One or more photo(s) has been virtually staged. If you are looking for a multi-family sanctuary, that offers everyone privacy and security, while also offering plenty of outdoor space to gather, this is the opportunity for you! This historic property offers a Spanish style main house with 3 additional private residences (casitas), all fully fenced with a courtyard and salt water lap pool on a triple lot in Winter Park. The pavered front porch welcomes you home, and the minute you step through the front door, you will realize that you have walked into something truly unique and special. This light and bright historic 2 bedroom, 2 bathroom main house has been lovingly renovated, with beautifully refinished hardwood floors, freshly painted interior and exterior walls and trim, new HVAC, new Renewal by Andersen windows, arched doorways and decorative wall sconces. The formal living room and dining room feature a wall of windows, and gas fireplaces in each room. The spacious kitchen is waiting for your personal touches, and features views of the pool, new appliances, a breakfast bar, plenty of cabinet and storage space and looks out over the great room leading out to the back porch. There is a bedroom downstairs along with a brand new, beautifully upgraded full bathroom.Take the staircase to the second floor to the large owner’s suite, featuring another gas fireplace, a fully upgraded ensuite bath, walk-in closet, a turret, which creates the perfect office / sitting space, and roof top access for tree lined, neighborhood views. This home also offers a rarity in Florida, a basement, providing for additional storage. Outside you will find a fully fenced yard that includes a saltwater pool with a new custom deck and landscaping, and a private courtyard with the 3 casitas on the perimeter. Each casita has its own character; there’s a studio apt with an updated kitchenette and renovated full bath with a screened porch with views of the pool. A fully renovated 1 bedroom, 1 bath apartment with an upgraded kitchen and living room area, and a 2 story apartment with 1 bedroom,1 bathroom, an upgraded kitchenette and a spiral staircase. You are situated on a triple lot (140 x 150) creating ½ acres of living space, with a large circular drive, for easy entry onto Orange Ave, and have plenty of room for parking. The courtyard can also be converted back into a 2 car carport, or you could potentially build a carport or garage on another part of the property, if needed. There is plenty of room to expand. This home is located in the Winter park “silent zone” so although you are close to the train, you will never hear any horns. You are a short walk or bike ride to plenty of shops and restaurants, and centrally located, with a short drive to all major roadways.