Oak Island Harbor
Homes for Sale in Kissimmee, FL

This is a mature, mid-1990s-vintage community with generously sized homes, where the mix of owner-occupied and non-homestead properties means condition varies house to house.

Stellar MLS sales records identify 38 homes in Oak Island Harbor that have changed hands since 2005, built between 1992 and 1998 (median 1996), with a median living area of about 2,045 sq ft and a typical 4-bedroom, 2.5-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 9 qualified sales in Oak Island Harbor across 2024–2024, median $454,000 — 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.

Oak Island Harbor is too small for its own price trend, so here is the market around it.

In ZIP 34747, 1,277 homes are on the market and 12% are under contract — a slower corner of Kissimmee.

Across Osceola County, 4,465 homes are active and 1,093 pending (20% under contract).

In ZIP 34747 (Kissimmee), 2,599 homes closed in the last 12 months at a median of $460K ($220/sq ft), down 3.8% year over year, with a median 75 days on market. Right now 581 active and 101 pending listings put supply at about 7.3 months — a buyer's market. See the live ZIP 34747 housing market and the Osceola County market.

ZIP and county figures describe the wider market, not Oak Island Harbor specifically. Momentum Research analysis of MLS records.

The build window closed over a decade ago, so there is no new construction to compete with resale here. The value question is straightforward: has a given home kept pace with its age? On homes built in the 1990s, roof age, HVAC, water heater, and kitchen and bath updates separate the strong listings from the ones that will sit. The living space is on the larger side for the era, which gives updated homes real appeal and gives dated ones more square footage to modernize.

The lower homestead share is the number to sit with. With roughly a third owner-occupied, the remainder skews toward investment and seasonal use, which can mean deferred maintenance in some cases and turnkey rental-grade finishes in others. Neither is good or bad on its own; it just means you underwrite each property individually and lean on inspection rather than assuming the block sets the standard.

In a community where condition, not a headline number, sets value, our job is to read the specific house: what has been updated, what is deferred, and where the negotiation leverage actually sits. We price and inspect on the merits of the individual home rather than a neighborhood shorthand, which matters most in older stock with a mixed ownership profile.

Listings in this community report association dues of about $54 per month ($648 a year) — the median AssociationFee across 22 MLS records, normalised to a monthly figure; most are billed annually. 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, 2026-10.

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