First Time Ever Offered by the Original Owners! Welcome to one of Sarasota's hidden gems-Oakleaf, a private enclave of custom homes tucked beneath mature oak trees just off Proctor Road. Lovingly maintained by the original owners since it was built, this exceptional custom Pruett-built residence showcases timeless craftsmanship, quality construction, and the pride of ownership that only comes from meticulous care over the years. This true 4-bedroom, 3-bathroom, 3-car garage pool home offers the spacious floor plan today's families are searching for. Unlike many homes that count an office or den as a fourth bedroom, this home features four genuine bedrooms along with generous living spaces designed for everyday comfort and effortless entertaining. Step outside to your own private Florida retreat where an oversized resort-style swimming pool and spa have been beautifully resurfaced and are surrounded by an elegant travertine pool deck, creating the perfect setting for relaxing weekends, family gatherings, and year-round outdoor living. The mature preserve behind the home provides exceptional privacy while lush tropical landscaping creates outstanding curb appeal from the moment you arrive. Major improvements have already been completed, allowing the next owner to simply move in and enjoy. Recent updates include a **new barrel tile roof (2022), resurfaced pool and spa with travertine pool deck (2022), fresh interior and exterior paint, new HVAC system (2025), and water heater (2021). This home truly reflects decades of careful maintenance and thoughtful investment. Oakleaf remains one of Sarasota's most desirable established communities, offering larger homesites, mature tree-lined streets, sidewalks, low HOA fees, and a peaceful neighborhood atmosphere that's increasingly difficult to find in newer developments. The location is second to none-just minutes to Siesta Key Beach, Lido Key, Downtown Sarasota, St. Armands Circle, UTC Mall, Interstate 75, Legacy Trail, Nathan Benderson Park, championship golf courses, waterfront dining, shopping, fitness centers, and countless restaurants. Healthcare is equally convenient with both Sarasota Memorial Hospital and Doctors Hospital of Sarasota just a short drive away, making this an outstanding location. Families will appreciate the home's proximity to Ashton Elementary School, Sarasota Middle School, and Sarasota High School (buyer to verify current school assignments), as well as several highly regarded private schools nearby including The Out-of-Door Academy, NewGate School, Sarasota Christian School, Classical Academy, and Sarasota Military Academy, offering exceptional educational opportunities from preschool through high school. If you've been searching for a move-in ready Sarasota pool home, 4-bedroom home in Sarasota, custom home near Siesta Key, family home with a private preserve view, or a centrally located Sarasota home close to beaches, shopping, dining, hospitals, and top schools, this is the opportunity you've been waiting for. Homes of this caliber, in this location, and with this level of care rarely become available. Already generating significant pre-market interest, this exceptional Oakleaf residence is not expected to remain on the market for long. Schedule your private showing today and discover why so many buyers have been waiting for a home exactly like this.