Oakland Trails
Single-family homes · Built 2017 to 2020 · about 1,850 to 3,500 sq ft
Newer Meritage homes with a pool, minutes from SR 50.
Oakland Trails at a glance
Location: Off J W Jones Road, north of SR 50 on the west side of town
Builder: Meritage Homes
Built: 2017 to 2020
Homes: About 305 homes in two phases
Home types: Single-family homes
Size: About 1,850 to 3,500 sq ft
Bedrooms: 3 to 5 bedrooms
Area: Johns Lake & SR 50
What Oakland Trails has
What is close to Oakland Trails
- SR 50 ~0.5 mi
- Florida's Turnpike at SR 50 ~1.5 mi
- Historic Downtown Winter Garden ~4.5 mi
- Clermont ~10 min
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
🏫 Tildenville Elementary
🏫 Lakeview Middle
🏫 West Orange High
Orange County Public Schools. Zoning changes, so verify every address.
Oakland Trails market snapshot
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 Trails homes for sale right now
Straight from Stellar MLS. Save the search and get new Oakland Trails listings the day they hit.
Start of list of properties
MLS# O6443027
Homevest Realty
MLS# S5156172
Exp Realty LLC
MLS# W7890380
Dalton Wade INC
Buying or selling in Oakland Trails?
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🏡 Buyer Guide
How buying in Oakland Trails 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 Trails.
Oakland Trails FAQ
Where is Oakland Trails in Oakland?
Oakland Trails is in south Oakland near Johns Lake and SR 50, at Off J W Jones Road, north of SR 50 on the west side of town.
How far is Oakland Trails 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 Trails built?
2017 to 2020, by Meritage Homes.
What amenities does Oakland Trails have?
Community pool, Playground, Green space and ponds, Quick access to the West Orange Trail, Energy-efficient Meritage construction.
Is Oakland Trails a gated community?
Oakland Trails is not listed as gated. Ask me about gated options nearby.
What schools serve Oakland Trails?
Schools commonly listed for this community: Tildenville Elementary, Lakeview Middle, West Orange High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.
Is Oakland Trails in the Town of Oakland?
Oakland Trails 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 Trails sell for?
Per Stellar MLS, the median sale price in Oakland Trails was $505,000 across 17 closed sales in the 12 months ending September 30, 2026. Call or text me at 407.502.4719 for recent sales that match your home.
Thinking about Oakland Trails?
Give me 30 minutes and tell me your timeline. I will send back:
- Recent closed sales in Oakland Trails, 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.