Mid-Century Modern Gem in Highly Desired Pasadena!!! *** NOT IN FLOOD ZONE *** NO FLOODING *** NO WIND DAMAGE *** Discover the allure of this original 1966 MID-CENTURY MODERN POOL HOME nestled on an expansive CORNER LOT in the heart of Pasadena. Enjoy the charming RED BRICK STREETS lined with mature trees, leading you to a welcoming circular driveway that adds both convenience and character. With vintage MCM details that take you back in time, this property is a true architectural treasure. As you step inside the double door entry, the opaque frosted glass in the foyer creates an inviting atmosphere with an incredible view of the sparkling pool through the SUNKEN LIVING ROOM featuring pocket sliders that open all the way, connecting to the outdoor living space. Marvel at the intricate vintage details throughout, including a glitter ceiling and décor switch plates that adds an extra touch of MCM glamour. Boasting over 2,000 square feet, this home has a large primary bedroom that opens up to the pool, primary bath with a walk-in shower, dual vanities, and in true MCM style, natural light and indoor planters. This home features not one, but two, classic ORIGINAL TERRAZZO FLOOR colors in captivating black opal and classic white hues, every step tells a story of its rich history. This multi-functional floorplan has enough space to transition one of the guest bedrooms into a stylish home office offering the ideal work-from-home environment, and the living area off of the kitchen and dining room could be easily renovated into a second primary suite, perfect for multi-generational living. Sellers have the ORIGINAL PLANS for this home! The kitchen is an absolute delight for any Mid-Century Modern enthusiast, showcasing the original appliances, including a double oven, 36-inch cooktop and a 36-inch vent hood. As you entertain, the floorplan features LARGE WINDOWS and three sets of POCKET SLIDING GLASS DOORS that allow for abundant natural light and a serve as seamless transition between indoor and outdoor spaces, creating an open flow between the dining and living rooms and covered lanai and pool, enhancing the home's social atmosphere. The home also features a designated dining area, perfect for enjoying meals with family and friends in a spacious and inviting setting. Relax in the screened-in pool area surrounded by BRICK PAVERS and lush, tropical landscaping… a true retreat, offering ample space for you to relax and unwind, making it the perfect poolside sanctuary for morning coffee or happy hour after a long day. Perfectly situated close to the Pinellas Trail, downtown St Pete, Gulfport and is just minutes from the stunning Gulf beaches, this mid-century modern home offers the ideal balance of modern potential and historic charm. RECENT UPDATES: new roof with hurricane straps (2020), HVAC system (2022), 50-gallon water heater (2020) and Seller has clear 4-point (Sep 2022). With its spacious, versatile layout, and inviting outdoor living spaces, 500 Oleander Way S is truly the perfect place to call home. Don’t miss your chance to own a piece of paradise! Schedule your private tour today and experience the enchanting lifestyle that awaits!