Oakland Parka
Homes for Sale in Winter Garden, FL

Oakland Park is a smaller, built-out enclave in Winter Garden with homes dating from 2008 to 2021 and a median build year of 2017, putting most of the community into a fairly consistent, contemporary construction era rather than a mix of old and new stock.

Stellar MLS sales records identify 11 homes in Oakland Parka that have changed hands since 2018, built between 2014 and 2022 (median 2017), with a median living area of about 2,718 sq ft and a typical 4-bedroom, 3.5-bath layout; 91% 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.

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.

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

In ZIP 34787, 957 homes are on the market and 30% are under contract — a steady corner of Winter Garden.

Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).

In ZIP 34787 (WINTER GARDEN), 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.

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

At 86 homes total, Oakland Park is not a high-turnover community, and the current single active listing underscores that - this is a place where inventory moves in trickles, not waves. The median living area runs a bit over 2,500 square feet, which points toward larger single-family floor plans rather than starter-sized homes, and the 2008 - 2021 build range means most buyers are shopping post-recession construction with modern codes and layouts rather than older stock needing updates.

A homestead share of 93% is notable: the overwhelming majority of homes here are owner-occupied primary residences rather than investment or seasonal-rental properties. That tends to correlate with more consistent upkeep and less turnover pressure, though it also means fewer homes cycle onto the market in any given stretch - reinforcing why supply here stays thin even when demand is present.

A community with one active listing and a single recent closing is not one where you can rely on a quick online search or a generic market report - you need someone pulling context from surrounding Winter Garden activity, tracking the HOA's actual amenity access, and ready to move the moment something new hits the market. That is the kind of on-the-ground tracking Momentum does for thin-inventory pockets like Oakland Park.

Listings in this community report association dues of about $206 per month ($2,472 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.