Welcome to 16239 Hillside Circle in Montverde, a beautifully updated property offering the perfect blend of modern upgrades, thoughtful improvements, and dual-living flexibility with a main home and private apartment on the same floor. Situated on a private, fenced lot with mature landscaping and a full irrigation system, this multi-family gem spans 2,756 square feet and is move-in ready with all major systems already updated. The home features luxury vinyl plank flooring installed in 2021, a 2017 roof with transferrable warranty through 2037, double-hung windows added in 2022, and new sliding glass doors and gutters in 2019. Both the main house and apartment have their own air conditioning systems (2015 and 2017) with warranty coverage through 2027, complemented by a mini-split A/C in the fully finished garage which also boasts epoxy flooring and an upgraded insulated garage door installed in 2017. Additional enhancements include two hot water heaters (2017), a whole-house water softener and dual Culligan reverse osmosis systems, lightning rods (2018), a privacy fence (2017), an 8x12 shed (2018), and a new exterior door for the apartment in 2022. The property is uniquely equipped with two septic systems, both pumped in 2021, ensuring convenience and peace of mind for multi-generational living or rental potential. Appliances convey with the sale, including a GE washer (2022), Speed Queen dryer (2016), Whirlpool dishwasher (2019), Samsung refrigerator and stove/oven (2019) in the main house, KitchenAid refrigerator and GE stove/oven in the apartment, along with two microwaves. With all major systems, appliances, and structural elements modernized, this home delivers worry-free living and versatile dual-family functionality. This rare Montverde opportunity is now fully upgraded and ready for its next chapter. Lake access within walking distance to Lake Florence creates a wonderful setting and close proximity to Montverde Academy adds an excellent option for education.