Winters Landing
Homes for Sale in Oakland, FL

A compact enclave of 69 homes in Oakland where construction dates span nearly a century, from 1928 to 2024, sitting alongside a median build year of 2006 and a median home size over 3,300 square feet.

Stellar MLS sales records identify 55 homes in Winters Landing that have changed hands since 2006, built between 2005 and 2007 (median 2006), with a median living area of about 3,133 sq ft and a typical 4-bedroom, 3-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

County records show 7 qualified sales in Winters Landing across 2024–2025 (5 in 2024, 2 in 2025), median $799,900 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Winters Landing is too small for its own price trend, so here is the market around it.

In ZIP 34787, 932 homes are on the market and 29% are under contract — a steady corner of Oakland.

Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).

In ZIP 34787 (Oakland), 811 homes closed in the last 12 months at a median of $600K ($249/sq ft), down 6.2% year over year, with a median 34 days on market. Right now 210 active and 125 pending listings put supply at about 3.1 months — a balanced market. See the live ZIP 34787 housing market and the Orange County market.

ZIP and county figures describe the wider market, not Winters Landing specifically. Momentum Research analysis of MLS records.

With only 69 homes total, Winters Landing Phase 2 is not a high-volume market, and the year-built range is the detail that deserves attention before anything else. Homes here date as far back as 1928 and as recently as 2024, with the median landing at 2006. That spread means two houses on the same street can carry very different construction standards, systems, and maintenance histories, so buyers should evaluate each property on its own age and condition rather than assuming a community-wide build standard.

Size is more consistent than age: the median living area of 3,349 square feet suggests larger-format homes are the norm rather than the exception. Combined with a homestead share near 80%, this reads as a community built around larger, owner-occupied residences rather than smaller or investment-oriented product. No community amenities are identified from current MLS listings, so any recreational or common-area features would need to be confirmed property by property rather than assumed as part of the package.

In a small, age-diverse pool like this, the details that separate a 1928-era structure from a 2024 build matter more than the address itself. We walk buyers through the construction era, condition, and systems of each specific home in Winters Landing Phase 2 rather than leaning on community-wide assumptions, and we help sellers position an individual property clearly against neighbors that may look nothing alike on paper.