Cobblestone
Single-family homes · Built 2006 to 2007 · about 1,900 to 3,900+ sq ft
A gated, wooded neighborhood minutes from Winter Garden Village.
Cobblestone at a glance
Location: Roper Rd & Cobblestone Pointe Dr
Builder: Custom and individual builders
Built: 2006 to 2007
Homes: 84
Home types: Single-family homes
Size: About 1,900 to 3,900+ sq ft
Bedrooms: Varies by floor plan
Entry: Gated
Area: Stoneybrook & East Winter Garden
What Cobblestone has
What is close to Cobblestone
- West Point Commons Shopping Center with Publix Grocery ~1.5 mi
- Winter Garden Village Retail Shopping Center with Super Target ~1 mi
- Downtown Winter Garden ~2 mi
- West Orange Trail ~7 mi
Approximate distances from the community entrance. Walt Disney World is roughly 15 to 20 minutes away off-peak. SR 50, the 429 interchanges and Avalon Road back up at rush hour, so send me your work address and I will map your real commute.
Schools
🏫 Maxey Elementary
🏫 SunRidge Middle
🏫 West Orange High
Orange County Public Schools. Zoning changes, so verify every address.
Cobblestone market snapshot
Cobblestone had 3 closed sales in the last 12 months. That is too few for a median that means anything, so I price homes here one at a time.
Get the real numbers for Cobblestone
Call or text me at 407.502.4719 and I will send every recent closed sale in and around Cobblestone, straight from Stellar MLS, with what each one tells us about value.
Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 16, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.
Cobblestone homes for sale right now
Straight from Stellar MLS. Save the search and get new Cobblestone listings the day they hit.
Buying or selling in Cobblestone?
Pick your guide, tell me where to send it, and it opens right away.
🏡 Buyer Guide
How buying in Cobblestone works, from new construction versus resale to what to verify on HOA, CDD and school zoning.
🔑 Seller Guide
Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.
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If it did not open, use the buttons below. It is yours to keep.
Next step: book a 30 minute call and we will walk through it together for Cobblestone.
Cobblestone FAQ
Where is Cobblestone in Winter Garden?
Cobblestone is in east Winter Garden near Stoneybrook West, Daniels Road and Tilden Road, at Roper Rd & Cobblestone Pointe Dr.
How far is Cobblestone from Walt Disney World?
Roughly 15 to 20 minutes off-peak from this part of Winter Garden. I will map the exact drive from the entrance before you choose.
When were homes in Cobblestone built?
2006 to 2007. Most homes were built by individual or custom builders.
What amenities does Cobblestone have?
Gated Community, Community Pond, Woodlands.
Is Cobblestone a gated community?
Yes. Cobblestone has a gated entry. I confirm gate type and access rules for any home before you write an offer.
What schools serve Cobblestone?
Schools commonly listed for this community: Maxey Elementary, SunRidge Middle, West Orange High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.
Is Cobblestone inside Winter Garden city limits?
Many homes with a Winter Garden 34787 address, including much of Horizon West, sit in unincorporated Orange County rather than the City of Winter Garden. Taxes, utilities and services differ, so I confirm the jurisdiction for every address.
What do homes in Cobblestone sell for?
Too few homes sold in Cobblestone in the last 12 months for a reliable median. Call or text me at 407.502.4719 and I will send recent closed sales in and around Cobblestone from Stellar MLS.
Thinking about Cobblestone?
Give me 30 minutes and tell me your timeline. I will send back:
- Recent closed sales in Cobblestone, straight from Stellar MLS
- City or county, HOA and CDD for the homes that fit
- Your real commute, mapped from the entrance
No pressure. If you are selling a home somewhere else first, we will plan both sides together.
Semper Fi to your real estate needs. Jorge Martinez, REALTOR®
Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify city or county jurisdiction, school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.