Explore Homes for Sale in Holiday, FL

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

2 Beds ⋅ 2 Baths ⋅ Eastwood Acres SubDv.

Virtually Staged. This inviting one-story home features a functional layout with an attached 1-car garage and comfortable living spaces ready for your personal touches. Step outside to enjoy the fenced backyard, offering plenty of space for outdoor activities, relaxing, or entertaining. Schedule your showing today! One or more photos may have been virtually staged.

3319 Cantrell Street, Holiday

Beacon Square SubDv.

Rare opportunity to own a buildable infill lot in Holiday with no HOA or restrictions. This 60' x 85' vacant lot is zoned R4 and offers flexibility for a single-family home or investment property. Ideal for first-time buyers looking for an affordable housing option or investors seeking a strong rental opportunity with no rental restrictions. Calling all developers—this property falls below the 20% acquisition threshold. Prime location near US Hwy 19 and SR 54 with quick access to shopping, dining, grocery stores, Holiday Mall, parks, and everyday conveniences. Bring your vision—this is a flexible infill opportunity in an established Holiday neighborhood with no HOA, no rental restrictions, and plenty of potential.

3621 Annona Court, Holiday

Ibis Sub SubDv.

Build your Florida dream home in the exclusive gated community of Ibis, an intimate enclave of just 13 homesites with only a handful of custom residences currently built. This .29-acre homesite offers a wonderful sense of privacy with no rear neighbors, along with an easement area directly to the north that provides additional open space and gives the property an even more spacious feel. A beautiful mature oak tree adds natural character to the homesite and offers the opportunity to incorporate its shade and beauty into the design and landscaping of your new home. For buyers looking for inspiration or a head start on the building process, the seller also has plans for a custom home designed for the property and is willing to share them with an interested buyer. Enjoy a location that combines privacy with easy access to some of the area's best outdoor recreation. J. Ben Harrill Recreation Complex is just down the road, offering indoor pickleball, tennis, soccer and baseball fields, a gymnasium and a variety of recreational programs. Nearby Key Vista Nature Park and the Anclote Coastal Trail offer opportunities for walking, biking and enjoying nature, while Anclote Gulf Park and Anclote River Park provide convenient access to public boat ramps, waterfront recreation and the Gulf. Both Downtown New Port Richey and historic Tarpon Springs are approximately 15 minutes away, putting waterfront dining, local shops, festivals, the famous Sponge Docks and more within easy reach. With no rear neighbors, additional open space to the north and very few homesites remaining, this property offers a unique opportunity to design and build a custom home in a private gated setting close to everything that makes Florida's Gulf Coast lifestyle so appealing.

3034 Sheppards Crook, Holiday

3 Beds ⋅ 2 Baths ⋅ Orangewood Village SubDv.

Beautifully updated throughout, this 3-bedroom, 2-bathroom home with a 1-car garage offers a bright, well-designed layout and low-maintenance living. Step inside to an open living area that flows seamlessly into the updated kitchen, featuring updated cabinetry, elegant granite countertops and backsplash, stainless-steel appliances, and abundant natural light. Durable wood-look tile flooring extends throughout the home, complemented by updated interior and exterior doors, including the overhead garage door and opener. Energy-efficient double-pane windows, modern textured walls and ceilings, and updated lighting and plumbing fixtures further enhance the home's comfort and appeal. The spacious primary bedroom features a private en-suite bathroom that has been completely updated, along with two generous closets. Two additional bedrooms and a fully updated guest bathroom provide comfortable accommodations for family or guests. A new roof, heating and cooling system, and water heater were installed in 2021. The covered, screened porch overlooks the fenced backyard, creating a private outdoor living space ideal for relaxing or entertaining. Conveniently located near public schools and just a short drive to Gulf beaches, shopping, dining, and other amenities. No HOA fees and no flood insurance required.

2332 Chancery Drive, Holiday

2 Beds ⋅ 2 Baths ⋅ La Villa Gardens SubDv.

Welcome to this beautifully updated 2-bedroom, 1.5-bath home offering extensive upgrades, energy efficiency, and exceptional outdoor living! Major improvements include a NEW ROOF, NEW HURRICANE-GRADE IMPACT WINDOWS with larger windows for abundant natural light, NEW HVAC/AC, NEW GUTTERS, and underground power lines. The impact windows also feature transferable lifetime warranties for added peace of mind. Inside, enjoy fresh paint throughout, a remodeled kitchen and bathroom, new carpet, updated interior door hardware, and new cabinet pulls. The oversized one-car garage features a freshly painted floor. Step outside to a freshly painted exterior, new landscaping, mature trees, a NEW DECK, and a new sliding glass door that seamlessly connects the living space to the backyard. The fully fenced yard also includes a storage shed and an irrigation system supplied by its own well. Additional highlights include NO HOA, NOT IN A FLOOD ZONE, and excellent insulation that helps keep the home remarkably quiet—even during storms and high winds. This home is also impressively energy-efficient, with the AC maintained between 68°–70°F and average summer electric bills of approximately $220. Move-in ready and thoughtfully upgraded throughout, this home is a must-see!

3420 Paloma Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ La Villa Gardens SubDv.

Charm and curb appeal abound for this Holiday home! Step inside the inviting foyer and into the well-appointed living room, positioned at the front of the home. Through the dining room you'll find the kitchen, which boasts stainless steel appliances, hard surface countertops, and ample storage. This split, ranch style floorplan is rounded out by the primary suite and two secondary bedrooms. Come and see for yourself the possibilities that this home has to offer!

5600 Andrea Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.

MOVE-IN READY! Welcome home to this charming 3-bedroom, 2-bathroom home featuring a desirable split-bedroom floor plan and spacious living areas. The large living room flows into the dining area, while the family room is open to both the dining room and kitchen, creating a great layout for everyday living and entertaining. Tile flooring runs throughout the home. The fenced backyard offers privacy and relaxation with a cute gazebo and no rear neighbors. An optional Civic Association offers access to a community pool. Enjoy an abundance of nearby recreational opportunities, including Anclote River Beach Park with boat ramp and fishing pier, Key Vista Nature Park, Eagle Point Park with playground and kayak trail, and Green Key Beach on the Gulf. Come enjoy your own piece of Paradise!

3431 Overland Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.

Virtually Staged. TROPICAL POOL & POND PARADISE HOME FEATURING A SPARKLING SWIMMING POOL, 3 BEDROOMS, 2 BATHROOMS AND A LARGE COVERED LANAI AND SCREEN-ENCLOSED POOL-DECK. NEW ROOF, NEW KITCHEN, NEW AC, NEW APPLIANCES, QUARTZ COUNTERSTOPS, NEW LUXURY WATERPROOF VINYL PLANK FLOORS, new electrical panel, new pool pump and new cartridge filter! All new interior paint and fixtures. Beautiful curb appeal with a spacious driveway and covered front porch. 22 Ft long garage with side entrance door. Private backyard with pond access and beautiful wildlife views. Perfectly located near great shopping, restaurants, parks and beaches! Enjoy the fun in the sun that a tropical paradise pool home offers!

3349 Overland Drive, Holiday

2 Beds ⋅ 1 Baths ⋅ Tahitian Gardens Condo SubDv.

Florida Living at its Best in Tahitian Gardens Welcome to this light and bright two-bedroom, one bath condo located in Tahitian Gardens, a 55+ gated community. This inviting home features a comfortable layout filled with natural light and is an excellent opportunity for those looking for low-maintenance Florida living. Low HOA fees and an array of community amenities make enjoying your time here even easier. Residents of Tahitian Gardens can take an advantage of the heated community pool, shuffleboard courts, clubhouse, and a variety of community activities and social gatherings. Whether you’re relaxing poolside, enjoying a game of shuffleboard, or getting together with neighbors, there are plenty of ways to stay active and connected. The location is another wonderful highlight. You’ll be just minutes from shopping, restaurants, parks, and the beautiful beaches of Tarpon Springs, giving you easy access to all that the area has to offer. Tampa Internation Airport is also approximately an hour away, making travel and visiting family and friends convenient. If you’ve been dreaming of a peaceful Florida lifestyle in a welcoming community, this charming Tahitian Gardens condo is one you’ll want to see.

4340 Tahitian Gardens Circle Unit D, Holiday

2 Beds ⋅ 2 Baths ⋅ Holiday Lake Villas Condo SubDv.

Come see this well-maintained 2-bedroom, 2-bath villa-style condo in the desirable Holiday Lake Villas community. This single-story home offers 1,114 square feet of comfortable living space with a practical layout and a number of attractive updates. The kitchen, fully redone in 2025, features bright white cabinetry, granite countertops, stainless steel appliances, and a convenient breakfast area overlooking the front of the home. The spacious living and dining areas feature durable wood-look flooring and open naturally to the enclosed Florida room through large sliding glass doors, creating an additional space to relax, entertain, or enjoy the Florida weather year-round. The Florida room also offers extra INTERIOR storage space that not every home in this community has. This home features all new windows replaced in 2025 as well, for YEARS of peace of mind. Both bedrooms are comfortably sized and offer ample closet space, while the two full bathrooms provide convenience for residents and guests. An interior laundry closet includes a full-size Samsung washer and dryer, and the home also comes with an assigned covered carport space. Outside, the property features a landscaped front entry and a private rear patio area overlooking a grassy common area. Holiday Lake Villas offers a low-maintenance lifestyle with community amenities including a clubhouse, pool, and recreational facilities. Conveniently located in Holiday with easy access to shopping, dining, parks, beaches, and the Tarpon Springs area, this home offers an excellent opportunity for anyone looking for a comfortable Florida residence in an established community.

3828 Sailmaker Lane, Holiday

3 Beds ⋅ 2 Baths ⋅ Vista Lks/Baileys Bluff SubDv.

Welcome to this well-maintained three-bedroom, two-bathroom home in Holiday, offering a comfortable split floor plan, spacious backyard, and no rear neighbors. A welcoming foyer entry leads into the open-concept living, dining, and kitchen areas, creating an ideal space for everyday living and entertaining. The kitchen features granite countertops, stainless steel appliances, a walk-in pantry, and a center island with room for meal preparation and casual dining. Tile flooring flows throughout the main living areas, while ceiling fans are found throughout the home for added comfort. Sliding glass doors open to a covered patio overlooking the large backyard, providing plenty of room to relax, play, or enjoy the outdoors. The private primary suite includes an en-suite bathroom with a dual-sink vanity, glass-enclosed shower, and walk-in closet. Two additional bedrooms share a second full bathroom, and a dedicated laundry room adds convenience. Major updates include a 2016 roof, HVAC system, and water heater. Located near a community playground and park and close to a variety of dining options, this home offers a great combination of comfort, convenience, and outdoor space. Schedule your showing today!

3123 Mela Court, Holiday

2 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv.

Welcome to your slice of the Florida waterfront lifestyle. This 2-bedroom, 2-bathroom home sits directly on the Anclote River with deeded Gulf of Mexico access, a rare opportunity to own true boating water at an approachable price point, on a nice block of well-kept homes. Step into your own private oasis with a screened, in-ground pool overlooking the river, a private dock with new wood decking ready for your boat, a seawall in good condition, and a spacious backyard made for sunset views and morning coffee on the water, while new windows across the back of the home flood the living space with natural light and frame those river views beautifully. This home has been well cared for where it counts most, with a new roof (2025), HVAC (approx. 2 years), fencing (1 year old), and pool pump (1.5 years old) already updated, making this a true opportunity for an investor or a buyer ready to add cosmetic value through new flooring, kitchen, and bath finishes and build significant equity, whether renovating to sell, to rent, or to make it your own. Tucked in the Flotilla Dr riverfront enclave of Holiday, the home is minutes from Anclote River Park, with its boat ramp, kayak launch, and Gulf-access swimming, and just a short drive from the world-famous Tarpon Springs Sponge Docks, known for its historic Greek waterfront district, dolphin cruises, and waterfront dining, with boaters able to head straight out the Anclote River to Anclote Key Preserve State Park or nearby Fred Howard Park and Sunset Beach. Families will also appreciate the school zoning for Sunray Elementary, Paul R. Smith Middle School, and Anclote High School. Homes with true river frontage and Gulf access rarely come to market at this price point, so bring your contractor and your vision, and turn this riverfront gem into something spectacular!

1332 Flotilla Drive, Holiday

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