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    Single Family Residence

    1024 KERSHAW DRIVE

    WINTER GARDEN, FL, 34787·OAKLAND PARK

    MLS# O6375448

    $925,700

    Listed at $949,900

    4

    Beds

    3.5

    Baths

    2,461

    Sq Ft

    Description

    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.

    Property Overview

    StatusClosed
    TypeSingle Family Residence
    Year Built2019
    CityWINTER GARDEN
    Area34787 - WINTER GARDEN
    SubdivisionOAKLAND PARK
    StateFL
    CountyOrange
    List Date01/30/2026
    MLS#O6375448
    List Price$949,900
    Sold Price$925,700

    Bedrooms & Bathrooms

    Bedrooms4
    Bathrooms3.5
    Full Bathrooms3
    Half Bathrooms1

    Structure

    Garage Capacity2
    ParkingAlley Access, Deeded, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Rear
    Construction MaterialsBlock, Other, Frame
    RoofShingle
    Foundation DetailsSlab
    FlooringCarpet, Hardwood, Laminate, Tile
    Private PoolNo
    BuilderDAVID WEEKLEY
    Patio & PorchCovered, Front Porch, Patio, Porch, Rear Porch, Screened

    Size & Lot

    Living Area2,461 sqft
    Lot Size5,850 sqft
    Acres0.13
    Lot DescriptionConservation Area, Greenbelt, Landscaped, Sidewalk, Paved
    Water FrontNo

    Utilities

    HeatingCentral, Electric
    CoolingCentral Air
    WaterPublic
    SewerPublic Sewer

    Additional Features

    Interior FeaturesBuilt-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Coffered Ceiling(s), Crown Molding, High Ceilings, In Wall Pest System, Open Floorplan, Other, Primary Bedroom Main Floor, Smart Home, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
    Exterior FeaturesFrench Doors, Lighting, Other, Outdoor Grill, Private Entrance, Private Yard, Rain Gutters, Sidewalk, Sprinkler Metered
    AppliancesDishwasher, Disposal, Exhaust Fan, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater

    Contact Agent

    Holiday Realty LLC

    Central Florida Real Estate Experts

    (800) 936-1754

    Our team typically responds within 1 hour during business hours.

    Neighborhood

    About OAKLAND PARK

    1024 KERSHAW DRIVE is located in the OAKLAND PARK community in WINTER GARDEN, FL. Part of Orange County.

    The OAKLAND PARK neighborhood offers convenient access to local schools, shopping, dining, parks, and major commute routes.

    HOA & Tax Information

    Annual Property Tax$6,141 (2025)

    HOA, Community & Pets

    HOA & Recurring Fees

    HOA Fee$625 / quarterly

    Ask About This Property

    Ask a question about this home and get quick, listing-based help from Holiday Realty.

    Answers are generated from listing data and may be incomplete — please verify details with a Holiday Realty agent.

    Listing courtesy of COLDWELL BANKER RESIDENTIAL RE · Erin Tompkins

    Properties displayed may be listed or sold by various participants in the MLS.

    Frequently Asked Questions

    What is the asking price for 1024 KERSHAW DRIVE?

    The listing price for 1024 KERSHAW DRIVE is $949,900.

    How many bedrooms and bathrooms does 1024 KERSHAW DRIVE have?

    This property features 4 bedrooms and 3 full bathrooms plus 1 half bath(s).

    What is the square footage of 1024 KERSHAW DRIVE?

    The living area is approximately 2,461 square feet.

    What community is 1024 KERSHAW DRIVE located in?

    This property is located in the OAKLAND PARK community in WINTER GARDEN, FL. The neighborhood offers convenient access to local schools, shopping, dining, and parks.

    When was 1024 KERSHAW DRIVE built?

    This property was built in 2019.

    What schools are near 1024 KERSHAW DRIVE?

    WINTER GARDEN is served by the Orange County Public Schools district. Contact us for details on nearby elementary, middle, and high schools, including ratings and enrollment information.

    How do I schedule a showing for 1024 KERSHAW DRIVE?

    You can schedule a private showing by clicking "Schedule a Showing" on this page or calling us at (800) 936-1754.

    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 2026-03-10. All data is obtained from various sources and may not have been verified by broker or MLS GRID.

    IDX information is provided exclusively for consumers' personal noncommercial use.

    © 2026 Stellar MLS. All rights reserved.