2019 to 2021Years built
1,450 to 2,500 sq ftHome size
2 to 4 bedroomsBedrooms
Pulte HomesBuilder
Why people move here

The most approachable way into a newer Oakland home.

Longleaf at Oakland is a Pulte community built between 2019 and 2021, with about 182 homes. Plans run from about 1,450 to 2,500 square feet, so it is the entry point for newer construction in town.
There is a waterfront pool, a park and a playground, and the Oakland Nature Preserve is a short walk or ride away. Mailing addresses read Winter Garden 34787, but the community is inside the Town of Oakland.
First-time buyers and downsizers who want newer and lower maintenance.

Longleaf at Oakland at a glance

Location: North of Oakland Avenue, between the Oakland Nature Preserve and Florida's Turnpike

Builder: Pulte Homes

Built: 2019 to 2021

Homes: About 182 homes

Home types: Townhomes and single-family homes

Size: About 1,450 to 2,500 sq ft

Bedrooms: 2 to 4 bedrooms

Area: Lake Apopka Shore & the Preserve

Life here

What Longleaf at Oakland has

🏊Waterfront community pool
🛠Park and playground
🌳Near the Oakland Nature Preserve
🚲Close to the West Orange Trail
Proximity

What is close to Longleaf at Oakland

  • Oakland Nature Preserve ~0.5 mi
  • West Orange Trail ~1 mi
  • Historic Downtown Winter Garden ~4 mi
  • Florida's Turnpike at SR 50 ~2 mi

Approximate distances from the community entrance. Walt Disney World is roughly 25 to 30 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

Longleaf at Oakland market snapshot

$519,000Median sale priceLast 12 months.
23 daysDays on marketMedian cumulative days on market.
9Closed salesLast 12 months.
98%Sale-to-list price ratioMedian for the last 12 months.

Stellar MLS, residential closed sales, Single-family homes, 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

Longleaf at Oakland homes for sale right now

Straight from Stellar MLS. Save the search and get new Longleaf at Oakland listings the day they hit.

Start of list of properties

Free guides

Buying or selling in Longleaf at Oakland?

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

🏡 Buyer Guide

How buying in Longleaf at Oakland 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

Longleaf at Oakland FAQ

Where is Longleaf at Oakland in Oakland?

Longleaf at Oakland is in north and west Oakland near the Lake Apopka shore and the Oakland Nature Preserve, at North of Oakland Avenue, between the Oakland Nature Preserve and Florida's Turnpike.

How far is Longleaf at Oakland from Walt Disney World?

Roughly 25 to 30 minutes off-peak from this part of Oakland. I will map the exact drive from the entrance before you choose.

When were homes in Longleaf at Oakland built?

2019 to 2021, by Pulte Homes.

What amenities does Longleaf at Oakland have?

Waterfront community pool, Park and playground, Near the Oakland Nature Preserve, Close to the West Orange Trail.

Is Longleaf at Oakland a gated community?

Longleaf at Oakland is not listed as gated. Ask me about gated options nearby.

What schools serve Longleaf at Oakland?

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 Longleaf at Oakland in the Town of Oakland?

Longleaf at Oakland 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 Longleaf at Oakland sell for?

Per Stellar MLS, the median sale price in Longleaf at Oakland was $519,000 across 9 closed sales in the Single-family homes, 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 Longleaf at Oakland?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Longleaf at Oakland, 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.