Experience timeless Olde Florida charm blended seamlessly with the refined coastal aesthetic of today in this beautifully curated cottage-style pool home. Situated on the desirable Woodside Avenue-just south of Thomasson and steps from Bayshore Drive-this property offers exceptional walkability to the Naples Botanical Gardens, making it a dream location for outdoor enthusiasts. A classic Southern-style front porch, complete with a charming porch swing and white picket fence, sets the tone for the warmth and character found inside. Thoughtfully designed landscaping enhances privacy while adding to the home's inviting curb appeal. Could be a great place to park money for investment purposes, as the sellers could have interest in renting it long term until they decide where they would like to go! Rare opportunity! Inside, an open-concept layout creates effortless flow between the living room, dining area, and chef-inspired kitchen-perfect for entertaining or relaxing with family and friends. The main level features a serene primary suite, a versatile office or fourth bedroom, a stylish powder room, and a spacious walk-in laundry room with valuable storage beneath the staircase. Upstairs, a Jack-and-Jill bedroom configuration (with one room currently serving as a second office) provides generous closet and storage space. Luxury vinyl flooring spans the entire home, complemented by custom detailing on the staircase for both beauty and durability. The garage has a private door and can be converted into a fabulous office space for 2, letting you use all the bedrooms, for well bedrooms. The pool area is a true highlight-this custom-designed above-ground “walk-in” pool eliminates the need for stairs and offers immediate access to a sun shelf for effortless enjoyment. An impact-glass banister adds a touch of modern elegance, while Azek decking and lush, low-maintenance landscaping create a private, resort-style retreat. The saltwater pool features both heating and cooling systems for year-round comfort. The property's outdoor layout has been carefully planned with functionality in mind, including a long brick-paved driveway that extends from the front to the rear of the home-ideal for additional secure parking, a boat, or a golf cart. A detached garage provides even more storage and flexibility to perhaps create your office space there vs in the office. Great use of space... Beautifully maintained, thoughtfully upgraded, and ideally located, this coastal cottage offers the perfect blend of character, comfort, and contemporary luxury.