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$949,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,461 Sq. Ft.
  • Updated 9 hours ago
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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.

Full Property Details for 1024 Kershaw Dr

General

  • Price: $949,900
  • HOA FEE: $208/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $6,141 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6375448
  • Updated: Today (1/30/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 12
  • Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fan(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
  • Appliances: Dishwasher, Disposal, Exhaust Fan, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater
  • Furnishings: Unfurnished
  • Flooring: Carpet, Engineered Hardwood, Laminate, Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Electric Dryer Hookup, Gas Dryer Hookup, Inside, Laundry Room, Washer Hookup

Additional Information

  • Shared Amenities: Clubhouse, Fence Restrictions, Park, Playground, Pool, Recreation Facilities, Trail(s), Vehicle Restrictions
  • Security/Safety: Security Lights, Security System, Smoke Detector(s)

Exterior

  • Exterior Features: French Doors, Irrigation System, Lighting, Other, Outdoor Grill, Private Entrance, Private Yard, Rain Gutters, Sidewalk, Sprinkler Metered
  • Deck/Patio: Covered, Front Porch, Patio, Porch, Rear Porch, Screened
  • Porch/Patio/Deck: Covered, Front Porch, Patio, Porch, Rear Porch, Screene

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Alley Access, Deeded, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Rear

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: OAKLAND PARK
  • Driving Directions: FROM HIGHWAY 50 (COLONIAL DRIVE), HEAD WEST ON COLONIAL DRIVE UNTIL YOU REACH TILDENVILLE SCHOOL ROAD (LIGHT), HEAD SOUTH ON TILDENVILLE SCHOOL ROAD, FOLLOW TO THE STOP SIGN WHICH IS CIVITAS WAY THEN HEAD WEST, TURN SOUTH ON LINEHART, TURN NORTH ON KERSHAW TO THE PROPERTY WHICH WILL BE ON YOUR RIGHT HAND SIDE.
  • Direction Faces: East

School Information

  • Elementary School: Tildenville Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Fishing, Lake, Water Access, Waterfront, Association Recreation - Owned, Clubhouse, Deed Restrictions, Dog Park, Golf Carts OK, Irrigation-Reclaimed Water, Park, Playground, Pool, Sidewalks
  • Optional Amenities: Clubhouse, Fence Restrictions, Park, Playground, Pool, Recreation Facilities, Trail(s), Vehicle Restriction
  • Association: Yes
  • Assoc. Name: ERIN LEWIS, LCAM
  • Assoc. Fees Include: Community Pool, Manager, Pool Maintenance, Recreational Facilities
  • Number of Pets: 10
  • Pet Restrictions: ALL PET RESTRICTIONS TO BE INDEPENDENTLY VERIFIED BY THE BUYER WITH THE GOVERNING AUTHORITIES WHICH MAY OR MAY NOT INCLUDE HOA, CITY AND / OR COUNTY.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water District: LAKE APOPKA, LAKE BRIM
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Cable Connected, Electricity Available, Electricity Connected, Natural Gas Available, Natural Gas Connected, Phone Available, Sewer Available, Sewer Connected, Spri

Structural Information

  • Builder: DAVID WEEKLEY
  • Exterior Const.: Block, Other, Wood Frame
  • Roof: Shingle
  • Windows: ENERGY STAR Qualified Windows, Low-Emissivity Windows, Shutters
  • Stories/Levels: Two
  • Square Feet: 2,461
  • Sq. Ft. Source: Appraiser
  • Year Built: 2019

Lot Features

  • Property View: Park/Greenbelt
  • Lot Size (Acres): 0.13
  • Lot Size (Sq. Ft.): 5,850
  • Lot Size: 5850
  • Lot Dimensions: 45 x 130
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Fenced, Vinyl

Water Features

  • Water Access: Yes
  • Water Access Desc: Lake
  • Water Extras: Yes
  • Water Front Name: LAKE APOPKA, LAKE BRIM
  • Water Front Desc.: Lake, Waterfront

Financial Considerations

  • Association Fee: $625
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $6,141
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: OAKLAND PARK UNIT 4A 87/105 LOT 376
  • Flood Zone Info: X
  • APN: 212227609803760
  • Property ID: 212227609803760
  • Block/Lot/Section: 21
Buyer's Brokerage Compensation: 2.5%
Not binding unless confirmed by separate agreement among applicable parties.

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— 1024 Kershaw Dr —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 1024 Kershaw Dr

School District:Orange County School District
NameGradesDistance
Tildenville Elementary School
1221 Brick Road, Winter Garden, FL 34787
PK-50.5 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-80.7 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-123.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1024 Kershaw Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/30/2026
Listed
$949,900
80.86%
MLS
2/22/2019
Sold
$525,200
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1024 Kershaw Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,835
—
$417,416
3%
2024
$5,835
4%
$405,652
3%
2023
$5,631
4%
$393,837
6%
2021
$5,393
-1%
$371,229
-3%
2022
$5,469
1%
$382,366
4%
2021
$5,393
265%
$366,104
266%
2019
$1,478
20%
$100,000
37%
2018
$1,231
5%
$73,000
4%
2017
$1,176
25%
$70,000
27%
2016
$944
—
$55,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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1024 Kershaw Drive, Winter Garden, FL 34787 (MLS# O6375448) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 1024 Kershaw Drive is currently listed for $949,900 and was received on January 30, 2026. This property is listed by Erin Tompkins, Realtor from our Winter Park Office.Want to learn more about 1024 Kershaw Drive? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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