Cobblestone Homes for Sale

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

Cobblestone – Winter Garden

Cobblestone is a gated single-family home community located off Roper Road, just east of Daniels Road in the central-north section of Winter Garden, Florida. Built mainly between 2006 and 2007 by KB Homes, Cobblestone offers contemporary, colonial, and traditional-style homes with spacious layouts and attractive architectural details.

The community is conveniently located near Winter Garden Village, providing shopping, dining, and entertainment. Residents also enjoy easy access to Hwy 50/Colonial Drive, connecting them to the Florida Turnpike, the 429 Expressway, Downtown Orlando, or Clermont.

Cobblestone Neighborhood Amenities

There is a mandatory HOA for Cobblestone, which includes:

  • • Sidewalks

Where Is Cobblestone in Winter Garden?

  • Cobblestone is located in the 34787 zip code, within the Central Winter Garden Village area of Winter Garden.
  • Neighborhood Borders:
  • North: Deerfield Place neighborhood

  • South: Regency Oaks neighborhood

  • East: Amberleigh neighborhood

  • West: Bradford Creek neighborhood

What’s Around & Nearby?

Grocery & Restaurants: West Point Commons

Shopping: Winter Garden Village

Hospital: AdventHealth Winter Garden

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 Cobblestone Home Features

Builder: KB Homes

Architectural Styles: Contemporary, Colonial, Traditional

Bedrooms: 3–5

Garage: 2–3 car garages

Living Area: Approximately 1,900–3,600 sq. ft.

Average Lot Size: Quarter-acre homesites

Interior Rooms & Features:

Attic

Ceiling fans

Eating space in kitchen

High ceilings

Kitchen/family room combo

Living room/dining room combo

Master bedroom (main floor)

Open floorplan

Split bedroom layout

Tray ceilings

Walk-in closets

Construction Material: Shingle

Roof: Shingle

Exterior Features: French doors, irrigation system, lighting, rain gutters. Some homes offer tree views or water views.

Thinking about a home in Cobblestone?

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

Winter Garden Village Area Neighborhoods

Country Lakes

Cypress Reserve

Daniels Landing

Deerfield Place

Emerald Ridge

Estates Lakeview Preserve

Foxcrest

Glynwood

Grove Park

Grovehurst

Hickory Hammock

Johns Lake Pointe

Lake Roberts Landing

Orange Cove

The Orchard

Oxford Chase

Regency Oaks

Reserve at Carriage Pointe

Roper Reserve

Sanctuary at Twin Waters

Southern Pines

Stone Creek

Stoneybrook West

Sunset Lakes

Tilden Place

Twinwaters

Waterside

Westfield Lakes

Windermere Crossing

Windward Cay

Wintermere Harbor

Wintermere Pointe

Woodbridge on the Green

Horizon West Area Neighborhoods

Avalon Cove

Cove At Hamlin

Del Webb Oasis (NEW)

Enclave at Hamlin

Encore at Ovation

Hamilton Gardens

Hamlin Reserve

Hawksmoor

Harvest at Ovation

Highland Ridge

Highlands Summerlake

Independence

Isles Of Lake Hancock

Lake Hancock Preserve

Lakeshore

Lakeside at Hamlin

Lakeview Pointe

Lakeview Preserve

Latham Park

Mezzano

Orchard Hills

Orchard Park

Osprey Ranch

Overlook At Hamlin

Panther View

Ravenna

Sanctuary at Hamlin

Storey Grove

Summerlake

Summerlake Groves

Waterleigh

Watermark

Westhaven Ovation

Wincey Groves

Winding Bay

Hamlin Pointe

Hamlin Ridge

Horizon Isle

Lake Star at Ovation

Northlake at Ovation

Parkview at Hamlin

Serenade at Ovation

Silverleaf Oaks

Silverleaf Reserve

Tribute at Ovation

Oakland Area Neighborhoods

Deer Island

Downtown Oakland

Hull Island

Johns Cove

Johns Landing

Lake Apopka Sound (NEW)

Longleaf at Oakland

Oakland Hills

Oakland Park

Oakland Trails

Trailside Station

Tucker Oaks

Verde Park

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