Oakland Heights
Single-family homes · Built 1940 to 2024, mostly 1957 to 1985 · about 1,200 to 2,450 sq ft
A small mid-century street on the east side of town.
Oakland Heights at a glance
Location: East side of the historic town, off Oakland Avenue
Builder: Custom and individual builders
Built: 1940 to 2024, mostly 1957 to 1985
Homes: About 20 homes and 3 vacant lots
Home types: Single-family homes
Size: About 1,200 to 2,450 sq ft
Bedrooms: 3 to 5 bedrooms
Area: East Oakland & Oakland Park
What Oakland Heights has
What is close to Oakland Heights
- West Orange Trail ~0.5 mi
- Oakland Town Hall and Speer Park ~0.5 mi
- Historic Downtown Winter Garden ~2.5 mi
- Oakland Nature Preserve ~1.5 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 Heights market snapshot
Oakland Heights had 2 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 Heights
Call or text me at 407.502.4719 and I will send every recent closed sale in and around Oakland Heights, 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 Heights homes for sale right now
Straight from Stellar MLS. Save the search and get new Oakland Heights listings the day they hit.
Buying or selling in Oakland Heights?
Pick your guide, tell me where to send it, and it opens right away.
🏡 Buyer Guide
How buying in Oakland Heights 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 Heights.
Oakland Heights FAQ
Where is Oakland Heights in Oakland?
Oakland Heights is in east Oakland along the Winter Garden line, at East side of the historic town, off Oakland Avenue.
How far is Oakland Heights 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 Heights built?
1940 to 2024, mostly 1957 to 1985. Most homes were built by individual or custom builders.
What amenities does Oakland Heights have?
Quarter-acre homesites, Established street with mature trees, Short ride to the West Orange Trail.
Is Oakland Heights a gated community?
Oakland Heights is not listed as gated. Ask me about gated options nearby.
What schools serve Oakland Heights?
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 Heights in the Town of Oakland?
Oakland Heights 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 Heights sell for?
Too few homes sold in Oakland Heights 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 Heights from Stellar MLS.
Thinking about Oakland Heights?
Give me 30 minutes and tell me your timeline. I will send back:
- Recent closed sales in Oakland Heights, 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.