Wilderness
Homes for Sale in Kissimmee, FL

A modest, established pocket of Kissimmee in Osceola County with 92 homes, a median living area just under 1,944 square feet, and a build era that mostly predates 1990 — with newer construction mixed in rather than clustered.

Stellar MLS sales records identify 160 homes in Wilderness that have changed hands since 2004, built between 1986 and 2023 (median 1990), with a median living area of about 1,578 sq ft and a typical 3-bedroom, 2-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 6 qualified sales in Wilderness across 2024–2025 (3 in 2024, 3 in 2025), median $325,000 — 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.

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

In ZIP 34746, 975 homes are on the market and 17% are under contract — a slower corner of Kissimmee.

Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).

In ZIP 34746 (Kissimmee), 1,623 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.3% year over year, with a median 67 days on market. Right now 435 active and 80 pending listings put supply at about 6.7 months — a buyer's market. See the live ZIP 34746 housing market and the Osceola County market.

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

The defining fact about Wilderness is its age spread. A median year built of 1989 against a range stretching to 2022 means this isn't a single-era subdivision — it's a base of older homes with scattered infill or rebuilds decades newer. Anyone shopping here should treat year built as a starting question, not an assumption: a home from the late 1980s and one from the 2010s will carry very different expectations around roofing, electrical, plumbing, and HVAC age, even at similar square footage.

Living space centers around 1,943 square feet, a size that fits a range of layouts without skewing toward oversized new construction. No community amenities were identified from current MLS listings, so this reads as a standalone residential subdivision rather than one built around a clubhouse, pool, or recreational package — worth confirming directly if amenities are a priority. With a high share of homestead-exempt owners and limited recent closing activity, inventory here tends to move at its own pace rather than in waves.

In a community with this much variation in build year and condition, a generic comparable-sales approach doesn't hold up — you need someone pulling the right subset of comps and walking the property with an eye for what era of systems and finishes you're actually buying or selling. We do that work directly rather than leaning on a one-size number.

Listings in this community report association dues of about $25 per month ($300 a year) — the median AssociationFee across 30 MLS records, normalised to a monthly figure; most are billed monthly. 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.