Osprey Ridge
Homes for Sale in Kissimmee, FL

Built out in 2018 and 2019, Osprey Ridge is a compact, newer-construction pocket of Kissimmee with homes averaging around 1,923 square feet - a size point that consistently attracts owner-occupants, reflected in a homestead share of roughly 76%.

Stellar MLS sales records identify 58 homes in Osprey Ridge that have changed hands since 2018, built between 2018 and 2019 (median 2018), with a median living area of about 1,651 sq ft and a typical 3-bedroom, 2-bath layout; 93% 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.

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

In ZIP 34744, 418 homes are on the market and 21% are under contract — a steady corner of Kissimmee.

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

In ZIP 34744 (KISSIMMEE), 785 homes closed in the last 12 months at a median of $406K ($215/sq ft), up 1.8% year over year, with a median 34 days on market. Right now 126 active and 26 pending listings put supply at about 6.6 months - a balanced market. See the live ZIP 34744 housing market and the Osceola County market.

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

Ninety-five homes is not a lot of ground to cover, and it shows in the market snapshot: one active listing, no closings in the tracked window, and a 12.0-month supply figure that reads more like 'we do not know yet' than 'inventory is piling up.' Buyers should not assume a soft market here - they should assume a quiet one, where the next listing sets the tone rather than confirms an existing trend.

The homestead share of about 76% is worth sitting with. It suggests most owners here are living in the home as a primary residence rather than holding it as a rental or seasonal property, which typically means better-maintained interiors and fewer investor-grade shortcuts at resale. No community amenities were identified from current MLS listings, so anyone drawn to this pocket for a clubhouse, pool, or gated feel should verify directly with the HOA rather than assume anything from the listing data.

In a community with one active listing and no recent closings, the comps you need will not be sitting in a public search - they will come from tracking off-market activity, tax roll turnover, and nearby Kissimmee sales that actually apply. That is the kind of legwork we do before you write an offer or set a list price, not after.

Listings in this community report association dues of about $62 per month ($744 a year) - the median AssociationFee across 3 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.