Baileys Bluff Estates Homes with Shingle Roof

Baileys Bluff Estates Homes with Shingle Roof

Welcome to Baileys Bluff Estates, a hidden gem nestled in the heart of Holiday, Florida, within the picturesque Pasco County. This charming subdivision is a perfect blend of serene living and vibrant community spirit, making it an ideal place for families, retirees, and anyone looking to enjoy the Florida lifestyle.

Baileys Bluff Estates showcases a variety of beautifully designed homes, each featuring classic shingle roofs that not only enhance their curb appeal but also provide durability and protection against Florida's elements. The homes here are thoughtfully crafted, offering spacious layouts that cater to modern living while maintaining a warm, welcoming atmosphere. With lush landscaping and well-maintained streets, the neighborhood exudes a sense of pride and community.

Residents of Baileys Bluff Estates enjoy the convenience of being close to local amenities, including shopping centers, dining options, and recreational facilities. The nearby Gulf Coast offers stunning beaches and outdoor activities, perfect for those who love to soak up the sun or explore nature. Whether you’re taking a leisurely stroll along the coastline or enjoying a day of fishing, the natural beauty surrounding this area is truly captivating.

In addition to the appealing homes and convenient location, Baileys Bluff Estates fosters a strong sense of community, with neighbors often coming together for events and gatherings. It’s a place where you can feel at home, surrounded by friendly faces and a supportive environment.

Explore the possibilities that await you in Baileys Bluff Estates, where your dream home and a vibrant lifestyle are just a doorstep away!

Newest Baileys Bluff Estates Homes with Shingle Roof

$799,000
2 Beds ⋅ 2 Baths ⋅ W7888180 MLS
"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
$509,000
2 Beds ⋅ 2 Baths ⋅ W7887224 MLS
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
$499,999
4 Beds ⋅ 3 Baths ⋅ TB8518437 MLS
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
$825,000
3 Beds ⋅ 3 Baths ⋅ TB8469784 MLS
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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