Winter Oaks Homes for Sale

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Browse Winter Oaks Homes for Sale in Winter Garden, FL. Discover community amenities, nearby attractions, schools, and the lifestyle this neighborhood offers.

Winter Oaks – Winter Garden

Winter Oaks is a non-gated neighborhood of single-family homes located off West Story Road and South Plant Street, just west of South Park Avenue in the northern section of Winter Garden, Florida. Most homes in Winter Oaks were built between 2003 and 2005 by Greater Construction Corp, offering a mix of contemporary, traditional, and Florida-style designs in a charming, established community.

Downtown Winter Garden is just minutes away, with easy access to Plant Street’s restaurants, boutiques, Farmers Market, and local events. Nearby Hwy 50/Colonial Drive connects residents east to the Florida Turnpike, the 429 Expressway, and Downtown Orlando, or west toward Clermont.

Winter Oaks Neighborhood Amenities

There is a mandatory HOA for Winter Oaks, which helps maintain the neighborhood and includes:

  • • Golf carts allowed

  • • Irrigation – reclaimed water

  • • Park

  • • Playground

  • • Community pool

Where Is Winter Oaks in Winter Garden?

  • Winter Oaks is located in the 34787 zip code, within the Northern Original and Downtown Winter Garden area of Winter Garden.

    Neighborhood Borders:

North: Individual homes

South: Hyde Park neighborhood

East: Winter Garden community park

West: Individual homes

What’s Around & Nearby?

  • Grocery & Restaurants: West Point Commons & Downtown Winter Garden

  • Shopping: Winter Garden Village

  • Hospital: Orlando Health

  • Schools: Orange County “Find My School”

  • Attractions: Walt Disney World & Universal Studios

  • Outdoor Fun: The West Orange Trail

  • Local Hangout: Downtown Winter Garden

  • Closest Beach: Cocoa Beach

Typical Winter Oaks Home Features

  • Builder: Greater Construction Corp

  • Architectural Styles: Contemporary, Traditional, Florida

  • Bedrooms: 3–5

  • Garage: 2-car garages

  • Living Area: Approximately 1,600–3,100 sq. ft.

  • Average Lot Size: Zero-lot-line homesites

  • Interior Rooms: Family room, formal dining room (separate), formal living room (separate), inside utility

  • Construction Material: Shingle

  • Roof: Shingle

  • Exterior Features: Balcony, irrigation system, sidewalks, sliding doors, sprinkler metered; some homes offer park, city, or water views.

Thinking about a home in Winter Oaks?

Call or text the Jared Jones Real Estate Team at 407-706-5000 to learn more today!

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