Baileys Bluff Estates Homes for Sale

Baileys Bluff Estates Homes for Sale

Welcome to Baileys Bluff Estates, a hidden gem nestled in the heart of Holiday, Florida. This charming subdivision offers a unique blend of tranquility and modern living, making it an ideal destination for families, retirees, and anyone seeking a peaceful lifestyle under the sun. With its picturesque surroundings and friendly community, Baileys Bluff Estates is a place where neighbors become friends and memories are made.

The homes for sale in Baileys Bluff Estates are as diverse as the residents who call it home. From cozy single-family residences to spacious layouts perfect for entertaining, each property is designed with comfort and style in mind. Many of these homes boast beautiful landscaping, inviting outdoor spaces, and modern amenities that cater to today’s lifestyle. Whether you're looking for a charming bungalow or a contemporary retreat, you’re sure to find a home that suits your needs.

Located in Pasco County, Baileys Bluff Estates is just a stone's throw away from stunning Gulf Coast beaches, vibrant parks, and a variety of shopping and dining options. Enjoy the convenience of nearby schools, medical facilities, and recreational activities that make life in this community both enjoyable and fulfilling.

If you're ready to discover your dream home in Baileys Bluff Estates, now is the perfect time to explore the listings available. Embrace the Florida lifestyle and make this welcoming community your own. Come and see why Baileys Bluff Estates is the perfect place to call home!

Newest Baileys Bluff Estates Homes for Sale

$849,900
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
$525,000
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
$549,000
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
$1,859,900
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
$825,000
3 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
Start Your Search