Winters Landing
Homes for Sale in Oakland, FL

Winters Landing market snapshot (as of September 12, 2026): the median sale price is about $850K ($250 per sq ft over the trailing 12 months of closed sales), and a median 44 days on market for closed sales.

In ZIP 34787 (Oakland), 2,162 homes closed in the last 12 months at a median of $595K ($251/sq ft), down 0.6% year over year, with a median 36 days on market. Right now 357 active and 169 pending listings put supply at about 3.8 months — a balanced market. See the live ZIP 34787 housing market and the Orange County market.

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.

Winters Lndg in Oakland (Orange County) is a small, uneven pool of homes where age and size vary widely, so the community rewards buyers who read each property on its own terms rather than the headline stats.

With only 39 homes and a build range from 1928 to 2024, this is a community defined by variety, not uniformity. A near-century of construction means everything from original older homes to recent builds sits under the same community name, and the median build year of 2006 sits roughly in the middle of that range. The median living area of 3,406 square feet points to substantial homes overall, but you will find real differences from one address to the next.

The homestead share of about 68% suggests most of these are owner-occupied primary residences rather than a rental-heavy pool. Combined with the 44-day median time on market, the picture is a slower, more considered market — one where turnover is modest and the right buyer is matching to a specific home, not fighting a crowd.

In a community this small, with construction spanning from 1928 to 2024, comps are thin and easy to misread. We underwrite each home against its own vintage, condition, and square footage rather than leaning on a single median, and we price sellers to move within a realistic window instead of guessing at the market.

Listings in this community report association dues of about $73 per month ($876 a year) — the median AssociationFee across 6 MLS records, normalised to a monthly figure; most are billed quarterly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.