots, ensure there’s never a dull moment for those who love adventure and entertainment.

The homes in Holiday Heights are designed with comfort and style in mind, featuring modern layouts and quality finishes. With a variety of options available, from cozy single-family homes to spacious properties perfect for growing families, there’s something for everyone in this welcoming community.

Experience the charm of Holiday Heights, where friendly neighbors and a vibrant community spirit come together to create the perfect backdrop for your Florida lifestyle. Discover your dream home today in this idyllic subdivision!

Newest Listings in Holiday Heights

$235,000
2 Beds ⋅ 1 Baths ⋅ Holiday Heights SubDv.
Tropical curb appeal, timeless construction, and endless backyard potential await at this charming block-built home. Framed by beautiful palm trees that instantly bring the Florida vibe, this property sits on a spacious, nearly quarter-acre fenced lot with room to relax, entertain, or create your dream outdoor oasis. Inside, you'll find an open-concept layout full of character, highlighted by a stunning brick accent wall, along with a one-car garage and washer and dryer for added convenience. The oversized screened-in lanai is the perfect place to enjoy your morning coffee or unwind in the evenings, while the expansive backyard offers endless possibilities for a pool, garden, or play space. Built with the quality and craftsmanship you don't often find today, this home is located outside of a flood zone, less than 20 minutes from the beautiful beaches of Anna Maria Island, and just minutes from Detwiler's Farm Market, giving you the perfect combination of classic charm, everyday convenience, and the Florida lifestyle. Schedule your showing today!

5123 20th Street W, West Bradenton
$1,674,500
Holiday Heights SubDv.
PREMIER BAYFRONT HOMESITE — BUILD YOUR DREAM HOME ON ESTERO BAY Paradise awaits on this rare, oversized Bayfront homesite offering direct Gulf access along the protected and prestigious Estero Bay Aquatic Preserve. Spanning 11,230 square feet with an impressive 95 feet of Bay frontage and 155 feet of depth, this exceptional property provides the ideal canvas to construct a new elevated two- or three-story Bayfront residence designed to capture sweeping water views and unforgettable sunsets. Enjoy front-row seating to nature’s daily show—dolphins and manatees gliding through the bay—right from your future private dock. Positioned on a quiet cul-de-sac and among the highest elevations on the island, this property is located within the highly desirable Holiday Heights neighborhood, offering both privacy and prestige. The existing structure is considered a teardown, and the property is being sold at lot value, allowing full creative freedom to design a custom home perfectly tailored to your lifestyle. Multiple builder introductions are available to assist in bringing your vision to life. Just a short stroll to deeded beach access, a nearby marina, and a grocery store, this one-of-a-kind bayfront parcel delivers the ultimate blend of boating, beach, and luxury island living. This is a rare opportunity to create a true coastal residence and be part of the ongoing Fort Myers Beach Renaissance.

5630 Williams Drive, Fort Myers Beach
$845,000
3 Beds ⋅ 2 Baths ⋅ Holiday Heights SubDv.
Newer construction built in 2023! Potential Income Producer. This Elevated Florida-Style Fully Furnished Turnkey Beach Home offers the rare combination of luxury living for a lifetime of Cherished Memories and provides potential Income in Weekly Zone that you need. Exceptional Rental History, highly rated on popular 3rd party rental sites. Close to the beach, Shopping and Dining. Absentee Ownership Made Easy. Room pool or Swim spa. Whether you want a personal Island Escape, a Second Home, or an Income Producing Investment Property, this home delivers lifestyle and revenue.

431 Lazy Way, Fort Myers Beach
$460,000
3 Beds ⋅ 2 Baths ⋅ Holiday Heights SubDv.
Rare opportunity to own a private, tree-lined retreat on nearly half an acre in the heart of Manatee County, where space, flexibility, and location come together in a way that's hard to find at this price point. This charming 3-bedroom, 2-bathroom home sits on an expansive .48-acre lot and has been lovingly maintained with meaningful updates throughout, including a brand new roof (2025), fresh interior paint (2026), a new vinyl privacy fence (2026), updated bathrooms, exterior security features, recently serviced mechanical systems, and a full PVC plumbing repipe throughout the entire home and all the way to the street. Located in an X flood zone, no flood insurance is required, a significant cost saving that sets this property apart from much of the surrounding area. With a 7-night minimum rental allowance, the income potential here is real, whether you're looking for a short-term rental investment, a seasonal Florida escape, or a full-time residence with the freedom to generate revenue when you're not using it. The oversized lot leaves room to dream big, think pool, outdoor entertainment space, guest house, or accessory dwelling unit. Positioned directly adjacent to commercial use to the west and established residential to the east, this property sits in a transitional corridor that forward-thinking buyers and investors will recognize as having strong long-term potential, including the possibility of future commercial rezoning, subject to Manatee County review and approval. Minutes to I-75, US-41, world-class Gulf Coast beaches, top-rated dining, shopping, and everything the Sarasota-Bradenton corridor has to offer, all tucked away on a quiet, private parcel that feels like your own little sanctuary. Properties like this don't last.

2503 53rd Avenue W, West Bradenton
$2,500,000
3 Beds ⋅ 2 Baths ⋅ Holiday Heights SubDv.
Newly built elevated gulf access pool home located in the desirable Holiday Heights neighborhood on Fort Myers Beach. Completed in 2025 and gently used since, this 3 bedroom 2 bathroom home offers a coastal feel with quality design and beautiful finishes. You may ascend to the living area using 1 of 2 composite staircases or call for your private elevator to transport you up to the property. Once inside you will admire the great room, teeming with natural light through the impact windows, complete with formal dining for 10, a comfy yet sophisticated living room, and sensational kitchen outfitted with stainless steel appliances, marble island, wine fridge, and 4-person breakfast bar. The spacious primary bedroom, with pocket sliders leading out to the deck and ensuite bathroom, provides a quiet sanctuary for the owners. You will find 2 guest bedrooms separated by a beautifully appointed bathroom on the other side of the home, perfect for families or guests. Once back downstairs and outside you can enjoy a large heated saltwater pool with sun shelf overlooking the canal with views of the bay. When you are ready to hit the water, the newly constructed dock with electric boat lift is the perfect spot to store your vessel. This beach property is located just minutes from Publix , shopping and dining options of Santini Plaza, and the Margaritaville Resort.

5545 Avenida Pescadora, Fort Myers Beach
$4,900,000
5 Beds ⋅ 5 Baths ⋅ Holiday Heights SubDv.
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 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.

5640 Williams Drive, Fort Myers Beach
$325,000
3 Beds ⋅ 2 Baths ⋅ Holiday Heights SubDv.
Virtually Staged. Welcome home to this bright and functional 3-bedroom, 2-bath residence situated on a generously sized, fully fenced 0.24-acre lot. With a 2019 roof, 2022 A/C, and recently pumped septic (late 2025), major systems are already taken care of. Tile flooring flows through the main living areas, making everyday living easy and low maintenance. The kitchen is equipped with stainless steel appliances and a window, overlooking the backyard. Natural light pours in through large windows and the sliding glass door, creating a warm and inviting atmosphere. Step outside to enjoy a large entertaining space in the large, fully fenced backyard, ideal for gatherings, grilling, or future outdoor projects. A 1-car garage, ample driveway parking, with room on the side of the home for a boat or trailer. Situated in a prime location less than 2.5 miles from I-4, 5 minutes from RDV Sportsplex and Costco, 15 minutes from Downtown Orlando and Advent health Altamonte, this home offers the complete package. Call and schedule your private showing today!

3008 Calumet Drive, Orlando
$79,000
Holiday Heights SubDv.
One or more photo(s) has been virtually staged. Vacant Land Opportunity in Bushnell!Beautiful 1.48-acre tree-shaded lot located on CR 476, just east of 9144 CR 476, offering privacy and a peaceful rural setting. The property is not located in a flood zone and has no HOA restrictions.Zoned for new home construction or manufactured home placement. Well and septic required. A great opportunity for buyers looking to build or place a manufactured home in a quiet area with flexible use.Bring your Cows,chickens and horses! Owner financing available.

00 W C 476, Bushnell
$1,795,000
Holiday Heights SubDv.
**PRICE IMPROVEMENT OF NEARLY $150,000!** STUNNING & EXPANSIVE unobstructed BAY & WATERFRONT VIEWS across Estero Bay Aquatic Preserve from this OVERSIZED cleared and buildable BAY FRONT lot! Over 100' of spectacular water frontage on over 1/3 of an acre which wakes up to beautiful sunrises across the bay and is only a short distance to Deeded Beach Access & sunsets on the Gulf! ONE OF THE MOST SOUGHT-AFTER WATERFRONT AND BOATING COMMUNITIES ON THE ISLAND, Holiday Heights, is KNOWN FOR ITS HIGHER ELEVATION AND GULF-ACCESS CANALS and warm & friendly community. Build your custom designed dream home on this oversized bay front lot offering awe inspiring views and the best in coastal living! Located mid-island close to Publix grocery store, trolley stop, full service marina, Fresh Catch Exquisite Waterfront Dining & Junkanoo Below Deck for the more casual waterfront dining experience. Don't miss out on this opportunity to own one of the few vacant bay front lots in this desirable mid island neighborhood location!

5636 Williams Drive, Fort Myers Beach
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