Welcome to this rarely available Cape Codstyle residence, comprised of a masterfully renovated main house and separate luxe guest house poised on an expansive 20,000 sq. ft. lot in Sarasotas prestigious Cherokee Park. Elevated 23 feet above sea level and nestled on a wide, tree lined street in the coveted West of Trail districtwithin the top rated Southside school zonethis 4 bedroom, 3 full/2 half bath +office private compound blends timeless architecture with designer curated sophistication. A stately front porch framed by lush landscaping and classic brick walkway introduces the home with understated grandeur. Handcrafted, glass inlaid iron double doors open to a refined foyer where natural light, elegant millwork, and soaring 10 foot ceilings set the tone for the bespoke interiors beyond. Inside, original hardwood floors, designer lighting by Arteriors, Eichholtz, and Kelly Wearstler, and high end finishes selected by Chelsea Dunbar of Blu Interiors create a sense of warmth and refinement throughout. The quartz clad chefs kitchen is as functional as it is beautiful, featuring a Wolf natural gas range, KitchenAid French door refrigerator, ample pantry space, and custom cabinetryperfectly suited for both intimate dining and entertaining. Anchored by a wood burning fireplace, the main living and dining spaces flow seamlessly outdoors to an inviting Pennsylvania bluestone patio, low maintenance Astroturf lawn, and wrap around Brazilian teak deckan idyllic setting for year round enjoyment. The serene first floor primary suite is a private retreat showcasing three custom designed walk in closets and a spa inspired bath with marble finishes, dual vanities, heated towel bar, and a zero entry shower with body sprays. Ascend the custom staircase to find 2 tailored guest retreats with spa like bath, each offering serene views and thoughtfully appointed details for ultimate comfort and privacy. Throughout the home, custom wallcoverings by Phillip Jeffries, Scalamandr, and litis add layers of texture and artistry, while upgraded systemsincluding a surround sound system, six climate zones, and multiple laundry areasenhance everyday comfort. Resort style living continues outdoors with a 9 foot deep pool framed by classic Bevolo gas lanterns and an extraordinary luxury guest house built in 2016. This refined space includes an entertaining area with custom built ins, full bar, refrigerator drawers, Scotsman icemaker, private guest suite, 1.5 baths, gym, and an outdoor teak shower. The fully equipped outdoor kitchen features a natural gas Lynx grill, XL Green Egg, quartzite prep counters, and a covered gazebo ideal for al fresco dining. All impact doors and windows, cedar shake roof, and Hardie Board siding add to the beauty and durability of the home. Completing this exceptional estate is an oversized 2.5 car detached garage and secure, fully fenced grounds with electric fence. Enjoy tree lined streets with sidewalks and a true sense of community, all just a short stroll or golf cart ride to Southside Village where residents enjoy boutique shops, Mortons Gourmet Market, cafs, and top rated restaurants, and minutes from downtown Sarasota and Siesta Key Beach. This is refined Gulf Coast livingwhere timeless architecture meets effortless luxury in one of Sarasotas most treasured neighborhoods.