The Cobblestone Estate - Historic Downtown Ocala!

A beloved piece of Ocala history, The Cobblestone is a one-of-a-kind luxury home where original architecture, local art and timeless character come together. Set beneath magnificent old trees in one of Ocala’s most beautifully preserved historic neighborhoods, it’s just minutes from Downtown Square. From gracious landscaping to magical fall and Christmas streets, this is Ocala charm at its finest.

Where old Ocala charm, gracious living and a little bit of magic come together!

Welcome to The Cobblestone, a remarkable historic luxury home tucked within one of Ocala’s most beautiful and lovingly maintained historic neighborhoods.

Rich in character and architectural detail, The Cobblestone offers the rare opportunity to experience a piece of Ocala’s history while enjoying the comfort and elegance of a thoughtfully curated stay. Original architectural features have been preserved throughout the home, giving each room a sense of history and individuality that simply cannot be recreated. Local artwork fills the spaces, celebrating Ocala’s culture, creativity, and unmistakable sense of place.

Outside, mature trees create a beautiful canopy over the neighborhood’s historic streets, where distinctive homes, established landscaping, and carefully maintained gardens make even an evening walk feel special. The setting changes beautifully with the seasons. In autumn, the neighborhood embraces the warmth and charm of fall, while Christmas brings beautifully decorated homes and streets that make the area especially magical during the holidays.

And while The Cobblestone feels tucked away in a gracious historic setting, its location is exceptionally convenient. Downtown Ocala Square is just minutes away, putting locally loved restaurants, boutiques, coffee shops, entertainment, and downtown events within easy reach.

Whether you`re visiting Ocala for an equestrian event, a romantic escape, a family gathering, the holidays, or simply a few days away, The Cobblestone offers something beyond an ordinary vacation rental. It is a home with history, character, art, and a genuine connection to the community surrounding it.

From the original architecture and locally curated artwork to the grand trees and beautifully landscaped surroundings, every part of the experience feels distinctly Ocala.

Historic character. Refined comfort. An exceptional location.

The Cobblestone is a timeless Ocala stay for every season.

Not suitable for children or infants due to the historic nature of the home, original architecture, delicate artwork, stairs, and features that have not been childproofed.

Please note, the pond is not accessible to guests; however, its beautiful oak-lined views can be enjoyed from your room, windows and porches.

The access to the home is on the 11th street side, lockbox located on the doors.

Please only use the 11th street parking . There is an asphalt parking pad.



Please note that The Cobblestone is a two-story home and is not suitable for children or pets. One bedroom and full bath are conveniently located on the first floor. The beautiful cobblestone lanai shown in the photos is fully enclosed and climate-controlled for year-round enjoyment. The entire property is strictly non-smoking. Guests may enjoy the picturesque oak-lined pond views from the home’s windows and porches; however, there is no guest access to the pond.
The Cobblestone is an adults-only property. We are unable to accommodate children or pets. Thank you for understanding and helping us preserve the peaceful atmosphere and special character of this historic home.


Please be mindful that the art, architecture and many custom details throughout The Cobblestone are very special and dear to our hearts. We want you to enjoy and appreciate them during your stay!

As with any historic home, you may notice a few imperfections here and there. We believe they’re part of its story—and simply add to the beauty, character and charm that make this home so special. ♡