Explore Homes for Sale in Holiday, FL

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Discover Homes for Sale in Holiday, FL with Joseph Sullivan Real Estate

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Explore a diverse range of homes for sale in Holiday, Florida, perfectly suited for various lifestyles. Joseph Sullivan Real Estate provides expertise and local knowledge to assist you in finding your dream home in this vibrant community. Begin your search today and discover the possibilities that await.

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Exploring the Holiday, FL Real Estate Market

The real estate market in Holiday, Florida, offers a unique blend of opportunities for homebuyers. From waterfront properties to cozy family homes, you'll find a variety of options tailored to your specific needs. Discover the charm and appeal of this growing community.

Finding Your Ideal Home

The search for the perfect home can be exciting and rewarding. Consider the factors that are most important to you, such as location, size, and amenities. Joseph Sullivan Real Estate is here to guide you through every step of the process, ensuring a smooth and successful experience.

Types of Homes for Sale in Holiday

Holiday boasts a wide selection of properties, providing options for various preferences and budgets. Explore the different types of homes available and discover what best suits your lifestyle.

Single-Family Homes

Enjoy the space and privacy of a single-family home in Holiday. These properties often feature spacious yards and are ideal for families seeking a comfortable and convenient living environment.

Condominiums and Townhouses

Consider the low-maintenance lifestyle offered by condominiums and townhouses. These properties provide access to community amenities and are often located in convenient locations near shopping, dining, and entertainment.

Waterfront Properties

Experience the beauty and tranquility of waterfront living in Holiday. Waterfront properties offer stunning views and access to recreational activities such as boating, fishing, and swimming.

The Benefits of Living in Holiday, FL

Holiday offers a desirable lifestyle with its beautiful surroundings, friendly community, and convenient access to amenities. Discover the many advantages of making Holiday your home.

Community and Lifestyle

Holiday is a close-knit community with a welcoming atmosphere. Enjoy local events, parks, and recreational facilities that contribute to a vibrant and fulfilling lifestyle.

Location and Accessibility

Located in a prime location, Holiday provides easy access to major highways, shopping centers, and entertainment venues. Enjoy the convenience of living close to everything you need.

Newest Homes for Sale in Holiday, FL

$229,900
2 Beds ⋅ 2 Baths ⋅ Holiday Gardens SubDv.
Virtually Staged. Water View living with NO HOA! From the charming covered front porch with decorative columns to the expansive screened lanai overlooking the pond, this beautifully updated 2-bedroom plus bonus room home offers the Florida lifestyle you've been searching for. Enjoy peaceful water views, a flexible floor plan, and a convenient Holiday location just minutes from shopping, restaurants, beaches, and major roadways for an easy commute. Step inside to an inviting open layout featuring easy-care tile flooring throughout the home. The spacious living room flows effortlessly into the dining area, creating a comfortable space for everyday living and entertaining. The beautifully updated kitchen is ready for its next chef with white cabinetry, solid surface countertops, stylish tile backsplash, new appliances, a modern black sink and fixtures, and a generous pantry that provides exceptional storage. The Bonus/Florida Room offers endless possibilities and can easily become a home office, hobby room, workout space, or additional family room. Whether you're working from home or simply need extra living space, this flexible room adapts to your lifestyle while enjoying beautiful views of the backyard and lake. The updated bathroom with an eye-catching vessel sink, and stylish finishes that create a fresh, modern feel. Wait until you see this outdoor living space! The nearly 20-foot screened lanai invites you to sip your morning coffee, read a good book, host friends, or simply unwind while taking in the peaceful waterfront scenery. Just beyond, the spacious open patio offers even more room for grilling, entertaining, or relaxing under the Florida sunshine. Located in Holiday with NO HOA, you'll enjoy convenient access to US-19, the Suncoast Parkway, shopping, restaurants, medical facilities, parks, golf courses, and the beautiful Gulf beaches. Whether you're looking for your first home, a winter retreat, or everyday waterfront living, this property offers comfort, flexibility, and a view you'll never grow tired of.

2044 Pamela Drive, Holiday
$575,000
4 Beds ⋅ 3 Baths ⋅ Glenwood Gulf Trace SubDv.
Welcome to this spacious 4-bedroom, 3-bath pool home offering approximately 2,857 square feet of comfortable living space in the desirable Gulf Trace community of Holiday. Designed with both everyday living and entertaining in mind, the home features a split-bedroom floor plan, an expansive family room with a cozy fireplace, a generous kitchen with abundant cabinetry, a bright breakfast nook, a formal dining room, separate living room, dedicated laundry room, and an oversized 2-car garage. The private primary suite includes a large walk-in closet and spacious en-suite bath, while three additional bedrooms and multiple bathrooms provide flexibility for family, guests, or a home office. Step outside to an impressive screen-enclosed pool and oversized lanai, creating the perfect setting for year-round Florida living. Ideally located just minutes from the Gulf of Mexico, you'll enjoy easy access to Key Vista Nature Park, Anclote River Park, Gulf beaches, boating, fishing, waterfront dining, and the historic Tarpon Springs Sponge Docks, with Clearwater Beach, Tampa, and Tampa International Airport all within an easy drive. Combining generous living space, a functional layout, and an exceptional location, this home offers the very best of Florida's Gulf Coast lifestyle.

3225 Glenwood Circle, Holiday
$799,000
2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv.
"Gulf Access Waterfront Home in Historic Baileys Bluff Estates" A rare opportunity to own a true waterfront gem with your own private boat ramp! Enjoy a quick 2-minute boat ride to the open Gulf and just 10 minutes more to Anclote Island—perfect for boating, fishing, and island adventures. This beautifully maintained 2-bedroom, 2-bath split floor plan home offers an open and inviting layout ideal for entertaining. The updated kitchen features granite countertops, solid maple wood cabinetry, and a spacious pantry. Rich dark wood flooring flows throughout the home, adding warmth and elegance. Wake up to Gulf views from the expansive primary suite, complete with a large walk-in closet and a luxurious en-suite bathroom featuring dual sinks and granite countertops. Relax in the Florida room overlooking a generous backyard and serene open water views of Anglers Cove, or unwind in the screened-in back porch while enjoying local wildlife. The ground level includes an oversized 2-car garage and an additional 1,360 sq ft of valuable storage space—perfect for all your recreational and boating needs. Recent updates provide added value and peace of mind, including a new roof (August 2022), new A/C system, and a brand-new paver driveway (July 2026). Baileys Bluff Estates is a vibrant, active community offering social gatherings at the Gulf-front clubhouse just across the street, where you can take in breathtaking sunsets. The Pinellas Trail is conveniently located at the community entrance, and Key Vista Nature Park is just a 15-minute walk away, offering scenic trails and shoreline exploration. The famous Tarpon Springs Sponge Docks, beaches, waterfront dining, shopping, are a short car drive away. Experience waterfront living at its best—schedule your private showing today!

2030 Gulfview Drive, Holiday
$205,000
2 Beds ⋅ 2 Baths ⋅ Holiday Lake Estates SubDv.
Welcome home to this charming 2-bedroom, 1.5-bath house offering comfort, convenience, and plenty of storage. Featuring two separate driveways and an oversized garage, there's ample room for multiple vehicles, a boat, camper, workshop, or extra storage. Inside, you'll find a bright and functional layout with spacious living areas, a comfortable kitchen, bonus room and generously sized bedrooms. The covered patio provides a great space to relax or entertain, while the large garage and additional parking make this property truly stand out. Conveniently located on the Pasco/Pinellas line putting you just down the road from the Sponge Docks and downtown Tarpon Springs which offer plenty of shopping and dining options. In the other direction you will find a number of parks, beaches, fishing piers, and nature trails. This home is ready to make your Florida living dream come true!

1023 Viking Drive, Holiday
$145,500
2 Beds ⋅ 2 Baths ⋅ Tanglewood Mobile Village SubDv.
Discover your own slice of paradise in this lakefront home in Tanglewood Mobile Village, this is a 55+ community with low monthly maintenance fee of $143.00 per month which includes lawn maintenance, garbage service, maintenance of year-around-heated pool, a very active clubhouse, shuffleboard courts, and much more. Home features load of storage shed, large, enclosed porch overlooking the lake, where you can watch all the wildlife, separate dining room, oh plus 2 walk-in closets, plus master bath in master bedroom. Home is furnished and ready for you to enjoy. Measurements are approx. Buyer to verify all information that is deemed to be accurate. Sold As Is.

3201 Brewster Drive, Holiday
$225,000
2 Beds ⋅ 1 Baths ⋅ Ridgewood Gardens SubDv.
Welcome to your next home! This charming two-bedroom, one-bath residence offers the perfect blend of comfort, style, and convenience. Featuring a beautifully renovated kitchen, timeless terrazzo flooring, a newer roof, and an updated A/C system, this home is truly move-in ready. Enjoy a spacious, fully fenced backyard with rear access, perfect for parking a boat, RV, or trailer. With no HOA and no rear neighbors, you’ll appreciate the added privacy and freedom. Conveniently located near shopping, dining, parks, beautiful Gulf Coast beaches, and the famous Tarpon Springs Sponge Docks. The seller is highly motivated and willing to consider contributing toward the buyer’s closing costs with an acceptable offer. Don’t miss this incredible opportunity!

2122 Holiday Drive, Holiday
$205,000
2 Beds ⋅ 1 Baths ⋅ Aloha Gardens Unit 12 Pb 17 Pgs 81-83 Lot 1572 SubDv.
Welcome home to this beautifully updated residence featuring modern finishes and a bright, open layout that’s perfect for everyday living and entertaining. Enjoy a stylish kitchen with shaker cabinets, granite countertops, stainless steel appliances, updated flooring throughout, and a beautifully renovated bathroom. Step outside to a spacious backyard with a screened-in patio—ideal for relaxing, entertaining, or enjoying Florida evenings. Whether you’re a first-time homebuyer, downsizing, or looking for an investment opportunity, this move-in-ready home is one you won’t want to miss!

3124 Lecanto Street, Holiday
$230,000
2 Beds ⋅ 1 Baths ⋅ Beacon Square SubDv.
Charming 2-bedroom, 1-bath single-family home offering comfortable living, practical updates, and no HOA or CDD fees. The carpet-free interior features ceramic tile flooring throughout, a bright living room, an eat-in kitchen with a lot of cabinets, a double sunny kitchen window, and double stainless-steel sink, plus a versatile Florida room for relaxing, working, or entertaining. Both bedrooms include ceiling fans, and the bathroom features updated wall tile, a single vanity, and a bathtub with shower. Enjoy indoor-outdoor living with a screened lanai, fenced backyard, patio, and garden area. A 1-car garage with garage door opener provides convenient parking and storage, with the washer and dryer included. Recent updates include air conditioning replaced in 2021, plumbing updated in 2022, a front exterior door replaced in 2022, and shingle and flat roof replacement completed in 2017. This low-maintenance home combines a functional layout, inviting outdoor spaces, and no flood zone noted. Schedule your showing today and see the opportunity this home offers.

3415 Clydesdale Dr Unit unit 5, Holiday
$459,900
4 Beds ⋅ 3 Baths ⋅ Forest Hills SubDv.
Welcome to true waterfront living in this beautifully remodeled 4-bedroom, 3-bath home with direct Gulf access, incredible privacy, and upgrades throughout. Located along a scenic bend of the river, the backyard overlooks a private island preserve, so there are no rear neighbors—just peaceful water views and frequent visits from dolphins, manatees, and local wildlife. The home has remained high and dry during recent storms, offering added peace of mind. Inside, the split floorplan includes two private en suites on opposite sides of the home, making it perfect for multigenerational living, guests, or anyone who wants extra privacy. The brand-new kitchen features updated appliances, a Moen motion-sensor faucet with WiFi controls, and a clean, modern design. Major improvements include a 2025 whole-home Halo water treatment system, Uponor PEX plumbing, propane tankless water heater, new doors and windows, added attic insulation, and a generator-ready electrical setup. Outside, enjoy the heated pool with new 2024 pump and heat pump, a gravity overflow drain, private dock, and 10,000-pound boat lift with new stainless-steel cables. Additional features include an EV charging outlet, commercial-grade garage door opener, rebuilt garage door, WiFi-controlled sprinkler system supplied by a private well, ADT security system, Ring doorbell, garage camera, 2018 roof, and 2018 HVAC system. This move-in-ready home combines modern updates, waterfront privacy, and the relaxed Florida lifestyle buyers are looking for. Schedule your private showing today!

1166 Chancellor Drive, Holiday
$84,900
1 Beds ⋅ 1 Baths ⋅ Buena Vista 2nd Add SubDv.
**MOBILE HOME OPPORTUNITY!** Enjoy affordable mobile home living on your own land! This 1-bedroom, 1-bath property features a newer roof and wall-unit air conditioning. A concrete block living room is attached to the mobile home, and you can step up into the kitchen and dining area with updated cabinets. Down the hall, you’ll find the bedroom with brand-new carpet and a full bathroom. Out the back door, there’s a block utility building with washer/dryer hookups and a small, low-maintenance backyard. The newer front door opens to a covered front porch with a privacy fence, and the 41-foot driveway provides plenty of parking under the covered carport for all your vehicles. Located in Zone X, it’s not in a flood zone and is conveniently close to shopping and restaurants!

1908 Shady Cove Drive, Holiday
$114,900
1 Beds ⋅ 1 Baths ⋅ Tahitian Gardens Condo SubDv.
Enjoy one of the most picturesque waterfront settings in the privately gated community of Tahitian Gardens! This beautifully maintained condominium sits directly on the lake overlooking the community fountain, offering peaceful water views from the comfort of your own home. A mature shade tree creates a relaxing outdoor setting, while the nearby cul-de-sac parking adds everyday convenience that few units enjoy. Inside, you'll find luxury vinyl flooring throughout, an updated bathroom with a new vanity, and updated fixtures throughout the home. Major improvements include a new A/C system (2024) and new water heater (2025), providing peace of mind for years to come. Expansive windows showcase the tranquil lake and fountain, filling the living space with natural light and beautiful views. Located within the 55+ Tahitian Gardens community, residents enjoy a clubhouse, community pool, beautifully maintained grounds, scenic walking paths, and a convenient location just minutes from shopping, dining, medical facilities, parks, beaches, and the Gulf Coast.

4318 Tahitian Gardens Circle Unit F, Holiday
$280,000
3 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.
Welcome home to this wonderfully maintained, move-in ready 3-bedroom, 1.5-bath home with a 1-car garage, offering 1,148 square feet of comfortable living space. Built in 1968 and located in Flood Zone X, this home is in a low-risk flood area where flood insurance is typically not required by lenders. Major improvements include a new roof (2022), paid-off solar panels, new windows (2023), a newer A/C system (2021), and fresh interior and exterior paint (2026). Inside, you'll find durable laminate flooring throughout and a well-equipped kitchen featuring an electric range, refrigerator, dishwasher, microwave, and a one-year-old front-loading washer and dryer—all included. Situated in Holiday, FL, this property comes with the added benefit of no HOA and no CDD fees, giving you more freedom and fewer monthly expenses. Conveniently located near beautiful Gulf beaches, parks, shopping, restaurants, and everyday amenities, this home offers the perfect combination of comfort, value, and location. Whether you're a first-time homebuyer, downsizing, or looking for an investment opportunity, this is one you won't want to miss!

3622 Winder Drive, Holiday
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