Holiday Heights Real Estate

Holiday Heights Real Estate

Welcome to Holiday Heights, a charming subdivision nestled in the heart of sunny Florida! Perfectly situated just minutes from the vibrant coastal beaches, this delightful community offers a serene escape while keeping you connected to all the excitement the Sunshine State has to offer.

Holiday Heights is characterized by its friendly atmosphere and beautifully landscaped surroundings. As you stroll through the tree-lined streets, you'll encounter a mix of contemporary and traditional homes, each exuding its own unique charm. The thoughtfully designed layouts cater to families, retirees, and everyone in between, making it an ideal place for anyone looking to settle down in a welcoming environment.

One of the standout features of Holiday Heights is its strong sense of community. Residents enjoy a variety of neighborhood events throughout the year, fostering connections and friendships that last a lifetime. The nearby parks and recreational areas provide ample opportunities for outdoor activities, whether it's a leisurely afternoon picnic, a morning jog, or a weekend barbecue with friends and family.

For those who appreciate convenience, Holiday Heights is just a short drive from shopping centers, dining options, and entertainment venues. With easy access to major highways, commuting to nearby cities or enjoying a day trip to Orlando’s world-renowned attractions is a breeze.

In Holiday Heights, you’ll find not just a house, but a place to call home. Experience the warmth of community living in this picturesque Florida subdivision, where every day feels like a vacation! Come and discover the joy of living in Holiday Heights – your dream home awaits!

Newest Listings in Holiday Heights

$422,000
3 Beds ⋅ 2 Baths ⋅ Holiday Heights SubDv.
Something Special in the Heart of Bradenton! Welcome to 5102 21st St W, a charming Florida home offering comfort, versatility, and an excellent location. Situated on a 0.22-acre lot with no HOA, this property provides the freedom and space that are increasingly difficult to find. The home features a functional layout complemented by inviting outdoor living areas, including a spacious screened enclosure that extends the living space and creates the perfect setting for morning coffee, casual gatherings, or simply enjoying Florida’s year-round lifestyle. The generous lot offers plenty of outdoor space and possibilities, while the property’s convenient Bradenton location places you close to shopping, dining, schools, everyday services, and major roadways, with easy access to the beautiful Gulf Coast beaches and everything the Sarasota–Bradenton area has to offer. Whether you are looking for a primary residence, seasonal Florida home, or investment opportunity, this property combines location, flexibility, and potential in one attractive package. No HOA and no known lease restrictions. A wonderful opportunity to make this Bradenton home your own.

5102 21st Street W, West Bradenton
$395,000
8 Beds ⋅ 4 Baths ⋅ Holiday Heights SubDv.
Bradenton duplex with two 2BR/1BA units. Live in one and rent the other, plus a large backyard near shopping and medical services. Built 1972. Bradenton duplex with two separate 2-bedroom, 1-bath units, offering flexibility for owner occupancy, rental use, or multi-generational living. Built in 1972, this two-unit property creates a straightforward opportunity to live in one side and rent the other or use both units as rentals. Each unit provides a practical 2-bedroom, 1-bath layout with separate living space. For buyers searching for a Bradenton duplex, an owner-occupied rental property, or a property with two distinct residences, this configuration provides multiple options under one ownership. A large backyard adds valuable outdoor space and is a standout feature of the property. The additional yard space complements both units and provides more room beyond the interior living areas. Convenience is another key benefit. The property is near restaurants, grocery stores, medical facilities, and everyday services, with access to area beaches and the airport. This Bradenton location puts daily necessities and popular Gulf Coast destinations within the surrounding area. Whether the goal is to live in one unit while renting the other, maintain two rental units, or create separate space for multi-generational living, this duplex offers versatility that a traditional single-family property does not. Two 2-bedroom, 1-bath units, a large backyard, and a convenient Bradenton location make this property worth considering for buyers seeking a duplex with multiple potential uses.

5014 & 5016 22nd Street W, West Bradenton
$2,825,000
3 Beds ⋅ 3 Baths ⋅ Holiday Heights SubDv.
WATERFRONT PARADISE! Magnificent luxury custom-built home situated on a wide Gulf-access canal with direct access to picturesque Estero Bay. Built by Gary Lau, this exceptional residence offers approximately 2,600 sq. ft. under air, featuring 3 bedrooms plus a den, 3 luxurious bathrooms, and an abundance of ground-level open space ideal for storage, recreation, entertaining, and more. An elevator provides effortless access to every level, blending convenience with sophisticated coastal living. The expansive great room features soaring ceilings and opens seamlessly to your private outdoor oasis. A spectacular two-story screened pool enclosure surrounds the inviting saltwater pool and spa, creating the perfect setting for relaxing, entertaining, and enjoying the year-round Florida lifestyle. BOATER'S DREAM LOCATION! Step outside to your impressive 16,000-lb. boat lift and dock, where endless aquatic adventures await. With direct Gulf access, you can enjoy boating, fishing, sunset cruises, and easy access to the beautiful waters of Estero Bay and beyond. Wake up to tranquil waterfront views and spend your days exploring Southwest Florida by boat. For the car enthusiast, boater, or outdoor lifestyle enthusiast, this property delivers with an oversized four-car garage, additional storage, and an RV electrical hookup. Every detail of this custom residence reflects quality craftsmanship, thoughtful design, and a commitment to luxury waterfront living. Ideally located within walking distance to the marina, restaurants, bars, shops, and more, this home offers the perfect combination of privacy and convenience. Enjoy easy access to the south end of Fort Myers Beach via Lovers Key, with convenient boating and driving access toward Bonita Springs, Naples, and Southwest Florida's renowned dining and entertainment destinations. From the lush surroundings and breathtaking water views to the resort-style pool, exceptional dockage, elevator, and generous garage space, this magnificent custom home offers an unparalleled waterfront lifestyle. Experience the ultimate blend of luxury, comfort, boating, and waterfront bliss. Welcome home.

5575 Avenida Pescadora, Fort Myers Beach
$464,000
6 Beds ⋅ 2 Baths ⋅ Holiday Heights SubDv.
Bradenton Duplex with two units, each with 3 bedrooms and 1 bath. Units renovated in 2024. Each unit has its own screened porch. Heat and air units are being installed in the back bedrooms. New electrical panels for both sides were installed a few months ago. A new roof was installed around last August. New PVC fence and Air conditioners were installed in 2020. New PEX piping installed in each shower and new windows were installed in each back bedroom. PVC services mains with clean outs for each side. A 4-pt inspection will be performed as soon as the heating and cooling units are installed.

4805 21st 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
$1,100,000
3 Beds ⋅ 2 Baths ⋅ Holiday Heights SubDv.
Newer construction built in 2023! Potential Income Producer. Rent includes land, no HOA, no land lease. 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
$440,000
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
$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
$315,000
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
$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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