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1024 Kershaw Drive, 
Winter Garden, FL 34787

$949,900


4

Beds


4

Baths


2,461

Sq Ft


Single Family


Virtual Tour

Active

Listed by

Erin Tompkins

Last updated:

January 30, 2026, 06:24 PM

MLS#

O6375448

Source:

MFRMLS

Company Logo

About This Home

1024 Kershaw Drive

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.

Home Facts

Single Family

4 Baths

4 Bedrooms

Built in 2019

Price Summary

949,900

$385 per Sq. Ft.

MLS #:

O6375448

Last Updated:

January 30, 2026, 06:24 PM

Added:

5 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

3

Interior

Living Area:

2,461 Sq. Ft.


Structure

Structure

Building Area:

5,844 Sq. Ft.

Year Built:

2019


Lot

Lot Size (Sq. Ft):

5,850


Finances & Disclosures

Finances

Price:

$949,900

Price per Sq. Ft:

$385 per Sq. Ft.

1024 Kershaw Drive
MLS Logo
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.