Winters Landing
Single-family homes · Built 2005 to 2007 · about 2,400 to 3,450 sq ft
Bigger mid-2000s homes on third-acre lots.
Winters Landing at a glance
Location: Largovista Drive and Strihal Loop, inside the Town of Oakland
Builder: Custom and individual builders
Built: 2005 to 2007
Homes: About 55 homes in two phases
Home types: Single-family homes
Size: About 2,400 to 3,450 sq ft
Bedrooms: 3 to 5 bedrooms
Area: East Oakland & Oakland Park
What Winters Landing has
What is close to Winters Landing
- West Orange Trail ~1 mi
- Tucker Oaks Village shopping ~2 mi
- Historic Downtown Winter Garden ~3 mi
- Oakland Nature Preserve ~2 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
🏫 Tildenville Elementary
🏫 Lakeview Middle
🏫 West Orange High
Orange County Public Schools. Zoning changes, so verify every address.
Winters Landing market snapshot
Winters Landing had 3 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 Winters Landing
Call or text me at 407.502.4719 and I will send every recent closed sale in and around Winters Landing, 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.
Winters Landing homes for sale right now
Straight from Stellar MLS. Save the search and get new Winters Landing listings the day they hit.
Buying or selling in Winters Landing?
Pick your guide, tell me where to send it, and it opens right away.
🏡 Buyer Guide
How buying in Winters Landing 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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If it did not open, use the buttons below. It is yours to keep.
Next step: book a 30 minute call and we will walk through it together for Winters Landing.
Winters Landing FAQ
Where is Winters Landing in Oakland?
Winters Landing is in east Oakland along the Winter Garden line, at Largovista Drive and Strihal Loop, inside the Town of Oakland.
How far is Winters Landing 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 Winters Landing built?
2005 to 2007. Most homes were built by individual or custom builders.
What amenities does Winters Landing have?
Third-acre homesites, Larger floor plans, Short drive to the West Orange Trail.
Is Winters Landing a gated community?
Winters Landing is not listed as gated. Ask me about gated options nearby.
What schools serve Winters Landing?
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 Winters Landing in the Town of Oakland?
Winters Landing 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 Winters Landing sell for?
Too few homes sold in Winters Landing 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 Winters Landing from Stellar MLS.
Thinking about Winters Landing?
Give me 30 minutes and tell me your timeline. I will send back:
- Recent closed sales in Winters Landing, 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.