*Seller is willing to give concessions towards closing costs!* Charming Renovated Home in the Heart of Historic Oakland! Welcome to 309 W Oakland Avenue, nestled in the storybook town of Oakland, which is celebrated for its Hallmark-like charm and strong sense of community. Located in the desirable 34760 zip code, this beautifully updated two-story home offers just under 2,400 square feet of thoughtfully designed living space with NO HOA restrictions! COMPLETELY RENOVATED IN 2020, upgrades include new dual A/C units, LVP flooring throughout the main floor, 42†kitchen cabinets with under cabinet lighting, Whirlpool appliances, granite countertops, fresh interior paint, and elegant crown molding throughout. The staircase and upstairs flooring were upgraded to LVP in 2024. Upon entry, you're greeted by a staircase with solid wood handrails and wrought iron detailing, adjacent to formal living/dinging room with soaring 30’ ceilings and abundant natural light. The open-concept kitchen and family room create the perfect gathering space, and a main-level bedroom with separate full bath offers flexibility as a guest suite or private office. Upstairs, the primary suite is a true retreat, complete with a walk-in closet, spa-like bathroom featuring a freestanding garden tub, an attached laundry room, and two additional bedrooms with a separate full bath. Enjoy outdoor living in the fully fenced backyard with a paver patio (2023), new sod (2024), storage shed, and ample space for pets, play, and entertaining. The driveway also offers an additional parking pad (2024), allowing space for 3+ vehicles in total. Residents of the 34760 zip code enjoy the unique charm of mail pickup at the historic Oakland Post Office, where you’ll also find the latest issue of the Orange Observer and a quaint Little Free Library out front. Oakland also hosts a variety of beloved community events, including Heritage Day, Santa meet-and-greets, Easter egg drops, and weekly farmers markets in-front of the Heritage Center, an ever changing art gala. The town is a scenic rest stop along the West Orange Bike Trail and is home to numerous parks and landmarks. Speer Park features two playgrounds, tennis, pickleball, and basketball courts. The Jake Voss public fishing pier provides a peaceful spot for watching sunsets on Lake Apopka. Prairie House Coffee serves local coffee, baked goods, floral arrangements, and gifts inside a charming 1860s residence. Disney enthusiasts will love Recycling the Magic, which offers an eclectic shopping experience filled with Walt Disney World props, resort decor, and memorabilia. Just 3.5 blocks from the upcoming boutique district at 300 S. Tubb Street, this location offers walkability to a future hub of shopping, dining, and community spaces—modeled after Winter Garden’s beloved Plant Street. Nearby, luxury estate communities like Briley Farm and The Grove are bringing multi-million-dollar homes to Oakland, setting the stage for strong equity growth. This is your chance to own a move-in ready gem in Oakland, call today to set up your exclusive showing!