Oakland Pointe
Single-family homes · Built 1996 to 2021, mostly 1998 to 2003 · about 1,800 to 3,100 sq ft
One quiet circle of homes with real yards.
Oakland Pointe at a glance
Location: Oakland Pointe Circle, inside the Town of Oakland (34760)
Builder: Custom and individual builders
Built: 1996 to 2021, mostly 1998 to 2003
Homes: About 31 homes
Home types: Single-family homes
Size: About 1,800 to 3,100 sq ft
Bedrooms: 3 to 4 bedrooms
Area: Historic Town Center
What Oakland Pointe has
What is close to Oakland Pointe
- West Orange Trail ~1 mi
- Oakland Nature Preserve ~1 mi
- Historic Downtown Winter Garden ~3.5 mi
- Florida's Turnpike at SR 50 ~2.5 mi
Approximate distances from the community entrance. Walt Disney World is roughly about 25 minutes away off-peak. SR 50 and the Turnpike interchange back up at rush hour, so send me your work address and I will map your real commute.
Schools
🏫 Oakland Avenue Charter School (K to 5, enrollment rules apply)
🏫 Tildenville Elementary
🏫 Lakeview Middle
🏫 West Orange High
Orange County Public Schools. Zoning changes, so verify every address.
Oakland Pointe market snapshot
Oakland Pointe had no 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 Oakland Pointe
Call or text me at 407.502.4719 and I will send every recent closed sale in and around Oakland Pointe, 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 15, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.
Oakland Pointe homes for sale right now
Straight from Stellar MLS. Save the search and get new Oakland Pointe listings the day they hit.
Buying or selling in Oakland Pointe?
Pick your guide, tell me where to send it, and it opens right away.
🏡 Buyer Guide
How buying in Oakland Pointe 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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Next step: book a 30 minute call and we will walk through it together for Oakland Pointe.
Oakland Pointe FAQ
Where is Oakland Pointe in Oakland?
Oakland Pointe is in the historic town center along Oakland Avenue and the West Orange Trail, at Oakland Pointe Circle, inside the Town of Oakland (34760).
How far is Oakland Pointe from Walt Disney World?
Roughly about 25 minutes off-peak from this part of Oakland. I will map the exact drive from the entrance before you choose.
When were homes in Oakland Pointe built?
1996 to 2021, mostly 1998 to 2003. Most homes were built by individual or custom builders.
What amenities does Oakland Pointe have?
One-circle street with no through traffic, Homesites from about a third to over half an acre, Short ride to the West Orange Trail.
Is Oakland Pointe a gated community?
Oakland Pointe is not listed as gated. Ask me about gated options nearby.
What schools serve Oakland Pointe?
Schools commonly listed for this community: Oakland Avenue Charter School (K to 5, enrollment rules apply), Tildenville Elementary, Lakeview Middle, West Orange High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.
Is Oakland Pointe in the Town of Oakland?
Oakland Pointe is inside the Town of Oakland, its own incorporated town since 1887 with its own government and police department. Many Oakland homes carry a Winter Garden 34787 mailing address, and a few nearby streets are in Winter Garden city limits or unincorporated Orange County, so I confirm the jurisdiction for every address.
What do homes in Oakland Pointe sell for?
Too few homes sold in Oakland Pointe 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 Oakland Pointe from Stellar MLS.
Thinking about Oakland Pointe?
Give me 30 minutes and tell me your timeline. I will send back:
- Recent closed sales in Oakland Pointe, straight from Stellar MLS
- Town of Oakland or Winter Garden, HOA, well and septic 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 Town of Oakland, 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.