Holiday Oceanfront Homes, Condos for Sale

Bailey's Bluff Estates Unit 1 SubDv. ⋅ 34691 Zip Code

GULF-FRONT OPPORTUNITY IN BEAUTIFUL BAILEY'S BLUFF! Rare opportunity to build your dream waterfront estate directly on the Gulf in the desirable Bailey's Bluff subdivision of Holiday, Florida. This 85x293 Gulf-front lot offers breathtaking, long-range views of Anclote Island and the open waters of the Gulf. Featuring an impressive 80 feet of seawall, this exceptional homesite is surrounded by distinguished gulf front properties ranging from approximately $760,000 to $2.8 million. Imagine designing a custom coastal residence that captures spectacular sunsets, panoramic water views, and the beauty of Florida's Gulf Coast. An outstanding opportunity to secure a premier waterfront location and create a truly extraordinary home in an established luxury neighborhood. Bring your vision and make the Florida waterfront lifestyle yours!

Bluff Boulevard, Holiday

$630,000

4 Beds ⋅ 3 Baths ⋅ Sand Bay SubDv. ⋅ 34691 Zip Code

Welcome to 2401 Sand Bay Dr — a truly one-of-a-kind property offering the perfect blend of Florida lifestyle, functionality, and flexibility. Situated in a peaceful waterfront-adjacent community in Holiday, this well-maintained home stands out with an incredible approximately 2,300 sq ft climate-controlled garage/workshop that is rarely found in the area. Fully finished with drywall throughout and equipped with dedicated mini-split cooling systems, the expansive garage space is ideal for car enthusiasts, contractors, hobbyists, or anyone seeking a versatile workspace with year-round comfort. The garage also features 8-foot garage doors, providing excellent functionality and accessibility. Properties offering this level of usable garage and workshop space are exceptionally hard to find. Inside, the home features bright and inviting living spaces with high ceilings, 8-foot interior doors, abundant natural light, and a functional layout designed for both everyday living and entertaining. The open indoor-outdoor flow creates a spacious and airy feel throughout the home. Major updates have already been completed, including a new roof (2024), one HVAC system (2023), and water heater (2022), providing peace of mind for years to come. Adding even more confidence for buyers, the property experienced no damage from the recent hurricanes, and flood insurance is not currently required — a rare and valuable benefit for a property located so close to the water. Step outside and enjoy the relaxed Gulf Coast lifestyle with backyard views overlooking the Gulf, creating the perfect setting to unwind and enjoy Florida sunsets. One of the home’s most impressive features is the rooftop terrace, offering breathtaking panoramic Gulf views and an incredible space for entertaining, relaxing, or enjoying peaceful evenings by the water. Conveniently located near marinas, waterfront dining, beaches, parks, and shopping, this property combines tranquility with accessibility while offering a truly unique lifestyle opportunity. Whether you're searching for a primary residence, seasonal retreat, or a property with unmatched workspace, storage, and coastal charm, 2401 Sand Bay Dr offers a rare opportunity to own a standout property in one of the Gulf Coast’s most desirable settings.

2401 Sand Bay Drive, Holiday

$474,900

3 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code

HUGE PRICE REDUCTION (OWNER MOTIVATED TO SELL) Waterfront Living at its Finest – Nestled in a luxury, family-friendly neighborhood in Holiday, Florida. This stunning 3-bedroom, 2-bath waterfront home with nearly 1,900 sq ft. It offers the perfect blend of comfort, style, and a ultimate Florida boating lifestyle with the bonus of having Multigenerational Living . This property is a true fisherman’s paradise with direct access to the Anclote River and just a short boat ride to the famous Tarpon Springs Sponge Docks then out to the Gulf of Mexico. A Home Designed for Comfort & Style. Step inside to an open-concept floor plan with seamless tile flooring throughout. This creates a clean and modern flow perfect for entertaining with everyday living. The custom kitchen is a true centerpiece, featuring: Striking waterfall marble countertops, black stainless steel appliances, generous prep including entertaining space and clear sightlines to the living and outdoor areas. The spacious primary suite is your private retreat, highlighted by a luxury wet steam room (5' x 9.5') large enough to accommodate multiple people-bringing spa-level relaxation right into your home. Additional upgrades include: Instant hot water heater – never run out of hot water, solar panels for energy savings, freshly painted, custom entry doors, newer roof, HVAC system, and windows. Outdoor Living Built for the Florida Lifestyle. This home truly shines outdoors. Relax or entertain from the screened-in patio overlooking the water, or take advantage of the huge covered patio with plenty of space for outdoor toys and gear. The beautifully maintained property also includes: New St. Augustine grass installed last year with irrigation system with its own well and on it's completely fenced side yard and backyard. Doggie door for convenient pet access, stamped cobblestone concrete driveway, super gutters installed around the entire home, two-car garage with professional epoxy flooring and warranty. Boater & Angler’s Dream! Situated at the end of the Anclote River, the property offers brackish waterfront known for abundant redfish and snook—often caught right off the dock. Your private waterfront setup includes: 10,000-lb boat lift, large oversized dock for entertaining, floating docks for kayaks, paddleboards, and water toys. double floating wave-runner dock available and recapped and stamped seawall. From your dock, enjoy a short scenic boat ride to the sponge docks, waterfront restaurants, and open Gulf waters. FYI this property has never flooded. Location Perks: You’re just minutes from: Gulf beaches, waterfront dining, boating and fishing hotspots, parks and local amenities. All while enjoying the tranquility of a quiet waterfront neighborhood perfect for families or those seeking the ultimate coastal lifestyle. Whether you’re a boater, fisherman, entertainer, or simply looking for the perfect waterfront retreat, this property delivers the Florida lifestyle at its absolute best.

1125 Fernwood Drive, Holiday

$799,000

Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

"BUILD YOUR DREAM HOME" on this exceptional Gulf-front property featuring 80 feet of direct water frontage and an impressive 206-foot depth. Perfectly positioned in the highly sought-after community of Baileys Bluff, this rare homesite is nestled within a true nature sanctuary, offering privacy, tranquility, and breathtaking coastal beauty. From your newly constructed home, you’ll enjoy spectacular, unobstructed views of the Gulf of Mexico—the perfect backdrop for everyday living. The property is completely fenced and comes with a Geotechnical Engineering soil report for a proposed residence. A proposed septic tank location is already identified, and no mound system is required for the drain field—making your building process even more seamless. Imagine spending your days island hopping, shelling, fishing, or enjoying peaceful sunset cruises right from your backyard. Take a short stroll to waterfront Key Vista Park for nature trails and scenic views, or enjoy a quick drive to Tarpon Springs for fine dining, boutique shopping, and the charm of this historic coastal town. This is more than a homesite—it’s a lifestyle. Don’t miss the opportunity to create your own waterfront retreat in one of the area’s most serene and desirable communities.

000 Bluff Boulevard, Holiday

$1,400,000

4 Beds ⋅ 4 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

Stunning Ocean views from this waterfront paradise. The opportunity has arisen to acquire the former home of the renowned local artist Elaine Hahn and AIA emeritus architect Byron G McIntyre. Located in the sought-after Bailey’s Bluff community, this stunning 4-bedroom, 4-bath elevated home offers 3,412 square feet of coastal living with panoramic water views throughout and 160 feet of private water frontage with direct access to the Gulf. Located at the very end of a Cul-de-sac the private driveway leads to a spacious 4 plus vehicle garage. Take the inside elevator to the open plan 2nd floor, with feature light maple hardwood flooring accentuating the amazing natural light that flows into the living room. This floor also contains an open-plan kitchen, dining area, master bedroom suite and artist studio which has the most amazing views you will find for any home office. There is a covered front balcony and wrap around back balcony where you can enjoy the wonderful Gulf breezes. The third floor has three further bedrooms and addition Den/office. Also, you will find a secluded third-floor balcony that looks out at more spectacular views across to Anclote Key. In addition to the ground level garage, there is a covered parking area. Inside the garage is workshop space with French doors onto the pool deck. The backyard has a tranquil, tropical and beach feel with floating dock and boat lift. Take a 15-minute stroll to Key Vista Nature Park with its many trails and observation tower overlooking the Gulf. Enjoy boating, fishing, scalloping and island hopping. A short drive to a recreational complex, parks, beaches and the charming community of Tarpon Springs, complete with shopping and dining options. This home is solidly built to withstand hurricanes, being elevated, and with concertina or roll down shutters to all windows. During 2024 storms only suffered minor damage, not even losing power. There is no HOA, but an optional Baileys Bluff Civic Assoc. membership is just $100 a year, providing a private beach, boat ramp, & clubhouse. Don't miss the opportunity to make this slice of paradise your own!

1906 Gulfview Drive, Holiday

$442,000

3 Beds ⋅ 2 Baths ⋅ Sand Bay SubDv. ⋅ 34691 Zip Code

Welcome to your entertainer’s dream home—a stunning 3-bedroom, 2-bath, 2-car garage oasis perfectly positioned on a unique oversized lot along the breathtaking Gulf of America. This one-of-a-kind property offers an unparalleled blend of resort-style amenities, natural Florida beauty, and a sense of peace and privacy that is simply unmatched. Step outside into your own private paradise, where beautifully landscaped, Florida-friendly gardens surround you with vibrant color and lush greenery. Designed for low maintenance and equipped with automatic watering, the grounds provide year-round natural beauty with minimal effort. At the heart of the backyard, the solar-heated pool sparkles under the Florida sun, inviting you to relax, entertain, and enjoy the ultimate in outdoor living. This backyard sanctuary has been thoughtfully designed to create an experience, not just a space. A charming outdoor gym offers a place to focus on your wellness, while a dedicated gardening area allows you to indulge your green thumb. For moments of peace and reflection, a tranquil meditation and yoga cathedral awaits, surrounded by tropical landscaping. Golf enthusiasts can enjoy a private driving area, and evenings come alive around the cozy firepit lounge with ample seating. A self-replenishing saltwater tidal pool adds a magical touch, attracting fish during the tides and connecting you to the surrounding natural beauty. From hammocks gently swaying in the breeze to spaces for cornhole, bocce ball, and a flourishing herb garden, every detail has been thoughtfully crafted to create your own personal resort. Inside, the home is equally captivating. The soaring cathedral ceilings in the living room create an airy, open ambiance, while large sliding glass doors invite endless views of the pool and gardens, seamlessly blending indoor and outdoor living. The split-bedroom floor plan offers privacy, with the primary suite tucked away as a true retreat. Enjoy a spa-like ensuite bathroom featuring a custom live-edge vanity, a generous walk-in closet, and sliding doors that open directly to the pool and gardens. The stylish kitchen boasts a custom live-edge peninsula, contemporary tile, and ample storage, flowing effortlessly into the dining area for easy entertaining. Throughout the home, newer flooring, fresh paint, and upgraded baseboards combine to create a polished, move-in-ready space. There is even a custom office conversion within the garage, offering flexibility to work from home or easily restore it for parking if desired. Best of all, this property offers peace of mind with no flood insurance required and no flooding during recent storms. No HOA or CDD! Imagine launching your kayak from your backyard and gliding through the mangrove-lined waterways out to Sand Bay and beyond to the Gulf. Every day feels like a vacation in this extraordinary home. This is more than a home—it’s a lifestyle, a retreat, and a personal sanctuary along the Gulf of America. The Anclote Trail that connects to the Pinellas Trial is right the around block for walking and biking. Don’t miss the chance to experience this exceptional property. Call your real estate professional today to schedule a private showing.

2257 Sand Bay Drive, Holiday

$750,000

3 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

"PRIVATE FLORIDA PARADISE: WATERFRONT ESTATE WITH BONUS BUILDING LOT & GULF ACCESS" Nestled at the end of a quiet cul-de-sac, situated on stunning property. The extra building lot conveys with the sale this Florida home which offers 180° water frontage on a peaceful bayou, with easy access to the Gulf in just 8 minutes. The home features 3 bedrooms, 2 baths, and an office, with 1,944 sq. ft. of living space and a 1,748 sq. ft. garage. The master suite includes a large walk-in closet, built-in closet, built-in shelving and a bath with a walk-in shower and double sinks. The great room boasts beautiful wood beams in the ceiling and a gas fireplace. The expansive screened-in back porch offers a great space to entertain while enjoying the soothing winds off the water . The private boat dock built in 2015 is a perfect place to park your boat to get ready for fishing, scalloping, and island-hopping adventures. The kitchen has solid wood cabinets, a new AC in 2022, and a reroof in 2016. No flood damage from Hurricane Helene. Additionally, the adjacent lot offers a unique opportunity to build a family compound. Located in the tranquil Baileys Bluff neighborhood, you're just minutes from parks, sports complex, beaches, restaurants, and the iconic Sponge Docks in Tarpon Springs. Enjoying the Florida lifestyle can be yours. Schedule a private showing today!

2020 Cove Court, Holiday

$1,800,000

3 Beds ⋅ 3 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

Nestled in a prime location with 171 FEET OF WATER FRONTAGE and its UNOBSTRUCTED GULF VIEWS AND DIRECT ACCESS from the brand-new BOAT DOCK this home is truly unmatched. From the moment you arrive, the paved driveway leads to an impressive seven-car garage, setting the stage for a remarkable residence. Access to the main living area is effortless with the choice of a grand front staircase or the convenience of a brand-new ELEVATOR that takes you from the garage to the second floor. Inside, an abundance of natural light pours through expansive windows, showcasing breathtaking Gulf views. The sunken living room is a showpiece, featuring luxury finishes and elegant underlighting. Just steps away, the gourmet kitchen is a chef’s dream, equipped with top-of-the-line appliances, a pot filler over the stove, a striking luxury hood vent, and sleek stone countertops. The adjacent dining room, framed by bay windows, offers a perfect setting for enjoying meals while overlooking the open Gulf waters. Designed with privacy in mind, the home features three distinct bedrooms, including a grand primary suite, a spacious guest suite, and a third bedroom. The primary suite is a retreat of its own, complete with an attached sitting room bathed in natural light and stunning Gulf views. A private door opens to a vast back patio deck, perfect for taking in breathtaking western sunsets. The spa-like en suite bathroom offers a luxurious escape with elegant MARBLE FLOORING, an oversized shower with multiple shower-heads, including a rain shower, and a stand-alone soaking tub perfectly positioned for water views. The guest suite also impresses with an oversized layout and an en suite bathroom featuring a beautifully marble surround walk-in shower. The outdoor living space is just as captivating, featuring a SALT WATER POOL overlooking endless water views, a cozy fire pit for evening gatherings, and a brand-new dock with a boat lift, providing effortless access to the Gulf. This home has been meticulously updated with two new HVAC units, a NEW ROOF, new gutters, brand-new HURRICANE-IMPACT WINDOWS, sliding doors and MUCH MORE. Nearly everything in this home is brand new, making it a rare opportunity for those seeking the ultimate Florida waterfront lifestyle.

1903 Gulfview Drive, Holiday

$700,000

3 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

" A RARE FIND IN BAILEYS BLUFF ESTATE" " NEVER FLOODED " Situated on a beautiful elevated lot over looking Anglers Cove on a tree lined cul-de-sac street. A well constructed single story home has a finished floor elevation of 12 feet. The open Gulf can be seen from the front of the house. From the new floating dock you can be in the open Gulf in 1 minute. This home has a split plan with 3 bedrooms, 2 baths, a great room with solid wood floor, vaulted ceiling with wood beam and wood burning fireplace. The master bedroom has a solid wood floor and master bathroom with two sinks, separate bath tub and a separate shower stall. The great room flows into a fabulous Florida room with new impact sliding glass doors that open to a large deck over looking the water and expansive back yard. Off the family room is a private office space. The roof has been replaced on 3/3/2021, the dock is new in 1/8/2021. The AC was replaced 6/27/2016. The home had a wind mitigation inspection. The third nail and H3 clips installed have been installed around the perimeter of the home. There are double pane windows throughout. Baileys Bluff Estate has its own private boat ramp and a community club house that is on the open Gulf. Enjoy a short walk to water front Key Vista Park with its many trails and observation tower. Recreation center, fishing pier, dog park, shopping, restaurants, beaches and downtown Tarpons Springs is a short drive away. The Florida life style can be yours. Don't miss the opportunity to make this house your home. Schedule a showing today!

1928 Gulfview Drive, Holiday

$662,000

2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

**Discover Your Dream Waterfront Oasis on the Gulf of Mexico!** Welcome to your coastal paradise! This charming concrete block 2-bedroom, 2-bathroom,1096 sq' home offers a fantastic opportunity to create your ideal retreat, featuring 141 feet of pristine waterfront and a well-constructed seawall with a generous 22-foot-wide cap—perfect for watching the stunning sunsets. The seawall has withstood the test of time, showing no damage from the recent Helene and Milton storms, providing you with peace of mind. The FLOOD INSURANCE IS TRANSFERABLE AND IS "PREPAID"THRU 27 NOV. 2027. While the home experienced water intrusion, all damaged drywall has been removed. County inspection determined the extent of damage at 19.8, allowing you to customize the space to your taste. The elevated AC unit remains untouched, and the roof was recently replaced in July 2023, giving you a solid foundation to build upon. This property is being sold as-is, inviting you to unleash your creativity and transform this house into your dream home. Situated in the serene bird sanctuary Bailey's Bluff Estates, this gem is nestled on a tree-lined cul-de-sac, just a 15-minute stroll to Key Vista Nature Park. Enjoy unparalleled outdoor experiences with your very own private boat ramp providing direct access to the Gulf of Mexico. Revel in a lifestyle rich with nature, from dolphins and manatee sightings to excellent fishing, scalloping, boating, and island hopping. Your waterfront paradise awaits—seize this rare opportunity!

1904 Gulfview Drive, Holiday

$400,000

3 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code

Enjoy a beautiful waterfront view from this 3/2 pool home. Beautiful updated home ready to move in(furniture is negotiable}Currently being used as an Air BnB . You’ll see manatees and dolphins in the canal, and the sunset views are unbelievable! This is a turn key business opportunity or a beautiful pool waterfront home for any family!

5424 Flora Avenue, Holiday

$1,030,000

4 Beds ⋅ 3 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

Discover the epitome of coastal living at 1931 Gulfview Dr in Bailey's Bluff Estates, where breathtaking, unobstructed views stretch before you. Nestled on .37 acres of prime real estate, this 2115 sqft haven has undergone a tasteful renovation, embracing contemporary design trends. Step inside to find a culinary masterpiece awaiting in the kitchen, adorned with quartz countertops, sleek stainless steel appliances, and luxurious solid wood cabinets featuring soft close hinges. The breakfast area overlooks serene water vistas, offering a tranquil start to your day. Boasting 4 bedrooms and 3 bathrooms, the ingenious three-way split floor plan ensures both versatility and seclusion. Ample closets throughout the home cater to your storage needs, while the unfinished bottom floor beckons as a canvas for your imagination. Savor glorious weather and stunning sunsets from your private balcony with newer PGT sliders, or descend the steps in your backyard during low tide to access the sandy beach just moments from your doorstep. HardiePlank siding adorns the exterior, ensuring both durability and style. The expansive backyard invites endless possibilities, whether envisioning a serene pool oasis or contemplating an accessory dwelling unit (ADU) in the front yard. Truly, this property must be seen to be fully appreciated – seize the opportunity to make it yours.

1931 Gulfview Drive, Holiday

$1,255,000

3 Beds ⋅ 3 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

DREAMING OF LIVING ON THE GULF OF MEXICO? YOU FOUND PARADISE! Panoramic open Gulf Front Water Views! Spectacular Sunsets, Dolphins Playing, World Class Fishing, Scalloping, Boating, Kayaking, or relaxing poolside on your own Private Beach! Nestled safely behind your own private electronic gate, this Charming Key West, 3 bedroom, 3 bathroom home sits on a beautiful .7 acre lot with 80 ft. of Gulf Frontage. Situated near the community club house on the peninsula of historic Bailey’s Bluff Estates. You will be in awe of the captivating sunsets cascading over open Gulf Waters. The open floor plan features a spacious updated kitchen with quartz counter tops and stainless steel appliances. The oversized living room overlooks the Gulf of Mexico with views continuing to the master bedroom with a beautifully remodeled bathroom and a huge walk in closet. This split floorpan home has two additional oversized bedrooms and a newly remodeled bathroom on the main living level. Entertaining and family space is abundant with a large wrap around deck and extends to the downstairs. Take the elevator to the ground floor where you will find a bonus room with kitchen and bathroom not included in the living square footage. There is also a separate 2 car garage. Plenty of room for your water toys on the large dock extending into the Gulf of Mexico… Currently set up with a boat lift and davits. Jump in your boat, it’s just a short ride to Anclote, Caladesi, 3 Rooker islands and the world famous Sponge Docks of Tarpon Springs, featuring waterfront dockage and dinning. This Gulf Front location is just minutes to shopping, parks, white sandy beaches, golf courses and all the amenities Tampa Bay has to offer. Schedule your private showing today!

2035 Gulfview Drive, Holiday

$?

3 Beds ⋅ 2 Baths ⋅ SubDv. ⋅ 34691 Zip Code

WOW WHAT A STEAL!! ... WHAT INCREDIBLE VALUE ... DIRECT OCEAN FRONT ...a chance to own direct Gulf Front property for a fraction of it's worth!! This charming home is in move-in condition with upgraded kitchen & baths, heated pool & spa onopen deck facing the Gulf, granite gas fireplace, real wood floors throughout the living area, newer roof, A/C, water heater, storm shutters. Located in Bailey's Bluffs, a quaint secluded waterfront community. LOCATION ... LOCATION ... LOCATION SPEAKS FOR ITSELF! This is what Florida is all about, white sand, blue ocean, captivating sea life, sailboat traffic, magical sunsets and more ... right in your own backyard ... a true storybook world! Don't pass up this dreamlikeopportunity!

1913 Gulfview Drive, Holiday

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