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Baileys Bluff, Holiday, FL – Homes for Sale

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About Baileys Bluff, Holiday, FL

If you’re looking for a beach community in Florida where you enjoy the glassy waters and enjoy the breathtaking trails nearby, look no further than Baily’s bluff. Living in a coastal neighborhood with waterfront access is a unique experience that many won’t be able to fathom.

Unlike most coastal communities, Baileys Bluff is quite secluded, located on the tips of Sand Bay in Holiday, Florida, near the coveted Key Vista Nature Park.

Housing here is pricey but offers a variety of amenities that make it worth it. Living in Baileys Bluff is perfect for beach bums, outdoor enthusiasts, and anyone looking to live a peaceful lifestyle away from the crowded city.

Housing Market in Baileys Bluff

These multi-room single-family residences for sale feature garages with up to two cars, and many have waterfront views.

Some properties have tropical landscapes that include private beaches and citrus trees. In addition, some of the higher-end homes for sale in Baileys Bluff include wide-open living and dining areas, vaulted ceilings, stainless steel appliances, and even hurricane shutters.

Living in such a dreamlike neighborhood does come with a cost. Many of the homes for sale are priced between $450,000 to $567,000. However, you’re getting up to 2,500 square feet and plenty of lot space. Also, these homes offer two to four bedrooms and up to 3 bathrooms. These properties sit on a private cul-de-sac with plenty of fully-grown trees, nicely manicured landscaping, and multiple-car garages.

On the inside, you can expect luxurious amenities such as high-end stainless steel appliances and cabinetry, granite countertops, and sliding doors to the patio and pool area. Most houses will have high-trey ceilings, walk-in closets, dual vanities in the bathroom, and cozy living space.

The neighborhood has walking trails that lead out to several beaches, parks, fishing piers, kayak trails, a recreation center, and a dog park.

Location & Accessibility

This tranquil and peaceful community of Baileys Bluff is located next to Key Vista Nature Park and nearby many entertainment and shopping facilities in the area. The houses are also located just minutes away from various hiking trails and the J. Bell Harrill Recreation Complex.

The best shopping areas are located down south to Tarpon Springs, where you’ll find unique Greek-inspired sponges and other souvenirs. However, for more casual shopping, there’s the Holiday mall, which is a standard shopping mall with local service providers, and clothing retailers.


As a resident of Baileys Bluff, you can truly appreciate the beauty of Key Vista Nature Park. This is a popular park for its scenic hiking trails that lead to beautiful creeks, forested areas, and white-sand beaches. You may also traverse the trail to Rocky Creek, where you’ll land on the Gulf of Mexico’s shorelines, the Anclote Gulf Park, and the salt marsh.

If you’re looking for a fun date night or outing with your buddies, we recommend grabbing some refreshing drinks and delicious food at Miss Vicki’s on the River Restaurant. This local outdoor hotspot is next to the Anclote River Park around the Anclote Village marina on Baillies Bluff Rd. It’s the perfect restaurant to unwind after a long week and watch the beautiful Florida sunset. You won’t regret ordering their delicious food ideas, from seafood and steaks to sandwiches and burgers.


Choosing the right school for your kids can be a major factor when deciding where to live. Fortunately, there are some prominent public schools less than ten minutes away from Bailey’s Bluff. You won’t have to sit in long hours of traffic to drop off and pick up your kids from school. Some of the most notable schools nearby are:

  • Gulf Trace Elementary School
  • Gulfside Elementary School
  • Paul R. Smith Middle School
  • Anclote High School
  • Web of Wisdom WOW School
  • Raintree Christian Academy

Bailey’s Bluff – A Secluded Paradise in Holiday, Florida

Bailey’s Bluff is truly a paradise. Everywhere you turn, you’ll find a wall of uniquely designed multi-story waterfront properties overlooking the Gulf of Mexico. There is uniquely designed tropical landscaping, such as citrus trees, palm trees, and other beautiful greenery.

If you enjoy the beaches, hiking trails, parks, and the smell of the ocean, there’s no doubt that Baileys Bluff is the right neighborhood in Holiday for you.