2017 to 2020Years built
1,850 to 3,500 sq ftHome size
3 to 5 bedroomsBedrooms
Meritage HomesBuilder
Why people move here

Newer Meritage homes with a pool, minutes from SR 50.

Oakland Trails is the largest newer community in town: about 305 Meritage homes built between 2017 and 2020. Most are two-story plans from about 1,850 to 3,500 square feet, with three to five bedrooms.
There is a community pool and a playground, and SR 50 and the Turnpike are close for the commute. Mailing addresses read Winter Garden 34787, but the community is inside the Town of Oakland.
Upsizers who want a newer home and a short commute without leaving the small-town feel.

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

Life here

What Oakland Trails has

🏊Community pool
🛠Playground
🌊Green space and ponds
🚲Quick access to the West Orange Trail
🏗Energy-efficient Meritage construction
Proximity

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.

The numbers

Oakland Trails market snapshot

$505,000Median sale priceDown 7.3% from $545,000 the year before.
73 daysDays on marketMedian cumulative days on market.
17Closed sales13 the year before.
98%Sale-to-list price ratioMedian for the last 12 months.

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.

Live MLS listings

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

Free guides

Buying or selling in Oakland Trails?

Pick your guide, tell me where to send it, and it opens right away.

🏡 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.

Questions buyers ask

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.

Your next step

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.