Baileys Bluff Homes for Sale in Holiday - 6 homes

Remarks: One or more photo(s) has been virtually staged. Open access to the Gulf!! Experience elevated waterfront living in this elegant 3 bed/2 bath residence with a versatile bonus room, thoughtfully designed to blend architectural charm, refined finishes, and seamless indoor–outdoor flow, all in the sought after Baileys Bluff Estates! The generously sized secondary bedrooms offer ample closet space and share a beautifully appointed full bath with a tub/shower combination. A hallway linen closet with built-in shelving provides additional storage. The primary suite is a true retreat, featuring sliding-door access to the lanai and a spa-inspired bath complete with a step-in shower with sliding glass doors—also opening to the exterior—dual-sink vanity, private water closet, and a dedicated dressing hallway with abundant closet space. A separate pool-access bath with sink and toilet can be closed off from the primary suite for added privacy. A nearby washer and dryer closet enhances everyday convenience. The main living areas impress with soaring volume ceilings, recessed lighting, and a striking corner stone fireplace anchoring the space. The chef’s kitchen is as functional as it is beautiful, showcasing wood soft-close cabinetry, granite countertops, stainless steel appliances, a breakfast bar, pantry closets with extensive shelving, a built-in corner desk, and a sun-filled breakfast nook. Architectural details add warmth and character, including a barn-style sliding door allowing the kitchen to be closed off when desired, and a decorative wicker-accent opening that enhances the home’s charm. A flexible dining area offers the option of formal dining and opens through sliding doors to a charming brick patio. The bonus room provides exceptional flexibility—ideal as a home office, media room, or optional fourth bedroom—complete with a utility sink closet, additional storage, and direct garage access. Outdoors, the expansive screened-in lanai and pool create a private oasis perfect for entertaining, complemented by an outdoor shower. The generous fenced backyard leads to your waterfront dock area, where tranquil water views can be enjoyed from the living room, breakfast nook, dining area, and kitchen. Additional highlights include light wood luxury vinyl flooring throughout; tile flooring in all bathrooms, oversized windows providing abundant natural light, ample storage throughout, and an oversized two-car garage. Located just two blocks from the Coastal Anclote Trail, which offers over four miles of scenic paths that connect to the Pinellas Trail in Tarpon Springs. Enjoy easy water access via the bayou and creek with just a five-minute boat ride to the Gulf. The area is also ideal for kayaking. Pickleball courts with weekly league play are located within one mile. This exceptional waterfront property offers the perfect blend of lifestyle, comfort, and convenience. Schedule your private showing today.

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

Listing Agent: Vanessa Leonard (727-647-2706)

Remarks: Discover the charm of Florida’s Gulf Coast in this beautifully crafted waterfront home, set along Rocky Creek within the private and sought-after Bailey’s Bluff neighborhood. Tucked away on a peaceful street, the property showcases wide-open water views, stunning sunsets, and easy access to the Gulf, making it an excellent choice for boating enthusiasts and those seeking a relaxed coastal lifestyle. A private dock equipped with a 12,000-pound boat lift allows for convenient days out on the water, while the home’s history of no flooding from past storms or hurricanes provides added reassurance. Designed with both comfort and entertaining in mind, the residence seamlessly blends indoor and outdoor spaces, featuring large screened-in area with a heated private in-ground saltwater pool and a fully fenced-in backyard—ideal for gatherings or unwinding in the coastal air. The primary suite serves as a serene escape, complete with dual walk-in closets, access to both front and back balconies, and a well-appointed bathroom featuring double vanities and a spacious walk-in shower. On the lower level, an air-conditioned space adds versatility and is currently utilized as a recreation and game area, along with laundry facilities, a pool bath, and extra storage, all connected to a split two-car garage. Recent updates include a new roof installed in April 2025. Residents also have the option to join the community HOA for $100 a year, granting access to a private beach, clubhouse, and boat ramp. Conveniently located near Key Vista Nature Park and the waterfront attractions of Tarpon Springs, this property presents a unique opportunity to enjoy upscale coastal living in a tranquil setting.

Listing is courtesy of: HOMEFRONT REALTY (727-641-4444)

Listing Agent: Michael Morton (727-580-0073)

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: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Nestled within the gated community of Vista Lakes at Bailey's Bluff, this beautifully maintained 3-bedroom, 2-bathroom home features a thoughtful split-floor plan. Manicured landscaping creates a welcoming first impression. Step inside to discover an open-concept layout perfect for entertaining, where the spacious living room flows seamlessly into the dining area and kitchen. The kitchen features beautiful wood cabinets, granite countertops, and an eat-in breakfast bar—ideal for casual meals and conversation. The primary suite is a private retreat with a generous walk-in closet and an en suite bathroom complete with a walk-in shower. Two additional bedrooms and a second full bath with matching wood cabinets and granite countertops provide flexible living space for your needs. Step outside to your own private oasis—an extra-large fenced backyard with a spacious screened lanai, perfect for unwinding after a long day while enjoying the Florida breeze. The 2-car garage offers convenient parking and storage, while hurricane shutters provide added peace of mind during storm season. Located just minutes from Key Vista Nature Park and Anclote Gulf Park, outdoor enthusiasts will love the easy access to biking, running, and walking trails. Plus, you'll enjoy an easy commute to local shopping, dining, and beaches. Whether you're relaxing at home or exploring the nearby natural beauty, this property delivers the best of Florida living in a secure, well-maintained community. Don't miss your opportunity to make Vista Lakes at Bailey's Bluff your home!

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

Listing Agent: Krystal Crichlow (816-590-4688)

Remarks: 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!

Listing is courtesy of: BANNER INT'L REAL ESTATE (407-574-5741)

Listing Agent: Nick Horton (407-733-7197)

Remarks: One or more photo(s) has been virtually staged. Discover unparalleled Gulf Front living in this stunning custom-built home with breathtaking OPEN 75’ Gulf front views and sunsets from multiple vantage points! This home features a BRAND NEW DOCK AND SEAWALL and with 3 bedrooms, 2.5 bathrooms, and a 2-car garage, this newly constructed home offers the perfect blend of luxury and modern convenience!! This home is a rare find offering the best waterfront living with high end finishes and thoughtful design including a fully equipped gourmet kitchen with new, elegant quartz countertops and backsplash, center island with pendulum lighting and farmer’s sink, new induction cooktop, new stainless steel double oven, sleek stainless steel hood vent and walk in pantry with custom shelving, family room with coffered ceilings and recess lighting perfect for entertaining, formal dining with coffered ceiling, new Luxury Vinyl floors and quad sliders leading you the oversized, raised, paved new patio and to the elongated NEW dock with a newer 7500lb boat lift! Wondrous master suite with astounding water views and walk in closets, exquisite master bath with Quartz countertops, pearl nickel fixtures and vast walk in shower with rainmaker shower head, modern lighting and mirror, immense guest quarters offer the 1st guest room with a walk in closet and impeccable views with a jack-n-jill bath boasting Quartz countertops, tiled floors and walk in shower with pebble flooring accents and rainmaker shower head, third guest room with double closets and beautiful view, NEW Luxury high end flooring throughout and electrical shades for added convenience and comfort and more! Don’t miss your chance to own this piece of paradise!

Listing is courtesy of: M3 REAL ESTATE PROFESSIONALS LLC (813-601-4752)

Listing Agent: Marsha Paul (813-601-4752)