Holiday Homes For Sale & Real Estate - 306 homes

Remarks: Do not hesitate on this meticulously maintained, one-owner villa in the Gulfwinds community. This exceptional corner-lot property is situated on a beautifully landscaped open space overlooking a pond, offering both privacy and scenic views. As one of the larger units available, the home features three bedrooms, two full bathrooms, and a dedicated den or office space complete with French doors and a decorative transom window. The interior is highlighted by high ceilings and porcelain plank tile flooring throughout. The kitchen is equipped with stainless steel appliances and quartz countertops, opening directly into a spacious great room. The split-bedroom layout ensures privacy for the owner’s suite, which includes dual vanities with updated granite tops, a garden tub, and a walk-in closet. Additional features of the home include a covered rear lanai, a brick paver patio, a separate laundry room with a washer and dryer, a generator, and a garage ceiling storage rack. The Gulfwinds community is an all-ages, pet-friendly neighborhood located in a no-flood zone. The monthly HOA provides significant value by covering lawn care, exterior maintenance (including the roof), internet, cable. Residents also enjoy access to a resort-style pool and recreation area, as well as lighted sidewalks and a bike trail connected to the Pinellas Trail. The location is conveniently situated just ten minutes from the Sponge Docks, local marinas, parks, and top-rated schools. Whether you are looking for a primary residence, a seasonal retreat, or an investment opportunity, this villa offers an incredible combination of luxury and convenience.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Jim Maiorano (727-580-5199)

Remarks: Wow—this stunning home truly has it all! Featuring 5 spacious bedrooms, 3 full baths, and an oversized 3-car garage, this beautifully maintained 3072 Sq. Ft. property is nestled on a cul-de-sac setting in the highly desirable Key Vista community. From the moment you step inside, you’re welcomed by bright, freshly painted interiors and soaring vaulted ceilings in the foyer. The open-concept layout flows effortlessly into the living room and kitchen, all overlooking your private pool—perfect for relaxing or entertaining. This home is truly turnkey and move-in ready. The outdoor living area is perfect for relaxing poolside; the expansive, fenced backyard and landscaping make this feel like your own private retreat. Whether your enjoying your morning coffee or a glass of wine at sunset, you'll love living the Florida lifestyle in this well-located home! Enjoy resort-style living with Key Vista’s exceptional amenities, including a beautiful clubhouse, large heated pool, fully equipped fitness center, pickleball courts, and a playground. Ideally located just minutes from the scenic Anclote River Beach, Park, where you can fish off the pier, enjoy a peaceful picnic, or take in breathtaking Gulf Coast sunsets. This home is located in a non-flood zone and has never had any damage from hurricanes. Homes like this don’t come around often—schedule your private showing today before it’s gone!

Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)

Listing Agent: Judi Pobst (727-808-0808)

Remarks: Under contract-accepting backup offers. Charm and curb appeal abound for this Holiday home! Step inside 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. Enjoy your private, enclosed backyard all year long! Come and see for yourself the possibilities that this home has to offer!

Listing is courtesy of: EVERYSTATE INC. (501-725-1234)

Listing Agent: Blake Keathley (661-900-9145)

Remarks: One or more photo(s) has been virtually staged. Affordable, updated, and ready for you! This move-in ready 3-bedroom, 2-bath home in Holiday, FL is a great opportunity for first-time homebuyers or investors. The home has been remediated following previous flood damage and renovated with numerous upgrades, including a new roof, new appliances, upgraded electrical panel, updated plumbing fixtures, new insulation, fresh drywall, and interior paint. Mold remediation was completed prior to renovation. Inside, the open-concept layout and ceramic tile flooring throughout create a clean, low-maintenance living space. Additional features include a one-car garage and a fully fenced backyard, perfect for relaxing, entertaining, or pets. Located just minutes from shopping, dining, parks, and beautiful Gulf Coast beaches, this home offers both convenience and value. Don’t miss this opportunity, make your appointment today!

Listing is courtesy of: ELLIOTT COASTAL REALTY LLC (727-576-4663)

Listing Agent: Linda Elliott (727-455-6743)

Remarks: Welcome to this Beautifully maintained 2 bedroom, 2 bathroom Single Family Home. This home is Move-In Ready! The home offers comfort, style, and space. Located in a very nice neighborhood, this property is clean, fully furnished, and ready for you to move in! Key Features: Beautiful bamboo floors throughout, Spacious Finished Florida Room. Relax and unwind in this bright and inviting space that adds extra living area for your enjoyment. Large kitchen and newer appliances for the cook. The home features a 2 car attached garage, a pad to park your RV or boat, and a work shed with electricity. This one has too many features to list. Come and check it out! Move in with ease! All furnishings are included, making this a hassle-free transition. THIS IS NOT A FLOOD ZONE. No flood insurance required.

Listing is courtesy of: CENTURY 21 COASTAL ALLIANCE (727-771-8880)

Listing Agent: Tom Schirr (727-916-4294)

Remarks: Under contract-accepting backup offers. Welcome to your own private Florida retreat at 4612 Flora Avenue in Holiday! This beautifully maintained 2-bedroom, 1-bath home offers 1,036 square feet of thoughtfully designed living space — plus incredible bonus features that make this property truly stand out. Inside, you’ll find a bright living room, a spacious family room for added flexibility, a dedicated dining area, and a well-appointed kitchen complete with appliances. The additional family room creates the perfect space for a home office, playroom, or second entertainment area — a rare find in homes of this size. Step outside and the real magic begins. The backyard is designed for enjoying the Florida lifestyle year-round, featuring a sparkling 6-foot-deep in-ground pool with a cool deck and full screen enclosure (2023). Whether you’re hosting summer gatherings or relaxing after a long day, this private oasis delivers. The screened back patio with ceiling fan offers yet another comfortable outdoor living space overlooking the pool. The front and backyard are beautifully finished with low-maintenance artificial turf, creating a clean, polished look without the upkeep. The PVC vinyl fencing adds both privacy and durability. Major upgrades provide peace of mind, including a brand-new roof and new septic system. The driveway and sidewalk feature cool deck coating for a cohesive and updated exterior feel. And that’s not all — the property also includes a detached 1-bedroom, 1-bath dwelling in the backyard. Perfect for guests, extended family, rental income potential, a private office, or creative studio space. Opportunities like this don’t come around often. Complete with a one-car garage and move-in-ready condition, this home offers exceptional value with upgrades already done for you. Schedule your private showing today and experience everything this Florida gem has to provide!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Laurie Rivera Robles (813-766-3941)

Remarks: Very nicely updated 3 bed/2 bath doublewide with large indoor air-conditioned storage room (3rd bedroom option), shed, carport, and screened porch in Tiki Village, a gated 55+ community where you own the land. NON-FLOOD ZONE with low $520/year HOA. Updates include new roof and A/C (Sept 2024), spacious new kitchen with granite countertops and new appliances, remodeled bathrooms including a master bathroom with jetted tub, utility room, new vinyl flooring, new interior/exterior paint. Home shows very well. PRIDE. Tiki Village is owner/member managed and has made significant improvements, including reducing the annual fee from $520 to $400 a year.

Listing is courtesy of: FLORIDA REAL ESTATE PARTNERS (727-409-4663)

Listing Agent: Randal Jenkins (727-409-4663)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated pool home in Holiday Lake Estates! This 3-bedroom, 2-bath home features a bright, open layout with a fully renovated kitchen with shaker cabinets, quartz countertops and new stainless steel appliances, new. Enjoy remodeled bathrooms with a double vanity in the primary suite, new luxury vinyl plank flooring and baseboards throughout, and updated major systems including HVAC and water heater. Step outside to your private in-ground pool—perfect for relaxing or entertaining. The converted garage offers additional flexible living space for a home office or bonus room. Situated on a corner lot with no HOA. Come see this home today, you'll love what it has to offer!

Listing is courtesy of: LEERDAM PROPERTIES INC. (407-740-0993)

Listing Agent: Philip Shaw (407-312-7366)

Remarks: Florida living at its finest! Tiki Village Mobile Home Park is a 55+ Gated Community where you OWN your LAND! Tiki Village is tucked back in off US 19 to enjoy the peace and quiet, yet convenient close to shopping, restaurants, medical, nature parks, beaches and so much more! The Home is move in ready, fully furnished and tastefully decorated. This 2 bedroom 2 bath is open and spacious Brand-NEW water heater!. Carport is large enough for 2 vehicles with plenty of storage with a back yard sitting area perfect for morning coffee, entertaining in the evenings or relaxing in the Florida sunshine. Schedule your private showing today!

Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-466-0800)

Listing Agent: Jon Dant (727-504-6727)

Remarks: Your next chapter begins now! 3030 Shadow Oaks Drive is ready for you to make it uniquely yours. This 3-bedroom, 2.5-bath, two-story pool home sits on a corner lot with minimal traffic. You’ll enjoy 2,510 sq. ft. of living (3,799 sq. ft. total) with an oversized three-car garage, ideal for a workshop or extra storage. Inside, vaulted ceilings complement a living room with a fireplace and sliders leading to the screened-in pool and inground spa. The first-floor primary suite includes a walk-in closet and ensuite bath, while upstairs you’ll find two bedrooms, a full bath, and a large family room with newer carpeting (2025). Updates include HVAC (2025), tankless water heater (2025), kitchen appliances (2024), and fresh interior paint in the garage (2026), front tree trimmed (2026),). A clean 4-point inspection (April 2026) ensures peace of mind. With space, updates, and potential, this home is ready for your vision. See it for yourself!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-799-2227)

Listing Agent: Erin Gwillim (727-409-1089)

Remarks: Holiday.. where the living is easy! This Community is positioned between Tarpon Springs and Trinity. This beautifully maintained 2-bedroom, 2.5-bath end-unit townhome offers privacy, space, and modern comforts coastal design. This townhome offers a open-concept layout featuring high ceilings and abundant natural light. The kitchen is thoughtfully designed with solid surface, stainless steel appliances, and generous cabinetry. Upstairs, the spacious primary suite includes a walk-in closet and a private ensuite bath. The other bedroom provides flexibility for guests, remote work, etc. The washer and dryer are conveniently located upstairs. This end unit offers enhanced privacy with a fenced in backyard, The private patio is perfect for morning coffee or winding down after a beach day. A spacious one-car garage with extra storage adds convenience. Located in a pet-friendly community with low HOA fees, this townhome also offers quick access to US-19, shopping, dining, and some of Florida’s most beautiful Gulf Coast beaches.

Listing is courtesy of: SUNCOAST SIGNATURE PROPERTIES (727-537-0797)

Listing Agent: Mike Nakelski (727-537-0797)

Remarks: Lovely setting on a spring-fed lake. Enjoy the spectacular sunsets and cool evening breezes off the lake as you sit in the bug-free zone of your caged pool yard. This unique home is one of the largest in the neighborhood, at over 1500+ square feet. Excellent floorplan with split bedrooms and lots of living space laid out with a separate living room, dining room, and family room. A very possibilities for a third bedroom, This is a rare pool home that's also got a beautiful water view just beyond and also boasts a two-car garage. House has been completely remodeled, kitchen, 2 bathrooms ,new flooring throughout and updating as well as resurfacing of the pool, the roof was just replaced as well as the electrical panel newer This is on the water-side of 19 and just a short trip up the road to Gulf Harbors beach Club, Green key beach. or Robert K Rees Memorial Park. Many restaurants and stores on 19 within a short distance. Wonderful primary or secondary home in a quiet neighborhood. Just Painted inside and out!! New flooring !! MOVE IN READY!! CALL TODAY!!

Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)

Listing Agent: Octavia Cheveresan (727-403-8948)

Remarks: Welcome to this beautiful, well maintained, must-see home in Holiday Lake Estates! This open-concept layout features a split-bedroom floor plan, a formal living area, and a versatile bonus room perfect for a home office, playroom, or additional lounge space. Durable wood-grain ceramic plank tile flooring runs throughout the main living areas, providing a modern look that’s both stylish and easy to maintain. The beautifully updated kitchen (2020) features modern cabinetry, granite countertops, barstool seating — perfect for cooking and entertaining. Both the primary and guest bathrooms have been tastefully updated, while the spacious primary suite includes luxury vinyl plank flooring, walk in closet. Buyers will appreciate the peace of mind that comes with major updates already completed, including a Roof replaced (2017), AC system (2018), and hot water heater (2018), along with energy-efficient upgraded double pane windows throughout. Step outside to a fully fenced backyard with a large storage shed with electricity, ideal for a workshop, hobby space, or additional storage — a feature that’s hard to find at this price point. See the backyard Garden beds producing broccoli, lettuce, onion, zucchini, squash, green beans, peas, parsley, sage, peppermint, and basil convey with sale. With all the big-ticket items already taken care of, this home is truly turnkey and ready for its next owner to move right in. Homes in this area with these updates and features don’t last long — schedule your private showing today.

Listing is courtesy of: COLDWELL BANKER REALTY (813-286-6563)

Listing Agent: Skyler Warden (813-777-5047)

Remarks: Welcome to this Stunning Townhouse, Built in 2023, Offering 1,634 square feet of Heated Living Space. This Beautiful Home Features Three Bedrooms and Two and a Half Baths, along with a One-Car Garage. Downstairs, you'll find an Open-Concept layout with a Bright Living Room, Dining area,and Kitchen, all adorned with elegant Ceramic Tile and High Ceilings. The Kitchen Boasts Stainless Steel Appliances, Granite Countertops, a Ton of Cabinets for Storage and Plenty of Counter Space for Preparation of Meals. At the Back of the Home a Sliding Glass Door provides access to a Large Covered Porch and a Fenced Backyard ( A unique feature not always allowed in Townhouse Communities)—Perfect for Privacy and Relaxation. A Convenient Half Bath and Garage access round out the First Floor. Upstairs, the Home Continues to Impress with Three Spacious Bedrooms and a Abundance of Natural Light. Two Bedrooms sit on one side and share a Full Bath, along with a versatile Loft Area ideal for a Reading Nook, Home Office, or Play Area. The Owner’s Retreat is on the Opposite Side, Offering a Spacious Layout, a Large Walk-In Closet, and a Ensuite with Dual sinks and a Walk-in Shower. Plus, this Community is out of the Flood Zone, with easy access to U.S. Highway 19 to travel North/South and Highways 54/56 to head East making commutes to Tampa a breeze. Conveniently close to shopping and all amenities, This home also boasts a LOW HOA fee of $249 a month, with no CDD fees. The HOA covers grounds maintenance, the park, and the exterior of the townhouse. This home truly has it all!

Listing is courtesy of: RE/MAX REALTY UNLIMITED (813-684-0016)

Listing Agent: Christina Vallianos (813-785-4741)

Remarks: **NO HOA**NO FLOOD ZONE** This beautifully updated 2-bedroom, 1.5-bath home in Holiday, Florida offers modern comfort with thoughtful upgrades throughout. Step inside to find a bright, refreshed interior featuring updated finishes, a clean, contemporary feel, and a layout that makes the most of every square foot. The home includes two well-sized bedrooms and a full bathroom inside, plus the added convenience of a half bath located in the one-car garage—perfect for guests, outdoor projects, or keeping the main living space tidy. A standout feature of the home is the large sunroom in the back, offering the perfect space to relax, entertain, or enjoy Florida living year-round with plenty of natural light. Out back, you’ll find a spacious, fully usable backyard with plenty of room for entertaining, pets, gardening, or even adding a pool. Whether you're hosting gatherings or enjoying a quiet evening outdoors, the large yard adds even more appeal. With its move-in-ready condition, practical layout, and generous indoor and outdoor living spaces, this home is a great opportunity for comfortable Florida living. All furniture is negotiable.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Elise Weber (727-418-9776)

Remarks: OPPORTUNITY IN POPULAR 55+ TIKI VILLAGE FOR A HANDY MAN FIXER UPPER.3 TON A/C UNITE NEW IN 2021, 200 AMP SERVICE, ROOF OVER IN 2005. FLOOR HAS SOME SOFT SPOTS. GREAT ROOM CONCEPT WITH ENCLOSED PORCH ON THE SIDE. AND YOU OWN THE LAND IN AN X FLOOD ZONE. A MUST SEE IF YOU ARE IN NEED OF A SUMMER HOME OR PERMANENT. COME AND TAKE A LOOK TO SEE IF ITS SOMETHING THAT YOU CAN UDATE YOURSELF WHILE LIVING IN IT. LOCATION IS MINUTES AWAY FROM SHOPPING AND THE SPONGE DOCKS OF TARPON SPRINGS. THIS ONE IS WORTH A LOOK.

Listing is courtesy of: CHARLES P CARTER (727-389-3418)

Listing Agent: Charles Carter (727-389-3418)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. NO HOA | NO FLOODING IN 2024 STORMS | Move-In Ready | Fully Renovated Welcome home to this beautifully updated 3-bedroom, 2-bathroom, 1-car garage residence located in Holiday, Florida—ideal for buyers seeking a low-maintenance, move-in ready home with no HOA restrictions. This property has been extensively renovated and features a NEW roof, NEW HVAC system, NEW tankless water heater, NEW hurricane-impact windows, and a NEW hurricane-rated garage door. The home has also been completely re-wired with a brand-new electrical panel, offering modern efficiency and long-term reliability. Inside, enjoy a fully remodeled kitchen and bathrooms, luxury vinyl plank flooring throughout, and fresh interior and exterior paint. The kitchen is equipped with brand-new stainless steel appliances, soft-close cabinetry, and quartz countertops, perfect for both everyday living and entertaining. Conveniently located just minutes from US-19, this home offers quick access to shopping, dining, and daily conveniences. The property did NOT flood during the 2024 storms, providing added peace of mind for today’s buyers. One or more photos have been virtually staged. Schedule your private showing today—this home is truly turn-key!

Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)

Listing Agent: Troy Hunter (812-205-0797)

Remarks: Under contract-accepting backup offers. $20,000 price reduction. All ages welcome. Own your own land. Low HOA (includes clubhouse/trash x2/Street lights) - Low Taxes! Mobile home (with exterior concrete wall(s) is 20'25" x 48'50". Live and play on every part of this fenced property with a palm tree, banana tree and a mature landscape. This unfurnished 2/2 with a carport has been improved with a resealed metal roof and recently painted. Septic tank has recently been pumped. Walk through the new security gated screen door on the front porch into the living room with slider doors. Enjoy a clean look with all new window blinds throughout the home. Home has been pest control treated. Enjoy a bright kitchen (no refrigerator/stove. Seller will give a concession of $1,000.00 toward a refrigerator and stove.) overlooks the front yard and a large dining area with a fan / light kit, mirror and shelf on the wall. The living room has 2 built-in bookshelves to hold your prized possessions. One bedroom has a closet and built-in dresser while the other large enormous GREAT room or 2nd bedroom has a concrete wall and exterior door into the back fenced yard. One bathroom has a double sink and shower tub. Enjoy an inside laundry room with washer/dryer hook-up, shower (needs hardware) toilet and small workbench with power. Make memorable memories under the carport's enormous sitting area. Next to the carport is a concrete building bearing shelves, electricity and workbenches. The back yard is secured by 2 side fences and a raised vegetable garden. Enjoy shopping, restaurants, Gulf of America, Suncoast Parkway, nearby MacDill AFB, hospitals, new VA Outpatient hospital, forthcoming H. Lee Moffitt Cancer Center and Research Institute will have a world-class expansion campus in Pasco County within a few years, beaches, and MORE at your fingertips! Tampa and St Pete Clearwater Airports are 30+ minutes away! Play anywhere in central Florida! Our playground awaits you !!

Listing is courtesy of: BILTMORE GROUP INC (727-559-2008)

Listing Agent: Shelly Hayden Mansfield (727-559-2008)

Remarks: HIGHLY Desirable & GATED, Tahitian Gardens 55+ Community, located right along US-19. Move-in ready, FIRST FLOOR CONDO!! Nobody above you or below you!! Competitive and LOW Monthly Fees!! 2 bed, 1 bath with 825 square feet of living space. Roof 2017. Water Heater 2023. Enjoy a seamless move-in experience—this CONDO can be offered with furnishings. Welcome to Tahitian Gardens, a well-kept gated 55+ community designed for easy living, convenience, and a vibrant social atmosphere. The HOA takes care of exterior maintenance, allowing for a low-maintenance, carefree Florida lifestyle. Conveniently located just minutes from Gulf beaches, the Tarpon Springs Sponge Docks, shopping, dining, and public transit, this condo offers exceptional access to everything in this area. Nice front patio—perfect for enjoying your morning coffee or connecting with neighbors. Residents of Tahitian Gardens enjoy a welcoming, walkable environment with a variety of amenities, including a heated pool, shuffleboard courts, billiards, a clubhouse with kitchen and gathering spaces, and scenic walking paths around a tranquil lake with a fountain. A full calendar of activities—like bingo, card games, crafts, and biking—ensures there’s always something to enjoy.

Listing is courtesy of: RE/MAX MARKETING SPECIALISTS (352-686-0540)

Listing Agent: Jarid Weddle (540-613-0744)

Remarks: Under contract-accepting backup offers. CHECK OUT THIS HOME WHERE YOU OWN YOUR OWN LAND WITH LOW MAINTAINMENT FEE ON $200.00 PER YEAR THIS HOME HAS BEEN IMMACULATELY MAINTAINED. BOTH BATHROOMS COMPLETELY REMODELED, KITCHEN REMODELED WITH LOADS OF STORAGE. NOT ONLY IN KITCHEN BUT THROUGHOUT THE HOME. HOME WAS BUILT TO HUD, AND FEMA STANDARD. INSIDE LAUNDRY, NEWER FLOORING. NEW METAL ROOF REPLACED IN 3/2025. THIS IS A LOT OF HOME FOR THE PRICE, AND IT'S READY FOR YOU TO MOVE IN. REALY MUST SEE TO APPRECIATE ALL THE GREAT FEATURES. Measurements are approx. Sold As Is. You Own your land. Golf carts allowed. Buyer to verify all information that is deemed to be accurate.

Listing is courtesy of: CITY BREEZE ACTION REALTY (727-372-9000)

Listing Agent: Stella Wooster (727-247-2790)