Introducing 2200 Bailey Ave, an exceptional 4 bedroom, 2.5 bath home nestled in popular Highland Park. Situated on a corner lot surrounded by mature trees, boasts remarkable curb appeal with an abundance of architectural charm in keeping with the Dutch Colonial Revival style. Steeped in Chattanooga history, this home was built around 1909/1910, although the exact construction date was partially affected by the courthouse fire in May 1910. It is thought to be the 1st home built on the block. Inside, you'll discover a world of early 1900's elegance with 10 ft ceilings, original hardwood floors, glass door knobs, solid wood doors, built-in pantry and original millwork, just to name a few. The main level features a spacious living room with fireplace, separate dining room with a stunning oversized wooden pocket door. The tastefully updated kitchen showcases modern stainless steel appliances, a subway tile backsplash, butcher block counters, and breakfast nook bathed in natural light. Ascending the staircase, you will find 3 generously sized bedrooms. The master suite is a true retreat, complete with renovated bathroom which features double sinks and walk-in shower. A unique sitting area within the master suite adds an extra touch of coziness. On the 3rd floor, a finished attic awaits which is perfect for a 4th bedroom, playroom, or home office. In addition to its charming interior, Bailey Avenue offers delightful outdoor spaces. An upstairs covered porch accessible by two sets of french doors, a welcoming front porch and a back deck all provide the perfect settings for enjoying fresh air and neighborhood charm. Noteworthy updates include new HVAC installed in 2022. The exterior has undergone significant improvements, with new HardiePlank siding, fresh paint, and added insulation for enhanced energy efficiency. The front porch decking and railings have been replaced and painted while the backyard has been transformed with the removal of several trees.