Under contract-accepting backup offers. Historic Cherokee Park: This prime, “West of the Trail†property with oak-lined boulevard streets and decorative light posts is located near Southside Village. At 20 feet elevation, this property has NO HISTORY OF FLOODING. There is a low annual HOA and no CDD’s. Situated on a picturesque lot, this home with a guest house boasts privacy and tranquility; surrounded by mature landscaping that provides a serene oasis. Both the main house and guest house have brand new roofs with certified GAF 25-year warranties. The main house has three bedrooms with two and a half baths, while the guest house has one full bath and kitchenette; totaling 3,227 square feet. Entering the home through the gated flagstone courtyard, you will find the openness of the home with authentic Saltillo tile flooring. The master bath has travertine flooring, dual sinks on a granite countertop, an open travertine shower and a tub. The guest bath flooring has custom multicolor tiles; embracing the “vintage†feel. The kitchen has granite countertops with stainless steel appliances, including a French door refrigerator/freezer (2022), and combination microwave/air fryer/convection oven with a Bluetooth-communicating combination range/oven/convection oven (11/2023.) The guest house flooring is wood looking wide ceramic tile. Three wood burning fireplaces, (two in the main house and one in the guest house), have been restored and are fully functional. Ample storage space includes a large walk-in closet with built-ins in the master bedroom and four cedar closets. No need for gutter cleaning, as both houses have Leaf Filter screens that come with a lifetime warranty. The multi-zone irrigation system is controlled by an automated clock and recently converted to metered city water (5/2025) due to the original surface well going dry due to drought. In the tranquil backyard, the large brick paver patio features an arbor and a fountain. Prior to Hurricane Milton on October 9, 2024, there were cascading bougainvillea on the arbor which had to be pruned back. Along the fenced and stucco wall back yard perimeter, there were traveler’s palms and white birds of paradise that further obstructed views to surrounding properties and gave the backyard a more private, tropical feel. An additional bonus is the yard’s double gate that backs up to Harmony Lane for tree trimming and construction access. A new custom front door with glass insets and updated hardware was installed in 1/2025. The proximity of this home to downtown and the world renowned Siesta Key beaches makes it the perfect base for enjoying all that Sarasota has to offer. The holiday parties and social gatherings promote a sense of community. Don't miss the opportunity to own this exceptional property, where prime location, a spacious lot, and unparalleled privacy come together to create a truly magnificent living experience.