Welcome to 185 Oakley Rd, a stunning oversized two-family home brimming with character and investment potential. Perfectly positioned on a coveted corner lot in Payson Park across from the middle school, this expansive property seamlessly blends timeless charm with modern convenience. Inside, both units boast soaring ceilings, French doors, elegant moldings, and abundant natural light that fills the bright, sun-drenched rooms. Unit 1 features 3 bedrooms, 1 bath, and an updated kitchen, while Unit 2 spans two levels with 4 bedrooms, 1.5 baths, and breathtaking Boston views from the third floor. Both units offer expansive living and dining areas, a sunroom perfect for a home office, and beautiful hardwood floors throughout. Recent upgrades include brand-new water heaters for both units, a new boiler, fresh paint, and refinished floors in Unit 2. A two-car attached garage plus two driveway spaces provide ample parking. With 15 spacious rooms and flexible living spaces, this home is ideal.