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

$123,500
2 Beds ⋅ 2 Baths ⋅ Dixie Grvs Estates SubDv.
Welcome to 1845 Dixie Lane! This move-in-ready home offers the perfect combination of modern updates and affordable living with NO HOA and NO lot rent. Recent improvements provide peace of mind, including a new roof (2024), new windows (2024), and beautiful new countertops (2024). The septic tank was professionally cleaned on June 15, 2026, making this home truly ready for its next owner. Whether you're a first-time homebuyer, downsizing, or looking for an investment opportunity, this property offers comfort, value, and the freedom of homeownership without additional monthly community fees. Conveniently located near shopping, dining, schools, and major roadways, this is a fantastic opportunity you won't want to miss. Schedule your private showing today!

1845 Dixie Lane, Holiday
$285,000
3 Beds ⋅ 2 Baths ⋅ La Villa Gardens SubDv.
Virtually Staged. Stunning Move-In Ready Home! Welcome to 5633 Andrea Dr — a beautifully updated gem in the heart of Holiday! This charming home features brand-new flooring and a fully remodeled master bathroom with modern finishes that create a true spa-like retreat. Enjoy an open, light-filled floor plan perfect for entertaining or relaxing with family. The kitchen offers ample cabinet space and flows effortlessly into the living and dining areas, brand new AC July 2026. Step outside to your spacious backyard, ideal for weekend barbecues or a quiet morning coffee. Conveniently located near shopping, dining, and the Gulf beaches — this home combines style, comfort, and location! ? Don’t miss your chance to own this newly refreshed beauty — schedule your private showing today!

5633 Andrea Drive, Holiday
$270,000
3 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.
Welcome Home!! From the moment you pull up to your new home, you’ll appreciate the inviting curb appeal and a driveway offering plenty of room for parking and everyday convenience. Lots of recent improvements & updates for this BEAUTIFUL home that include a Newer Re-Roof (2025), Newer HVAC System (2025), Newer Water Heater (2025), and Newer Stainless Steel Appliances. Step inside through the foyer, where you will discover an open and inviting layout perfect for everyday living and entertaining! The thoughtful split-bedroom layout provides the perfect balance of space and privacy. The primary suite is located on one side of the home and features a walk-in closet and private primary bathroom, while the additional two bedrooms and second bathroom are conveniently located on the opposite side of the home. A hallway walk-in closet provides further storage and benefit for the additional two bedrooms too! The spacious living room welcomes you with sliding glass doors leading to the enclosed Florida Room with A/C, creating the perfect space to relax, entertain, or enjoy Florida’s beautiful weather year-round. Step outside to the large fenced backyard offering endless possibilities for outdoor enjoyment. Plus, this home comes with NO HOA! Location is everything, and this home truly does deliver! Conveniently located near Anclote River Park with boat ramps and fishing piers, Anclote Gulf Dog Park, Key Vista Nature Park, the historic Tarpon Springs Sponge Docks, and Fred Howard Park Beach. It's also just a short drive or bike ride from the Pinellas Trail, offering miles of scenic biking, walking, and outdoor recreation. You'll also enjoy easy access to shopping, dining, medical facilities, churches, and major roadways, including US-19. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this very well-maintained home offers everything needed for enjoying the wonderful Florida lifestyle! Don’t miss your chance to make this beautiful home yours! This home could truly be everything you've been looking for!!

3543 Rockaway Drive, Holiday
$579,000
3 Beds ⋅ 4 Baths ⋅ Ibis Sub SubDv.
"Luxury Living in an Exclusive Gated Community" Experience coastal elegance in this custom-built executive residence, privately situated on a quiet cul-de-sac within an exclusive gated community. Offering 2,367 square feet of thoughtfully designed living space, this exceptional three-story home combines luxury, comfort, and functionality with partial Gulf views from multiple balconies. From the moment you arrive, the impressive stamped concrete driveway and striking architectural design create unforgettable curb appeal. Inside, you'll find soaring ceilings, custom 8-foot doors, elegant crown molding, engineered hardwood flooring, marble and travertine finishes, and an open-concept floor plan designed for both entertaining and everyday living. The gourmet kitchen is truly the heart of the home, featuring granite countertops, abundant custom cabinetry, a walk-in pantry, breakfast bar, and newer stainless-steel appliances—perfect for preparing meals while staying connected with family and guests. Escape to the luxurious owner's retreat occupying the entire upper level. This private sanctuary offers partial Gulf views, a spacious walk-in closet, and a spa-inspired ensuite featuring dual vanities, an oversized walk-in shower, and a relaxing whirlpool tub. Step outside and enjoy Florida living at its finest. Four travertine balconies provide multiple places to relax and enjoy the coastal breeze, while the beautiful in-ground pool and expansive paver patio create the perfect setting for entertaining family and friends. The oversized garage offers room for multiple vehicles, a workshop, abundant storage, and even includes a convenient full pool bath.Recent upgrades provide peace of mind and modern convenience, including: New roof (2021), Newer-zone HVAC system, Updated stainless-steel kitchen appliances Central vacuum system Premium flooring throughout. Ideally located enjoy indoor pickleball, weekly gymnasium schedule, summer camp, soccer fields, baseball, tennis and more at J. Ben Harrill Recreation Center is a short walk from your front gate. Just minutes from Anclote Gulf Park, public boat ramps, Gulf beaches, the Pinellas Trail, and the world-famous Tarpon Springs Sponge Docks, you'll also enjoy convenient access to shopping, dining, and endless waterfront recreation. Luxury, location, and lifestyle come together in one extraordinary home. Schedule your private showing today and discover why this exceptional property is one you won't want to miss.

3020 Sheppards Crook Court, Holiday
$239,900
2 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.
NEW PRICE + A RARE 3.625% ASSUMABLE FHA MORTGAGE OPPORTUNITY! Qualified buyers could have the opportunity to assume the existing FHA mortgage at 3.625%, offering a financing advantage that is increasingly difficult to find in today's market. Now offered at $239,900, this 2-bedroom, 2-bath home in the established Beacon Square community offers more space and flexibility than you might expect. The spacious bonus room provides exciting potential for a 3rd bedroom, home office, fitness room, hobby space, or even an expanded primary suite. The flexible layout allows you to reimagine the space to fit your lifestyle. Step outside to a private backyard with no rear neighbors, plus a screened lanai that's perfect for morning coffee, outdoor dining, or relaxing at the end of the day. Even better—NO HOA and the property is not located in a designated flood zone. Conveniently located near shopping, dining, parks, medical facilities, Gulf beaches, and the famous Tarpon Springs Sponge Docks, with easy access to US-19 and the surrounding Tampa Bay area. Whether you're purchasing your first home, downsizing, or just looking for an affordable Florida home with room to make it your own, 3920 Beacon Square Drive deserves another look. Schedule your private showing today!

3920 Beacon Square Drive, Holiday
$214,000
2 Beds ⋅ 1 Baths ⋅ Beacon Square SubDv.
Virtually Staged. Potential Zero-Down Financing Available! Qualified buyers may be eligible to purchase this home with up to 100% financing. Welcome to 4312 Beacon Square Drive — a bright, refreshed home with stylish updates and a backyard full of possibilities. Step inside to a semi-open layout featuring wide-plank wood-look flooring, crisp white walls, and great natural light throughout. The spacious living room flows easily into the dining area and updated kitchen, creating a comfortable setup for everyday living or entertaining. The kitchen offers white shaker-style cabinetry, stainless steel appliances, modern backsplash, updated fixtures, and a convenient breakfast bar for casual seating. This home features 2 bedrooms plus a bonus room that can function as a 3rd bedroom, office, guest space, hobby room, or playroom. The bathroom has been nicely updated with subway tile, a modern vanity, gold-tone fixtures, and a clean, timeless look. The screened lanai adds extra usable space and leads out to a private, tree-shaded backyard with plenty of room to relax, garden, play, or create your own outdoor retreat. Additional highlights include a 1-car garage, neutral design choices, and a layout that lives larger than expected. Conveniently located near shopping, dining, and major roadways, this home is a great opportunity for buyers looking for move-in ready style with room to make it their own. Clean, bright, flexible, and full of potential — this Holiday home is ready for its next chapter. **NO SELLER FINANCING!!!**

4312 Beacon Square Drive, Holiday
$189,000
2 Beds ⋅ 1 Baths ⋅ Buena Vista Lullaby Gardens Add SubDv.
Move-in ready and beautifully updated, this inviting home combines modern finishes, low HOA fees, and an outstanding location just minutes from Historic Tarpon Springs. The renovated kitchen features white shaker cabinetry, quartz countertops, a designer tile backsplash, a stainless steel refrigerator and microwave, updated lighting, and tile flooring throughout the main living areas. The updated bathroom includes a granite vanity, and ceiling fans are installed throughout the home for year-round comfort. One of the property's standout features is the side yard bordering a heavily wooded area, creating a peaceful natural backdrop and added privacy. The screened lanai provides the perfect space for relaxing or entertaining, while the adjacent bonus room offers flexible living space ideal for a home office, media room, fitness room, guest space, or playroom. A detached storage building provides ample room for tools, lawn equipment, bicycles, or a workshop. Excellent opportunity for homeowners, seasonal residents, or investors. The HOA fee is only $88.50 per quarter, covering trash collection and street lighting. According to the HOA, there are no breed restrictions, and lease agreements are simply submitted to the management office, which offers owner-friendly leasing policies. Conveniently located just off US Highway 19, you'll enjoy quick access to shopping, dining, grocery stores, banking, pharmacies, and healthcare, including HCA Florida Trinity Hospital, AdventHealth North Pinellas, and Morton Plant North Bay Hospital. Historic Downtown Tarpon Springs is approximately 4 minutes away, the famous Sponge Docks about 8 minutes, Sunset Beach approximately 10 minutes, Fred Howard Park and Beach about 12 minutes, Honeymoon Island State Park approximately 20 minutes, Clearwater Beach about 25 minutes, Downtown Tampa approximately 40 minutes, and Tampa International Airport approximately 45 minutes away. Enjoy boating, fishing, kayaking, paddleboarding, waterfront dining, festivals, and Florida's beautiful Gulf Coast beaches, all within easy reach.

1650 Bold Lane, Holiday
$234,900
3 Beds ⋅ 2 Baths ⋅ Aloha Gardens SubDv.
Welcome to this 3-bedroom, 2-bathroom home located in the Aloha Gardens neighborhood! The interior features a thoughtful layout designed for everyday comfort. The kitchen comes equipped with stainless steel appliances and durable countertops, providing a functional space for cooking and meal preparation. In the primary bedroom, you will find the added convenience of a large walk-in closet, offering ample storage space. Step outside to enjoy the privacy of a fully fenced-in backyard. Ideally located close to parks, beaches, restaurants, hospitals, and recreational facilities, this home combines comfort and functionality. Schedule your private showing today!

3609 Truman Drive, Holiday
$200,000
2 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv.
Virtually Staged. BACK on the Market- Buyer's financing fell through. Tucked into the established Forest Hills neighborhood, this 1969 block-built single-family home offers a smart opportunity in the heart of Holiday. Two bedrooms, two full baths, plus a half bath and an attached garage, with an enclosed Florida-style porch made for easy mornings. No flood-zone headaches here. Close to US-19, Gulf beaches, Tarpon Springs' Sponge Docks, and everyday shopping. Bring your vision and make it yours.

1248 Ermine Drive, Holiday
$259,900
2 Beds ⋅ 2 Baths ⋅ Holiday Gardens SubDv.
Welcome to this beautifully updated 2-bedroom, 2-bath home located in the desirable Holiday Gardens subdivision of Holiday, Florida. Thoughtfully renovated with quality finishes throughout, this move-in-ready home offers peace of mind with a new water heater (2020), brand-new roof (2025), new A/C system (2026), and fresh interior and exterior paint. Best of all, the property is not located in a flood zone, offering added value and potential savings on insurance. The stunning kitchen has been completely remodeled with custom shaker-style cabinetry featuring new plywood construction, dovetailed drawers, soft-close doors and drawers, elegant quartz countertops, and a full suite of stainless steel GE appliances. Throughout the home, you'll find high-quality commercial-grade luxury flooring with a durable 30-mil wear layer, providing both style and long-lasting performance. The spacious floor plan includes two comfortable bedrooms and two full bathrooms, with the second bathroom conveniently located inside the home—not in the garage. A bright Florida room provides additional living space and could easily be converted into a third bedroom, home office, hobby room, or flex space to fit your needs. Step outside to enjoy Florida living from the screened rear porch or relax on the inviting covered front porch. The oversized one-car garage offers plenty of room for parking, storage, or a workshop. The beautifully maintained yard is a gardener's paradise, featuring a mature fig tree, fragrant rosemary, lemongrass, roses, bird of paradise, and an array of colorful flowering plants that create a peaceful outdoor retreat. Conveniently located close to shopping, restaurants, parks, and public bus service, this home offers easy access to everything you need while nestled in an established neighborhood. Whether you're looking for a year-round residence, seasonal getaway, or investment opportunity, this beautifully updated Holiday Gardens home is truly move-in ready. Schedule your private showing today!

2109 Shannon Drive, Holiday
$178,000
2 Beds ⋅ 2 Baths ⋅ Pinewood Villas SubDv.
Virtually Staged. Back on the market—buyer financing fell through. Discover this charming and spacious 2-bedroom, 2 full-bathroom villa in a truly tranquil, amenity-rich, ALL-AGES community. With a remarkably LOW HOA fee of $50 per month, this property is ideal whether you’re seeking a permanent residence or a seasonal retreat, and could be the perfect STARTER HOME for those just starting their homeowner journey. On arrival appreciate the well maintained exterior, pleasing front patio, three parking spaces with one covered. You will also note that this villa is in one of the quietest parts of the community with no through traffic, and it is just steps away from the beautiful community pool, the clubhouse and the community mailboxes. Step inside to a bright, open floor plan with soaring vaulted ceilings and clerestory windows that bathe the home with natural light. The well maintained kitchen features, newer stainless steel appliances, a double sink and a breakfast bar. The inside laundry room, which includes washer and dryer also serves as a storage room or pantry. Enjoy outdoor living in the expansive screened-in lanai—one of the largest in the neighborhood and a sizeable back yard—which offer the perfect spaces to relax or entertain year round. This home also features a - NEWER WATER HEATER, recently re-done ROOF 2022 and a well maintained HVAC system for peace of mind. The super low HOA fee of only $50 covers enjoyment of the sparkling community pool, shuffleboard, horseshoes, grilling area, shaded picnic tables complete with gated entry and restroom facilities all just steps away. Don’t miss your chance to own this well situated villa—convenient to all kinds shopping and restaurants and ~10 minutes from the world-famous sponge docks in Tarpon Springs, several coastal parks, fishing piers and beaches

4320 Fern Glen St, Holiday
$210,000
3 Beds ⋅ 1 Baths ⋅ Crest Ridge Gardens SubDv.
Virtually Staged. Discover the possibilities in this charming Holiday home, offering a comfortable layout and plenty of potential to make it your own. Whether you’re a first-time homebuyer, investor, or looking to downsize, this property provides a great opportunity to add your personal style and create the perfect space. Enjoy the convenience of being just minutes from shopping, dining, parks, beaches, and major roadways, making everyday living and commuting a breeze. Don’t miss your chance to own a home in a well-established neighborhood with easy access to everything the Gulf Coast has to offer.

4922 Panorama Avenue, Holiday
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