Baileys Bluff Estates Real Estate

Baileys Bluff Estates Real Estate

Welcome to Baileys Bluff Estates, a hidden gem nestled in the serene landscape of Holiday, Florida, within the charming Pasco County. This vibrant subdivision offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and anyone seeking a peaceful retreat in the Sunshine State.

Baileys Bluff Estates is characterized by its picturesque surroundings, featuring lush greenery and scenic waterways that invite you to explore the great outdoors. Residents can enjoy leisurely strolls along the nearby nature trails or take a short drive to the stunning Gulf Coast beaches, where sun-soaked days and breathtaking sunsets await.

The community boasts a welcoming atmosphere, with friendly neighbors and a strong sense of camaraderie. With well-maintained homes and beautifully landscaped yards, Baileys Bluff Estates exudes charm and warmth, making it a delightful place to call home. Families will appreciate the proximity to reputable schools, parks, and recreational facilities, ensuring that there’s always something to do for residents of all ages.

Conveniently located near major highways, Baileys Bluff Estates offers easy access to the bustling cities of Tampa and St. Petersburg, where you can enjoy a wealth of dining, shopping, and entertainment options. Whether you’re looking for a quiet retreat or a vibrant community, Baileys Bluff Estates provides the perfect backdrop for your Florida lifestyle.

Discover the allure of Baileys Bluff Estates today, and let this enchanting community be the place where your next chapter unfolds!

Newest Listings in Baileys Bluff Estates

3138 Bluff Boulevard, Holiday
$649,000
2 Beds ⋅ 3 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
GULF ACCESS AND AN OVERSIZED, ELEVATED WATERFRONT LOT IN BAILEYS BLUFF ESTATES! Discover waterfront living in Baileys Bluff Estates, a coastal community known for boating, fishing, and a relaxed Florida lifestyle. Set on an impressive 0.40-acre waterfront lot, this property features a residence positioned on the lot’s highest point, along with a seawall, existing dock, and space for a potential boat lift. The distinctive multi-level design takes advantage of the property’s natural elevation. The main living area offers comfortable living spaces, while the former lower-level garage has been converted into a flexible space with bathroom, spacious recreation room, and laundry area—ideal for guests, entertaining. This lower level got 4" of water during hurricane Helene. The expansive lot provides room to create a tropical retreat, outdoor entertaining area, or peaceful waterfront escape. Shopping, dining, beaches, a recreation center, and numerous parks are just a short drive away. THE REAL VALUE IS THE LOCATION! BRING YOUR BOAT AND MAKE YOUR WATERFRONT DREAMS A REALITY!

3138 Bluff Boulevard, Holiday
2123 Bayou Drive, Holiday
$579,900
3 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
Waterfront living with Gulf access in Holiday. This 3-bedroom, 2-bathroom pool home at 2123 Bayou Dr sits on a saltwater canal with a private dock and seawall. It has 1,962 square feet of living space and a backyard made for the Florida boating lifestyle. Inside, the comfortable layout gives you room to spread out, with bright living areas for everyday living and hosting friends and family. The primary suite has its own private bath, and the two other bedrooms work well for guests, a home office, or hobbies. Step outside to your private pool overlooking the canal, the perfect spot to unwind and catch the breeze off the water. Tie up at your own dock, protected by a seawall, and cruise straight out to the Gulf of Mexico for fishing, sandbar days, and sunset rides. Boaters, kayakers, and anglers will love having the water right at their back door. You're minutes from Key Vista Nature Park, Anclote River Park, Gulf beaches, the historic Tarpon Springs Sponge Docks, and the shopping and dining along US-19. Clearwater, Tampa, and Tampa International Airport are an easy drive. Saltwater canal homes with a pool, dock, and Gulf access are hard to find. Schedule your private showing today.

2123 Bayou Drive, Holiday
Bluff Boulevard, Holiday
$133,500
Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
Rare opportunity in Bailey’s Bluff! Build your dream Florida home on this vacant lot surrounded by mature trees and established homes. Enjoy the added benefit of private boat ramp access from the road behind the property, making it easy to take advantage of the beautiful waterways and coastal lifestyle. A peaceful setting with a great sense of privacy, yet close to everything Holiday and the Gulf Coast have to offer. Bring your plans and make this special property your own! **Located between 3028 and 3038 Bluff Blvd**

Bluff Boulevard, Holiday
3143 Pineview Drive, Holiday
$1,265,000
4 Beds ⋅ 4 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
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.

3143 Pineview Drive, Holiday
2030 Gulfview Drive, Holiday
$774,900
2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
"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
3318 Pineview Drive, Holiday
$499,000
2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
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
2210 Bayou Drive, Holiday
$499,999
4 Beds ⋅ 3 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
Perfectly designed for family living and entertaining, this house boasts an array of features that cater to every need. The primary bedroom is a true retreat, featuring a whirlpool tub, a stand-up shower, and a vanity that all contribute to a spa-like atmosphere. The room is generously sized with vaulted ceilings, creating an airy and open feel. Additionally, a bonus room with slider doors and bay window provides direct access to the pool deck, making it perfect for unwinding after a long day. The dining room is a charming space with a built-in buffet and French doors that lead out to the pool deck, enhancing the indoor-outdoor flow. The kitchen is a chef's delight, equipped with ample cabinetry, all stainless-steel appliances, and granite countertops. An eat-in counter extends into the living area, which is adorned with more slider doors opening to the pool deck, perfect for seamless entertaining. Comfortable Bedrooms and Private Spaces, in addition to the primary suite, the house includes another bedroom with two closets and a private bathroom, offering privacy and convenience. The final oversized bedroom is located at the far end of the house, featuring two large closets and more sliders that lead to the pool deck. This bedroom is accompanied by a bathroom with a stand-up shower and an oversized bathtub. The backyard is an entertainer's paradise, fully fenced with an inground pool that is lanai covered, set on an oversized pool deck. It provides the perfect setting for hosting friends and family or enjoying a quiet evening by the water. Additional Features are High elevation ensures no past flooding, providing peace of mind. 2-car garage with a brand-new garage door opener for convenience. This house is conveniently located just minutes away from the Bailys Bluff community BOAT RAMP with Gulf access, a Clubhouse with beautiful Gulf views with access to set sail your Kayak.

2210 Bayou Drive, Holiday
000 Bluff Boulevard, 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
2138 Bayou Drive, Holiday
$775,000
4 Beds ⋅ 3 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
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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