Nestled in the heart of coveted Bungalow Hill and the sought-after Southside School district and WEST OF THE TRAIL, this charming 1935 cottage is the epitome of Old Florida charm. Situated on a 0.13-acre lot, this home seamlessly blends the intimacy of past home scale with modern comforts, making it an inviting space. As you step inside, the wood floors add character and warmth to the space. The living room, complete with a wood-burning fireplace, provides a cozy retreat for relaxation and entertainment. The adjacent dining area offers an intimate space for enjoying meals or hosting a party. The current kitchen features leather-finished stone countertops, stainless steel appliances, gas cooking and a rich stone backsplash. The versatility of the flex space off the kitchen is ideal for an additional family room, sitting area, reading nook or office. The tranquil primary suite boasts a vaulted ceiling and sliding glass doors that lead to the enchanting private backyard. Two closets provide ample storage including a walk-in closet with fully custom built-ins. The updated en-suite bathroom exudes charm featuring double vanities with granite countertops and a floor-to-ceiling tiled walk-in shower with frameless glass. With two additional bedrooms and a full bathroom, the home has plenty of space for guests or a growing family. A spacious laundry room with extra storage space makes household chores a breeze. Stepping into the backyard, a private heated in-ground cocktail pool awaits, providing the perfect spot to relax and unwind. Additionally, an air-conditioned cabana/studio or office space offers further flexibility. The secluded lush landscaping completely surrounds the property, creating a sense of privacy and serenity. Attached is a one-car enclosed carport. The metal roof was replaced in 2008 with a 20-year warranty. There are two well maintained A/C zones. Ideally located West of the Trail, this residence is within walking distance to Southside Village, renowned for its shops and restaurants, as well as beautiful Marie Selby Botanical Gardens and vibrant downtown Sarasota. Minutes from Sarasota Memorial Hospital and a brief drive to St. Armands Circle and the stunning beaches of Siesta Key and Lido, you will be in the most desirable lifestyle location in Sarasota. This adorable home in Bungalow Hill is a true gem for those seeking the quintessential West of the Trail lifestyle on Florida's Gulf Coast.