1024 Kershaw Drive Winter Garden, FL 34787

Welcome to Oakland Park, where nature and architectural charm collide creating a colorful canvas that looks like majestic live oak trees, shady front porches, grassy open spaces and breathtaking golden hours. This Florida Vernacular two story home is nestled in the heart of 258 acres and overlooks a Conservation Green Space. This Shoreline B was constructed by David Weekley and is occupied by the original owners. The floor plan delivers 4 Bedrooms with the Primary Bedroom location on level one, Private Office, Dining Room with Custom Built-In Features, Gourmet Kitchen with Stainless Steel Appliances, Backsplash, Farmhouse Sink, Designer Upgrades and Quartz Counters, Living Room with Custom Shiplap accent wall, Laundry Room with Built In Cabinets and a Spacious Bonus Room. All additional Bedrooms and Bonus Room are located on level two. Bedroom Two and Three have optimal privacy with En-Suite Bathrooms. Bedroom Four is currently being used as a home exercise platform, it has a closet. The Primary Bedroom was thoughtfully designed with Coffer Ceilings, Custom Walk-In Closet and an En-Suite Bathroom with Dual Sinks, Quartz Counters, A bathtub worthy of a Lush Bathbomb and Large seperate shower. Throughout the home you will find Plantation Shutters, Upgraded Interior Lighting, Designer Mirrors and Fans, Built-In and thoughtful Features such as Coat Closet, Drop Spot with Benches and organization System. A full exterior painting and sealing was performed in 2025. Enjoy a cozy screened porch that overlooks a fenced yard with fresh sod, Einstien Lighting and BBQ grill. The alleyway detached garage includes a 40 amp circuit and receptacle for a Tesla charger, Garage shelving, Cabinets and Refrigerator. The Hoa covers all the main areas of Oakland Park, Green Spaces, Parks, Clubhouse, Trails, Fields, Pathways, Playgrounds 2 Pool and Amenities. Each homeowner is responsible for maintaining their property. All mechanicals are 2019. On the shore of Lake Brim, the West Orange Trail entices residents to explore the outdoors—walk, jog, bike, skate or take a drive in a golf cart. There are 22 miles of walkways, trails and preserved wetlands that connect residents to nature, local shopping (including the nationally heralded Farmers Market), dining, culture and entertainment in charming Winter Garden. I invite you to take a moment on our front porch and believe that a dream can turn into reality.