1024 KERSHAW DRIVE, Winter Garden, FL 34787

• 4 beds |
• 4 baths |
• 2,461 sqft

Property Description

Under contract-accepting backup offers. 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.

Listing Status:

Pending

Date Added:

January 30, 2026

Data Last Updated:

February 18, 2026 at 7:21AM

Listing Office:

COLDWELL BANKER RESIDENTIAL RE : 407-647-1211

Listing Agent:

Erin Tompkins : 321-231-2262

MLS ID:

O6375448

Interior

• General: Built-in FeaturesCathedral Ceiling(s)Ceiling Fans(s)Coffered Ceiling(s)Crown MoldingHigh CeilingsIn Wall Pest SystemOpen FloorplanOtherPrimary Bedroom Main FloorSmart HomeSolid Surface CountersSolid Wood CabinetsSplit BedroomStone CountersThermostatWalk-In Closet(s)Window Treatments
• Rooms: AtticBonus RoomDen/Library/OfficeFormal Dining Room SeparateFormal Living Room SeparateInside Utility
• Appliances: DishwasherDisposalExhaust FanGas Water HeaterMicrowaveRangeRange HoodRefrigeratorTankless Water Heater
• Laundry: Electric Dryer HookupGas Dryer HookupInsideLaundry RoomWasher Hookup
• Flooring: CarpetHardwoodLaminateTile
• A/C: Central Air
• Heating: CentralElectric

Exterior

• General: French DoorsLightingOtherOutdoor GrillPrivate EntrancePrivate YardRain GuttersSidewalkSprinkler Metered
• Other Structures: PorchFront PorchRear PorchScreenedPatioCovered
• Parking: Alley AccessDeededDrivewayElectric Vehicle Charging Station(s)Garage Door OpenerGarage Faces Rear

Construction

• Roofing: Shingle
• Windows: ENERGY STAR Qualified WindowsLow-Emissivity WindowsShutters
• General: BlockOtherFrameTwoSlab

Location

• Road/Access: AsphaltPaved
• HOA Amenities: ClubhouseFence RestrictionsParkPlaygroundPoolRecreation FacilitiesTrail(s)Vehicle RestrictionsPoolManagementRecreational Facilities625.0Quarterly
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: PUDOAKLAND PARK UNIT 4A 87/105 LOT 37621-22-27-6098-03-760
• View: Park/Greenbelt
• Fencing: FencedVinyl

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableCable ConnectedElectricity AvailableElectricity ConnectedNatural Gas AvailableNatural Gas ConnectedPhone AvailableSewer AvailableSewer ConnectedSprinkler MeterUnderground UtilitiesWater AvailableWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple