Holiday Homes For Sale & Real Estate - 325 homes

Remarks: 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.

Listing is courtesy of: RE/MAX CHAMPIONS (727-807-7887)

Listing Agent: Jennifer Tobey, Pa (727-871-1064)

Remarks: WELCOME TO THE MOST UNIQUE PROPERTY IN PASCO COUNTY at 6345 Lost Trail, Holiday, FL. This AMAZING .76 acre property is a HIDDEN GEM with virtually untouched, PRIME WATERFRONT of about 880 feet of ANCLOTE RIVER. Get away from the hustle & bustle & come EXPLORE the properties offered for sale the first time in decades at LOST TRAIL. The pictures of this RIVER landscape do not do justice as this land is simply indescribable. Some of the countless TROPICAL plants include a pair of MAJESTIC royal palms, bromeliads, bamboo & banana. The 2-story block & wood frame home features 5 bedrooms, 2 bathrooms & a MASSIVE garage of 36'x24'. The 864 sqft garage can be easily converted to an in-law suite/separate apartment. The laundry hookups are in the garage & there is a back door exit. You'll LOVE the design of the etched front door & the A-frame covered front porch with wood deck landing. The kitchen, living room, dining room, primary bedroom & bathroom are all found on the 1st level. There is a utility closet & a hall closet with a water heater (manufacture date 4/2019) on the first level too. The second level features 4 SPACIOUS bedrooms each with a ceiling fan & a built-in closet. One of these bedrooms has glass sliders to a wooden deck/balcony overlooking the river. The full bathroom consists of a tub/shower combo & a linen closet with an additional coat closet in the loft/landing. The sweet seller used to host outdoor parties & guests would DIVE into the river as some areas of the river are 20-30ft deep! Manatees, otters, plentiful fish, deer, turkey & even a bobcat call this area home. The property features a wooden dock at the water, a BOAT LAUNCH (currently overgrown), rock steps to the river & a GIGANTIC concrete pad for parking of all your vehicles like cars, work trucks, boats, kayaks, jet skis, RV. Roof is 5/2004. The adjacent parcel of 50.5 acres to the north is owned by Copperspring CDD so it is going to stay as undeveloped land adding to the privacy of the LUCKY NEW OWNER. Are you a buyer with a vision for the potential of this GREAT OPPORTUNITY? This property lies on the Anclote River which meanders eventually to the Gulf of Mexico!! Combine it with adjacent 1-acre property at 6331 Lost Trail to expand your private residence. MAKE THIS YOUR FUTURE HOME!

Listing is courtesy of: FUTURE HOME REALTY (800-921-1330)

Listing Agent: Janina Wozniak (727-888-3889)

Remarks: Welcome to this brand new listing in Holiday!!! Large and spacious home offers big rooms with an open feeling kitchen, living room and den. Full Garage, fully fenced oversized lot located on cul de sac providing safer low traffic for young children and pets to play! Enjoy morning coffee on front porch and relaxing evenings on your back porch. The back and side yard is equipped with a swing set and a jungle gym for the little ones making it wonderful space for family fun! All hurricane shutters are included for added peace of mind. Conveniently located close to beaches, restaurants, shopping and hospitals. Priced very attractively and full potential - this is a fantastic home for years to come!!

Listing is courtesy of: F I GREY & SON RESIDENTIAL (727-495-2424)

Listing Agent: Grace Pineyro (727-608-9600)

Remarks: The opportunity you’ve been waiting for in Pasco County! This stunning, fully remodeled, turnkey residence seamlessly blends modern sophistication with everyday warmth. Step inside to a beautiful and bright layout designed for a fresh start. The heart of the home features a beautifully upgraded kitchen and main living areas adorned with premium contemporary finishes. Outside, your private oasis awaits: a spectacular backyard tailored for enjoying Florida’s enviable year-round climate, hosting weekend barbecues, and entertaining family and friends. Strategically located with fast access to major commuter routes, top-tier shopping, and entertainment. Don't miss this move-in-ready gem—schedule your showing today!

Listing is courtesy of: JPT REALTY LLC (813-325-4177)

Listing Agent: Yaima Diaz Moya (813-770-9847)

Remarks: Skip the projects, skip the surprises, and step into a home that already feels dialed-in. Built in 2023, this 3-bedroom townhome delivers that crisp, like-new vibe—without the builder waitlist or the premium price tag. The main level has an easy, open flow from the living area into a kitchen designed for real everyday use. This one upgrades the standard package with stainless steel appliances, a granite countertop, and a clean, neutral backsplash that ties everything together. Your enclosed patio sits just off the living room, giving you a private spot for morning coffee or unwinding after work, all without the upkeep of a yard. Upstairs, the layout keeps life simple and functional. The primary suite has its own private bath, while the two additional bedrooms flex perfectly for guests, a roommate, or a dedicated office. And with blonde laminate flooring throughout the second floor—no carpet anywhere—the space feels bright, modern, and easy to maintain. Laundry is right where it should be: upstairs near the bedrooms. Your monthly overhead stays low thanks to NO CDD fee, and the HOA covers exterior maintenance, high-speed internet, and cable. A 1-car garage and metal storm shutters check off the practical boxes. The location puts you in the sweet spot between convenience and coastal living. You’re minutes from grocery stores, retail, medical facilities, and US-19 for an easy commute. And when you want to get out and enjoy the area, you’re right near the Pinellas County line—close to the Tarpon Springs Sponge Docks, Anclote River Park, boat launches, waterfront dining, and scenic trails. Clean, modern, low-maintenance, and move-in ready—this is the kind of home that gives you your weekends back.

Listing is courtesy of: QUICKSILVER REAL ESTATE GROUP (813-288-0300)

Listing Agent: Erica Antonakos (813-455-0946)

Remarks: One or more photo(s) has been virtually staged. Forget the endless weekend honey-do lists and the hidden costs of an older home. Built in 2023, this 3-bedroom townhome gives you that clean, brand-new feel without the builder’s waitlist. The main floor is wide open, flowing from the living room right into a kitchen that actually has room to move. The owners upgraded the kitchen past the builder-grade standard by adding a custom tile backsplash that pairs with the neutral white quartz counters and breakfast bar. Just past the living area, you can step out onto your enclosed patio space—perfect for morning coffee or unwinding in the evening with the rare perk of having zero backyard neighbors directly behind you. Upstairs keeps life practical: the primary suite features its own private bath, while the other two bedrooms work perfectly for guests, roommates, or a dedicated home office. Plus, the laundry closet is upstairs right where the clothes actually are. Your monthly overhead is incredibly lean here. There is NO CDD fee, and the low HOA covers your exterior maintenance, high-speed internet, and cable TV package right out of the gate. Metal storm shutters and a 1-car garage are already checked off the list for you. Location-wise, you are right in the sweet spot for everyday convenience and weekend fun. For daily needs, you’re just minutes from major grocery chains, retail shopping, medical facilities, and US-19 for an easy commute. When you want to head out, you're a stone's throw from the Pinellas County line, putting the historic Tarpon Springs Sponge Docks, Anclote River Park boat launches, coastal trails, and local waterfront dining practically in your backyard. Clean, modern, private, and zero yard work to eat up your weekends.

Listing is courtesy of: QUICKSILVER REAL ESTATE GROUP (813-288-0300)

Listing Agent: Alexandros Antonakos (813-428-1907)

Remarks: Don't miss out on this opportunity! LOCATION! LOCATION! LOCATION! This home is located in beautiful Holiday Lakes Estates, Just minutes from the beautiful Tarpon Springs Sponge Docks, beaches, and Pinellas County Line. You will be delighted at the amount of space this home offers. There is ample room here with this 4 Bedroom, 2 bath home! Bring your pets, the backyard is fully fenced. Recently updated with hurricane rated windows in 2021 as well as HVAC 2021. Call Today!

Listing is courtesy of: MCPEAK REAL ESTATE FIRM (813-495-3875)

Listing Agent: Jim Mcpeak (813-495-3875)

Remarks: Welcome to on Lake Conley a large Mobile Home Park in the city of Holiday Florida of Pasco County! This is a Gated 55+ Community with MULTIPLE amenities and a very low community fee. **No lot Rent here so you own the land** The Amenities include: Community Boat Ramp, Fishing Pier, Clubhouse, heated Pool, Shuffleboard Court, Horseshoe Court, Lakefront Dock to sit and enjoy sunset, RV/Boat Parking and much more! This double wide mobile home is 1,056sqft and bright with a lot of natural light all throughout the home. From the exterior you have a large Carport, Large Shed with Shelves and the Washer & Dryer plus the Whole Home Water Softener System. The Inside is charming with a great layout complete with 2 Bedrooms, 2 Bathrooms, Kitchen, large Living room, Dining Space with Built In cabinets, and an enclosed patio. Some of the Updates include: NEW ROOF 2026, AC SYSTEM Replaced 2024, New Electrical Panel, New Carpet, New GFCI throughout, New Hot Water Neater added 2024, Plumbing Updated throughout with New toilets, New sub flooring 3/4 plywood in living and dining room areas, Skirting around home coming June 2026, and more, Priced to Sell! Add to your short list to see and buy before its gone. *Lake Conley is a Golf Cart Friendly updated Community with a very low HOA fee of only $60 a month* Reminder that this versatile space, featuring Updated Sliders, can be used as an office or casual hangout area. Also this home offers a relaxed Florida living lifestyle that is centrally located to all shopping, restaurants, less than 20 minutes to Florida's most beautiful beaches, Places of worship, nature trails, Parks and many outdoor entertainment. to sum it up: Lake Conley is highly sought after for its privacy, amenities, low HOA fees, location, Gated, Golf carts welcome, Storage, Boast ramp, own your lot, and peaceful surroundings! Call for additional information!

Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)

Listing Agent: Bert Baalbaki, Cdp (813-507-8348)

Remarks: Built in 2024, this beautifully designed 3 bedroom, 2 bathroom home in Holiday Lake Estates features an open floor plan with modern finishes and a relaxing back porch perfect for enjoying the Florida lifestyle plus no CDD or HOA fees! Conveniently located near Downtown New Port Richey, shopping, dining, parks, and entertainment, while also close to Key Vista Nature Park for scenic walking trails and outdoor activities. Schedule your showing today!

Listing is courtesy of: PEOPLE'S TRUST REALTY (727-946-0904)

Listing Agent: Ali Kochno (813-766-7143)

Remarks: Stunning fully remodeled 4-bedroom, 3-bath waterfront home offering privacy, functionality, and true Gulf-access living. This exceptional property has remained high and dry with no flooding during recent storms, providing peace of mind along with an unbeatable natural setting. Set along a scenic bend of the river, the backyard overlooks a private island preserve—meaning no rear neighbors, just nature. Dolphins, manatees, and a wide variety of birds are frequent visitors, creating a tranquil waterfront backdrop rarely found. The thoughtfully designed split floorplan features two complete en suites located on opposite sides of the home, ideal for multigenerational living, guests, or added privacy. The home has been meticulously maintained and extensively upgraded. Outdoor & Waterfront Features include: 10,000 lb boat lift with dock Heated chlorine pool with new variable-speed pool pump (2024) New pool heat pump (2024) Gravity overflow pool drain to prevent overfilling New stainless steel boat lift cables (2025) Interior & Systems Upgrades: Brand-new kitchen with ventless hood, microwave, dishwasher (2026), refrigerator, and stove (2025) Moen motion-sensor kitchen faucet with WiFi/app control (2025) Propane tankless hot water heater on demand (2025) Additional electric on-demand water heater available (can be reconnected) Whole-home 5-stage Halo water treatment system (2025) Entire home repiped with Uponor PEX water lines (2025) Efficiency, Safety & Storm Readiness: Generator-ready electrical setup EV charging outlet in garage Commercial-grade garage door opener and fully rebuilt garage door (springs, rollers, hinges – 2025) Electrical panel installed 2018 Roof (2018) Air handler and heat pump (2018) Additional blown-in attic insulation (2025) New doors and windows (2025) Additional Features: New 4-zone front yard sprinkler system with WiFi-controlled pump (private well water – 2025) ADT security system with fire and carbon monoxide detection Nest Ring doorbell and garage camera convey This home offers true waterfront privacy, modern systems, and extensive upgrades, making it ideal for full-time living or a refined coastal retreat with direct Gulf access.

Listing is courtesy of: SNAP REALTY LLC (727-457-5453)

Listing Agent: Shawn Poole (813-967-3837)

Remarks: Move-in ready opportunity in Holiday! This beautifully maintained home features 2 bedrooms, 2 bathrooms, central HVAC, and vinyl flooring throughout. Enjoy a fenced backyard, patio area, and a one car garage. Conveniently located near everyday shopping, dining, and entertainment with easy access to major roadways and the Gulf Coast. Easy to show!

Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)

Listing Agent: William Figueroa (305-662-1502)

Remarks: Auction Property. Welcome to Holiday Lake Condos and enjoy peaceful water views right from your own living room! This well-maintained GROUND FLOOR unit features an open floor plan with plenty of natural light. Galley kitchen with eat-in space. Inside utility closet. Living room. Separate dining room. Bonus Florida room with wonderful views of the pond. Split bedroom plan. Master suite is quite large with full master bathroom. Bedroom #2 is adjacent to bathroom #2 for privacy. The community offers a relaxing atmosphere complete with a pool, clubhouse, shuffleboard courts, and a recreational facility! Whether you're looking for a vacation home or a year-round residence, this condo provides the perfect balance of comfort, convenience, and tranquility. Premium location as it has easy access to multiple stores and restaurants. Just 4 miles away from Holidays pride and joy for recreation; The J. Ben Harrill Recreation Complex. This Large Park offers tennis courts, basketball courts, hockey roller rink, soccer fields and is the home of the Greater Holiday Little League. Just minutes away from Key Vista Nature Park. A 101-acre park with nature trails, boardwalk and observation tower. Head 4 miles south and you can enjoy the World-Famous Sponge Docks of Tarpon Springs. Known for its fishing, food and entertainment. * * PLEASE NOTE * * It is buyer’s responsibility to verify all information. Information posted in MLS or any marketing information is not guaranteed.

Listing is courtesy of: RE/MAX ELITE REALTY (727-785-7653)

Listing Agent: Matthew Brashear (727-403-3900)

Remarks: Welcome to your turnkey coastal retreat in the highly desirable Gulfwinds community, where homes rarely become available and the Florida lifestyle takes center stage. This spacious 4-bedroom, 3-bath home offers over 2,600 square feet of living space with a bright open layout, soaring ceilings, and a functional split-bedroom floorplan designed for both everyday living and entertaining. Located in an X flood zone where flood insurance is typically not required, this move-in ready home combines peace of mind with comfort and convenience. Inside, you'll find an open-concept living area, solid wood cabinetry, solid surface countertops, walk-in closets, and a spacious kitchen that flows seamlessly into the main living spaces. The home also features a 3-car garage, hurricane shutters, irrigation system, indoor laundry room, and comes turnkey furnished for an easy move right in experience. Perfectly positioned just minutes from historic downtown Tarpon Springs and the famous Sponge Docks along the Anclote River, this location offers the ideal blend of laid-back coastal charm and everyday convenience. Enjoy quick access to local restaurants, boating, waterfront parks, golf cart rides through the neighborhood, nearby Gulf beaches, and the scenic Coastal Anclote Trail connecting you to parks, nature, and downtown Tarpon Springs. Local schools are also just a short walk away, making this an ideal setting for full-time residents, seasonal owners, or anyone looking to enjoy the best of Florida living. Whether you're looking for more space, a low-maintenance Florida home, or a peaceful coastal community close to it all, this property delivers. Schedule your private showing today!

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

Listing Agent: Sheri Harris (609-462-8358)

Remarks: Move in ready 3 bedroom 1.5 bathroom home located in Holiday Fl. This home has and update kitchen with quartz countertops and shaker style cabinets. The seller has taken care of all the big ticket items! These include the Roof (2023), Electric Panel (2022), Water Heater (2022), Impact rated garage door (2022), HVAC(2023), and Windows (2023). Conveniently located near restaurants and shopping, this home is ready to go!

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

Listing Agent: Trevor Skeens (813-531-3713)

Remarks: Welcome to this one-of-a-kind Holiday retreat on 0.74 acres, where a private park-like setting, tranquil pond views, wildlife in your backyard and thoughtful interior features create a truly special place to call home. Nestled among mature trees, this property offers a peaceful setting rarely found in today's market. Inside, you'll find all tile flooring throughout and a warm, inviting living area highlighted by a stone veneer fireplace, perfect for relaxing evenings at home. A versatile recreation room currently serves as a family room and office, providing flexible space to fit your lifestyle. Designed with both function and style in mind, the kitchen features granite countertops, abundant cabinet space, modern appliances, a double oven, and an island-mounted electric cooktop with exhaust. Whether preparing everyday meals or entertaining guests, this kitchen is ready to meet your needs. The natural beauty of this property truly sets it apart. Front and rear covered porches overlook the picturesque pond and surrounding landscape, creating the perfect places to enjoy morning coffee or unwind at the end of the day. A charming bridge crosses a small stream, while the firepit area offers a peaceful gathering spot surrounded by nature. Located in Holiday, this home offers convenient access to the Tampa Bay area while maintaining a quieter, more affordable lifestyle. Enjoy nearby parks, nature preserves, boating, fishing, waterfront dining, and outdoor recreation, including Anclote River Park and Key Vista Nature Park. The home is located in FEMA Zone AE; however, the owner states that the property has never flooded. With pond views, mature landscaping, covered porches, a fireplace, flexible living space, and a truly unique natural setting, this property offers privacy, comfort, and a lifestyle that is difficult to find. Schedule your private showing today.

Listing is courtesy of: CENTURY 21 ALLIANCE REALTY (352-686-0000)

Listing Agent: Marie Mclaughlin (727-858-7569)

Remarks: Welcome to this beautifully updated two-bedroom, two-bathroom home with a one-car garage. This home features a remodeled kitchen with updated cabinets and countertops, complemented by two fully renovated bathrooms. Enjoy new wood laminate flooring throughout and fresh interior paint, creating a clean and modern feel. Major updates include an updated AC system and a brand-new roof to be installed prior to closing, providing added value and reassurance for the next owner. Step outside to a screened, covered back patio-perfect for relaxing or entertaining year-round. The home is also equipped with rollaway shutters on nearly every window and door opening for added protection and convenience. Best of all, this property did not flood during Hurricane Helene or Hurricane Milton.

Listing is courtesy of: RICHEY REALTY (727-849-1000)

Listing Agent: Allan Safranek, Iii (727-849-1000)

Remarks: Built in 2023, this well maintained two story townhome offers a low maintenance lifestyle with modern finishes throughout. Positioned on a desirable corner lot, the home features hurricane impact windows and is located in a no flood zone. Inside, the open concept kitchen and dining area are designed for both functionality and style, featuring stainless steel appliances, a center island, and a seamless flow into the main living space. Plantation shutters add a clean, upscale touch to the main living areas. The home offers 3 bedrooms and 2.5 bathrooms, with tile flooring in the main living areas and carpet in the bedrooms for added comfort. A screened lanai provides a relaxing outdoor space, while the covered front porch enhances curb appeal. Additional features include a one car garage and convenient guest parking nearby. The HOA covers exterior maintenance, allowing for easy low maintenance living. Ideally located in Holiday, approximately 4.5 miles from the Tarpon Springs Sponge Docks, local marinas, and waterfront dining, and about 7 miles from Fred Howard Park beach. A great opportunity to own a newer home in a growing area.

Listing is courtesy of: TREASURED HOME COLLECTION (727-210-3282)

Listing Agent: Shelby Baker (727-916-2299)

Remarks: Under contract-accepting backup offers. This updated lakefront home is located in the desirable Aloha Gardens subdivision. Meticulously maintained and surrounded by lush landscaping, this beautiful property sits at the end of a quiet cul-de-sac. Featuring a spacious open floor plan, the home offers the perfect gathering space for family and friends. It includes 2 split bedrooms, 2 renovated bathrooms, and a 2-car garage, with 1,432 square feet of living area. Exquisite wood-look ceramic tile flooring flows throughout the home. The lovely kitchen is equipped with wood cabinetry, granite countertops, and stainless steel appliances. Both bathrooms have been recently updated with tasteful finishes. Conveniently located just minutes from the Pinellas Trail and the world-famous Sponge Docks, this home is also close to shopping areas, medical centers, hospitals, Pinellas County beaches, and Tampa International Airport. Enjoy Florida living at its best! Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (727-381-2345)

Listing Agent: Christian Pezey Llc (727-515-7102)

Remarks: Charming 3-bedroom, 2-bath, 1-car garage home in Holiday offering approximately 1,600 sq ft of living space and a desirable Eldorado floorplan featuring a welcoming front courtyard—perfect for enjoying Florida’s beautiful weather. This well-maintained home is in great condition and move-in ready with a newer roof (4 yo) and numerous updates throughout. Interior features include all tile flooring, newer windows, a spacious living room filled with natural light, and a functional kitchen with solid wood cabinets and a convenient breakfast counter. The home offers a split comfort setup with a dedicated mini-split unit in the third bedroom. The primary suite features a walk-in closet and direct access to a Jack-and-Jill style bathroom with double sinks and a tub with shower. Step outside to a large fenced backyard with plenty of room to relax, garden, or entertain. Unique privacy surrounds this property with vacant lots on both sides of the home, creating extra space and openness. One of the neighboring lots is available for purchase from a separate owner, presenting a potential opportunity for expansion or added privacy. Located just minutes from a county waterfront park with public boat launches, this home offers easy access to boating, fishing, and outdoor recreation. Enjoy comfortable Florida living in a well-cared-for home that is ready for its next owner.

Listing is courtesy of: FUTURE HOME REALTY (800-921-1330)

Listing Agent: Vera Ziegler (800-921-1330)

Remarks: ON THE LAKE!!! A RARE FIND, One Bedroom, One Bath CORNER unit that needs a little TLC. Enjoy maintenance free living in Tahitian Gardens a beautiful Resort-Style GATED 55+ community. The open floor plan is tiled throughout with a carpeted bedroom. Large floor to ceiling front windows let you enjoy the view of the lake as well as letting in an abundance of natural light. This unit also includes a large washer/dryer for your convenience. Relax and enjoy the Resort-Style amenities including a large, heated swimming pool, two club houses, pool tables, wood shop or walk on the many sidewalks throughout the community and by the lake. Other activities include shuffleboard, arts and crafts, a bicycling club, bingo, horseshoes, bocce ball, dominoes, card groups and more. Easy access to dining, shopping and public transportation. Tampa and Clearwater International airports are less than an hour’s drive. Walking distance to CVS, Walgreens and Aldi's. Minutes away from Tarpon Springs, the Sponge Docks and the beach at Howard Park. Easy to see and immediate possession available. Make this your new home before somebody else does!

Listing is courtesy of: COASTAL FLORIDA REAL ESTATE (727-471-9115)

Listing Agent: Michael Mcauley (727-471-9115)