Rare gem in Sarasota's highly desirable Southgate neighborhood, East of the Trail. Just minutes from Siesta Key Beach, Lido Beach, St. Armands Circle, downtown Sarasota, and Sarasota Memorial Hospital, this 5-bedroom, 4-bathroom residence offers the perfect blend of space, flexibility, and long-term value. Situated on a private corner lot, the home provides versatile living space designed to support multigenerational living and generational wealth opportunities. Whether accommodating extended family, aging parents or long-term guests, the layout offers privacy, comfort, and independence under one roof. Enjoy two oversized driveways ideal for multiple vehicles, a boat and RV. The resort-style backyard features an Olympic-size, 8-foot-deep heated pool, recently resurfaced and surrounded by lush tropical landscaping, fruit trees, palms - perfect for gatherings that bring generations together. In-law suite with private entrance includes two master suites, a full kitchen, and laundry-an ideal setup for live-in relatives, or future income potential. Recent upgrades include a new roof (2022), new AC unit, two new water heaters, new pool water heater, fresh interior and exterior paint, modern lighting, granite countertops, all new appliances, pavers, fencing, gutters, and storage sheds, along with full replumbing and rewiring completed in 2012. No HOA and no flood zone. Fully fenced with room for a boat, RV. Close to historic Southside Elementary A-rated schools, beaches, dining, shopping, and cultural attractions. This is more than a home-it's a long-term lifestyle and legacy property, offering flexibility, privacy, and the opportunity to build multigenerational wealth in one of Sarasota's most desirable locations.