Welcome to this rarely available Cape Cod style residence, a masterfully renovated home situated on an expansive 20,000 sq. ft. lot in Sarasotas prestigious Cherokee Park. Perched 23 feet above sea level and nestled on a quiet extra wide tree lined street with sidewalks in one of the areas most coveted West of Trail neighborhoods in the top rated Southside school district. This 4 bedroom, 3 full/2 half bathroom home blends timeless charm with luxurious, designer curated updates. Combining durability and sophistication, the home boasts all impact windows and doors, new Hardy Board siding and cedar shake roof, and features high end finishes throughout thoughtfully modernized by designer Chelsea Dunbar from Blu Interiors where every detail has been considered. The custom handcrafted, glass inlaid, iron double front doors welcome you to the warm and inviting interior which showcases original wood flooring in the main home, Italian porcelain tile in the guest house, soaring 10 foot ceilings in the living room, and designer lighting from Arteriors, Eichholtz, and Kelly Wearstler. The heart of the home is the quartz clad kitchen, outfitted with a Wolf natural gas range, KitchenAid French door refrigerator, and ample pantry spaceideal for everyday living or entertaining. Anchored by a wood burning fireplace, the main living and dining areas flow seamlessly to the outdoors, where a lush, low maintenance Astroturf lawn, Pennsylvania bluestone slate patio, and expansive wrap around Brazilian teak deck create the perfect setting for year round enjoyment. The serene primary suite features three gorgeous custom designed walk in closets, and a spa like bathroom with marble finishes, and a zero entry shower with body sprays. Throughout the home, custom wallpaper by Phillip Jeffries, Scalamandr, and litis adds layers of sophistication and style. Additional thoughtful upgrades include: surround sound system, six climate zones, a security system, and three laundry areas. The propertys resort style amenities continue with a large, 9' deep pool framed by classic Bevolo gas lanterns and an impressive luxury guest house built in 2016. This beautifully designed space includes an entertaining area with custom built ins including full bar, dishwasher, refrigerator drawers and Scotsman icemaker, private guest suite,1.5 baths, outdoor teak shower, and gym. The fully equipped outdoor kitchen includes a natural gas Lynx grill, an extra large Green Egg, generous quartzite prep counters, and covered gazebo making it the perfect setting for al fresco dining and entertaining. Completing the fully fenced estate is an oversized 2.5 car detached garage, providing ample storage and convenience. No flood insurance is required, thanks to the homes elevation at 23 feet above sea level. Take a short walk or golf cart ride to the highly desirable Southside Villageone of Sarasotas most sought after town centers known for its charming, walkable atmosphere and vibrant energy. This premier area blends historic charm with modern convenience. Enjoy tree lined streets, a true sense of community, and close proximity to Mortons Gourmet Market, boutique shops, sidewalk cafs, and top rated local restaurants. Dont miss this extraordinary opportunity to own a legacy property in one of Sarasotas most beloved neighborhoods just minutes to world renowned Siesta Key Beach, downtown Sarasota & cultural venuesthis is Gulf Coast living at its best.