Holiday Real Estate

Holiday Real Estate

Welcome to Holiday, Florida – a hidden gem nestled in the heart of Pasco County! This charming community offers a unique blend of suburban tranquility and vibrant coastal living, making it an ideal destination for families, retirees, and everyone in between.

Holiday is perfectly situated along the Gulf Coast, just a stone's throw away from beautiful sandy beaches and picturesque waterfront parks. Residents and visitors alike can enjoy the stunning sunsets over the Gulf of Mexico, making every evening a picturesque experience. With its warm climate, outdoor enthusiasts can indulge in a variety of activities year-round, from fishing and boating to hiking and biking along the scenic trails.

The city boasts a rich tapestry of amenities, including local shops, restaurants, and recreational facilities. The nearby Gulf View Square Mall offers a fantastic shopping experience, while local eateries serve up delicious cuisine that reflects the diverse culture of the area. For those who appreciate nature, the nearby Anclote River Park and Jay B. Starkey Wilderness Park offer lush landscapes and abundant wildlife, perfect for a weekend escape.

Education is a priority in Holiday, with access to quality schools and community programs that foster growth and development for all ages. The friendly atmosphere and strong sense of community make Holiday a welcoming place to call home.

Whether you’re seeking a serene retirement haven or a lively family-friendly neighborhood, Holiday, Florida, has something for everyone. Discover the charm of this delightful city and find your perfect home in this beautiful slice of paradise!

Newest Listings in Holiday

$220,000
2 Beds ⋅ 1 Baths ⋅ TB8550815 MLS
Move in and add your personality to this solid block 2 bedroom Holiday home west of US 19. Situated mid block on a quiet street close to everything a new homeowner needs. This home has been well maintained and features 2 generous bedrooms, one full bath, large family room, kitchen and dining room combo, and a flex room that can be utilized as office space, media room or possibly a guest bedroom. The home also features a 1 car garage with laundry area and fenced back yard. Conveniently located close to major highways 19 and 54, outdoor recreation, night life, shopping, restaurants and a short drive to world class beaches.

3415 Monticello Street, Holiday
$265,000
3 Beds ⋅ 2 Baths ⋅ TB8552102 MLS
Short Sale. COMING SOON! MOVE IN READY 3/2/1 PLUS BONUS ROOM HOME IN HOLIDAY on a MASSIVE LOT! CALL FOR MORE DETAILS

5404 Front Drive, Holiday
$399,000
3 Beds ⋅ 2 Baths ⋅ TB8551484 MLS
Welcome to this Amazing Waterfront 3-bedroom, 2-bathroom residence, complete with a versatile bonus room! This home features an oversized two-car garage and a wealth of exceptional upgrades. Step inside to find new tile flooring throughout the entryway, kitchen, bonus room, and recent remodeled guest bath. Enjoy the elegance of crown molding and ample closet space, including his and her walk-in closets in the Primary suite. The remodeled baths boast luxurious finishes, with a heated whirlpool tub in the master bath for your relaxation. Safety and convenience are paramount, with hurricane-proof replacement windows and a new garage door. Outdoor living is at its finest with a boat lift, floating dock, and davits, perfect for boating enthusiasts. Dive into your large in-ground pool while enjoying breathtaking views of the Anclote River and the vibrant local wildlife, all set against the backdrop of a wide canal and a high seawall. This home is a true gem for anyone seeking a waterfront lifestyle. Don't miss your chance to make it yours! CALL TODAY FOR YOUR PRIVATE TOUR...

1117 Rushmore Drive, Holiday
$229,900
2 Beds ⋅ 2 Baths ⋅ TB8550934 MLS
Welcome home to this beautifully updated 2-bedroom, 2-bath home in Tahitian Homes with NO HOA! An inviting covered front porch opens to a bright interior featuring wood-look tile flooring, contemporary lighting, and a flowing layout for comfortable living and entertaining. The kitchen showcases crisp white cabinetry, stone countertops, a tile backsplash, and stainless steel appliances. Generously sized bedrooms and tastefully updated bathrooms complete the home’s welcoming feel. Step outside to a spacious backyard with a fenced area and room for outdoor dining, gardening, or simply enjoying the Florida sunshine. Conveniently located near shopping, dining, and US-19, this home also puts coastal recreation within easy reach. Enjoy boating at Anclote River Park, explore the shops and waterfront restaurants at Tarpon Springs’ historic Sponge Docks, or unwind on the beach at Fred Howard Park. Schedule your private showing and discover everything this home has to offer!

4149 Darlington Road, Holiday
$269,900
3 Beds ⋅ 2 Baths ⋅ TB8550921 MLS
Just minutes from Tarpon Springs, the Sponge Docks, Fred Howard Park, Gulf beaches, shopping, dining, and everyday conveniences, this updated 3-bedroom, 2-bath Holiday home offers an easygoing lifestyle. Major improvements include a roof in 2016; A/C system in 2019; electrical inspection and upgrades in 2021, including outlets and GFCI protection, plus a newer electrical main panel; septic system improvements in 2022; and a water heater and well-water tank in 2023. Additional updates include a refreshed kitchen and bathrooms, granite countertops, updated appliances, luxury vinyl and tile flooring, blinds, lighting, interior and exterior paint, fencing, gates, and front and rear outdoor living areas. 1,102 heated square feet, the home also features an attached one-car garage, additional carport parking, a private well, a septic system, a fenced yard, and a storage shed. An extra-wide gate on the north side provides convenient access for storing a boat, trailer, or other recreational equipment, a great feature for enjoying the Florida Gulf Coast lifestyle. Nearby public schools include Sunray Elementary, approximately 1.4 miles; Paul R. Smith K-8, approximately 2.2 miles; and Anclote High School, approximately 2.5 miles. School zone enrollment eligibility should be independently verified. Located in Flood Zone X, this home combines practical improvements, useful outdoor space, and convenient access to beaches, boating, parks, and some of the area's most popular Gulf Coast destinations.

1408 Jennings Drive, Holiday
$298,900
3 Beds ⋅ 3 Baths ⋅ TB8551707 MLS
Virtually Staged. IN-LAW suite! Meticulously renovated 3-bedroom, 3-bathroom move-in ready and ready! This stunning home features countless upgrades, including a new HVAC system, smart STAINLESS steel appliances, new kitchen cabinets, sparkling white MARBLE countertops, a smart stainless steel washer and dryer, oversized 24” x 48” TILE flooring, 5-inch baseboards, new doors and trim, newer windows, a newer electrical panel, and fresh interior and exterior paint. Enjoy the bright, open floor plan that seamlessly connects the living and dining areas, enhanced by modern fixtures and recessed lighting throughout. All three bathrooms have been beautifully updated with designer tile and high-end finishes. The spacious primary suite features a walk-in closet, a private en-suite bathroom, and direct access to the backyard. The private mother-in-law suite includes a brand-new mini-split A/C system, a kitchenette with a full-size refrigerator, cooktop, microwave, and sink, a separate entrance, and a full bathroom - making it ideal for guests, extended family, or potential rental income. Outside, you’ll find a brand-new vinyl privacy fence, fresh sod, and decorative landscaping, creating the perfect outdoor space to enjoy. Located in a prime area near the world-famous Tarpon Springs Sponge Docks, the historic Greek community, beautiful Gulf beaches, shopping, dining, and all that the Tampa Bay area has to offer, this truly turnkey home is a rare opportunity you won’t want to miss! One or more photo(s) was virtually staged.

3215 Kilburn Road, Holiday
$225,000
2 Beds ⋅ 2 Baths ⋅ TB8551580 MLS
Fresh updates, a generous corner lot, and an unbeatable price tag make this Holiday Lake Estates home an opportunity too hard to ignore! This 2-bedroom, 1.5-bath home welcomes you with a recently renovated interior featuring LVP Flooring, natural light, and a modern kitchen with white shaker cabinetry, tile backsplash, and stainless steel appliances (2024). French doors open to the screened back patio, creating an inviting spot for indorr/ outdoor living. The large corner lot offers space to garden, entertain, and enjoy the outdoors, while a one-car garage adds practical parking and storage. Beyond your doorstep, explore nearby Key Vista Nature Park, launch a boat or kayak at Anclote River Park, or head to the Tarpon Springs Sponge Docks for waterfront shops and Greek dining. Convenient access to US-19 keeps everyday shopping and restaurants within reach. With an updated interior, usable outdoor space, and an accessible price point, 2055 Norfolk Drive brings together the features that make owning a home feel within reach. Schedule your showing and see how much this home has to offer!

2055 Norfolk Drive, Holiday
$1,299,999
4 Beds ⋅ 4 Baths ⋅ W7889727 MLS
Welcome to your dream waterfront estate in the sought-after Baileys Bluff community! This stunning custom mini mansion is perched high and dry with no HOA, offering unparalleled privacy and luxury. Enjoy direct Gulf access with a new dock equipped with electric and water, a seawall, and a serene backyard oasis featuring a lagoon-style saltwater pool, spa, waterfall, expansive Belgard paver deck, outdoor shower, travertine rear porch, and cedar trellis dining area—all with no rear neighbors. Step inside to soaring 10-14 foot ceilings, nine sets of French doors, and rare Santos Mahogany floors that exude timeless elegance. The chef’s kitchen is a masterpiece with granite counters, custom cabinetry, a large island, and a high counter perfect for entertaining. The first-floor primary suite is a true retreat with dual walk-in closets, private pool access, and an opulent spa bath with whirlpool tub and dual shower. Upstairs features a full secondary residence with three bedrooms, two baths, a massive living area, balcony with stunning sunset views, and a second laundry. The home also includes three spacious porches, a four-car garage with 14-foot ceilings, a six-inch slab, lift potential, and abundant workshop space. Luxury upgrades include impact windows, full hurricane strapping, exterior insulation, three new AC systems (2024), and a new tankless water heater. Baileys Bluff offers a community boat ramp, clubhouse, and parks, with nearby Anclote boat launch, marinas, waterfront dining, and the world-famous Tarpon Springs Sponge Docks accessible via quiet neighborhood roads. This estate blends sophistication, comfort, and waterfront living in one spectacular package.

3143 Pineview Drive, Holiday
$249,900
3 Beds ⋅ 1 Baths ⋅ TB8551298 MLS
LOCATION, UPDATES & FLEXIBILITY! Welcome to this beautifully updated and completely remodeled 3-bedroom, 1-bathroom home in a fantastic Holiday location with convenient access to Pinellas County and everything the Tampa Bay area has to offer! Step inside to find a fresh, move-in-ready interior featuring brand-new laminate flooring installed throughout the home. The fully updated galley-style kitchen is equipped with modern stainless-steel appliances, creating a functional and inviting space for everyday living and entertaining. The home offers three bedrooms, with the third bedroom created from a portion of the garage. For buyers who prefer additional garage space, this area can easily be converted back, providing valuable flexibility to suit your needs. Additional highlights include a newer roof, newer A/C, interior laundry room, spacious backyard, and ample driveway parking. The large backyard provides plenty of room for entertaining, gardening, pets, or simply relaxing and enjoying Florida’s beautiful weather. Conveniently located near parks, beaches, shopping, restaurants, medical facilities, and major conveniences, this home offers the perfect combination of comfort, updates, location, and versatility. Don’t miss this opportunity to make this move-in-ready Holiday home your own. Schedule your private showing today!

1400 Jennings Drive, Holiday
$219,000
2 Beds ⋅ 1 Baths ⋅ W7889682 MLS
WELCOME HOME to this charming and MOVE-IN READY 2-bedroom, 1-bath home located on Beachwood Drive in Holiday, Florida! Tucked away on a NON-THROUGH STREET with limited traffic, this well-maintained home offers a comfortable, functional floor plan along with numerous updates throughout. Major improvements include a 2025 A/C, NEWER WINDOWS, a newer garage door and an updated water heater. Step inside to a bright and inviting interior featuring UPDATED FLOORING, fresh paint and large windows that bring in plenty of natural light. The traditional layout provides defined KITCHEN, DINING and FAMILY ROOM spaces, creating an easy flow for everyday living. Both bedrooms offer generous windows, while the UPDATED BATHROOM features newer tile and an updated vanity. The kitchen has also been refreshed with UPDATED CABINETRY AND COUNTERTOPS, providing a clean and functional space for cooking and entertaining. Even the sliding glass door has been replaced and opens to the backyard, where you'll find a spacious outdoor area and BACK DECK perfect for relaxing, grilling or enjoying the Florida sunshine. A welcoming FRONT PORCH adds even more outdoor living space. With its updated mechanicals, newer windows, refreshed interior and convenient Holiday location, this 2-bedroom Florida home is ready for its next owner!

3811 Beechwood Drive, Holiday
$270,000
2 Beds ⋅ 2 Baths ⋅ TB8550647 MLS
Short Sale. Great Opportunity in Holiday, FL – Short Sale Property! This single-family home offers fantastic potential for investors, primary buyers, or anyone looking to customize a home to their liking. 2 Bedrooms & 1.5 Bathrooms, Comfortable lay-out with great functional space. A bright and spacious Florida room, perfect for relaxing, entertaining, or enjoying sunny days indoors. Versatile extra room that can easily serve as a home office, playroom, den, or guest area. Additional outdoor shed/storage building providing plenty of space for tools, equipment, or extra belongings. Features a charming exterior design with nice accent stone, a welcoming front porch, and plenty of yard space.

1918 Villa Rosa Drive, Holiday
$285,000
2 Beds ⋅ 2 Baths ⋅ TB8547590 MLS
Enjoy peaceful pond views and effortless Florida living in this beautifully updated, move-in-ready home in Holiday! From the stylish interior to the tranquil waterfront setting, this home offers an inviting place to relax, recharge, and feel right at home. The stunning kitchen features high-end cabinetry and elegant granite countertops, creating a beautiful space for everyday cooking and entertaining. Both bathrooms have been tastefully remodeled with contemporary vanities and stylish finishes. Thoughtful updates include a newer AC unit and ductwork, washer and dryer, gutters, garage door, and front entry door—adding comfort, convenience, and curb appeal. The true highlight awaits out back, where picturesque pond views provide a relaxing backdrop to your day. Enjoy your morning coffee by the water, cast a fishing line, or simply unwind while taking in the peaceful surroundings. This is the Florida lifestyle you’ve been looking for! Conveniently located just a short drive from Tarpon Springs, you can explore the historic Sponge Docks, enjoy delicious Greek dining, and discover charming local shops. Gulf Coast beaches and convenient airport access put recreation and travel within easy reach. Beautiful updates, a serene pondfront setting, and a convenient location—this home is ready for you to move in and start enjoying it all. Schedule your private showing today!

3532 Overland Drive, Holiday
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