Baileys Bluff Estates Homes with Waterfront

Baileys Bluff Estates Homes with Waterfront

Welcome to Baileys Bluff Estates, an enchanting subdivision nestled in the scenic landscapes of Holiday, Florida, within Pasco County. This charming community is the perfect blend of serene living and vibrant outdoor recreation, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle by the water.

Baileys Bluff Estates is renowned for its stunning waterfront properties, offering residents breathtaking views and direct access to the shimmering waters of the Gulf of Mexico. Imagine waking up to the gentle sound of waves lapping against the shore and enjoying picturesque sunsets from the comfort of your own backyard. The homes in this community are designed to embrace the beauty of their surroundings, featuring spacious layouts, modern amenities, and lush landscaping that enhances the inviting atmosphere.

In addition to the captivating homes, Baileys Bluff Estates boasts a variety of recreational opportunities. Residents can indulge in boating, fishing, and kayaking, all just steps away from their front doors. The nearby parks and nature reserves provide ample space for hiking, picnicking, and exploring Florida’s unique wildlife.

With its prime location in Holiday, you'll find yourself just a short drive from the vibrant culture and entertainment of Tampa Bay, while still enjoying the peace and quiet that comes with waterfront living. Whether you’re looking for a permanent residence or a seasonal getaway, Baileys Bluff Estates offers a unique lifestyle that celebrates the beauty of Florida's coast. Come explore your dream home in this idyllic waterfront community today!

Newest Baileys Bluff Estates Homes with Waterfront

$849,900
2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv.
"Gulf Access Waterfront Home in Historic Baileys Bluff Estates" A rare opportunity to own a true waterfront gem with your own private boat ramp! Enjoy a quick 2-minute boat ride to the open Gulf and just 10 minutes more to Anclote Island—perfect for boating, fishing, and island adventures. This beautifully maintained 2-bedroom, 2-bath split floor plan home offers an open and inviting layout ideal for entertaining. The updated kitchen features granite countertops, solid maple wood cabinetry, and a spacious pantry. Rich dark wood flooring flows throughout the home, adding warmth and elegance. Wake up to Gulf views from the expansive primary suite, complete with a large walk-in closet and a luxurious en-suite bathroom featuring dual sinks and granite countertops. Relax in the Florida room overlooking a generous backyard and serene open water views of Anglers Cove, or unwind in the screened-in back porch while enjoying local wildlife. The ground level includes an oversized 2-car garage and an additional 1,360 sq ft of valuable storage space—perfect for all your recreational and boating needs. Recent updates provide added value and peace of mind, including a new roof (August 2022), new A/C system, and a brand-new paver driveway (July 2026). Baileys Bluff Estates is a vibrant, active community offering social gatherings at the Gulf-front clubhouse just across the street, where you can take in breathtaking sunsets. The Pinellas Trail is conveniently located at the community entrance, and Key Vista Nature Park is just a 15-minute walk away, offering scenic trails and shoreline exploration. The famous Tarpon Springs Sponge Docks, beaches, waterfront dining, shopping, are a short car drive away. Experience waterfront living at its best—schedule your private showing today!

2030 Gulfview Drive, Holiday
$525,000
2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv.
NEVER FLOODED DURING HURRICANE HELENE! This is a rare opportunity to own a Gulf-access waterfront home that offers both an exceptional boating lifestyle and added peace of mind. According to the seller, the home has never experienced flooding or water intrusion, making it an outstanding choice for buyers seeking waterfront living with confidence. Nestled in the highly desirable Baileys Bluff Estates, this move-in-ready waterfront home sits on an oversized 0.31-acre lot with approximately 55 feet of saltwater canal frontage, offering direct Gulf access in about one minute. Bring your boat, kayaks, paddleboards, and fishing gear—your waterfront adventures begin right in your own backyard. Boaters will appreciate the private boat ramp, 10,000-pound boat lift, with, stationary dock, and concrete seawall, making launching and storing your boat effortless. Spend your days fishing, scalloping, island hopping to Anclote Key, or watching spectacular Gulf sunsets just minutes from home. Inside, you'll find an inviting floor plan featuring 2 bedrooms, 1.5 baths, an updated kitchen with solid wood cabinetry, updated bathrooms, comfortable living spaces, and a bright Florida room overlooking the tranquil canal. The home has been well maintained and is ready for its next owner. Major recent improvements provide outstanding value, including a brand-new roof (2025) and a brand-new air conditioning system, helping reduce future maintenance costs while increasing buyer confidence. The spacious backyard provides plenty of room to entertain, garden, or simply relax while enjoying peaceful waterfront views and abundant Florida wildlife. Located just minutes from Anclote River, the Gulf of Mexico, Key Vista Nature Park, the famous Tarpon Springs Sponge Docks, beaches, waterfront dining, shopping, and medical facilities, this home offers the perfect balance of recreation and convenience. Whether you're looking for a year-round residence, seasonal retreat, or waterfront investment, opportunities like this are becoming increasingly difficult to find. No HOA, Move-in ready. Schedule your private showing today and discover why this exceptional Gulf-access waterfront property is one of Holiday's best boating values.

3318 Pineview Drive, Holiday
$799,000
Baileys Bluff Estates SubDv.
"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
$1,859,900
4 Beds ⋅ 4 Baths ⋅ Baileys Bluff Estates SubDv.
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
$825,000
3 Beds ⋅ 3 Baths ⋅ Baileys Bluff Estates SubDv.
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.

2138 Bayou Drive, Holiday
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